Topological, hydrophobicity, and other descriptors on α-glucosidase inhibition: A QSAR study on xanthone derivatives

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 26, Issue 6, 2011, Pages 755-766

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

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

glucosidase inhibitor; Electrotopological; Hydrophobicity; QSAR; Xanthone derivatives

Indexed keywords

ALPHA GLUCOSIDASE; XANTHONE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME LOCALIZATION; HYDROGEN BOND; HYDROPHOBICITY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ALPHA-GLUCOSIDASES; ENZYME INHIBITORS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; XANTHONES;

EID: 81355149312     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2010.549089     Document Type: Article

References (48)

1. 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)
2. Fischer PB, Collin M, Karlsson GB, James W, Butters TD, Davis SJ et al. The alpha-glucosidase inhibitor N-butyldeoxynojirimycin inhibits human immunodeficiency virus entry at the level of post- CD4 binding. J Virol 1995;69:5791-5797.
3. Taylor DL, Kang MS, Brennan TM, Bridges CG, Sunkara PS, Tyms AS. Inhibition of alpha-glucosidase I of the glycoproteinprocessing enzymes by 6-O-butanoyl castanospermine (MDL 28,574) and its consequences in human immunodeficiency virus-infected T cells. Antimicrob Agents Chemother 1994;38:1780-1787. (Pubitemid 24250724)
4. Jung-Hum P, Sungmin K, Hwangseo P. Toward the virtual screening of α-glucosidase inhibitors with the homology-modelled protein structure. Bull Korean Chem Soc 2008;29:921-927.
5. Wang S, Yan J, Wang X, Yang Z, Lin F, Zhang T. Synthesis and evaluation of the alpha-glucosidase inhibitory activity of 3-[4-(phenylsulfonamido)benzoyl] -2H-1-benzopyran-2-one derivatives. Eur J Med Chem 2010;45:1250-1255.
6. Hwangseo P, Kyo YH, Kyung HO, Young HK, Jae YL, Keun K. Discovery of novel α-glucosidase inhibitors based on the virtual screening with the homology-modelled protein structure. Bioorg Med Chem 2008;16:284-292.
7. Humphries MJ, Matsumoto K, White SL, Olden K. Inhibition of experimental metastasis by castanospermine in mice: blockage of two distinct stages of tumor colonization by oligosaccharide processing inhibitors. Cancer Res 1986;46:5215-5222. (Pubitemid 16008292)
8. Rudd PM, Storr, SJ, Royle L, Chapman CJ, Hamid UM, Robertson JF et al. The O-linked glycosylation of secretory/shed MUC1from an advanced breast cancer patient's serum. Glycobiol 2008;18:456-462. (Pubitemid 351753549)
9. 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)
10. 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)
11. 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 Graph Model 2008;26:1202-1212.
12. Rawling AJ, Lomas H, Adam WP, Marvin JRL, Dominic SA, Shane JSR et al. Synthesis and biological characterization of novel N-alkyl deoxynojirimycin α-glucosidase inhibitors. ChemBioChem 2009;10:1101-1105.
13. Joseph R, Florent B, Catia T, Froncois M. 2D and 3D QSAR studies of diarylpyrimidine HIV-1 reverse transcriptase inhibitors. J Comput Aided Mol Des 2008;22:831-841.
14. Karthikeyan C, Moorthy NSHN, Piyush T. QSAR study of substituted 2-pyridinyl quanidine as selective urokinase-type plasminogen activator (uPA) inhibitors. J Enz Inhibit Med Chem 2009;24:6-13.
15. Cho DH, Lee SK, Kim BT, No KT. Quantitative structure activity relationship (QSAR) study of new fluorovinyloxyacetamides. Bull Korean Chem Soc 2001;22:388-394. (Pubitemid 32436156)
16. Yan L, Zhuofeng K, Jianfang C, Wen-Hua C, Lin M, Bo W. Synthesis, inhibitory activities and QSAR study of xanthone derivatives as α-glucosidase inhibitors. Bioorg Med Chem 2008;16:7185-7192.
17. Eun JS, Maecus JCL, Byong WL, Hoi YK, Young BR, Tae SJ, Woo SL, Ki HP. Xanthones from Cudrania tricuspidata displaying potent α-glucosidase inhibition. Bioorg Med Chem Lett 2007;17:6421-6424.
18. 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)
19. Raymond AD, Terry DB, Frances MP, Nicole Z. Targeting glycosylation as a therapeutic approach. Nat Rev Drug Dis 2002;1:65-75.
20. Moorthy NSHN, Ramos MJ, Fernandes PA. Prediction of relationship between structural features of andrographolide derivatives and α-glucosidase inhibitory ctivity: a QSAR study. J Enz Inhibit Med Chem 2011;8:14-25.
