Log in

Relevant bibliographies by topics / Berberine derivatives / Journal articles

Journal articles on the topic 'Berberine derivatives'

To see the other types of publications on this topic, follow the link: Berberine derivatives.

Author: Grafiati

Published: 10 March 2023

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the top 50 journal articles for your research on the topic 'Berberine derivatives.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Browse journal articles on a wide variety of disciplines and organise your bibliography correctly.

1

Olleik, Hamza, Taher Yacoub, Laurent Hoffer, Senankpon Martial Gnansounou, Kehna Benhaiem-Henry, Cendrine Nicoletti, Malika Mekhalfi, et al. "Synthesis and Evaluation of the Antibacterial Activities of 13-Substituted Berberine Derivatives." Antibiotics 9, no. 7 (July 6, 2020): 381. http://dx.doi.org/10.3390/antibiotics9070381.

Full text

Abstract:

The biological activities of berberine, a natural plant molecule, are known to be affected by structural modifications, mostly at position 9 and/or 13. A series of new 13-substituted berberine derivatives were synthesized and evaluated in term of antimicrobial activity using various microorganisms associated to human diseases. Contrarily to the original molecule berberine, several derivatives were found strongly active in microbial sensitivity tests against Mycobacterium, Candida albicans and Gram-positive bacteria, including naïve or resistant Bacillus cereus, Staphylococcus aureus and Streptococcus pyogenes with minimal inhibitory concentration (MIC) of 3.12 to 6.25 µM. Among the various Gram-negative strains tested, berberine’s derivatives were only found active on Helicobacter pylori and Vibrio alginolyticus (MIC values of 1.5–3.12 µM). Cytotoxicity assays performed on human cells showed that the antimicrobial berberine derivatives caused low toxicity resulting in good therapeutic index values. In addition, a mechanistic approach demonstrated that, contrarily to already known berberine derivatives causing either membrane permeabilization, DNA fragmentation or interacting with FtsZ protein, active derivatives described in this study act through inhibition of the synthesis of peptidoglycan or RNA. Overall, this study shows that these new berberine derivatives can be considered as potent and safe anti-bacterial agents active on human pathogenic microorganisms, including ones resistant to conventional antibiotics.

APA, Harvard, Vancouver, ISO, and other styles

2

Milata, Viktor, Alexandra Svedova, Zuzana Barbierikova, Eva Holubkova, Ingrid Cipakova, Dana Cholujova, Jana Jakubikova, et al. "Synthesis and Anticancer Activity of Novel 9-O-Substituted Berberine Derivatives." International Journal of Molecular Sciences 20, no. 9 (May 1, 2019): 2169. http://dx.doi.org/10.3390/ijms20092169.

Full text

Abstract:

Berberine is a bioactive isoquinoline alkaloid derived from many plants. Although berberine has been shown to inhibit growth and induce apoptosis of several tumor cell lines, its poor absorption and moderate activity hamper its full therapeutic potential. Here, we describe the synthesis of a series of 9-O-substituted berberine derivatives with improved antiproliferative and apoptosis-inducing activities. An analysis of novel berberine derivatives by EPR spectroscopy confirmed their similar photosensitivity and analogous behavior upon UVA irradiation as berberine, supporting their potential to generate ROS. Improved antitumor activity of novel berberine derivatives was revealed by MTT assay, by flow cytometry and by detection of apoptotic DNA fragmentation and caspase-3 activation, respectively. We showed that novel berberine derivatives are potent inhibitors of growth of HeLa and HL-60 tumor cell lines with IC50 values ranging from 0.7 to 16.7 µM for HL-60 cells and 36 to >200 µM for HeLa cells after 48 h treatment. Further cell cycle analysis showed that the observed inhibition of growth of HL-60 cells treated with berberine derivatives was due to arresting these cells in the G2/M and S phases. Most strikingly, we found that berberine derivative 3 (9-(3-bromopropoxy)-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a] isoquinolin-7-ylium bromide) possesses 30-fold superior antiproliferative activity with an IC50 value of 0.7 µM and 6-fold higher apoptosis-inducing activity in HL-60 leukemia cells compared to berberine. Therefore, further studies are merited of the antitumor activity in leukemia cells of this berberine derivative.

APA, Harvard, Vancouver, ISO, and other styles

3

Ali, Farak, Shahnaz Alom, and Md Kamaruz Zaman. "Berberine: A Comprehensive Review on its Isolation, Biosynthesis, Chemistry and Pharmacology." Asian Journal of Chemistry 33, no. 11 (2021): 2548–60. http://dx.doi.org/10.14233/ajchem.2021.23365.

Full text

Abstract:

The isoquinoline compounds from alkaloidal class have been excellent source of important phytoconstituents having wide range of pharmacological activities. Berberine is a protoberberine alkaloidal compound obtained from Berberis genus plants which belongs to family Barberidaceae. Due to its unique structural properties, berberine and its derivatives has been exploited extensively for its potential uses in various pharmacological targets such as cancer, inflammation, diabetes, gastrointestinal disorder, viral and microbial infections, neurological disorder like Alzheimer, anxiety, schizophrenia, depression, etc. This review illustrates the updated information on berberine with respect to its isolation, biosynthesis, chemical synthesis, structural modification and pharmacological activities. An extensive literature search were carried out in various search engine like PubMed, Google Scholars, Research Gate and SCOPUS by using keywords like Berberine, protoberberine alkaloids, isoquinoline derivatives, pharmacological effects, etc. Prephenic acid is the starting material for biosynthesis of berberine. Structural modifications lead to generation of various potential derivatives, which earn patents by researchers. Besides toxicities, the complications of low solubility and bioavailability should be eliminated. To improve its safety, efficacy and selectivity the berberine should be carefully derivatized.

APA, Harvard, Vancouver, ISO, and other styles

4

Mittal, J., K. Chaudhary, N. Kumar, and D. Pathak. "EXTRACTION, ISOLATION, CHARACTERIZATION, SEMISYNTHESIS AND BIOLOGICAL EVALUATION OF BERBERINE FROM ROOTS OF BERBERIS ARISTATA." INDIAN DRUGS 50, no. 09 (September 28, 2013): 18–24. http://dx.doi.org/10.53879/id.50.09.p0018.

Full text

Abstract:

A methanolic extract of roots of Berberis aristata was prepared by using hot percolation method. Berberine was isolated from the above extract and characterized by IR, 1HNMR, mass spectrometry and elemental analysis. A series of 8-(substituted acetophenone) berberine derivatives was synthesized by introducing various acetophenone derivatives at 8th position of berberine and analyzed by melting point and TLC. The structures of all the synthesized compounds were characterized by IR, 1HNMR, mass spectrometry and elemental analysis. The semisynthesized compounds were screened for in vitro antibacterial and antifungal activity using disc (5mm) diffusion method on nutrient agar medium against Gram-positive (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacterial strains (Pseudomonas aeruginosa and Escherichia coli) and fungal strains (Aspergillus niger and Candida albicans) respectively. The zone of inhibition was compared with standard drugs berberine and kanamycin. All the above compounds showed significant activity in comparison to the standards berberine and kanamycin.

