3D-QSAR studies of Dipeptidyl peptidase IV inhibitors using a docking based alignment

Journal of Molecular Modeling

Volumn 13, Issue 10, 2007, Pages 1047-1071

  Pissurlenkar, Raghuvir R S ^a   Shaikh, Mushtaque S ^a   Coutinho, Evans C ^a  

^a BOMBAY COLLEGE OF PHARMACY   (India)

Author keywords

3D QSAR; CoMFA; CoMSIA; Dipeptidyl peptidase IV inhibitors; Docking receptor based alignment

Indexed keywords

1 (2 AMINO 3 BIPHENYL 4 YL PROPIONYL)PYRROLIDINE 2 CARBONITRILE; 2 AMINO 3 METHYL 1 PYRROLIDIN 1 YL BUTAN 1 ONE; 4 OXO 4 [3 (TRIFLUOROMETHYL) 5,6 DIHYDRO[1,2,4] TRIAZOLO[4,3 A]PYRAZIN 7(8H) YL] 1 (2,4,5 TRIFLUOROPHENYL)BUTAN 2 AMINE; DIPEPTIDYL PEPTIDASE IV; DIPEPTIDYL PEPTIDASE IV INHIBITOR; FLUOROPYRROLIDINE DERIVATIVE; HETEROCYCLIC COMPOUND; N [[1 [3 AMINO 4 (2 FLUOROPHENYL)BUTANOYL]PYRROLIDIN 2 YL]METHYL]BENZAMIDE; PEPTIDE HYDROLASE INHIBITOR; PHENYLALANINE; PYRROLIDINE DERIVATIVE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME STRUCTURE; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; PHARMACOPHORE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL SIGNIFICANCE; THREE DIMENSIONAL IMAGING;

ANIMALS; ANTIGENS, CD26; BINDING SITES; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; GLUCOSE; HORMONES; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34548167100     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-007-0227-2     Document Type: Article

References (58)