21. Moorthy NSHN, Ramos MJ, Fernandes PA. QSAR analysis of isosteviol derivatives as α-glucosidase inhibitors with element count and other descriptors. Lett Drug Des Dis (In Press).
22. Bonchev D. Novel indices for the topological complexity of molecules. SAR/QSAR Environ Res 1997;7:23-43.
23. Gálvez J, García-Domenech R, Julian-Ortiz J V de, Soler R. Topological approach to drug design. J Chem Inf Comput Sci 1995;35:272-284
24. Schultz HP, Schultz EB, Schultz TP. Topological organic chemistry. 9. Graph theory and molecular topological indices of stereoisomeric organic compounds. J Chem Inf Comput Sci 1995;35:864-870.
25. Biye R. Atomic level based AI topological descriptors for structure property correlations. J Chem Inf Comput Sci 2003;43:161-169
26. Jarmo H. QSAR modeling with the electrotopological state: TIBO derivatives. J Chem Inf Comput Sci 2001;41:425-429.
27. Yan L, Lan Z, Lin M, Wen HC, Bo W, Zun LX. Synthesis and pharmacological activities of xanthone derivatives as α-glucosidase inhibitors. Bioorg Med Chem 2006;14:5683-5690.
28. Chem BioOffice 2008, CambridgeSoft Corp, Cambridge, UK.
29. V-Life Technologies, molecular design suite 3.5, 2008, Pune, India.
30. Statistica 8.0 statistical software, StatSoft, Inc. 2006, OK, USA
31. Balaji S, Karthikeyan C, Moorthy NSHN, Trivedi P. QSAR modelling of HIV-1 reverse transcriptase inhibition by benzoxazinones using a combination of P-VSA and pharmacophore feature descriptors. Bioorg Med Chem Lett 2004;14:6089-6094. (Pubitemid 39531278)
32. Gramatica P. Principle of QSAR model validation: internal and external. QSAR Comb Sci 2007;26:694-701. (Pubitemid 46932857)
33. Tropsha A, Gramatica P, Gombar VK. The importance of earnest, validation is the absolute essential application and interpretation of QSPR models. QSAR Comb Sci 2003;22:69-77. (Pubitemid 36717473)
34. Erikkson L, Jaworsha J, Worth AP, Mark TDC, Robert MM, Gramatica P. Methods for reliability and uncertainty assessment and for applicability evaluation of classification and regression based QSARs. Envirn Health Perspect 2003;111:1361-1375. (Pubitemid 37021142)
35. Alexander G, Alexander T. Beware of Q2. J Mol Graphs Model 2002;20:269-276.
36. Tuppurainen K, Viisas M, Laatikainen R, Peräkylä M. Evaluation of a novel electronic eigenvalue (EEVA) molecular descriptor for QSAR/QSPR studies: validation using a benchmark steroid data set. J Chem Inf Comput Sci 2002;42:607-613. (Pubitemid 35359017)
37. Durbin J, Watson GS. Testing for serial correlation in least squares regression. II. Biometrika 1951;38:159-178.
38. Prasanna S, Manivannan E, Chaturvedi SC. QSAR analysis of some fused pyrazoles as selective cyclooxygenase-2 inhibitors: a Hansch approach. Arch Pharm (Weinheim) 2004;337:440-444. (Pubitemid 39243534)
39. Gnanadesikan R, Kettenring JR. Robust estimate, residuals and outlier detection with multipurpose data. Biometrics 1972;28:81-124.
40. Santiago V, Humberto GD, Lourdes S, Eugenio U. QSAR model for alignment-free prediction of human breast cancer biomarkers based on electrostatic potentials of protein pseudofolding HP-lattice networks. J Comput Chem 2008;29:2613-2622.
41. Cook RD. Influential observation in linear regression. J Am Stat Assoc 1979;74:169-174.
42. Rotriquez G. Chapter 2, Linear models for continuous data, 1993- 2000:49-58. http://data.princeton.edu/wws509/notes
43. Dogra, Shailay K. Script for computing linear regression diagnostics from QSAR world-free online resources for QSAR modelling. http://www.qsarworld.com/ virtualworkshop.php
44. Gough JD, Hall LH. Modeling antileukemic activity of carboquinones with electrotopological state and chi indices. J Chem Inf Comput Sci 1999;39:356-361. (Pubitemid 129538927)
45. Andersson PM, Michael SM, Svante W, Torbjo, Rn L. Comparison between physicochemical and calculated molecular descriptors. J Chemometrics 2000;14:629-642.
46. Hliang HM, Hall LA. E-state modeling of corticosteroids binding affinity validation of model for small data set. J Chem Inf Comput Sci 2001;41:1248-1254.
47. Hall LM, Hall LH, Kier LB. Modeling drug albumin binding affinity with e-state topological structure representation. J Chem Inf Comput Sci 2003;43:2120-2128.
48. Maw HH, Hall LH. E-state modeling of HIV-1 protease inhibitor binding independent of 3D information. J Chem Inf Comput Sci 2002;42:290-298. (Pubitemid 35355304)