APA, Harvard, Vancouver, ISO, and other styles

5

Parcha, Versha, Diveya J. Singh, Deepak Kumar, and Jaswinder K. Saini. "EVALUATION OF ANTI-MICROBIAL POTENTIAL OF STRUCTURALLY MODIFIED DERIVATIVES OF LEAD COMPOUND BERBERINE ISOLATED FROM ROOTS OF BERBERIS ARISTATA." INDIAN DRUGS 58, no. 09 (December 4, 2021): 59–64. http://dx.doi.org/10.53879/id.58.09.12262.

Full text

Abstract:

The alkaloid berberine, the chief constituent of Berberis aristata, has been reported to have antimicrobial activity associated with it. Structural changes can be made to this lead compound to try to improve its effi cacy in terms of antimicrobial activity. In the present study, attempts have been made to evaluate anti-microbial potential of structurally modifi ed derivatives of berberine. The derivatives so synthesized were characterized on the basis of spectral techniques like 1H,13C NMR, UV, IR and MASS and by comparison with standard berberine. Structure-activity relationship studies revealed that methoxyl group is pharmacophore of berberine and is thus needed to be retained in the skeleton. Further incorporation of the electron-withdrawing group has pronounced effect on the antimicrobial activity. Further attempts could be made to extend the series with the incorporation of such electron-withdrawing groups to get potent antimicrobial agents.

APA, Harvard, Vancouver, ISO, and other styles

6

Jamshaid, Faisal, Jun Dai, and Li Xi Yang. "New Development of Novel Berberine Derivatives against Bacteria." Mini-Reviews in Medicinal Chemistry 20, no. 8 (May 17, 2020): 716–24. http://dx.doi.org/10.2174/1389557520666200103115124.

Full text

Abstract:

: Many berberine derivatives have been synthesized for their antibacterial activity in the past years. In order to elucidate their new Structural Activity Relationship (SAR), the recently synthesized berberine derivatives are reviewed. The newly synthesized berberine derivatives are reported in this review with novel modifications on the berberine structure at various positions. It is hoped that this article would help scientists to design and synthesize new berberine derivatives with high potency and a broad spectrum of antimicrobial activities, more effectiveness and lower toxicity for improved antimicrobial therapy. These berberine derivatives could be developed as novel antibacterial agents to treat patients with infectious diseases, especially caused by resistant bacteria.

APA, Harvard, Vancouver, ISO, and other styles

7

Chen, Chunqiu, Zhen Yu, Yongyu Li, Jakub Fichna, and Martin Storr. "Effects of Berberine in the Gastrointestinal Tract — A Review of Actions and Therapeutic Implications." American Journal of Chinese Medicine 42, no. 05 (January 2014): 1053–70. http://dx.doi.org/10.1142/s0192415x14500669.

Full text

Abstract:

Berberine is an isoquinoline alkaloid present in several plant species, including Coptis sp. and Berberis sp. In traditional medicine, extracts of berberine are used in the treatment of diarrhea of different origins. Recent studies have shown that berberine and its derivatives have significant biological effects on gastrointestinal (GI) and other functions and may become therapeutics for the treatment of diarrhea, gastroenteritis, diabetes, hyperlipidemia, cardiovascular diseases and inflammatory conditions. This paper summarizes the current knowledge on the actions of berberine in the GI tract. Binding and target sites, activated intracellular pathways, as well as the absorption and metabolism of berberine are discussed. Effects that may be useful in future clinical treatment, like antidiarrheal, anti-inflammatory and antitumor effects are critically reviewed and potential clinical applications are presented in detail.

APA, Harvard, Vancouver, ISO, and other styles

8

Giorgini, Giorgia, Gianmarco Mangiaterra, Nicholas Cedraro, Emiliano Laudadio, Giulia Sabbatini, Mattia Cantarini, Cristina Minnelli, et al. "Berberine Derivatives as Pseudomonas aeruginosa MexXY-OprM Inhibitors: Activity and In Silico Insights." Molecules 26, no. 21 (November 2, 2021): 6644. http://dx.doi.org/10.3390/molecules26216644.

Full text

Abstract:

The natural alkaloid berberine has been demonstrated to inhibit the Pseudomonas aeruginosa multidrug efflux system MexXY-OprM, which is responsible for tobramycin extrusion by binding the inner membrane transporter MexY. To find a structure with improved inhibitory activity, we compared by molecular dynamics investigations the binding affinity of berberine and three aromatic substituents towards the three polymorphic sequences of MexY found in P. aeruginosa (PAO1, PA7, and PA14). The synergy of the combinations of berberine or berberine derivatives/tobramycin against the same strains was then evaluated by checkerboard and time-kill assays. The in silico analysis evidenced different binding modes depending on both the structure of the berberine derivative and the specific MexY polymorphism. In vitro assays showed an evident MIC reduction (32-fold and 16-fold, respectively) and a 2–3 log greater killing effect after 2 h of exposure to the combinations of 13-(2-methylbenzyl)- and 13-(4-methylbenzyl)-berberine with tobramycin against the tobramycin-resistant strain PA7, a milder synergy (a 4-fold MIC reduction) against PAO1 and PA14, and no synergy against the ΔmexXY strain K1525, confirming the MexY-specific binding and the computational results. These berberine derivatives could thus be considered new hit compounds to select more effective berberine substitutions and their common path of interaction with MexY as the starting point for the rational design of novel MexXY-OprM inhibitors.

APA, Harvard, Vancouver, ISO, and other styles

9

Gladkova, Elizaveta D., Nicolae Valutsa, Sergey A. Borisov, Mikhail V. Khvostov, Olga A. Luzina, Tatiana G. Tolstikova, and Nariman F. Salakhutdinov. "Synthesis of a Novel 9-O Berberine Derivative and Evaluation of Its Hypoglycemic Effect." Molbank 2023, no. 1 (February 24, 2023): M1597. http://dx.doi.org/10.3390/m1597.

Full text

Abstract:

Berberine is a phytogenic isoquinoline alkaloid which demonstrates several pharmacological effects, including a hypoglycemic effect. Its medical use is limited by its very low bioavailability. Synthesizing new berberine derivatives might help in overcoming this problem. In this work, we report on the synthesis and biological evaluation of a novel berberine 9-O-derivative. At an oral dose of 25 mg/kg, the compound demonstrated hypoglycemic activity in an oral glucose tolerance test performed using C57BL/6 mice.

APA, Harvard, Vancouver, ISO, and other styles

10

Lin, Hong-Jhih, Jinn-Hsuan Ho, Li-Chen Tsai, Fang-Yu Yang, Ling-Ling Yang, Cheng-Deng Kuo, Lih-Geeng Chen, Yi-Wen Liu, and Jin-Yi Wu. "Synthesis and In Vitro Photocytotoxicity of 9-/13-Lipophilic Substituted Berberine Derivatives as Potential Anticancer Agents." Molecules 25, no. 3 (February 5, 2020): 677. http://dx.doi.org/10.3390/molecules25030677.

