Bibliographies thématiques / QUERCETIN ANALOGUES

Littérature scientifique sur le sujet « QUERCETIN ANALOGUES »

Auteur : Grafiati
Publié le 26 octobre 2023

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Articles de revues sur le sujet "QUERCETIN ANALOGUES"

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Otieno, Filex, et Richard Kagia. « Virtual screening for chemical analogues similar to phytochemicals that inhibit aldose reductase in the development of diabetic microvascular complications ». F1000Research 12 (21 mars 2023) : 314. http://dx.doi.org/10.12688/f1000research.129663.1.

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Background: The polyol pathway contributes to the development of diabetic complications but can be inhibited by plant phytochemicals. This study aimed at assessing analogs of specific flavonoids that delay onset of microvascular complications with better pharmacokinetic and toxicology profiles. Methods: An in silico study design was employed. The phytochemicals luteolin and quercetin were selected. Analogs were obtained from ZINC database and prepared using Avogadro software. Docking analysis was done using AutoDock Vina embedded in Chimera. Ligand enzyme interaction was carried out using Biovia Discovery studio. Pharmacokinetic and toxicological profiling was carried out using SWISSADME and protox server. A total of 40 analogues were analyzed. Sulindac was used as the comparator besides original phytochemicals. Results: Docking analysis showed both luteolin and quercetin (-9.7) had a slightly stronger affinity for inhibiting aldose reductase compared with sulindac (-9.6). Eight analogues of luteolin and 14 analogues of quercetin showed stronger affinity with the highest registered at -10.6. Both luteolin and quercetin did not violate the Lipinski rule, had high GI absorption, did not cross the blood brain barrier nor were p-glycoprotein substrates, and inhibited CYP1A2, CYP2D6 and CYP3A4. The LD50 of luteolin (3,919 mg/kg) was high indicating excellent safety profile. Quercetin had a low LD50 (159 mg/kg). All 22 analogues exhibited similar pharmacokinetic profiles to their respective phytochemical. However, they did differ in terms of docking strength and toxicology analysis. Six out of the eight luteolin analogues had LD50=3,919 mg/kg, while the remaining had LD50=159 mg/kg. Five quercetin analogues had LD50 of 159 mg/kg, another five had LD50=3,919 mg/kg and the rest had LD50=4,000 mg/kg, while the other two had a LD50 of 5,000 mg/kg. Conclusions: In conclusion, six ZINC compounds similar to luteolin and nine similar to quercetin had stronger binding affinity for aldose reductase and superior toxicological profile compared to parent phytochemicals.
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Pardo, Antonelle, Thomas Josse, Laetitia Mespouille, Bertrand Blankert, Philippe Dubois et Pierre Duez. « Synthesis of Quercetin-imprinted Polymer Spherical Particles with Improved Ability to Capture Quercetin Analogues ». Phytochemical Analysis 28, no 4 (26 janvier 2017) : 289–96. http://dx.doi.org/10.1002/pca.2674.

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Biler, Michal, David Biedermann, Kateřina Valentová, Vladimír Křen et Martin Kubala. « Quercetin and its analogues : optical and acido–basic properties ». Phys. Chem. Chem. Phys. 19, no 39 (2017) : 26870–79. http://dx.doi.org/10.1039/c7cp03845c.

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Imai, Kohei, Ikuo Nakanishi, Kei Ohkubo, Yusuke Ohba, Takuya Arai, Mirei Mizuno, Shunichi Fukuzumi, Ken-ichiro Matsumoto et Kiyoshi Fukuhara. « Synthesis of methylated quercetin analogues for enhancement of radical-scavenging activity ». RSC Advances 7, no 29 (2017) : 17968–79. http://dx.doi.org/10.1039/c7ra02329d.

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Duan, Yu, Na Sun, Min Xue, Xiaolan Wang et Hu Yang. « Synthesis of regioselectively acylated quercetin analogues with improved antiplatelet activity ». Molecular Medicine Reports 16, no 6 (12 octobre 2017) : 9735–40. http://dx.doi.org/10.3892/mmr.2017.7781.

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Fernández-Aparicio, Mónica, Marco Masi, Alessio Cimmino, Susana Vilariño et Antonio Evidente. « Allelopathic Effect of Quercetin, a Flavonoid from Fagopyrum esculentum Roots in the Radicle Growth of Phelipanche ramosa : Quercetin Natural and Semisynthetic Analogues Were Used for a Structure-Activity Relationship Investigation ». Plants 10, no 3 (13 mars 2021) : 543. http://dx.doi.org/10.3390/plants10030543.

