Development of a robust QSAR model to predict the affinity of pyrrolidine analogs for dipeptidyl peptidase IV (DPP-IV)

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 26, Issue 1, 2011, Pages 129-140

  Paliwal, Sarvesh ^a   Seth, Deepika ^a   Yadav, Divya ^a   Yadav, Rakesh ^a   Paliwal, Shailendra ^b  

^a BANASTHALI UNIVERSITY   (India)

^b LLRM MEDICAL COLLEGE   (India)

Author keywords

anti diabetic agents; Dipeptidyl Peptidase IV (DPP IV); MLR; PLS; QSAR; TSAR

Indexed keywords

DIPEPTIDYL PEPTIDASE IV INHIBITOR; PYRROLIDINE DERIVATIVE;

ARTICLE; DIPOLE; DRUG ACTIVITY; IC 50; LIPINSKI RULE; MATHEMATICAL MODEL; MULTIPLE LINEAR REGRESSION ANALYSIS; PARTIAL LEAST SQUARES REGRESSION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATIC ELECTRICITY;

DIABETES MELLITUS, TYPE 2; DIPEPTIDYL PEPTIDASE 4; DIPEPTIDYL-PEPTIDASE IV INHIBITORS; HUMANS; LEAST-SQUARES ANALYSIS; LINEAR MODELS; MODELS, THEORETICAL; PYRROLIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SMALL MOLECULE LIBRARIES; SOFTWARE;

EID: 79851489024     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756361003777057     Document Type: Article

References (35)