Full text

Abstract:

The objective of this study was to synthesize the 9-/13-position substituted berberine derivatives and evaluate their cytotoxic and photocytotoxic effects against three human cancer cell lines. Among all the synthesized compounds, 9-O-dodecyl- (5e), 13-dodecyl- (6e), and 13-O-dodecyl-berberine (7e) exhibited stronger growth inhibition against three human cancer cell lines, (HepG2, HT-29 and BFTC905), in comparison with structurally related berberine (1). These three compounds also showed the photocytotoxicity in human cancer cells in a concentration-dependent and light dose-dependent manner. Through flow cytometry analysis, we found out a lipophilic group at the 9-/13-position of berberine may have facilitated its penetration into test cells and hence enhanced its photocytotoxicity on the human liver cancer cell HepG2. Further, in cell cycle analysis, 5e, 6e, and 7e induced HepG2 cells to arrest at the S phase and caused apoptosis upon irradiation. In addition, photodynamic treatment of berberine derivatives 5e, 6e, and 7e again showed a significant photocytotoxic effects on HepG2 cells, induced remarkable cell apoptosis, greatly increased intracellular ROS level, and the loss of mitochondrial membrane potential. These results over and again confirmed that berberine derivatives 5e, 6e, and 7e greatly enhanced photocytotoxicity. Taken together, the test data led us to conclude that berberine derivatives with a dodecyl group at the 9-/13-position could be great candidates for the anti-liver cancer medicines developments.

APA, Harvard, Vancouver, ISO, and other styles

11

Guamán Ortiz, Luis Miguel, Micol Tillhon, Michael Parks, Ilaria Dutto, Ennio Prosperi, Monica Savio, Andrea G. Arcamone, Franco Buzzetti, Paolo Lombardi, and Anna Ivana Scovassi. "Multiple Effects of Berberine Derivatives on Colon Cancer Cells." BioMed Research International 2014 (2014): 1–12. http://dx.doi.org/10.1155/2014/924585.

Full text

Abstract:

The pharmacological use of the plant alkaloid berberine is based on its antibacterial and anti-inflammatory properties; recently, anticancer activity has been attributed to this compound. To exploit this interesting feature, we synthesized three berberine derivatives, namely, NAX012, NAX014, and NAX018, and we tested their effects on two human colon carcinoma cell lines, that is, HCT116 and SW613-B3, which are characterized by wt and mutatedp53, respectively. We observed that cell proliferation is more affected by cell treatment with the derivatives than with the lead compound; moreover, the derivatives proved to induce cell cycle arrest and cell death through apoptosis, thus suggesting that they could be promising anticancer drugs. Finally, we detected typical signs of autophagy in cells treated with berberine derivatives.

APA, Harvard, Vancouver, ISO, and other styles

12

Vennerstrom, J. L., J. K. Lovelace, V. B. Waits, W. L. Hanson, and D. L. Klayman. "Berberine derivatives as antileishmanial drugs." Antimicrobial Agents and Chemotherapy 34, no. 5 (May 1, 1990): 918–21. http://dx.doi.org/10.1128/aac.34.5.918.

Full text

APA, Harvard, Vancouver, ISO, and other styles

13

BUYUKAKINCI, YESIM BANU, RECEP KARADAG, and EMINE TORGAN GUZEL. "Organic cotton fabric dyed with dyer's oak and barberry dye by microwave irradiation and conventional methods." Industria Textila 72, no. 01 (February 28, 2021): 30–38. http://dx.doi.org/10.35530/it.072.01.1755.

Full text

Abstract:

In this work, organic cotton fabrics were dyed using barberry (Berberis vulgaris L.), dyer’s oak (Quercus infectoria Olivier) and dyer’s oak + barberry (Quercus infectoria Olivier + Berberis vulgaris L.) by microwave irradiation and conventional dyeing methods. They were used in equal percentages. The dyed fabrics were analyzed by different analytical and technical methods. Colouring compounds were analyzed in the dyed fabrics, dye extractions (before dyeing bath and after dyeing bath) by High Performance Liquid Chromatography with Diode Array Detector (HPLC-DAD). Identified coloring compounds based on the dyestuff analysis were berberine, berberine derivative, phenolic acid, ellagic acid, ellegic acid derivatives, gallic acid and gallic acid derivative. Colour characteristics of all the dyed fabrics were measured by CIEL*a*b* spectrophotometer and pH values were determined by surface-pH meter. Scanning Electron Microscopy equipped with Energy Dispersive X-ray Spectrometer (SEM-EDX) was used for imaging and elemental analysis of the surfaces of the dyed organic cotton fabrics. The colouristic and colour fastness properties of the dyed fabrics were investigated and compared with each other. No damage was observed in the fabrics dyed by the microwave and conventional dyeing methods. Almost the same colour yields were obtained in both dyeings using different processing times. According to the analyses and test results, microwave irradiation method is very eligible compared to conventional dyeing methods, considering coloristic properties of dyed fabrics, time saving and the cost effectiveness wise.

APA, Harvard, Vancouver, ISO, and other styles

14

Khvostov, Mikhail V., Elizaveta D. Gladkova, Sergey A. Borisov, Marina S. Fedotova, Nataliya A. Zhukova, Mariya K. Marenina, Yulia V. Meshkova, et al. "9-N-n-alkyl Berberine Derivatives: Hypoglycemic Activity Evaluation." Pharmaceutics 15, no. 1 (December 22, 2022): 44. http://dx.doi.org/10.3390/pharmaceutics15010044.

Full text

Abstract:

Several novel 9-N-n-alkyl derivatives of berberine (C5, C7, C10, C12) were synthesized. They were analyzed in vitro and in vivo for their hypoglycemic activity. In vitro studies showed that the derivatives with shorter alkyl substitutes at concentrations ranging from 2.5 to 10 μM were able to stimulate glucose consumption by HepG2 cells more prominently than the derivatives with longer substitutes (C10 and C12). All compounds demonstrated a better effect compared to berberine. Their impact on cells’ viability also depended on the alkyl substitutes length, but in this case, C10 and C12 derivatives demonstrated the best results. A similar correlation was also found in the OGTT, where the C5 derivative demonstrated a pronounced hypoglycemic effect at a dose of 15 mg/kg and C12 was less effective. This compound was further investigated in C57BL/6Ay mice for four weeks and was administered at a dose of 15 mg/kg. Pronounced effect of C12 on carbohydrate metabolism in mice was discovered: there was a decrease in fasting glucose levels and an increase in glucose tolerance in OGTT on the 14th and 28th days of the experiment. However, at the end of the experiment, signs of hepatosis exacerbation and an increase in the content of hepatic aminotransferases in blood were found.

APA, Harvard, Vancouver, ISO, and other styles

15

Kotani, Kenta, Mio Matsumura, Yuji Morita, Junko Tomida, Ryo Kutsuna, Kunihiko Nishino, Shuji Yasuike, and Yoshiaki Kawamura. "13-(2-Methylbenzyl) Berberine Is a More Potent Inhibitor of MexXY-Dependent Aminoglycoside Resistance than Berberine." Antibiotics 8, no. 4 (November 6, 2019): 212. http://dx.doi.org/10.3390/antibiotics8040212.