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Allelopathic potential of buckwheat roots on the radicle growth of the broomrape weed species Orobanche cumana and Phelipanche ramosa was studied. Buckwheat root exudates induced a significant growth inhibition in P. ramosa radicles but radicles of O. cumana were not affected. Among the metabolites present in the root organic extract we identified the flavonol quercetin and the stilbene p-coumaric acid methyl ester with only quercetin showing inhibitory effect on P. ramosa. The activity of quercetin was compared with other two similar flavanoids, the flavone apigenin and the dihydroflavanol 3-O-acetylpadmatin extracted respectively from Lavandula stoechas and Dittrichia viscosa plants. In this comparative assay only 3-O-acetylpadmatin besides quercetin, showed inhibition activity of radicle growth while apigenin was inactive. These results indicated that the presence of two ortho-free hydroxy groups of C ring, like catechol, could be an important feature to impart activity while the carbon skeleton of B ring and substituents of both A and B rings are not essential. Besides reduction of radicle growth, haustorium induction was observed at the tip of P. ramosa radicles treated with quercetin which swelled and a layer of papillae was formed. Activity of quercetin on haustorium induction in P. ramosa was assayed in comparison with the known haustorium-inducing factor 2,6-dimethoxy-p-benzoquinone (DMBQ) and a three partial methyl ether derivatives semisynthetized from quercetin. Results indicated that P. ramosa haustorium was induced by DMBQ at concentrations of 1–0.5 mM and quercetin and its derivatives at concentration range 0.1–0.05 mM.
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Litvin, V. A., et R. A. Njoh. « Quercetin as a precursor in the synthesis of analogues of fulvic acids and their antibacterial properties ». Voprosy Khimii i Khimicheskoi Tekhnologii, no 2 (mars 2021) : 56–64. http://dx.doi.org/10.32434/0321-4095-2021-135-2-56-64.

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A simple, fast and effective method for producing synthetic substances with properties similar to natural humic substances has been proposed. The synthesis method is based on the oxidation of quercetin by molecular oxygen in an alkaline medium, followed by conversion to the acid form by passing through a cation exchange column. Study of elemental and functional compositions, spectral properties (UV/Vis and IR range) and redox characteristics allowed qualifying the resulting product as a synthetic fulvic acid. The enhanced antibacterial properties of the obtained synthetic product were established. The minimum concentration of inhibition of synthetic fulvic acid derived from quercetin is 25 g mL–1, which is in 100 times less than for natural humic substances.
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Atala, Elias, Jocelyn Fuentes, Maria Jose Wehrhahn et Hernan Speisky. « Oxidation of Quercetin and Its Structural Analogues Differentially Affects Its Antioxidant Properties ». Free Radical Biology and Medicine 100 (novembre 2016) : S93. http://dx.doi.org/10.1016/j.freeradbiomed.2016.10.231.

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Nayak, Yogendra, Venkatachalam Hillemane, Vijay Kumar Daroji, B. S. Jayashree et M. K. Unnikrishnan. « Antidiabetic Activity of Benzopyrone Analogues in Nicotinamide-Streptozotocin Induced Type 2 Diabetes in Rats ». Scientific World Journal 2014 (2014) : 1–12. http://dx.doi.org/10.1155/2014/854267.

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Benzopyrones are proven antidiabetic drug candidate in diabetic drug discovery. In this view novel synthetic benzopyrone analogues were selected for testing in experimental diabetes. Type 2 diabetes (T2D) was induced in Wistar rats by streptozotocin (60 mg/kg, i.p.) followed by nicotinamide (120 mg/kg i.p.). Rats having fasting blood glucose (FBG) >200 mg/dL, 7 days after T2D-induction, are selected for the study. Test compounds and standard treatment were continued for 15 days. FBG, oral glucose tolerance test (OGTT), and insulin tolerance test (ITT) were determined on 21st day after induction of T2D. Plasma lipids and serum insulin were estimated. Homeostatic model assessment (HOMA-IR) was then calculated from serum insulin. Rats were sacrificed and pancreas was isolated for histopathological observations. Oxidative stress markers were estimated in liver homogenate. Quercetin, a natural product with benzopyrone ring, showed significant hypoglycemic activity comparable to glibenclamide. Treatment with test compounds lowered the FBG and insulin resistance was significant alleviated as determined by OGTT, HOMA-IR, and ITT. There was significant normalisation of liver antioxidant enzymes compared to diabetic rats indicating that all the synthesised benzopyrone analogues are beneficial in reducing oxidative stress and are on par with the standard quercetin and glibenclamide in experimental T2D.
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Primikyri, Alexandra, Eleftheria Hatzimichael, Evdoxia Karali, Eleftherios Kostaras, Michalis Manztaris, Jae-Sun Shin, Seung-Wook Chi et al. « Decoding The BH3-Mimetic Pro-Apoptotic Activity Of Quercetin In Jurkat Cells ». Blood 122, no 21 (15 novembre 2013) : 1672. http://dx.doi.org/10.1182/blood.v122.21.1672.1672.

