Structural analysis of structurally diverse α-glucosidase inhibitors for active site feature analysis

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 5, 2012, Pages 649-657

  Narayana Moorthy, N S Hari ^a   Ramos, Maria J ^a   Fernandes, Pedro A ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

glucosidases; Polarizability; QSAR; Validation methods

Indexed keywords

ALPHA GLUCOSIDASE INHIBITOR; ANDROGRAPHOLIDE; CHROMENE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; MATHEMATICAL MODEL; POLARIZATION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

ALPHA-GLUCOSIDASES; CATALYTIC DOMAIN; ENZYME INHIBITORS; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84866120433     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.605359     Document Type: Article

References (32)

1. Gamblin DP, Scanlan EM, Davis BG. Glycoprotein synthesis: An update. Chem Rev 2009;109:131-163.
2. Park H, Hwang KY, Kim YH, Oh KH, Lee JY, Kim K. Discovery and biological evaluation of novel alpha-glucosidase inhibitors with in vivo antidiabetic effect. Bioorg Med Chem Lett 2008;18:3711-3715. (Pubitemid 351794515)
3. Rawlings AJ, Lomas H, Pilling AW, Lee MJ, Alonzi DS, Rountree JS et al. Synthesis and biological characterisation of novel N-alkyldeoxynojirimycin alpha-glucosidase inhibitors. Chembiochem 2009;10:1101-1105.
4. Silva CH, Taft CA. Computer-aided molecular design of novel glucosidase inhibitors for AIDS treatment. J Biomol Struct Dyn 2004;22:59-63. (Pubitemid 39095283)
5. Shen Q, Shao J, Peng Q, Zhang W, Ma L, Chan ASC, Gu L. Hydroxycoumarin derivatives: Novel and potent α-glucosidase inhibitors. J Med Chem 2010;53:8252-8259.
6. Karpas A, Fleet GW, Dwek RA, Petursson S, Namgoong SK, Ramsden NG et al. Aminosugar derivatives as potential antihuman immunodeficiency virus agents. Proc Natl Acad Sci USA 1988;85:9229-9233. (Pubitemid 19001870)
7. Zitzmann N, Mehta AS, Carrouée S, Butters TD, Platt FM, McCauley J et al. Imino sugars inhibit the formation and secretion of bovine viral diarrhea virus, a pestivirus model of hepatitis C virus: Implications for the development of broad spectrum anti-hepatitis virus agents. Proc Natl Acad Sci USA 1999;96:11878-11882. (Pubitemid 29502826)
8. Kavitha B, Nagakumar B, Ki HP, Keun WL. Binding mode analyses and pharmacophore model development for sulphonamide chalcone derivatives, a new class of α-glucosidase inhibitors. J Mol Graphs Model 2008;26:1202-1212.
9. Tomich CH, da Silva P, Carvalho I, Taft CA. Homology modeling and molecular interaction field studies of alpha-glucosidases as a guide to structure-based design of novel proposed anti-HIV inhibitors. J Comput Aided Mol Des 2005;19:83-92. (Pubitemid 40974009)
10. Park JH, Ko S, Park H. Towards the virtual screening of α-glucosidase inhibitors with the homology-modeled protein structure. Bull Korean Chem Soc 2008;29:921-927.
11. Cardona F, Parmeggiani C, Faggi E, Bonaccini C, Gratteri P, Sim L et al. Total syntheses of casuarine and its 6-O-alphaglucoside: Complementary inhibition towards glycoside hydrolases of the GH31 and GH37 families. Chemistry 2009;15: 1627-1636.
12. Sim L, Jayakanthan K, Mohan S, Nasi R, Johnston BD, Pinto BM et al. New glucosidase inhibitors from an ayurvedic herbal treatment for type 2 diabetes: Structures and inhibition of human intestinal maltase-glucoamylase with compounds from Salacia reticulata. Biochemistry 2010;49:443-451.
