Chemical function-based pharmacophore generation of selective κ-opioid receptor agonists by catalyst and phase

Journal of Molecular Modeling

Volumn 15, Issue 9, 2009, Pages 1027-1041

  Zhang, Jing ^a   Liu, Guixia ^a   Tang, Yun ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

opioid receptor agonists; Catalyst HypoGen; Pharmacophore models; Phase; QSAR

Indexed keywords

3,4 DICHLORO N METHYL N [1 PHENYL 2 (1 PYRROLIDINYL)ETHYL]BENZENEACETAMIDE; 3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; KAPPA OPIATE RECEPTOR AGONIST;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; CATALYST; COMPUTER PREDICTION; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; HYDROGEN BOND; HYDROPHOBICITY; INFORMATION RETRIEVAL; PHARMACOPHORE; PRIORITY JOURNAL; PROCESS OPTIMIZATION; RELIABILITY; SCORING SYSTEM; STRUCTURE ANALYSIS; VALIDITY;

3,4-DICHLORO-N-METHYL-N-(2-(1-PYRROLIDINYL)-CYCLOHEXYL)-BENZENEACETAMIDE, (TRANS)-ISOMER; ANALGESICS, NON-NARCOTIC; CATALYSIS; DRUG DESIGN; MODELS, MOLECULAR; PYRROLIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, OPIOID, KAPPA; SOFTWARE;

EID: 67849114231     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-008-0418-5     Document Type: Article

References (42)

