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Academic literature on the topic 'Berberine derivatives'

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Published: 10 March 2023

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Journal articles on the topic "Berberine derivatives"

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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.

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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.
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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.

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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.
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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.

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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.
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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.

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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.
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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.

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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.
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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.

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: 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.
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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.

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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.
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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.

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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.
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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.

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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.
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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.

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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.
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Dissertations / Theses on the topic "Berberine derivatives"

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Samosorn, Siritron. "Development of berberine-based derivatives as novel antimicrobial agents." Access electronically, 2005. http://www.library.uow.edu.au/adt-NWU/public/adt-NWU20050819.161843/index.html.

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Mari, Giacomo. "Synthesis of various and interesting heterocycles included berberino derivatives." Doctoral thesis, Urbino, 2018. http://hdl.handle.net/11576/2656415.

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3

Yu, Chengyin. "Berberine8998, a new derivative of berberine, improves hyperlipidemia through additional mechanisms." Thesis, University of Portsmouth, 2018. https://researchportal.port.ac.uk/portal/en/theses/berberine8998-a-new-derivative-of-berberine-improves-hyperlipidemia-through-additional-mechanisms(56cfdae2-12ba-4080-9c3b-10f96f9d511c).html.

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Berberine (BBR), an herbal originated compound, has lipid-lowering activity. However, its low bioavailability and poor absorption characteristics have limited its clinical application. The aim of this research study was to investigate the lipid lowering effect of a novel berberine derivative, namely berberine8998, and its properties and underlying mechanisms. For the purpose of this study, the pharmacodynamics of berberine8998 was evaluated on a hamster model of hypercholesterolemia by a high-fat diet. Our results showed that, compared with the other structurally related derivatives of the berberine group, berberine8998 significantly lowered the serum lipid levels in hamsters. Berberine8998 stimulated the uptake of low-density lipoprotein (LDL) in HepG2 cells in a dose-dependent manner. Isobaric tags for the relative and absolute quantitation (iTRAQ) labeling proteome methods was applied, using a TripleTOF 5600 mass spectrometer to compare the pharmacological basis of both berberine and berberine8998. The mechanisms of the actions of these two compounds were investigated by identifying and quantifying the differences in the proteins that were expressed (with respect to the untreated animals) in the liver tissues of hamsters treated with the compounds. The result of proteome study showed that peroxisomal acyl-coenzyme A oxidase 1 (ACOX1) and long-chain fatty acid-CoA ligase 1 (ACSL1), involved in fatty acid metabolism, were regulated by using berberine and berberine8998. Moreover, western blot validation results showed that ACOX1 and ACSL1, which are proteins involved in fatty acid metabolism, were expressed differently in the berberine8998 group than in the untreated group and the berberine treatment group. Biochemistry results showed that berberine8998 significantly lowered the non-esterified fatty acid (NEFA) levels, which may lead to a reduction in TG levels in the berberine8998 treatment group and the differences observed in proteomics analyses. Furthermore, a pharmacokinetic study was applied to investigate the absorption of two formulations of berberine8998. These findings suggested that berberine8998 lowered cholesterol and lipid levels via different mechanisms from berberine, and its improved absorption made it a promising therapeutic candidate for the treatment of hypercholesterolemia and obesity.
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Hung, Shu-fen, and 洪淑芬. "Antihypertensive Action of Berberine and Its Derivatives in The Rat." Thesis, 1996. http://ndltd.ncl.edu.tw/handle/10682306990338171747.

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碩士
國立成功大學
藥理學研究所
84
Berberine is an isoquinoline alkaloid contained in plants of Ranuculaceae and Berberidaceae. Extracts of berberine-containing plants have been used as Chi nese folk remedies for centuries. After screening the antihypertensive activit y in spontaneously hypertensive rats ( SHRs ), 6-protoberberine ( PTB-6 ) was found to be most effective in the synthetic compounds from berberine. In cons cious SHRs, PTB-6 lowered the systemic arterial blood pressure ( SBP ) in a do se-dependent manner. The possible mechanisms were then investigated in the pr esent study. Cardiac output in PTB-6-treated anesthetized SHRs, using thermodi lution method, was modified slightly with an decrease of heart rate. Also, th e total peripheral resistance was attenuated by PTB-6. In isolated aortic rin gs from normotensive rats, PTB-6 produced relaxation in a precontraction-depen dent manner in both the presence and absence of endothelium. Specific effect on a-adrenoceptor by PTB-6 was characterized using radioligand binding study. PTB-6 also can dose-dependently inhibit the effect of KCl-induced membrane dep olarization. Using fura-2 to study the calcium influx into vascular smooth mu scle cells, this work observed that high concentration of PTB-6 inhibited calc ium influx into vascular smooth muscle cells. Moreover, PTB-6 was found to in hibit left ventricular pressure in isolated rat heart. Another hand, injectio n of PTB-6 into the intracerebral ventricula of the brain ( i.c.v. ) can lower the systemic arterial blood pressure and heart rate of SHRs. The results indi cate that PTB-6 works more effective than other derivatives of berberine to lo wer the SBP in SHRs via an influence on cardiac output and vascular tone.
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Yang, Fang-Yu, and 楊芳俞. "Synthesis and biological evaluation of 13-lipophilic substituted berberine derivatives for photocytotoxicity in human colon cancer cells." Thesis, 2018. http://ndltd.ncl.edu.tw/handle/5tzr4q.