13. Moorthy NSHN, Trivedi P. QSAR modelling of some 2-methoxy acridones: Cytotoxic in multidrug resistant cells. Int J Cancer Res 2006;2:267-276. (Pubitemid 46705976)
14. Moorthy NSHN, Cerqueira NMFS, Ramos MJ, Fernandes PA. QSAR and pharmacophore analysis of thiosemicarbazone derivatives as ribonucleotide reductase inhibitors. Med Chem Res 2011; DOI: 10.1007/s00044-011-9580-x.
15. Moorthy NSHN, Ramos MJ, Fernandes P.A. QSAR analysis of isosteviol derivatives as α-glucosidase inhibitors with element count and other descriptors. Lett Drug Des Dis 2011;8:14-25.
16. Moorthy NS, Ramos MJ, Fernandes PA. Prediction of the relationship between the structural features of andrographolide derivatives and α-glucosidase inhibitory activity: A quantitative structure-activity relationship (QSAR) study. J Enz Inhibit Med Chem 2011;26:78-87.
17. Moorthy NSHN, Ramos MJ, Fernandes PA. Topological, hydrophobicity and other descriptors on α-glucosidase inhibition: A QSAR study on xanthone derivatives. J Enz Inhibit Med Chem 2011; DOI:10.3109/14756366.2010.549089.
18. Moorthy NSHN, Ramos MJ, Fernandes PA. Analysis of α-glucosidase inhibitory activity of chromenone derivatives by its molecular features: A computational study. Med Chem 2011 (In Press).
19. Raju BC, Tiwari AK, Kumar JA, Ali AZ, Agawane SB, Saidachary G et al. α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Bioorg Med Chem 2010;18:358-365.
20. Xu HW, Dai GF, Liu GZ, Wang JF, Liu HM. Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors. Bioorg Med Chem 2007;15:4247-4255.
21. Ferreira SB, Sodero AC, Cardoso MF, Lima ES, Kaiser CR, Silva FP et al. Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as α-glucosidases inhibitors. J Med Chem 2010;53:2364-2375.
22. Dai GF, Xu HW, Wang JF, Liu FW, Liu HM. Studies on the novel α-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues. Bioorg Med Chem Lett 2006;16:2710-2713.
23. Lin A. QuaSAR-descriptors. J Chem Comput Group 2002; http://www.chemcomp. com/Journal-of-CCG/Features/descr.htm
24. Kiralj R, Ferreira MMC. Basic validation procedures for regression models in QSAR and QSPR studies: Theory and applications. J Braz Chem Soc 2009;20:770-787.
25. Gramatica P. Principle of QSAR model validation: Internal and external. QSAR Comb Sci 2007;26:694-701. (Pubitemid 46932857)
26. Golbraikh A, Tropsha A. Beware of q2! J Mol Graph Model 2002;20:269-276.
27. Moorthy NSHN, Sousa SF, Ramos MJ, Fernandes PA. Structural feature study of benzofuran derivatives as farnesyltransferase inhibitors. DOI: 10.3109/14756366.2011.552885.
28. Cook R, Dennis. Influential observation in linear regression. J Am Stat Assoc 1979;74:169-174.
29. Moorthy NSHN, Cerquira NM, Ramos MJ, Fernandes PA. QSAR analysis of 2-benzoxazolyl hydrazone derivatives for anticancer activity and its possible target prediction. Med Chem Res 2011; DOI: 10.1007/s00044-010-9510-3.
30. Durbin J, Watson GS. Testing for serial correlation in least squares regression. I. Biometrika 1950;37:409-428.
31. Manoj Kumar P, Karthikeyan C, Moorthy NSHN, Quantitative structure-activity relationships of selective antagonists of glucagon receptor using QuaSAR descriptors. Chem Pharm Bull 2006;54:1586-1591. (Pubitemid 44703987)
32. Cruciani C, Crivori P, Carrupt PA, Testa B. Molecular fields in quantitative structure-permeation relationships: The VolSurf approach. J Mol Struct (Theochem) 2000;503:17-30.