Synthesis and characterizations of novel quinoline derivatives having mixed ligand activities at the κ and μ receptors: Potential therapeutic efficacy against morphine dependence

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 16, 2009, Pages 5782-5790

  Deb, Ishani ^a   Paira, Priyankar ^a   Hazra, Abhijit ^a   Banerjee, Sukdeb ^a   Dutta, Pradip Kumar ^a   Mondal, Nirup Bikash ^a   Das, Sumantra ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

Morphine; Opioid; Quinoline; Receptor; Withdrawal

Indexed keywords

2 (2 METHYLQUINOLIN 4 YLAMINO) N PHENYLACETAMIDE; DELTA OPIATE RECEPTOR; DYNORPHIN; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; IODINE 125; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; NALOXONE; QUINOLINE DERIVATIVE; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; IC 50; MORPHINE ADDICTION; MOUSE; NONHUMAN; PHARMACOPHORE; QUANTITATIVE ANALYSIS; RADIOASSAY; RECEPTOR AFFINITY; STEREOTYPY; WEIGHT REDUCTION; WITHDRAWAL SYNDROME;

ACETANILIDES; AMINOQUINOLINES; ANIMALS; CELL LINE, TUMOR; COMPETITIVE BIDDING; HUMANS; LIGANDS; MICE; MICE, INBRED BALB C; MORPHINE DEPENDENCE; NARCOTIC ANTAGONISTS; QUINOLINES; RATS; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU;

EID: 68249103079     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.07.024     Document Type: Article

References (47)