1. Morral N. Novel targets and therapeutic strategies for type 2 diabetes. Trends Endocrinol Metab 2003; 14:169-75. (Pubitemid 36733902)
2. Ross S A, Gulve E A, and Wang M. Chemistry and biochemistry of Type 2 Diabetes. Chem Rev. 2004; 104 (3):1255-1282.
3. Skyler JS. Diabetes Mellitus: Pathogenesis and Treatment Strategies. J Med Chem. 2004; 47: 4113-4117. (Pubitemid 39045414)
4. Vilsbøll T, Knop FK. Efect of incretin hormones GIP and GLP-1 for the pathogenesis of type 2 diabetes mellitus. Ugeskr Laeger 2007; 169: 2101-5.
5. Drucker DJ. Te biology of incretin hormones, Cell Metabolism 2006; 3:153-165.
6. Nauck MA, Bartels E, Orskov C, Ebert R, Creutzfeldt W. Additive insulinotropic efects of exogenous synthetic human gastric inhibitory polypeptide and glucagon-like peptide-1-(7-36) amide infused at near-physiological insulinotropic hormone and glucose concentrations. J Clin Endocrinol Metab 1993; 76: 912-917. (Pubitemid 23110837)
7. Lynn FC, Pamir N, Ng EHC, McIntosh CH.S, Pederson RA. Defective glucose-dependent insulinotropic polypeptide receptor expression in diabetic fatty Zucker rats. Diabetes 2001; 50:1004-1011. (Pubitemid 32374530)
8. Jones I R, Owens DR, Moody A J, Luzio SD; Morris T, Hayes, TM. Te efects of glucose-dependent insulinotropic polypeptide infused at physiological concentrations in normal subjects and Type 2 (non-insulin-dependent) diabetic patients on glucose tolerance and B-cell secretion. Diabetologia 1987; 30: 707-712. (Pubitemid 17155776)
9. Meier JJ, Hucking K, Holst JJ, Deacon CF, Schmiegel WH, Nauck MA. Reduced insulinotropic efect of gastric inhibitory polypeptide in frst-degree relatives of patients with type 2 diabetes. Diabetes 2001; 50: 2497-2504. (Pubitemid 33642767)
10. Knudsen LB. Glucagon-like Peptide-1: Te Basis of New Class of Treatment for Type 2 Diabetes. J Med Chem 2004; 47: 4128-4134. (Pubitemid 39045416)
11. Eng J, Kleinman WA, Singh L, Singh G, Raufman JP. Isolation and characterization of exendin 4, an exendin 3 analogue from Heloderma suspectum venom. J Biol Chem 1992; 267: 7402-7405.
12. Mentlein R, Gallwitz B, Schmidt WE. Dipeptidyl-peptidase IV hydrolyses gastric inhibitory polypeptide, glucagon-like peptide-1(7-36) amide, peptide histidine methionine and is responsible for their degradation in human serum. Eur J Biochem 1993; 214: 829-835. (Pubitemid 23188160)
13. Kiefer TJ, McIntosh CH, Pederson RA. Degradation of glucose-dependent insulinotropic polypeptide and truncated glucagon-like peptide 1 in vitro and in vivo by dipeptidyl peptidase IV. Endocrinology 1995; 136: 3585-3596.
14. Hansen L, Deacon CF, Orskov C, Holst JJ. Glucagon-like peptide-1-(7-36)amide is transformed to glucagon-like peptide-1-(9-36) amide by dipeptidyl peptidase IV in the capillaries supplying the L cells of the porcine intestine. Endocrinology 1999; 140: 5356-5363.
15. Mentlein R. Dipeptidyl-peptidase IV (CD26)-role in the inactivation of regulatory peptides. Regul Pept 1999; 85: 9-24. (Pubitemid 29505281)
16. http://accelrys.com/products/accord/desktop/tsar.html: TSAR 3.3, Oxford Molecular Limited
17. Takashi K, Sugimoto I, Nekado T, Ochi K, Ohtani T, Tajima Y, Yamamoto S, Kawabata K, Nakai H. Toda M (2007) Design and synthesis of long-acting inhibitors of Dipeptidyl peptidase IV, Biorg Med Chem 2007; 15: 2715-2735. (Pubitemid 46367700)
18. Takashi K, Sugimoto I, Nekado T, Ochi K, Takai S, Kinoshita A, Hatayama A, Yamamoto S, Kawabata K, Nakai H., Toda M. Discovery of long-acting N-(cyanomethyl)-N-alkyl-L-prolinamide inhibitors of dipeptidyl peptidase IV. Biorg Med Chem 2008; 16: 190-208.
19. Takashi K, Sugimoto I, Nekado T, Ochi K, Takai S, Kinoshita A, Hatayama A, Yamamoto S, Kishikawa K, Nakai H., Toda M. Design and synthesis of DPP IV inhibitors lacking the electrophilic nitrile group. Biorg Med Chem 2008; 16: 1613-1631. (Pubitemid 351226600)
20. Sadowski J, Gasteiger J. From Atoms and Bonds to Tree-Dimensional Atomic Coordinates: Automatic Model Builders. Chem Rev 1993; 93: 2567-2581.
21. Benfenati E, Quantitative structure activity relationships [QSAR]. for pesticide regulatory purposes. Elsevier 2007:186.
22. Balakrishnan N; Childs A. "Outlier", in Hazewinkel, Michiel, Encyclopaedia of Mathematics, 2001, Kluwer Academic Publishers, ISBN 978-1556080104
23. Kim KH. Outliers in SAR and QSAR: 2. Is a fexible binding site a possible source of outliers? J Comput Aided Mol Des 2007; 21: 421-435. (Pubitemid 47423276)
24. Spanier A M, Okai H, Tamura M. Food Flavor and Safety: Molecular Analysis and Design. ACS Symposium Series 1993; 103-104.
25. Paliwal S, Narayan A, Paliwal Shailendra. Quantitative Structure Activity Relationship Analysis of Dicationic Diphenylisoxazole as Potent Anti-Trypanosomal Agents. QSAR Comb Sci 2009; 28: 1367-1375.
26. Kohavi, Ron. A study of cross-validation and bootstrap for accuracy estimation and model selection. Proceedings of the Fourteenth International Joint Conference on Artifcial Intelligence 1995; 2 (12): 1137-1143.(Morgan Kaufmann, San Mateo).
27. Chang J, Luo Y, Su, K. GPSM: a Generalized Probabilistic Semantic Model for ambiguity resolution. In Proceedings of the 30th Annual Meeting on Association For Computational Linguistics (Newark, Delaware, June 28-July 02, 1992). Annual Meeting of the ACL. Association for Computational Linguistics, Morristown, NJ,1992; 177-184.
28. Devijver P A, Kittler J. Pattern Recognition: A Statistical Approach, Prentice-Hall, London, 1982
29. Quinn RJ, Carroll AR, Pham NB, Baron P, Palframan ME, Suraweera L, Pierens GK, Muresan M. Developing a Drug-like Natural Product Library. J Nat Prod 2008; 71: 464-468. (Pubitemid 351549376)
30. Dessalew N. QSAR study on aminophenylbenzamides and acrylamides as histone deacetylase inhibitors: An insight into the structural basis of antiproliferative activity. Med Chem Res 2007; 16:449-460.
31. Paliwal SK, Pal M, Siddiqui AA. Quantitative structure activity relationship analysis of angiotensin II AT1 receptor antagonists. Med Chem Res DOI 10.1007/s00044-009-9205-9.
32. Karelson M. Molecular Descriptors in QSAR/QSPR, Wiley Interscience, New York, February. 2000.
33. Peters, Jens-Uwe. 11 years of Cyanopyrrolidines as DPP-IV Inhibitors. Current topics in Med Chem 2007;7: 579-595.
34. Hall L H, Kier LB. Te molecular connectivity chi indexes and kappa shape indexes in structure-property modeling. Reviews in Computational Chemistry II 1991; 367-422.
35. Sapre NS, Pancholi N Gupta S, Sapre N. Computational modeling of tetrahydroimidazo-[4,5,1-jk][1,4]. benzodiazepinone derivatives: an atomistic drug design approach using Kier-Hall electrotopological state (E-state) indices. J Comput Chem 2008; 29: 1699-706.