Full text

Abstract:

We previously showed that berberine attenuates MexXY efflux-dependent aminoglycoside resistance in Pseudomonas aeruginosa. Here, we aimed to synthesize berberine derivatives with higher MexXY inhibitory activities. We synthesized 11 berberine derivatives, of which 13-(2-methylbenzyl) berberine (13-o-MBB) but not its regiomers showed the most promising MexXY inhibitory activity. 13-o-MBB reduced the minimum inhibitory concentrations (MICs) of various aminoglycosides 4- to 128 fold for a highly multidrug resistant P. aeruginosa strain. Moreover, 13-o-MBB significantly reduced the MICs of gentamicin and amikacin in Achromobacter xylosoxidans and Burkholderia cepacia. The fractional inhibitory concentration indices indicated that 13-o-MBB acted synergistically with aminoglycosides in only MexXY-positive P. aeruginosa strains. Time-kill curves showed that 13-o-MBB or higher concentrations of berberine increased the bactericidal activity of gentamicin by inhibiting MexXY in P. aeruginosa. Our findings indicate that 13-o-MBB inhibits MexXY-dependent aminoglycoside drug resistance more strongly than berberine and that 13-o-MBB is a useful inhibitor of aminoglycoside drug resistance due to MexXY.

APA, Harvard, Vancouver, ISO, and other styles

16

Gladkova, Elizaveta D., Ivan V. Nechepurenko, Roman A. Bredikhin, Arina A. Chepanova, Alexandra L. Zakharenko, Olga A. Luzina, Ekaterina S. Ilina, et al. "The First Berberine-Based Inhibitors of Tyrosyl-DNA Phosphodiesterase 1 (Tdp1), an Important DNA Repair Enzyme." International Journal of Molecular Sciences 21, no. 19 (September 28, 2020): 7162. http://dx.doi.org/10.3390/ijms21197162.

Full text

Abstract:

A series of berberine and tetrahydroberberine sulfonate derivatives were prepared and tested against the tyrosyl-DNA phosphodiesterase 1 (Tdp1) DNA-repair enzyme. The berberine derivatives inhibit the Tdp1 enzyme in the low micromolar range; this is the first reported berberine based Tdp1 inhibitor. A structure–activity relationship analysis revealed the importance of bromine substitution in the 12-position on the tetrahydroberberine scaffold. Furthermore, it was shown that the addition of a sulfonate group containing a polyfluoroaromatic moiety at position 9 leads to increased potency, while most of the derivatives containing an alkyl fragment at the same position were not active. According to the molecular modeling, the bromine atom in position 12 forms a hydrogen bond to histidine 493, a key catalytic residue. The cytotoxic effect of topotecan, a clinically important topoisomerase 1 inhibitor, was doubled in the cervical cancer HeLa cell line by derivatives 11g and 12g; both displayed low toxicity without topotecan. Derivatives 11g and 12g can therefore be used for further development to sensitize the action of clinically relevant Topo1 inhibitors.

APA, Harvard, Vancouver, ISO, and other styles

17

Becher, Jonas, Daria V. Berdnikova, Heiko Ihmels, and Christopher Stremmel. "Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives." Beilstein Journal of Organic Chemistry 16 (November 18, 2020): 2795–806. http://dx.doi.org/10.3762/bjoc.16.230.

Full text

Abstract:

A small series of five novel berberine derivatives was synthesized by the Cu-catalyzed click reaction of 9-propargyladenine with 9-O-(azidoalkyl)berberine derivatives. The association of the resulting berberine–adenine conjugates with representative quadruplex-forming oligonucleotides 22AG dA(G3TTA)3G3 and a2 d(ACAG4TGTG4)2 was examined with photometric and fluorimetric titrations, thermal DNA denaturation analysis, and CD spectroscopy. The results from the spectrometric titrations indicated the formation of 2:1 or 1:1 complexes (ligand:G4-DNA) with log K b values of 10–11 (2:1) and 5–6 (1:1), which are typical for berberine derivatives. Notably, a clear relationship between the binding affinity of the ligands with the length of the alkyl linker chain, n, was not observed. However, depending on the structure, the ligands exhibited different effects when bound to the G4-DNA, such as fluorescent light-up effects and formation of ICD bands, which are mostly pronounced with a linker length of n = 4 (with a2) and n = 5 (with 22AG), thus indicating that each ligand–G4-DNA complex has a specific structure with respect to relative alignment and conformational flexibility of the ligand in the binding site. It was shown exemplarily with one representative ligand from the series that such berberine–adenine conjugates exhibit a selective binding, specifically a selectivity to quadruplex DNA in competition with duplex DNA, and a preferential thermal stabilization of the G4-DNA forms 22AG and KRAS. Notably, the experimental data do not provide evidence for a significant effect of the adenine unit on the binding affinity of the ligands, for example, by additional association with the loops, presumably because the adenine residue is sterically shielded by the neighboring triazole unit.

APA, Harvard, Vancouver, ISO, and other styles

18

Chang, Jia-Ming, Kam-Hong Kam, Wen-Ying Chao, Pei-Wen Zhao, Shu-Hsin Chen, Hui-Chen Chung, Yi-Zhen Li, Jin-Yi Wu, and Ying-Ray Lee. "Berberine Derivatives Suppress Cellular Proliferation and Tumorigenesis In Vitro in Human Non-Small-Cell Lung Cancer Cells." International Journal of Molecular Sciences 21, no. 12 (June 13, 2020): 4218. http://dx.doi.org/10.3390/ijms21124218.

Full text

Abstract:

Lung cancer is the leading cause of death in the world, and the most common type of lung cancer is non-small-cell lung cancer (NSCLC), accounting for 85% of lung cancer. Patients with NSCLC, when detected, are mostly in a metastatic stage, and over half of patients diagnosed with NSCLC die within one year after diagnosis; the 5-year survival rate is 24%. However, in patients with metastatic NSCLC, the 5-year survival rate is 6%. Therefore, development of a new therapeutic agent or strategy is urgent for NSCLCs. Berberine has been illustrated to be a therapeutic agent of NSCLC. In the present study, we synthesized six derivatives of berberine, and the anti-NSCLC activity of these agents was examined. Some of them exert increasing proliferation inhibition comparing with berberine. Further studies demonstrated that two of the most effective agents, 9-O-decylberberrubine bromide (B6) and 9-O-dodecylberberrubine bromide (B7), performed cell cycle regulation, in-vitro tumorigenesis inhibition and autophagic flux blocking, but not induction of cellular apoptosis in NSCLC cells. Moreover, B6 and B7 were determined to be green fluorescent and could be penetrated and localized in cellular mitochondria. Herein, B6 and B7, the berberine derivatives we synthesized, revealed better anti-NSCLC activity with berberine and may be used as therapeutic candidates for the treatment of NSCLCs.

APA, Harvard, Vancouver, ISO, and other styles

19

Och, Anna, Rafał Podgórski, and Renata Nowak. "Biological Activity of Berberine—A Summary Update." Toxins 12, no. 11 (November 12, 2020): 713. http://dx.doi.org/10.3390/toxins12110713.

Full text

Abstract:

Berberine is a plant metabolite belonging to the group of isoquinoline alkaloids with strong biological and pharmacological activity. Currently, berberine is receiving considerable interest due to its anticancer activity based on many biochemical pathways, especially its proapoptotic and anti-inflammatory activity. Therefore, the growing number of papers on berberine demands summarizing the knowledge and research trends. The efficacy of berberine in breast and colon cancers seems to be the most promising aspect. Many papers focus on novel therapeutic strategies based on new formulations or search for new active derivatives. The activity of berberine is very important as regards sensitization and support of anticancer therapy in combination with well-known but in some cases inefficient therapeutics. Currently, the compound is being assessed in many important clinical trials and is one of the most promising and intensively examined natural agents.