1. Dole V.P., Nyswander M.E., and Kreek M.J. Arch. Intern. Med. 118 (1966) 304
2. Gold M.S., Redmond D.E.Jr., and Kleber H.D. Lancet 1 (1978) 929
3. Contreras E., Tamayo L., and Amigo M. Eur. J. Pharmacol. 148 (1988) 463
4. Zharkovsky A., and Cebers G. Alcohol Alcohol. (1993) 483
5. Koyuncuoglu H., and Saydam B. Int. J. Clin. Pharmacol. Ther. Toxicol. 28 (1990) 147
6. Trujillo K.A., and Akil H. Science 251 (1991) 85
7. Rasmussen K., Fuller R.W., Stockton M.E., Perry K.W., Swinford R.M., and Ornstein P.L. Eur. J. Pharmacol. 197 (1991) 9
8. Koyuncuoglu H., Dizdar Y., Aricioglu F., and Sayin U. Pharmacol. Biochem. Behav. 43 (1992) 487
9. Rossetti Z.L., Hmaidan Y., and Gessa G.L. Eur. J. Pharmacol. 221 (1992) 227
10. Cappendijk S.L., de Vries R., and Dzoljic M.R. Eur Neuropsychopharmacol. 3 (1993) 111
11. Kolesnikov Y.A., Maccechini M.L., and Pasternak G.W. Life Sci. 55 (1994) 1393
12. Jasinski D.R., Pevnick J.S., and Griffith J.D. Arch. Gen. Psychiatry 35 (1978) 501
13. Grüsser S.M., Thalemann C.N., Platz W., Gölz J., and Partecke G.A. Biol. Psychol. 71 (2006) 231
14. Thalemann C.N., Platz W., Golz J., and Partecke G. Biol. Psychol. 71 (2006) 231
15. Kolesnikov Y.A., Pick C.G., Ciszewska G., and Pasternak G.W. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 5162
16. Bhargava H.N. Gen. Pharmacol. 26 (1995) 1049
17. Lutfy K., Hurlbut D.E., and Weber E. Brain Res. 616 (1993) 83
18. Capasso A., Piacente S., De Tommasi N., Rastrelli L., and Pizza C. Curr. Med. Chem. 13 (2006) 807
19. Broadbent J., Gaspard T.M., and Dworkin S.I. Pharmacol. Biochem. Behav. 51 (1995) 379
20. Glick S.D., Maisonneuve I.M., Raucci J., and Archer S. Brain Res. 681 (1995) 147
21. El Daly E., Chefer V., Sandill S., and Shippenberg T.S. J. Neurochem. 74 (2000) 1553
22. Vanderschuren L.J., Schoffelmeer A.N., Wardeh G., and De Vries T.J. Psychopharmacol. (Berl) 150 (2000) 35
23. Mello N.K., and Negus S.S. Ann. N.Y. Acad. Sci. 909 (2000) 104
24. Neumeyer J.L., Gu X.-H., van Vliet L.A., DeNunzio N.J., Rusovici D.E., Cohen D.J., Negus S., Mello N.K., and Bidlack J.M. Bioorg. Med. Chem. Lett. 11 (2001) 2735
25. Bowen C.A., Negus S.S., Zong R., et al. Neuropsychopharmacology 28 (2003) 1125
26. Filizola M., Villar H.O., and Loew G.H. Bioorg. Med. Chem. 9 (2001) 69
27. Kane B.E., Svensson B., and Ferguson D.M. The AAPS J. 8 (2006) E126
28. Schmidhammer H., Aeppli L., Atwell L., Fritsch F., Jacobson A.E., Nebuchla M., and Sperk G. J. Med. Chem. 27 (1984) 1575
29. Greiner E., Spetea M., Krassnig R., Schullner F., Aceto M., Harris L.S., Traynor J.R., Woods J.H., Coop A., and | Schmidhammer H. J. Med. Chem. 46 (2003) 1758
30. Peng X., Knapp B.I., Bidlack J.M., and Neumeyer J.L. J. Med. Chem. 49 (2006) 256
31. Neumeyer J.L., Zhang A., Xiong W., Gu X.-H., Hilbert J.E., Knapp B.I., Negus S., Mello N.K., and Bidlack J.M. J. Med. Chem. 46 (2003) 5162
32. Makman M.H., Lyman W.D., and Dvorkin B. Brain Res. 762 (1997) 247
33. Li L.Y., and Chang K.J. Mol. Pharmacol. 50 (1996) 599
34. Bohn L.M., Belcheva M.M., and Coscia C.J. J. Neurochem. 74 (2000) 564
35. Belcheva M.M., Tan Y., Heaton V.M., Clark A.L., and Coscia C.J. Mol. Pharmacol. 64 (2003) 1391
36. Belcheva M.M., Clark A.L., Haas P.D., Serna J.S., Hahn J.W., Kiss A., and Coscia C.J. J. Biol. Chem. 280 (2005) 27662
37. Ho I.K., Loh H.H., and Way E.L. J. Pharmacol. Exp. Ther. 185 (1973) 347
38. Mamiya T., Noda Y., Ren X., Nagai T., Takeshima H., Ukai M., and Nabeshima T.J. Neural. Trans. 108 (2001) 1349
39. Cui C.-L., Wu L.-Z., and Han J.-S. Neurosci. Lett. 295 (2000) 45
40. Sahu N.P., Pal C., Mondal N.B., Banerjee S., Raha M., Kundu A.P., Basu P.A., Ghosh M., Roy K., and Bandyopadhyay S. Bioorg. Med. Chem. 10 (2002) 1687
41. Lowry O.H., Rosebrough N.J., Farr A., and Randall R.J. J. Biol. Chem. 193 (1951) 265
42. Greenwood F.C., Hunter W.M., and Glover J.S. Biochem. J. 89 (1963) 114
43. Jin W.Q., Tai K.K., Chan T.K., and Wong T.M. J. Mol. Cell Cardiol. 27 (1995) 1507
44. Kest B., Jenab S., Brodsky M., Sadowski B., Belknap J.K., Mogil J.S., and Inturrisi C.E. Brain Res. 816 (1999) 381
45. Paul S., Gharami K., Das S., and Sakar P.K. J. Neurochem. 73 (1999) 1964
46. Paul S., Das S., Poddar R., and Sarkar P.K. Eur. J. Neurosci. 8 (1996) 2361
47. Belcheva M.M., Tan Y., Heaton V.M., Clark A.L., and Coscia C.J. Mol. Pharmacol. 64 (2003) 1391