1. Ogata S, Misumi Y, Ikehara YS (1959) J Biol Chem 264:596-601
2. Bjelke RJ, Christensen J, Branner S, Wagtmann N, Olsen C, Kanstrup AB, Rasmussen HB (2004) J Biol Chem 279:34691-34697
3. Abbott CA, Gorrell MD (2002) Ectopeptidases: CD13/Aminopeptidase N and CD26/Dipeptidylpeptidase IV. In: Langner J, Ansorge S (eds) Medicine and biology. Kulwer/Plenum, New York, pp 171-184
4. Lambeir AM, Diaz Pereira JF, Chacon P, Vermeulen G, Heremans K, Devreese B, Van Beeumen J, De Meester I, Scharpe S (1997) Biochim Biophys Acta 1340:215
5. Duke-Cohan JS, Morimoto C, Rocker JA, Schlossman SF (1996) J Immunol 156:1714-1721
6. Hartel S, Gossrau R, Hanski C, Reutter W (1988) Histochemistry 89:151-161
7. Engel M, Hoffmann T, Wagner L, Wermann M, Heiser U, Keifersauer R, Huber R, Bode W, Demuth H-U, Brandstetter H (2003) Proc Natl Acc Sci 100:5063-5068
8. Pederson RA, White HA, Schlenzig D, Pauly RP, McIntosh CH, Demuth H-U (1998) Diabetes 47:1253-1258
9. Pospisilik JA, Stafford SG, Demuth HU, McIntosh CH, Pederson RA (2002) Diabetes 51:2677-2683
10. Cheng JD, Dunbrack RL, Valianou M, Rogatko A, Alpaugh RK, Weiner LM (2002) Cancer Res 62:4767-4772
11. Kajiyama H, Kikkawa F, Suzuki T, Shibata K, Ino K, Mizutani S (2002) Cancer Res 62:2753-2757
12. Ho L, Aytac U, Stephens LC, Ohnuma K, Mills GB, McKee KS, Neumann C, LaPushin R, Cabanillas F, Abbruzzese JL, Morimoto C, Dang NH (2001) Clinic Cancer Res 7:2031-2040
13. Frohman LA, Downs TR, Heimer EP, Felix AM (1989) J Clinic Invest 83:1533-1540
14. Nausch I, Heymann E (1985) J Neurochem 44:1354-1357
15. Ahmad S, Wang L, Ward PE (1992) J Pharmacol Exp Ther 260:1257-1261
16. Nauck MA, Niedereichholz U, Ettler R, Holst JJ, Ørskov C, Ritzel R, Schmiegel WH (1997) Am J Physiol 273:E981-E988
17. Ahrén B (1998) BioEssays 20:642-651
18. Meier JJ, Nauck MA, Schmidt WE, Gallwitz B (2002) Regul Pept 107:1-13
19. Jörnvall H, Carlquist M, Kwauk S, Otte SC, McIntosh CH, Brown JC, Mutt V (1981) FEBS Lett 123:205-210
20. Adelhorst K, Hedegaard BB, Knudsen LB, Kirk O (1994) J Biol Chem 269:6275-6278
21. Rolin B, Deacon CF, Carr RD, Ahrén B (2004) Eur J Pharmacol 494:283-288
22. Green BD, Flatt PR, Bailey CJ (2006) Expert Opin Emerg Drugs 11:525-539
23. Kendall DM, Kim D, Maggs D (2006) Diabetes Technol Ther 8:385-396
24. Ahren B, Landin-Olsson M, Jansson PA, Svensson M, Holmes D, Schweizer A (2004) J Clin Endocrinol Metab 89:2078-2084
25. Pratley R, Galbreath E (2004) Diabetes 53:A83
26. Herman GA, Zhao P-L, Dietrich G (2004) Diabetologia 47:794-805
27. Triplitt C, Wright A, Chiquette E (2006) Pharmacotherapy 26:360-374
28. Brandt W, Lehmann T, Barth A, Fittkaui S (1993) J Mol Graphics 11:277-278
29. Brandt W, Lehmann T, Thondor I, Born I, Schutkowski M, Rahfeld JU, Neubert K, Barth A (1995) Int J Peptide Prot Res 46:494-507
30. Rasmussen HB, Branner S, Wiberg FC, Wagtmann NR (2003) Nat Struct Biol 10:19-25
31. Qiao L, Baumann CA, Crysler CS, Ninan NS, Abad MC, Spurlino JC, Desjarlais RL, Kervinen J, Neeper MP, Bayoumy SS, Williams R, Deckman IC, Dasgupta M, Reed RL, Huebert ND, Tomczuk BE, Moriarty KJ (2006) Bioorg Med Chem Lett 16:123-128
32. Kim D, Wang L, Beconi M, Eiermann GJ, Fisher MH, He H, Hickey GJ, Kowalchick JE, Leiting B, Lyons K, Marsilio F, Mccann ME, Patel RA, Petrov A, Scapin G, Patel SB, Roy RS, Wu JK, Wyvratt MJ, Zhang BB, Zhu L, Thornberry NA, Weber AE (2005) J Med Chem 48:141-151
33. Nordhoff S, Cerezo-Galvez S, Feurer A, Hill O, Matassa VG, Metz G, Rummey C, Thiemann M, Edwards PJ (2006) Bioorg Med Chem Lett 16:1744-1748
34. GOLD 3.0.1 CCDC Ltd., UK
35. Sybyl version 7.1 Tripos Inc., USA
36. Cerius2 version 4.8, Accelrys Inc., USA
37. Nayyar A, Malde A, Jain R, Coutinho EC (2006) Bioorg Med Chem 14:847-856
38. Tanimoto TT, Trans NY (1961) Acad Sci Ser 2(23):576-578
39. Nikolova N, Jaworska J (2003) QSAR Comb Sci 22:1006-1026
40. Xu J, Ok HO, Gonzalez EJ, Colwell LF Jr, Habulihaz B, He H, Leiting B, Lyons KA, Marsilio F, Patel RA, Wu JK, Thornberry NA, Weber AE, Parmee ER (2004) Bioorg Med Chem Lett 14:4759-4762
41. Edmondson SD, Mastracchio A, Duffy JL, Eiermann GJ, He H, Ita I, Leiting B, Leone JF, Lyons KA, Makarewicz AM, Patel RA, Petrov A, Wu JK, Thornberry NA, Weber AE (2005) Bioorg Med Chem Lett 15:3048-3052
42. Xu J, Wei L, Mathvink R, He J, Park Y-J, He H, Leiting B, Lyons KA, Marsilio F, Patel RA, Wu JK, Thornberry NA, Weber AE (2005) Bioorg Med Chem Lett 15:2533-2536
43. Hulin B, Cabral S, Lopaze MG, Van Volkenburg MA, Andrews KM, Parker JC (2005) Bioorg Med Chem Lett 15:4770-4773
44. InsightII version 2005L, Accelrys Inc, USA
45. Datar PA, Coutinho EC (2004) J Mol Graph Model 23:239-251
46. Cramer RD, Patterson DE, Bunce JD (1988) J Am Chem Soc 110:5959-5967
47. Klebe G, Abraham U, Mietzner T (1994) J Med Chem 37:4130-4146
48. Klebe G (1998) Drug Discov Des 12:87-104
49. Böhm M, Stürzebecher J, Klebe G (1999) J Med Chem 42:458-477
50. Wold S, Johansson E, Cocchi M (1993) PLS-partial least squares projections to latent structures in 3D-QSAR. In: Kubinyi H (ed) Drug design; theory methods and applications. ESCOM Lieden, The Netherlands, pp 523-550
51. Bush BL, Nachbar RB (1993) J Comput Aided Mol Des 7:587-619
52. Legar C, Politis DN, Romano JP (1992) Technometrics 34:378-399
53. Edmondson SD, Mastracchio A, Beconi M, Colwell LF, Habulihaz B, He H, Kumar S, Leiting B, Lyons KA, Mao A, Marsilio F, Patel RA, Wu JK, Zhu L, Thornberry NA, Weber AE, Parmee ER (2004) Bioorg Med Chem Lett 14:5151-5155
54. Ludwig K, Yan S, Fan H, Reutter W, Bottcher C (2003) Biochem Biophys Res Commun 304:73-77
55. Mentlein R (1999) Regul Pept 85:9-24
56. Ogata S, Misumi Y, Tsuji E, Takami N, Oda K, Ikehara Y (1992) Biochemistry 31:2582-2587
57. Abbott CA, McCaughan GW, Gorrell MD (1999) FEBS Letters 458:278-284
58. Datar PA, Khedkar SA, Malde AK, Coutinho EC (2006) J Comput Aided Mol Des 20:343-360