APA, Harvard, Vancouver, ISO, and other styles

20

Mahapatra, Anita, Vijay Maheswari, Nitin Pal Kalia, Vikrant S. Rajput, and Inshad Ali Khan. "Synthesis and Antitubercular Activity of Berberine Derivatives." Chemistry of Natural Compounds 50, no. 2 (May 2014): 321–25. http://dx.doi.org/10.1007/s10600-014-0942-8.

Full text

APA, Harvard, Vancouver, ISO, and other styles

21

Fu, Shengnan, Yanqi Xie, Jue Tuo, Yalong Wang, Wenbo Zhu, Sihan Wu, Guangmei Yan, and Haiyan Hu. "Discovery of mitochondria-targeting berberine derivatives as the inhibitors of proliferation, invasion and migration against rat C6 and human U87 glioma cells." MedChemComm 6, no. 1 (2015): 164–73. http://dx.doi.org/10.1039/c4md00264d.

Full text

APA, Harvard, Vancouver, ISO, and other styles

22

Wang, Lizhen, Haotian Kong, Meng Jin, Xiaobin Li, Rostyslav Stoika, Houwen Lin, and Kechun Liu. "Synthesis of disaccharide modified berberine derivatives and their anti-diabetic investigation in zebrafish using a fluorescence-based technology." Organic & Biomolecular Chemistry 18, no. 18 (2020): 3563–74. http://dx.doi.org/10.1039/d0ob00327a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

23

Liu, Yanfei, Shuo Long, Shanshan Zhang, Yifu Tan, Ting Wang, Yuwei Wu, Ting Jiang, Xiaoqin Liu, Dongming Peng, and Zhenbao Liu. "Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives." RSC Advances 11, no. 29 (2021): 17611–21. http://dx.doi.org/10.1039/d1ra01339d.

Full text

APA, Harvard, Vancouver, ISO, and other styles

24

Han, Liwen, Wenlong Sheng, Xiaobin Li, Attila Sik, Houwen Lin, Kechun Liu, and Lizhen Wang. "Novel carbohydrate modified berberine derivatives: synthesis andin vitroanti-diabetic investigation." MedChemComm 10, no. 4 (2019): 598–605. http://dx.doi.org/10.1039/c9md00036d.

Full text

APA, Harvard, Vancouver, ISO, and other styles

25

Bremner, John B., and Siritron Samosorn. "8-Allyldihydroberberine as an Alternative Precursor for the Synthesis of 13-Substituted Berberine Derivatives." Australian Journal of Chemistry 56, no. 9 (2003): 871. http://dx.doi.org/10.1071/ch03054.

Full text

APA, Harvard, Vancouver, ISO, and other styles

26

Huang, Mei-Yan, Jing Lin, Zhi-Jian Huang, Hong-Gui Xu, Juan Hong, Ping-Hua Sun, Jia-Liang Guo, and Wei-Min Chen. "Design, synthesis and anti-inflammatory effects of novel 9-O-substituted-berberine derivatives." MedChemComm 7, no. 4 (2016): 658–66. http://dx.doi.org/10.1039/c5md00577a.

Full text

Abstract:

A series of novel 9-O-substituted-berberine derivatives were synthesized and their anti-inflammatory activities were evaluated. Among them, compounds 3i and 5e exhibited excellent anti-inflammatory potential.

APA, Harvard, Vancouver, ISO, and other styles

27

Man, Stanislav, Milan Potáček, Marek Nečas, Zdirad Žák, and Jiří Dostál. "Molecular and Crystal Structures of Three Berberine Derivatives." Molecules 6, no. 5 (April 30, 2001): 433–41. http://dx.doi.org/10.3390/60500433.

Full text

APA, Harvard, Vancouver, ISO, and other styles

28

Franceschin, Marco, Luigi Rossetti, Anna D’Ambrosio, Stefano Schirripa, Armandodoriano Bianco, Giancarlo Ortaggi, Maria Savino, Christoph Schultes, and Stephen Neidle. "Natural and synthetic G-quadruplex interactive berberine derivatives." Bioorganic & Medicinal Chemistry Letters 16, no. 6 (March 2006): 1707–11. http://dx.doi.org/10.1016/j.bmcl.2005.12.001.

Full text

APA, Harvard, Vancouver, ISO, and other styles

29

Wang, Jian-Ta, Jin-Gang Peng, Ji-Quan Zhang, Zhong-Xiao Wang, Yi Zhang, Xun-Rong Zhou, Jing Miao, and Lei Tang. "Novel berberine-based derivatives with potent hypoglycemic activity." Bioorganic & Medicinal Chemistry Letters 29, no. 23 (December 2019): 126709. http://dx.doi.org/10.1016/j.bmcl.2019.126709.

Full text

APA, Harvard, Vancouver, ISO, and other styles

30

Wang, Bo, An-Jun Deng, Zhi-Hong Li, Nan Wang, and Hai-Lin Qin. "Syntheses and Structure–Activity Relationships in Growth Inhibition Activity against Human Cancer Cell Lines of 12 Substituted Berberine Derivatives." Molecules 25, no. 8 (April 18, 2020): 1871. http://dx.doi.org/10.3390/molecules25081871.

Full text

Abstract:

In this study, quaternary berberine chloride is used as a lead compound to design and synthesize a series of berberine-12-amine derivatives to evaluate the growth inhibition activity against human cancer cell lines. Forty-two compounds of several series were obtained. The quaternary berberine-12-N,N-di-n-alkylamine chlorides showed the targeted activities with the IC50 values of most active compounds being dozens of times those of the positive control. A significant structure–activity relationship (SAR) was observed. The activities of quaternary berberine-12-N,N-di-n-alkylamine chlorides are significantly stronger than those of the reduced counterparts. In the range of about 6-8 carbon atoms, the activities increase with the elongation of n-alkyl carbon chain of 12-N,N-di-n-alkylamino, and when the carbon atom numbers are more than 6-8, the activities decrease with the elongation of n-alkyl carbon chain. The activities of the tertiary amine structure are significantly higher than that of the secondary amine structure.

APA, Harvard, Vancouver, ISO, and other styles

31

Chang, Jia-Ming, Jin-Yi Wu, Shu-Hsin Chen, Wen-Ying Chao, Hsiang-Hao Chuang, Kam-Hong Kam, Pei-Wen Zhao, Yi-Zhen Li, Yu-Pei Yen, and Ying-Ray Lee. "9-O-Terpenyl-Substituted Berberrubine Derivatives Suppress Tumor Migration and Increase Anti-Human Non-Small-Cell Lung Cancer Activity." International Journal of Molecular Sciences 22, no. 18 (September 13, 2021): 9864. http://dx.doi.org/10.3390/ijms22189864.

