CoMFA and CoMSIA analysis of 2,4-thiazolidinediones derivatives as aldose reductase inhibitors

Journal of Molecular Modeling

Volumn 15, Issue 7, 2009, Pages 837-845

  Liu, Hong Yan ^a   Liu, Shu Shen ^a,b   Qin, Li Tang ^b   Mo, Ling Yun ^a  

^a GUILIN UNIVERSITY OF TECHNOLOGY   (China)

^b Tongji University ^*  (China)

Author keywords

2,4 Thiazolidinedione derivative; 3D QSAR; Aldose reductase inhibitor; CoMFA; CoMSIA

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; ALDEHYDE REDUCTASE;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; DRUG DESIGN; DRUG STRUCTURE; INHIBITION KINETICS; NON INSULIN DEPENDENT DIABETES MELLITUS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; THREE DIMENSIONAL IMAGING;

ALDEHYDE REDUCTASE; ALGORITHMS; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REPRODUCIBILITY OF RESULTS; TECHNOLOGY, PHARMACEUTICAL; THIAZOLIDINEDIONES;

EID: 67349254122     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-008-0439-0     Document Type: Article

References (39)

1. Zimmet P, Alberti KGMM, Shaw J (2001) Global and societal implications of the diabetes epidemic. Nature 414:782-787
2. Grubb T (2006) Diabetes Epidemic Out Of Control. http://diabetic-diet-secrets.com
3. Diamond J (2003) The double puzzle of diabetes. Nature 423:599-605
4. Koukoulitsa C, Zika C, Geromichalos GD et al (2006) Evaluation of aldose reductase inhibition and docking studies of some secondary metabolites, isolated from Origanum vulgare L. ssp. hirtum. Bioorg Med Chem 14:1653-1659
5. Brownlee M (2001) Biochemistry and molecular cell biology of diabetic complications. Nature 414:813-820
6. Ishii H, Tada H, Isogai S (1998) An aldose reductase inhibitor prevents glucose-induced increase in transforming growth factor-b and protein kinase C activity in cultured human mesangial cells. Diabetologia 41:362-364
7. Kasuya Y, Ito M, Nakamura J et al (1999) An aldose redutase inhibitor prevents the intimal thickening in coronary arteries of galactose-fed beagle dogs. Diabetologia 42:1404-1409
8. Calcutt NA, Freshwater JD, Mizisin AP (2004) Prevention of sensory disorders in diabetic Sprague-Dawley rats by aldose reductase inhibition or treatment with ciliary neurotrophic factor. Diabetologia 47:718-724
9. Cameron NE, Cotter MA, Basso M et al (1997) Comparison of the effects of inhibitors of aldose reductase and sorbitol dehydrogenase on neurovascular function, nerve conduction and tissue polyol pathway metabolites in streptozotocin-diabetic rats. Diabetologia 40:271-281
10. Petrash JM (2004) All in the family: Aldose reductase and closely related aldoketo reductases. Cell Mol Life Sci 61:739-749
11. Hotta N (1995) New approaches for treatment in diabetes: Aldose reductase inhibitors. Biomed Pharmacother 49:232-243
12. Settimo FD, Primofiore G, Motta CL et al (2005) Spirohydantoin derivatives of thiopyrano [2,3-#1b] pyridin-4(4H)-one as potent in vitro and in vivo aldose reductase inhibitors. Bioorg Med Chem 13:491-499
13. Gabbay KH (1973) The sorbitol pathway and the complications of diabetes. New Engl J Med 288:831-836
14. Fernández M, Caballero J, Helguera AM et al (2005) Quantitative structure-activity relationship to predict differential inhibition of aldose reductase by flavonoid compounds. Bioorg Med Chem 13:3269-3277
15. Prabhakar YS, Gupta MK, Roy N et al (2006) A high dimensional QSAR study on the aldose reductase inhibitory activity of some flavones: topological descriptors in modeling the activity. J Chem Inf Model 46:86-92
16. Hu L, Chen G, Chau RMW (2006) A neural networks-based drug discovery approach and its application for designing aldose reductase inhibitors. J Mol Graph Model 24:244-253