1. Schwalbe H, Wess G (2002) Chem Bio Chem 3:915-919. doi: 10.1002/ 1439-7633(20021004)3:10<915::AID-CBIC915>3.0.CO;2-L
2. Gether U (2000) Endocr Rev 21:90-113. doi: 10.1210/er.21.1.90
3. Ulloa-Aguirre A, Stanislaus D, Janovick JA, Conn PM (1999) Arch Med Res 30:420-435. doi: 10.1016/S0188-0128(99)00041-X
4. Kieffer BL (1995) Cell Mol Neurobiol 15:615-635. doi: 10.1007/BF02071128
5. Dhawan BN, Cesselin F, Raghubir R, Reisine T, Bradley PB, Portoghese PS, Hamon M (1996) Pharmacol Rev 48:567-592
6. DeHaven-Hudkins DL, Dolle RE (2004) Curr Pharm Des 10:743-757. doi: 10.2174/1381612043453036
7. Holzgrabe U, Brandt W (2003) J Med Chem 46:1383-1389. doi: 10.1021/ jm0210360
8. Soukara S, Maier CA, Predoiu U, Ehret A, Jackisch R, Wunsch B (2001) J Med Chem 44:2814-2826. doi: 10.1021/jm0108395
9. Szmuszkovicz J, Von Voigtlander PF (1982) J Med Chem 25:1125-1126. doi: 10.1021/jm00352a005
10. Costello GF, James R, Shaw JS, Slater AM, Stutchbury NCJ (1991) J Med Chem 34:181-189. doi: 10.1021/jm00105a027
11. Chu GH, Gu M, Cassel JA, Belanger S, Graczyk TM, DeHaven RN, Conway-James N, Koblish M, Little PJ, DeHaven-Hudkins DL, Dolle RE (2007) Bioorg Med Chem Lett 17:1951-1955. doi: 10.1016/j.bmcl.2007.01.053
12. Chu GH, Gu M, Cassel JA, Belanger S, Stabley GJ, DeHaven RN, Conway-James N, Koblish M, Little PJ, DeHaven-Hudkins DL, Dolle RE (2006) Bioorg Med Chem Lett 16:645-648. doi: 10.1016/j.bmcl.2005.10.034
13. Le Bourdonnec B, Ajello CW, Seida PR, Susnow RG, Cassel JA, Belanger S, Stabley GJ, DeHaven RN, DeHaven-Hudkins DL, Dolle RE (2005) Bioorg Med Chem Lett 15:2647-2652. doi: 10.1016/j.bmcl.2005.03.020
14. Chu GH, Gu M, Cassel JA, Belanger S, Graczyk TM, DeHaven RN, Conway-James N, Koblish M, Little PJ, DeHaven-Hudkins DL, Dolle RE (2005) Bioorg Med Chem Lett 15:5114-5119. doi: 10.1016/j.bmcl.2005.08.094
15. Kumar V, Guo D, Cassel JA, Daubert JD, Dehaven RN, Dehaven-Hudkins DL, Gauntner EK, Gottshall SL, Greiner SL, Koblish M, Little PJ, Mansson E, Maycock AL (2005) Bioorg Med Chem Lett 15:1091-1095. doi: 10.1016/ j.bmcl.2004.12.018
16. Tuthill PA, Seida PR, Barker W, Cassel JA, Belanger S, DeHaven RN, Koblish M, Gottshall SL, Little PJ, DeHaven-Hudkins DL, Dolle RE (2004) Bioorg Med Chem Lett 14:5693-5697. doi: 10.1016/j.bmcl.2004.08.041
17. Kumar V, Marella MA, Cortes-Burgos L, Chang AC, Cassel JA, Daubert JD, DeHaven RN, DeHaven-Hudkins DL, Gottshall SL, Mansson E, Maycock AL (2000) Bioorg Med Chem Lett 10:2567-2570. doi: 10.1016/ S0960-894X(00)00519-9
18. Kurogi Y, Guner OF (2001) Curr Med Chem 8:1035-1055
19. Li H, Sutter J, Hoffman R, HypoGen (2000) An automated system for generating 3D predictive pharmacophore models. In: Guner O (ed) Pharmacophore perception, development and use in drug design. International University Line, La Jolla, CA
20. Dixon SL, Smondyrev AM, Knoll EH, Rao SN, Shaw DE, Friesner RA (2006) J Comput Aided Mol Des 20:647-671. doi: 10.1007/s10822-006-9087-6
21. Phase 2.0, Schrodinger, LLC: New York
22. Fischer R (1966) The principle of experimentation, illustrated by a PSYcho-Physical Experiment. Hafner, New York, Chap. II
23. CATALYST 4.10, Accelrys, http://www.accelrys.com: San Diego, CA
24. Funk OF, Kettmann V, Drimal J, Langer T (2004) J Med Chem 47:2750-2760. doi: 10.1021/jm031041j
25. Krovat EM, Langer T (2003) J Med Chem 46:716-726. doi: 10.1021/jm021032v
26. Tafi A, Costi R, Botta M, Santo R, Corelli F, Massa S, Ciacci A, Manetti F, Artico M (2002) J Med Chem 45:2720-2732. doi: 10.1021/jm011087h
27. Sybyl 7.0, Triops, St Louis, MO
28. Martin YC Distance comparisons (DISCO): A new strategy for examining 3D structure-activity relationships. American Chemical Society, Washington DC, 1995
29. Jones G, Willett P, Glen RC (1995) J Comput Aided Mol Des 9:532-549. doi: 10.1007/BF00124324
30. Richmond NJ, Abrams CA, Wolohan PR, Abrahamian E, Willett P, Clark RD (2006) J Comput Aided Mol Des 20:567-587. doi: 10.1007/s10822-006-9082-y
31. Ockham WO English philosopher and Franciscan Monk, 1285, see http://www.britannica.com/EBchecked/topic/424706/Ockhams-razor
32. de Costa BR, Bowen WD, Hellewell SB, George C, Rothman RB, Reid AA, Walker JM, Jacobson AE, Rice KC (1989) J Med Chem 32:1996-2002. doi: 10.1021/jm00128a050
33. Halfpenny PR, Horwell DC, Hughes J, Hunter JC, Rees DC (1990) J Med Chem 33:286-291. doi: 10.1021/jm00163a047
34. de Costa BR, Radesca L, Di Paolo L, Bowen WD (1992) J Med Chem 35:38-47. doi: 10.1021/jm00079a004
35. Thirstrup K, Hjorth SA, Schwartz TW (1996) In: Investigation of the binding pocket in the kappa opioid receptor by a combination of alanine substitutions and steric hindrance mutagenesis. 27th Meeting of the International Narcotics Research Conference, poster M30, 21-26 July 1996, Long Beach, CA
36. Kong H, Raynor K, Reisine T (1994) Reg Pept 54:155-156. doi: 10.1016/ 0167-0115(94)90437-5
37. Surratt CK, Johnson PS, Moriwaki A, Seidleck BK, Blaschak CJ, Wang JB, Uhl GR (1994) J Biol Chem 269:20548-20553
38. Uhl GR, Childers S, Pasternak G (1994) Trends Neurosci 17:89-93. doi: 10.1016/0166-2236(94)90110-4
39. Lavecchia A, Greco G, Novellino E, Vittorio F, Ronsisvalle G (2000) J Med Chem 43:2124-2134. doi: 10.1021/jm991161k
40. Singh N, Nolan TL, McCurdy CR (2008) J Mol Graph Model. doi: 10.1016/j. jmgm.2008.03.007
41. Singh N, Cheve G, Mccurdy CR, Ferguson DM (2006) J Comput Aided Mol Des 20:471-493. doi: 10.1007/s10822-006-9067-x
42. Flizola M, Villar HO, Loew GH (2001) J Comput Aided Mol Des 15:297-307. doi: 10.1023/A:1011187320095