Full text

Abstract:

Lung cancer is one of the most common cancers and the leading cause of death in humans worldwide. Non-small-cell lung cancer (NSCLC) accounts for approximately 85% of lung cancer cases and is often diagnosed at a late stage. Among patients with NSCLC, 50% die within 1 year after diagnosis. Even with clinical intervention, the 5-year survival rate is only approximately 20%. Therefore, the development of an advanced therapeutic strategy or novel agent is urgently required for treating NSCLC. Berberine exerts therapeutic activity toward NSCLC; therefore, its activity as an antitumor agent needs to be explored further. In this study, three terpenylated-bromide derivatives of berberrubine were synthesized and their anti-NSCLC activities were evaluated. Each derivative had higher anti-NSCLCs activity than berberrubine and berberine. Among them, 9-O-gernylberberrubine bromide (B4) and 9-O-farnesylberberrubine bromide (B5) showed greater growth inhibition, cell-cycle regulation, in vitro tumorigenesis suppression, and tumor migration reduction. In addition, some degree of apoptosis and autophagic flux blocking was noted in the cells under B4 and B5 treatments. Our study demonstrates that the berberrubine derivatives, B4 and B5, exhibit impressive anti-NSCLC activities and have potential for use as chemotherapeutic agents against NSCLC.

APA, Harvard, Vancouver, ISO, and other styles

32

Wang, Lizhen, Xueliang Yang, Xiaobin Li, Rostyslav Stoika, Xue Wang, Houwen Lin, Yukui Ma, Rongchun Wang, and Kechun Liu. "Synthesis of hydrophobically modified berberine derivatives with high anticancer activity through modulation of the MAPK pathway." New Journal of Chemistry 44, no. 33 (2020): 14024–34. http://dx.doi.org/10.1039/d0nj01645d.

Full text

APA, Harvard, Vancouver, ISO, and other styles

33

Bazzicalupi, Carla, Alessandro Bonardi, Tarita Biver, Marta Ferraroni, Francesco Papi, Matteo Savastano, Paolo Lombardi, and Paola Gratteri. "Probing the Efficiency of 13-Pyridylalkyl Berberine Derivatives to Human Telomeric G-Quadruplexes Binding: Spectroscopic, Solid State and In Silico Analysis." International Journal of Molecular Sciences 23, no. 22 (November 14, 2022): 14061. http://dx.doi.org/10.3390/ijms232214061.

Full text

Abstract:

The interaction between the series of berberine derivatives 1–5 (NAX071, NAX120, NAX075, NAX077 and NAX079) and human telomeric G-quadruplexes (G4), which are able to inhibit the Telomerase enzyme’s activity in malignant cells, was investigated. The derivatives bear a pyridine moiety connected by a hydrocarbon linker of varying length (n = 1–5, with n number of aliphatic carbon atoms) to the C13 position of the parent berberine. As for the G4s, both bimolecular 5′-TAGGGTTAGGGT-3′ (Tel12) and monomolecular 5′-TAGGGTTAGGGTTAGGGTTAGGG-3′ (Tel23) DNA oligonucleotides were considered. Spectrophotometric titrations, melting tests, X-ray diffraction solid state analysis and in silico molecular dynamics (MD) simulations were used to describe the different systems. The results were compared in search of structure–activity relationships. The analysis pointed out the formation of 1:1 complexes between Tel12 and all ligands, whereas both 1:1 and 2:1 ligand/G4 stoichiometries were found for the adduct formed by NAX071 (n = 1). Tel12, with tetrads free from the hindrance by the loop, showed a higher affinity. The details of the different binding geometries were discussed, highlighting the importance of H-bonds given by the berberine benzodioxole group and a correlation between the strength of binding and the hydrocarbon linker length. Theoretical (MD) and experimental (X-ray) structural studies evidence the possibility for the berberine core to interact with one or both G4 strands, depending on the constraints given by the linker length, thus affecting the G4 stabilization effect.

APA, Harvard, Vancouver, ISO, and other styles

34

Kumar, Manu, Sang-Min Chung, Ganuskh Enkhtaivan, Rahul V. Patel, Han-Seung Shin, and Bhupendra M. Mistry. "Molecular Docking Studies and Biological Evaluation of Berberine–Benzothiazole Derivatives as an Anti-Influenza Agent via Blocking of Neuraminidase." International Journal of Molecular Sciences 22, no. 5 (February 27, 2021): 2368. http://dx.doi.org/10.3390/ijms22052368.

Full text

Abstract:

In this study, we have introduced newly synthesized substituted benzothiazole based berberine derivatives that have been analyzed for their in vitro and in silico biological properties. The activity towards various kinds of influenza virus strains by employing the cytopathic effect (CPE) and sulforhodamine B (SRB) assay. Several berberine–benzothiazole derivatives (BBDs), such as BBD1, BBD3, BBD4, BBD5, BBD7, and BBD11, demonstrated interesting anti-influenza virus activity on influenza A viruses (A/PR/8/34, A/Vic/3/75) and influenza B viral (B/Lee/40, and B/Maryland/1/59) strain, respectively. Furthermore, by testing neuraminidase activity (NA) with the neuraminidase assay kit, it was identified that BBD7 has potent neuraminidase activity. The molecular docking analysis further suggests that the BBD1–BBD14 compounds’ antiviral activity may be because of interaction with residues of NA, and the same as in oseltamivir.

APA, Harvard, Vancouver, ISO, and other styles

35

Leyva-Peralta, Mario A., Ramón E. Robles-Zepeda, Rodrigo S. Razo-Hernández, Laura P. Á. Berber, Karen O. Lara, Eduardo Ruiz-Bustos, and Juan C. Gálvez-Ruíz. "Berberine as Source of Antiproliferative Hybrid Compounds: In Vitro Antiproliferative Activity and Quantitative Structure-activity Relationship." Anti-Cancer Agents in Medicinal Chemistry 19, no. 15 (January 10, 2019): 1820–34. http://dx.doi.org/10.2174/1871520619666190503121820.

Full text

Abstract:

Background: Despite advances for cancer treatment, it still remains a major worldwide public health problem. Compounds derived from natural sources are important alternatives to combat this mortal disease. Berberine is an isoquinoline alkaloid with a wide variety of pharmacological properties, including antiproliferative activity. Previously, we have found that fatty acids also show antiproliferative activity against cancer cell lines. Background: Despite advances for cancer treatment, it still remains a major worldwide public health problem. Compounds derived from natural sources are important alternatives to combat this mortal disease. Berberine is an isoquinoline alkaloid with a wide variety of pharmacological properties, including antiproliferative activity. Previously, we have found that fatty acids also show antiproliferative activity against cancer cell lines. Objective: To combine berberine and fatty acids, or carboxylic acids, in order to improve their antiproliferative properties. Objective: To combine berberine and fatty acids, or carboxylic acids, in order to improve their antiproliferative properties. Methods: We synthetized six new hybrid derivatives through a simple methylenedioxy group-cleavage method followed by the reaction with fatty acids, or carboxylic acids. The structure of the compounds was elucidated by IR, NMR and HRMS. The in vitro antiproliferative activity against four human cancer cell lines (HeLa, A-549, PC-3 and LS-180) and one normal cell line (ARPE-19), was evaluated by the MTT method. Chemical structures were drawn using SPARTAN '08 software and the conformational analysis was carried out with a molecular mechanic level of theory and the SYBIL force field. All molecular structures were subjected to geometrical optimization at the semi-empirical method PM3. Molecular descriptors were calculated using DRAGON 5.4 and SPARTAN ´08 programs. Methods: We synthetized six new hybrid derivatives through a simple methylenedioxy group-cleavage method followed by the reaction with fatty acids, or carboxylic acids. The structure of the compounds was elucidated by IR, NMR and HRMS. The in vitro antiproliferative activity against four human cancer cell lines (HeLa, A-549, PC-3 and LS-180) and one normal cell line (ARPE-19), was evaluated by the MTT method. Chemical structures were drawn using SPARTAN '08 software and the conformational analysis was carried out with a molecular mechanic level of theory and the SYBIL force field. All molecular structures were subjected to geometrical optimization at the semi-empirical method PM3. Molecular descriptors were calculated using DRAGON 5.4 and SPARTAN ´08 programs. Results: The geranic acid and berberine hybrid compound (6) improved the antiproliferative activity shown by natural berberine, even more than the 16- to 18-carbon atoms fatty acids. Compound 6 showed IC50 values of 2.40 ± 0.60, 1.5 ± 0.24, 5.85 ± 1.07 and 5.44 ± 0.24 μM, against HeLa, A-549, PC-3 and LS-180 human cancer cell lines, respectively. Using this information, we performed a quantitative structure-activity relationship (QSAR) of the hybrid molecules and found that the molecular descriptors associated with the antiproliferative activity are: hydrophobic constant associated with substituents (!(!) = 6.5), molecular volume descriptor (!"#!"#$%& ≈ 700 Å!), !!"#", number of rotatable bonds (!"#) and number of 6-membered rings (!"06). Results: The geranic acid and berberine hybrid compound (6) improved the antiproliferative activity shown by natural berberine, even more than the 16- to 18-carbon atoms fatty acids. Compound 6 showed IC50 values of 2.40 ± 0.60, 1.5 ± 0.24, 5.85 ± 1.07 and 5.44 ± 0.24 μM, against HeLa, A-549, PC-3 and LS-180 human cancer cell lines, respectively. Using this information, we performed a quantitative structure-activity relationship (QSAR) of the hybrid molecules and found that the molecular descriptors associated with the antiproliferative activity are: hydrophobic constant associated with substituents (!(!) = 6.5), molecular volume descriptor (!"#!"#$%& ≈ 700 Å!), !!"#", number of rotatable bonds (!"#) and number of 6-membered rings (!"06). Conclusion: The methylendioxy and methoxyl groups in berberine are important for the antiproliferative activity shown by its derivatives. Better results in antiproliferative activity were obtained in compound 6 with the prenyl moiety. The QSAR indicates that the molecular descriptors which associated positively with the antiproliferative activity are: hydrophobic constant associated with substituents (! ! = 6.5), molecular volume descriptor (!"#!"#$%& ≈700 Å3) and !!"#". This research gave the basis for the design and preparation of new, easily afforded molecules derived from berberine and carboxylic acids, with improved antiproliferative activity. Conclusion: The methylendioxy and methoxyl groups in berberine are important for the antiproliferative activity shown by its derivatives. Better results in antiproliferative activity were obtained in compound 6 with the prenyl moiety. The QSAR indicates that the molecular descriptors which associated positively with the antiproliferative activity are: hydrophobic constant associated with substituents (! ! = 6.5), molecular volume descriptor (!"#!"#$%& ≈700 Å3) and !!"#". This research gave the basis for the design and preparation of new, easily afforded molecules derived from berberine and carboxylic acids, with improved antiproliferative activity.

APA, Harvard, Vancouver, ISO, and other styles

36

Zagrebaev, Alexander D., Oleg N. Burov, Mikhail Е. Kletskii, Anton V. Lisovin, Sergey V. Kurbatov, and Oleg D. Demekhin. "The Synthesis and Investigation of New Electroneutral Berberine Derivatives." Chemistry of Heterocyclic Compounds 58, no. 1 (January 2022): 45–57. http://dx.doi.org/10.1007/s10593-022-03055-0.

Full text

APA, Harvard, Vancouver, ISO, and other styles

37

Demekhin, Oleg D., Oleg N. Burov, Mikhail E. Kletskii, Anton V. Lisovin, Sergey V. Kurbatov, Elena A. Bereznyak, and Alena V. Trishina. "New 13-vinyl derivatives of berberine: synthesis and characterization." Chemistry of Heterocyclic Compounds 58, no. 2-3 (February 2022): 144–52. http://dx.doi.org/10.1007/s10593-022-03067-w.

Full text

APA, Harvard, Vancouver, ISO, and other styles

38

Ding, Yangping, Xiaoli Ye, Jie Zhou, Sai Luo, Mengfei Lian, and Xuegang Li. "Progress in Synthesis and Physiological Activity of Berberine Derivatives." Chinese Journal of Organic Chemistry 32, no. 4 (2012): 677. http://dx.doi.org/10.6023/cjoc1108152.

Full text

APA, Harvard, Vancouver, ISO, and other styles

39

Xiao, Daipeng, Zhenbao Liu, Shanshan Zhang, Mi Zhou, Fen He, Ming Zou, Junying Peng, Xiong Xie, Yanfei Liu, and Dongming Peng. "Berberine Derivatives with Different Pharmacological Activities via Structural Modifications." Mini-Reviews in Medicinal Chemistry 18, no. 17 (September 13, 2018): 1424–41. http://dx.doi.org/10.2174/1389557517666170321103139.

Full text

APA, Harvard, Vancouver, ISO, and other styles

40

Guamán Ortiz, Luis Miguel, Anna Leta Croce, Francesca Aredia, Simone Sapienza, Gaetano Fiorillo, Tanjia Monir Syeda, Franco Buzzetti, Paolo Lombardi, and Anna Ivana Scovassi. "Effect of new berberine derivatives on colon cancer cells." Acta Biochimica et Biophysica Sinica 47, no. 10 (September 3, 2015): 824–33. http://dx.doi.org/10.1093/abbs/gmv077.

Full text

APA, Harvard, Vancouver, ISO, and other styles

41

Han, Xie, Kaiyuan Shao, and Wenxiang Hu. "Synthesis of 9-Substituted Berberine Derivatives with Microwave Irradiation." Chemical Research in Chinese Universities 34, no. 4 (July 11, 2018): 571–77. http://dx.doi.org/10.1007/s40242-018-7425-6.

Full text

APA, Harvard, Vancouver, ISO, and other styles

42

Singh, Inder Pal, and Shivani Mahajan. "Berberine and its derivatives: a patent review (2009 – 2012)." Expert Opinion on Therapeutic Patents 23, no. 2 (December 12, 2012): 215–31. http://dx.doi.org/10.1517/13543776.2013.746314.

Full text

APA, Harvard, Vancouver, ISO, and other styles

43

Liu, Cui, Siyuan Liu, Yuechai Wang, Shuxiang Wang, Jinchao Zhang, Shenghui Li, Xinying Qin, Xiaoliu Li, Kerang Wang, and Quoqiang Zhou. "Synthesis, cytotoxicity, and DNA-binding property of berberine derivatives." Medicinal Chemistry Research 23, no. 4 (September 24, 2013): 1899–907. http://dx.doi.org/10.1007/s00044-013-0796-9.

Full text

APA, Harvard, Vancouver, ISO, and other styles

44

Nechepurenko, I. V., U. A. Boyarskikh, M. V. Khvostov, D. S. Baev, N. I. Komarova, M. L. Filipenko, T. G. Tolstikova, and N. F. Salakhutdinov. "Hypolipidemic Berberine Derivatives with a Reduced Aromatic Ring C." Chemistry of Natural Compounds 51, no. 5 (September 2015): 916–22. http://dx.doi.org/10.1007/s10600-015-1447-9.