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Abstract Deregulation of apoptosis contributes largely to the pathogenesis of lymphoid neoplasms allowing the expansion of cell clones that develop resistance to drug-induced cell death. Therefore, subverting inherent resistance to apoptosis is a very challenging therapeutic issue and developing small molecules that can mimic the BH3 domain of the pro-apoptotic Bcl-2 family proteins appears to offer such potentials. Natural products, a rich source of compounds with BH3 mimetic activity, make a sound basis for such an approach. Quercetin, a natural polyphenol, has drawn much attention because it exerts anticancer cytotoxic effects, while sparing normal cells. Pro-apoptotic effects of quercetin have been shown in human lymphoma and leukemic cells and have been associated with Bcl-2 and Mcl-1 downregulation and Bax conformational activation. We undertook a multidisciplinary approach to elucidate the mode of action of quercetin, including cytotoxicity cell assays, biochemical approaches (pull down assays), NMR spectroscopy and docking calculations. We demonstrate that quercetin binds directly to the BH3 domain of the anti-apoptotic Bcl-2 and Bcl-xL proteins, exhibiting BH3-mimetic properties. Specifically, functional cytotoxicity assays of quercetin in Jurkat T-cell leukemic lines, Jurkat Bcl-2 and Jurkat Puro, indicated that quercetin binds to Bcl-2 protein. The direct binding of quercetin to Bcl-2 and to Bcl-xL was biochemically validated using pull down assays. NMR chemical shift perturbation experiments and docking calculations finally revealed that quercetin was bound to the pro-apoptotic BH3-binding site of the anti-apoptotic Bcl-2 family proteins (Figure 1). This property classifies quercetin as a natural flavonoid with BH3 mimetic activity, capable of driving leukemic cells to apoptosis. These results explain the cytotoxic effects of quercetin on Jurkat cells. These data can serve as a basis to consider studying BH3 mimetic natural products as adjuncts in the therapeutic approaches of lymphoid neoplasms in combination with chemotherapy, and can also provide a starting structure for developing novel potent analogues for the treatment of blood cancers.Figure 1Modeling (3D) the complex of quercetin with Bcl-2 (A) and Bcl-xl (B). Quercetin occupies the deep hydrophobic cleft in both proteins making an extended interaction network. The relevant residues are normally occupied by the pro-apoptotic Bak/Bad BH3 binding site in the complexFigure 1. Modeling (3D) the complex of quercetin with Bcl-2 (A) and Bcl-xl (B). Quercetin occupies the deep hydrophobic cleft in both proteins making an extended interaction network. The relevant residues are normally occupied by the pro-apoptotic Bak/Bad BH3 binding site in the complex Disclosures: No relevant conflicts of interest to declare.
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Thèses sur le sujet "QUERCETIN ANALOGUES"

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DAS, NIVEDITA. « IN SILICO SCREENING OF QUERCETIN ANALOGUES AS POTENTIAL INHIBITORS OF TUMOR NECROSIS FACTOR-ALPHA FOR DIARRHEA MITIGATION IN IRINOTECAN CANCER TREATMENT ». Thesis, 2023. http://dspace.dtu.ac.in:8080/jspui/handle/repository/19909.

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Diarrhea can be caused due to many reasons in an oncological patient. It could be due to radiation therapy, graft vs host infections, chemotherapeutic agents. Early diagnosis of causative agent can help to prevent diarrhea in cancer patients. Chemotherapeutic agents such as 5 fluorouracil with leucovorin, capecitabine and irinotecan are main causative agent of diarrhea. Loperamide and Octreotide are two recommended treatments for chemotherapy induced diarrhea. Loperamide can only treat grade 1 or 2 diarrhea, it becomes ineffective in severe cases of diarrhea. Octreotide is especially for treating grade 3 or 4 diarrhea but one drawback is that it requires hospitalization for fluid resuscitation due to dehydration in patients which thus increases the cost of treatment. The therapeutic potential of TNF- alpha inhibition for conditions including cancer, diabetes, and particularly autoimmune illnesses is significant. Even though there are several small molecule inhibitors of TNF- that have been discovered, no orally active treatment has yet been revealed that necessitates the urgent need for a small molecule drug against TNF- alpha. This research paper presents a comprehensive analysis of autodocking results obtained from virtual screening experiments conducted on a library of plant natural compound as inhibitor - Quercetin. The objective was to identify potential lead compounds with high binding affinities and favourable binding modes against the Tumor Necrosis Factor – alpha. Our findings reveal promising candidates for further investigation as potential therapeutics in the treatment of chemotherapy induced diarrhoea.
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Actes de conférences sur le sujet "QUERCETIN ANALOGUES"

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Cordonnier, Guy, Christian Rolando et Didier Barbry. « Access to a Key Intermediate for the Synthesis of 1-thia-analogue of Quercetin ». Dans The 9th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland : MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01509.

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