Synthesis, induced-fit docking investigations, and in vitro aldose reductase inhibitory activity of non-carboxylic acid containing 2,4-thiazolidinedione derivatives

Background: Breast Cancer (BC), a common death-causing disease and the deadliest cancer next to lung cancer, is characterized by an abnormal growth of cells in the tissues of the breast. BC chemotherapy is marked by targeting the activities of some receptors such as Estrogen Receptor alpha (ER-α). At present, one of the most commonly used and approved marketed therapeutic drug for BC is tamoxifen. Despite the short term success of tamoxifen usage, its long time treatment has been associated with significant side effects. Therefore, there is a pressing need for the development of novel anti-estrogens for the prevention and treatment of BC. Objective: In this study, we evaluate the inhibitory effect of Cannabis Sativa phyto-constituents on ER-α. Method: Glide and Induced Fit Docking followed by ADME, Automated QSAR and Binding free energy (ΔGbind) studies were used to evaluate the anti-breast cancer and ER-α inhibitory activity of Cannabis sativa, which has been reported to be effective in inhibiting breast cancer cell proliferation. Results: Phyto-constituents of Cannabis sativa possess lower docking scores and good ΔGbind when compared to that of tamoxifen. ADME and AutoQSAR studies revealed that our lead compounds demonstrated the properties required to make them promising therapeutic agents. Conclusion: The results of this study suggest that Naringenin, Dihydroresveratrol, Baicalein, Apigenin and Cannabitriol could have relatively better inhibitory activity than tamoxifen and could be a better and patent therapeutic candidate in the treatment of BC. Further research such as in vivo and/or in vitro assays could be conducted to attest the ability of these compounds.

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Induced Fit Docking (IFD) Study of the Solid State Structure of (2E)-1-(5- bromothiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one – Fragment Based Design Approach for Human Aldose Reductase Inhibition

Letters in Drug Design & Discovery ◽

10.2174/157018012802652949 ◽

2012 ◽

Vol 9 (8) ◽

pp. 789-796

Author(s):

Suresh B. Vepuri ◽

H. C. Devarajegowda ◽

S. Anbazhagan ◽

Y. Rajendra Prasad

Keyword(s):

Solid State ◽

Aldose Reductase ◽

Design Approach ◽

State Structure ◽

Induced Fit Docking ◽

Induced Fit ◽

Solid State Structure ◽

Aldose Reductase Inhibition

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Constituents of the flowers of Platycodon grandiflorum with inhibitory activity on advanced glycation end products and rat lens aldose reductase in vitro

Archives of Pharmacal Research ◽

10.1007/s12272-010-0610-x ◽

2010 ◽

Vol 33 (6) ◽

pp. 875-880 ◽

Cited By ~ 27

Author(s):

Dae Sik Jang ◽

Yun Mi Lee ◽

Il Ha Jeong ◽

Jin Sook Kim

Keyword(s):

Aldose Reductase ◽

Advanced Glycation End Products ◽

Inhibitory Activity ◽

Advanced Glycation ◽

Platycodon Grandiflorum ◽

Rat Lens Aldose Reductase ◽

Glycation End Products ◽

End Products

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A New Monoterpenoid and a New Flavonoid Glycoside from the Peels of Clausena lansium

Natural Product Communications ◽

10.1177/1934578x1601100502 ◽

2016 ◽

Vol 11 (5) ◽

pp. 1934578X1601100 ◽

Cited By ~ 1

Author(s):

Hui-Dong Deng ◽

Cai-Hong Cai ◽

Shuai Liu ◽

Yan-Bo Zeng ◽

Wen-Li Mei ◽

...

Keyword(s):

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Carboxylic Acid ◽

Inhibitory Activity ◽

2D Nmr ◽

Flavonoid Glycoside ◽

Esi Ms ◽

Inhibition Zones

One new monoterpenoid, nerol oxide-8-carboxylic acid (1), and one new flavonoid glycoside, claulansoside A (2), together with six known compounds, clausenamide (3), quercetin (4), isorhamnetin (5), dihydromyric (6), 2′',3′'-dihydroxyanisolactone (7) and ( E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen (8), have been isolated from the peels of Clausena lansium (Lour.) Skeels. Their structures were determined using a combination of 1D, and 2D NMR (HMQC, HMBC, COSY and NOESY) techniques, and HR-ESI-MS analyses. Compounds 1 and 7 exhibited antibacterial activity against Staphylococcus aureus with the diameter of inhibition zones of 11.5 mm and 14.2 mm. Compounds 3 and 6 showed α-glucosidase inhibitory activity in vitro.