Full text

APA, Harvard, Vancouver, ISO, and other styles

45

Hao, Wenhui, Shiying Che, Jinsheng Li, Jingyi Luo, Wanqiu Zhang, Yang Chen, Zijian Zhao, Hao Wei, and Weidong Xie. "Synthesis of Berberine and Canagliflozin Chimera and Investigation into New Antibacterial Activity and Mechanisms." Molecules 27, no. 9 (May 5, 2022): 2948. http://dx.doi.org/10.3390/molecules27092948.

Full text

Abstract:

Berberine is an isoquinoline alkaloid isolated from Chinese herbal medicines such as Coptis chinensis. It has many pharmacological actions, such as antibacterial, hypoglycemic, anti-inflammatory, and so on. However, due to the low lipophilicity of berberine, it is difficult to penetrate the bacterial cell membrane and also difficult to be absorbed orally and usually needs a relatively high dose to achieve the ideal effect. The purpose of this study is to transform the structure of berberine in order to improve the bioavailability of berberine and reduce the dosage. Moreover, we introduce a pharmacophore named Canagliflozin, a hypoglycemic drug (which was also found to have potential anti-bacterial activity) into BBR to see whether this new compound has more existed activities. We at first connected berberine with Canagliflozin, to form a new compound (BC) and see whether BC has synergic effects. We use microbroth dilution method to determine the minimum inhibitory concentration of BC, determine the bacterial growth with the enzyme labeling instrument, observe the formation of bacterial biofilm with crystal violet staining method, observe the bacterial morphology with field emission scanning electron microscope, and determine the intracellular protein with SDS-PAGE. The above indicators reflect the damage of BC to bacteria. New compound BC was successfully obtained by chemical synthesis. The minimal inhibitory concentration of compound BC on three bacteria was significantly better than that of berberine and canagliflozin alone and the combination of berberine and canagliflozin. Moreover, compound BC has obvious destructive effect on bacterial morphology and biofilm, and the compound also has destructive effect on intracellular proteins. Therefore, new compound BC has broad-spectrum antibacterial activity and the inhibitory effect of BC might play a role by destroying the integrity of biofilm and the intracellular protein of bacteria. In conclusion, we create a new molecular entity of berberine and Canagliflozin chimera and open up a new prospect for berberine derivatives in the treatment of bacterial infection.

APA, Harvard, Vancouver, ISO, and other styles

46

Wickhorst, Peter Jonas, Mathilda Blachnik, Denisa Lagumdzija, and Heiko Ihmels. "Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties." Beilstein Journal of Organic Chemistry 17 (May 4, 2021): 991–1000. http://dx.doi.org/10.3762/bjoc.17.81.

Full text

Abstract:

Eleven novel 10-O-aryl-substituted berberrubine and berberine derivatives were synthesized by the Cu2+-catalyzed Chan–Evans–Lam coupling of berberrubine with arylboronic acids and subsequent 9-O-methylation. The reaction is likely introduced by the Cu2+-induced demethylation of berberrubine and subsequent arylation of the resulting 10-oxyanion functionality. Thus, this synthetic route represents the first successful Cu-mediated coupling reaction of berberine substrates. The DNA-binding properties of the 10-O-arylberberine derivatives with duplex and quadruplex DNA were studied by thermal DNA denaturation experiments, spectrometric titrations as well as CD and LD spectroscopy. Fluorimetric DNA melting analysis with different types of quadruplex DNA revealed a moderate stabilization of the telomeric quadruplex-forming oligonucleotide sequence G3(TTAG3)3. The derivatives showed a moderate affinity towards quadruplex DNA (Kb = 5–9 × 105 M−1) and ct DNA (Kb = 3–5 × 104 M−1) and exhibited a fluorescence light-up effect upon complexation to both DNA forms, with slightly higher intensity in the presence of the quadruplex DNA. Furthermore, the CD- and LD-spectroscopic studies revealed that the title compounds intercalate into ct DNA and bind to G4-DNA by terminal stacking.

APA, Harvard, Vancouver, ISO, and other styles

47

Gladkova, Elizaveta D., Arina A. Chepanova, Ekaterina S. Ilina, Alexandra L. Zakharenko, Jóhannes Reynisson, Olga A. Luzina, Konstantin P. Volcho, Olga I. Lavrik, and Nariman F. Salakhutdinov. "Discovery of Novel Sultone Fused Berberine Derivatives as Promising Tdp1 Inhibitors." Molecules 26, no. 7 (March 30, 2021): 1945. http://dx.doi.org/10.3390/molecules26071945.

Full text

Abstract:

A new type of berberine derivatives was obtained by the reaction of berberrubine with aliphatic sulfonyl chlorides. The new polycyclic compounds have a sultone ring condensed to C and D rings of a protoberberine core. The reaction conditions were developed to facilitate the formation of sultones with high yields without by-product formation. Thus, it was shown that the order of addition of reagents affects the composition of the reaction products: when sulfochlorides are added to berberrubine, their corresponding 9-O-sulfonates are predominantly formed; when berberrubine is added to pre-generated sulfenes, sultones are the only products. The reaction was shown to proceed stereo-selectively and the cycle configuration was confirmed by 2D NMR spectroscopy. The inhibitory activity of the synthesized sultones and their 12-brominated analogs against the DNA-repair enzyme tyrosyl-DNA phosphodiesterase 1 (Tdp1), an important target for a potential antitumor therapy, was studied. All derivatives were active in the micromolar and submicromolar range, in contrast to the acyclic analogs and 9-O-sulfonates, which were inactive. The significance of the sultone cycle and bromine substituent in binding with the enzyme was confirmed using molecular modeling. The active inhibitors are mostly non-toxic to the HeLa cancer cell line, and several ligands show synergy with topotecan, a topoisomerase 1 poison in clinical use. Thus, novel berberine derivatives can be considered as candidates for adjuvant therapy against cancer.

APA, Harvard, Vancouver, ISO, and other styles

48

Jin, Yifeng, Daulat B. Khadka, and Won-Jea Cho. "Pharmacological effects of berberine and its derivatives: a patent update." Expert Opinion on Therapeutic Patents 26, no. 2 (December 4, 2015): 229–43. http://dx.doi.org/10.1517/13543776.2016.1118060.

Full text

APA, Harvard, Vancouver, ISO, and other styles

49

Wang, Zhi-Cheng, Jing Wang, Huang Chen, Jie Tang, Ai-Wu Bian, Ting Liu, Li-Fang Yu, Zhengfang Yi, and Fan Yang. "Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives." Bioorganic & Medicinal Chemistry Letters 30, no. 2 (January 2020): 126821. http://dx.doi.org/10.1016/j.bmcl.2019.126821.

Full text

APA, Harvard, Vancouver, ISO, and other styles

50

Chen, Zhu, Xiaoli Ye, Jun Yi, Xin Chen, and Xuegang Li. "Synthesis of 9-O-glycosyl-berberine derivatives and bioavailability evaluation." Medicinal Chemistry Research 21, no. 8 (June 3, 2011): 1641–46. http://dx.doi.org/10.1007/s00044-011-9678-1.

Full text

APA, Harvard, Vancouver, ISO, and other styles

We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!