17. Ko K, Won H, Won Y (2006) Quantitative structure-activity relationship of spirosuccinimide type aldose reductase inhibitors diminishing sorbitol accumulation in vivo. Bioorg Med Chem 14:3090-3097
18. Ko K, Won Y (2005) Quantitative structure and aldose reductase inhibitory activity relationship of 1,2,3,4-tetrahydropyrrolo[1,2-a] pyrazine-4-spiro-3′-pyrrolidine-1,2′,3,5′-tetrone derivatives. Bioorg Med Chem 13:1445-1452
19. Bruno G, Costantino L, Curinga C et al (2002) Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg Med Chem 10:1077-1084
20. Maccari R, Ottana R, Curinga C et al (2005) Structure-activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors. Bioorg Med Chem 13:2809-2823
21. Sambasivarao SV, Soni LK, Gupta AK et al (2006) Quantitative structure-activity analysis of 5-arylidene-2,4-thiazolidinediones as aldose reductase inhibitors. Bioorg Med Chem Lett 16:512-520
22. Maccari R, Ottanà R, Ciurleo R et al (2007) Evaluation of in vitro aldose redutase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg Med Chem Lett 17:3886-3893
23. Rakowitz D, Maccari R, Ottanà R et al (2006) In vitro aldose reductase inhibitory activity of 5-benzyl-2,4-thiazolidinediones. Bioorg Med Chem 14:567-574
24. Pan HJ, Lin Y, Chen YE et al (2006) Adverse hepatic and cardiac responses to rosiglitazone in a new mouse model of type 2 diabetes: relation to dysregulated phosphatidylcholine metabolism. Vasc Pharmacol 45:65-71
25. ÓMoore-Sullivan TM, Prins JB et al (2002) Thiazolidinediones and type 2 diabetes: New drugs for an old disease. Med J Australia 176:381-386
26. Maccari R, Ottanà R, Curinga C, Vigorita MG et al (2005) Structure-activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors. Bioorg Med Chem 13:2809-2823
27. Cramer RD, Patterson DE, Bunce JD (1988) Comparative Molecular Field Analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959-5967
28. Klebe G, Abraham U, Mietzner T (1994) Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 37:4130-4146
29. SYBYL Molecular Modeling Software, Version 6.9, Tripos Inc., St. Louis, MO
30. Benabadji HS, Chen HF et al (2003) 3D-QSAR study on diindolylmethane and its analogues with comparative molecular field analysis (CoMFA). Chinese J Chem 21:20-24
31. Wellsow J, Machullab HJ, Kovar KA (2002) 3D QSAR of serotonin transporter ligands: CoMFA and CoMSIA studies. Quant Struct-Act Relatsh 21:577-589
32. 2! J Mol Graph Model 20:269-276
33. Golbraikh A, Tropsha A (2002) Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection. J Comput Aided Mol Des 16:357-369
34. Golbraikh A, Tropsha A (2000) Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection. Mol Divers 5:231-243
35. Afantitis A, Melagraki G, Sarimveis H et al (2006) A novel simple QSAR model for the prediction of anti-HIV activity using multiple linear regression analysis. Mol Divers 10:405-414
36. Roy PP, Roy K (2008) On some aspects of variable selection for partial least squares regression models. QSAR Comb Sci 27:302-313
37. Murthy VS, Kulkarni VM (2002) 3D-QSAR CoMFA and CoMSIA on protein tyrosine phosphatase 1B inhibitors. Bioorg Med Chem 10:2267-2282
38. Equbal T, Silakari O, Ravikumar M (2008) Exploring three-dimensional quantitative structural activity relationship (3D-QSAR) analysis of SCH 66336 (Sarasar) analogues of farnesyltransferase inhibitors. Eur J Med Chem 43:204-209
39. Subbiah Ramar SB, Tawari NR, Degani MS (2007) 3-D-QSAR analysis of 2-(oxalylamino) benzoic acid class of protein tyrosine phosphatase 1B inhibitors by CoMFA and Cerius2 GA. QSAR Comb Sci 26:608-617