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碩士
國立嘉義大學
微生物免疫與生物藥學系研究所
106
Berberine, a quaternary ammonium salt isoquinoline alkaloids. It has a wide range of biochemical and pharmacological effects. The objective of this study was to synthesize 13-O-lipophilic substituted berberine derivatives and evaluate their photocytotoxic effects against human colon cancer cell lines. The modified berberine at 13-O-position by n-alkyl lipophilic substitution was synthesized and in vitro investigated for cytotoxicity and photocytotoxicity by MTT assay. The introduction of lipophilic substituents at 13-O-position of the berberine scaffold led to potent inhibition against human colon cancer cells. Among 8 synthesized compounds, compound 4e exhibit strongest growth inhibition against human colon cancer cells. HPLC analysis showed that the lipophilic modification of 4e enhanced the cellular uptake in DLD-1 cells. Cell viability assay showed that 4e inhibited the cell growth of SW480, DLD-1 and HT-29 cells in a dose- and time-dependent manner and in a light dose- and time-dependent manner after visible light (420 nm) irradiation. Flow cytometry analysis was employed to evaluate the photocytotoxic effects of berberine (1) and 4e for cell cycle effect, cell death, intracellular reactive oxygen species (ROS) and mitochondrial membrane potential (ΔΨm) charge in DLD-1 cells. In cell cycle analysis, 4e induced remarkable SubG1 phase in DLD-1 cells after light irradiation. In cell death analysis, 4e induced cell both apoptosis and necrosis after light irradiation. Compound 4e also distinctly induced intracellular ROS and reduced mitochondrial membrane potential in DLD-1 cells after light irradiation. In conclusion, photodynamic treatment of 4e demonstrated a significant photocytotoxic effects in SW480, DLD-1 and HT-29 cells, induced remarkable cell apoptosis and necrosis, increased intracellular ROS level and triggered mitochondrial membrane potential depolarization. The conclusion revealed that berberine derivatives at 13-O-position bearing n-alkyl group had the potential as a candidate of anticancer agent and phototherapeutic drugs.
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Papi, Francesco. "Structural investigations on the adducts formed by natural and synthetic compounds with non-canonical DNA foldings." Doctoral thesis, 2018. http://hdl.handle.net/2158/1114320.

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Non-canonical DNA structures are involved in fundamental biological processes as replication, transcription and repair. Their dysregulation is indeed connected to the development of several human diseases, including cancer. As more and more information about their existence and function in living cells are documented, such DNA structures have emerged as promising therapeutic targets. In the last decades, the G-quadruplex folding has caught the attention of scientists because of its implication in the origin and growth of various cancer forms. The stabilization of G-quadruplex structures at human telomeres is thought to be particularly attractive as it might lead to the identification of potential drug candidates with wide-spectrum anticancer activity and reduced side effects in comparison to classical chemotherapies. The research project underlying this thesis concerns the structural investigation on the interaction of non-canonical DNA foldings, especially of the human telomeric G-quadruplex, with natural and synthetic compounds in order to select potential anticancer drugs. The characterization of ligand-DNA adducts has been carried out primarily by X-ray crystallography which provides detailed structural information. In addition, alternative techniques, as CD spectroscopy and in silico calculations, have supplied complementary data with particular reference to the formation of adducts in solution.
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Books on the topic "Berberine derivatives"

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Potopalʹskiĭ, A. I. Barbaris i ego preparaty v biologii i medet͡s︡ine. Kiev: Nauk. dumka, 1989.

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Conference papers on the topic "Berberine derivatives"

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"Inhibitors of tyrosyl-DNA phosphodiesterase 1 (Tdp1) leelamine and berberine derivatives as prototypes of antitumor drugs." In SYSTEMS BIOLOGY AND BIOINFORMATICS. Institute of Cytology and Genetics, Siberian Branch of the Russian Academy of Sciences, 2019. http://dx.doi.org/10.18699/sbb-2019-24.

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Xu, Beibei, Tian hui Hu, and jing Xiong. "Abstract 1868: B-125, a novel berberine derivative, acts as a better retinoid X receptor a agonist with stronger anti-tumor activity in colon cancer." In Proceedings: AACR Annual Meeting 2019; March 29-April 3, 2019; Atlanta, GA. American Association for Cancer Research, 2019. http://dx.doi.org/10.1158/1538-7445.sabcs18-1868.

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Xu, Beibei, Tian hui Hu, and jing Xiong. "Abstract 1868: B-125, a novel berberine derivative, acts as a better retinoid X receptor a agonist with stronger anti-tumor activity in colon cancer." In Proceedings: AACR Annual Meeting 2019; March 29-April 3, 2019; Atlanta, GA. American Association for Cancer Research, 2019. http://dx.doi.org/10.1158/1538-7445.am2019-1868.

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