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Exploration of Diosmin to control diabitis and its complications-an in vitro and in silico approach

Current Computer - Aided Drug Design ◽

10.2174/1573409916666200324135734 ◽

2020 ◽

Vol 16 ◽

Author(s):

Kushagra Dubey ◽

Raghvendra Dubey ◽

Revathi Gupta ◽

Arun Gupta

Keyword(s):

Molecular Docking ◽

Aldose Reductase ◽

Inhibitory Activity ◽

Blood Lipid ◽

Docking Studies ◽

Alpha Amylase ◽

Lipid Lowering ◽

Molecular Docking Studies ◽

Alpha Glucosidase

Background: Diosmin is a flavonoid obtained from the citrus fruits of the plants. Diosmin has blood lipid lowering activities, antioxidant activity, enhances venous tone and microcirculation, protects capillaries, mainly by reducing systemic oxidative stress. Objective: The present study demonstrates the potential of Diosmin against the enzymes aldose reductase, α-glucosidase, and α-amylase involved in diabetes and its complications by in vitro evaluation and reverse molecular docking studies. Method: The assay of aldose reductase was performed by using NADPH as starting material and DL-Glyceraldehyde as a substrate. DNS method was used for alpha amylase inhibition and in alpha glucosidase inhibitory activity p-nitrophenyl glucopyranoside (pNPG) was used as substrate. The reverse molecular docking studies was performed by using Molegro software (MVD) with grid resolution of 30 Å. Result: Diosmin shows potent inhibitory effect against aldose reductase (IC50:333.88±0.04 µg/mL), α-glucosidase (IC50:410.3±0.01 µg/mL) and α-amylase (IC50: 404.22±0.02 µg/mL) respectively. The standard drugs shows moderate inhibitory activity for enzymes. The MolDock Score of Diosmin was -224.127 against aldose reductase, -168.17 against α-glucosidase and -176.013 against α-amylase respectively, which was much higher than standard drugs. Conclusion: From the result it was concluded that diosmin was a potentially inhibitor of aldose reductase, alpha amylase and alpha glucosidase enzymes then the standard drugs and it will be helpful in the management of diabetes and its complications. This will also be benevolent to decrease the socio economical burden on the middle class family of the society.

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In vitro aldose reductase inhibitory activity of 5-benzyl-2,4-thiazolidinediones

Bioorganic & Medicinal Chemistry ◽

10.1016/j.bmc.2005.08.056 ◽

2006 ◽

Vol 14 (2) ◽

pp. 567-574 ◽

Cited By ~ 42

Author(s):

Dietmar Rakowitz ◽

Rosanna Maccari ◽

Rosaria Ottanà ◽

Maria Gabriella Vigorita

Keyword(s):

Aldose Reductase ◽

Inhibitory Activity

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Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

RSC Advances ◽

10.1039/c6ra24651f ◽

2016 ◽

Vol 6 (115) ◽

pp. 114879-114888 ◽

Cited By ~ 10

Author(s):

Ailong Shi ◽

Defa Wang ◽

He Wang ◽

Yue Wu ◽

Haiqiu Tian ◽

...

Keyword(s):

Carboxylic Acid ◽

Xanthine Oxidase ◽

Carboxylic Acids ◽

Inhibitory Activity ◽

Xanthine Oxidase Inhibitors

A series of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acids/carbohydrazides as analogues of febuxostat were synthesized and evaluated for their in vitro xanthine oxidase (XO) inhibitory activity.

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Aldose reductase and advanced glycation end products formation inhibitory activity of standardized extracts of Picrorhiza kurroa (Royle ex benth) and Hibiscus rosa-sinensis (Linn.)

Pharmaceutical and Biological Evaluations ◽

10.26510/2394-0859.pbe.2017.28 ◽

2017 ◽

Author(s):

Anasuri Santhosh ◽

C. Veeresham ◽

A. Rama Rao

Keyword(s):

Aldose Reductase ◽

Advanced Glycation End Products ◽

Inhibitory Activity ◽

Reference Compound ◽

Advanced Glycation ◽

Hibiscus Rosa Sinensis ◽

Glycation End Products ◽

End Products

Objective: The objectives were to study the in-vitro and in-vivo aldose reductase and in-vitro advanced glycation end products formation inhibitory activities of the standardized extracts of Picrorhiza kurroa roots and Hibiscus rosa-sinensis flowers.Methods: In-vitro Aldose reductase inhibitory activity was studied by using isolated rat lens and kidney Aldose reductase by UV-Visible spectro photo metric method by using Quercetin as reference compound. In-vivo Aldose reductase inhibitory activity was evaluated by using experimental rat models of galactosemia and the final lens galactitol was evaluated by High performance liquid chromatography and Gas chromatography methods by using Quercetin as reference compound. In-vitro advanced glycation end products formation inhibitory activity was estimated by using laboratory test reaction with protein and sugars by spectro fluorimetric method by sung aminoguanidine as reference compound. Statistical analysis of the results was done by using Analysis of the variance method.Results: The plant extracts were found to possess significant aldose reductase and advanced glycation end products formation inhibitory activity.Conclusions: More study is required for isolation and characterization of the chief chemical constituents responsible for the biological activity of the plant extracts.

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