14-O-Heterocyclic-substituted naltrexone derivatives as non-peptide mu opioid receptor selective antagonists: Design, synthesis, and biological studies

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 6, 2009, Pages 1825-1829

  Li, Guo ^a   Aschenbach, Lindsey C K ^a   He, Hengjun ^a   Selley, Dana E ^a   Zhang, Yan ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Antagonist; Mu opioid receptor; Naltrexone; Opioid

Indexed keywords

DELTA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR ANTAGONIST; NALTREXONE DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING;

BINDING, COMPETITIVE; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; KINETICS; LIGANDS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NALTREXONE; NARCOTIC ANTAGONISTS; NITROGEN; PEPTIDES; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, OPIOID, MU;

EID: 61349201712     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.12.093     Document Type: Article

References (52)

1. Goldstein A., and Naidu A. Mol. Pharmacol. 36 (1989) 265
2. Dhawan B.N., Cesselin F., Raghubir R., Reisin T., Bradley P.B., Portoghese P.S., and Hamon M. Pharmacol. Rev. 48 (1996) 567
3. Minami M., and Satoh M. Neurosci. Res. 23 (1995) 121
4. Zimmerman D.M., and Leander J.D. J. Med. Chem. 33 (1990) 895
5. Schmidhammer H. Prog. Med. Chem. 35 (1998) 83
6. Eguchi M. Med. Res. Rev. 242 (2004) 182
7. Skoubis P.D., Matthes H.W., Walwyn W.M., Kieffer B.L., and Maidment N.T. Neuroscience 106 (2001) 757
8. Matthes H.W., Maldonado R., Simonin F., Valverde O., Slowe S., Kitchen I., Befort K., Dierich A., Le Meur M., Dollé P., Tzavara E., Hanoune J., Roques B.P., and Kieffer B.L. Nature 383 (1996) 819
9. Gold M.S., Dackis C.A., Pottash A.L., Sternbach H.H., Annitto W.J., Martin D., and Dackis M.P. Med. Res. Rev. 23 (1982) 211
10. Gonzalez J.P., and Brogden R.N. Drugs 35 (1988) 192
11. Goodman A.J., Le Bourdonnec B., and Dolle R.E. ChemMedChem 2 (2007) 1552
12. Schwyzer R. Ann. N.Y. Acad. Sci. 297 (1977) 3
13. Portoghese P.S., Lipkowski A.W., and Takemori A.E. Life Sci. 40 (1987) 1287
14. Jones R.M., Hjorth S.A., Schwartz T.W., and Portoghese P.S. J. Med. Chem 41 (1998) 4911
15. Portoghese P.S., Sultana M., Nagase H., and Takemori A.E. J. Med. Chem. 31 (1988) 281
16. Schmidhammer H., Burkard W.P., Eggstin-Aeppli L., and Smith C.F.C. J. Med. Chem. 32 (1989) 418
17. Schmidhammer H., Smith C.F., Erlach D., Koch M., Krassnig R., Schwetz W., and Wechner C. J. Med. Chem. 33 (1990) 1200
18. Schmidhammer H., Smith C.F., Erlach D., Koch M., Krassnig R., Schwetz W., and Wechner C. Prog. Clin. Biol. Res. 328 (1990) 37
19. Lewis J.W., Smith C.F.C., McCarthy P.S., Kobylecki R.J., Myers M., Haynes A.S., Lewis C.J., and Waltham K. NIDA Res. Monogr. 90 (1988) 136
20. Portoghese P.S., and Takemori A.E. NIDA Res. Monogr. 69 (1986) 157
21. Burke T.F., Woods J.H., Lewis J.W., and Medzihradsky F. J. Pharmacol. Exp. Ther. 2712 (1994) 715
22. Xue J.-C., Chen C., Zhu J., Kunapuli S.P., De Riel J.K., Yu L., and Liu-Chen L.-Y. J. Biol. Chem 27022 (1995) 12977
23. Zhu J., Xue J.-C., Law P.-Y., Claude P.A., Luo L.-Y., Yin J., Chen C., and Liu-Chen L.-Y. FEBS Lett. 384 (1996) 198
24. Bonner G., Meng F., and Akil H. Eur. J. Pharmcol. 403 (2000) 37
25. Xu H., Lu Y.F., Partilla J.S., Zheng Q.X., Wang J.B., Brine G.A., Carroll F.I., Rice K.C., Chen K.X., Chi Z.Q., and Rothman R.B. Synapse (New York) 32 (1999) 23
26. Okada T., Le Trong I., Fox B.A., Behnke C.A., Stenkamp R.E., and Palczewski K. J. Struct. Biol. 130 (2000) 73
27. Teller D.C., Okada T., Behnke C.A., Palczewski K., and Stenkamp R.E. Biochemistry. 40 (2001) 7761
28. Salom D., Le Trong I., Pohl E., Ballesteros J.A., Stenkamp R.E., Palczewski K., and Lodowski D.T. J. Struct. Biol. 156 (2006) 497
29. Salom D., Lodowski D.T., Stenkamp R.E., Le Trong I., Golczak M., Jastrzebska B., Harris T., Ballesteros J.A., and Palczewski K. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 16123
30. Park J.H., Scheerer P., Hofmann K.P., Choe H.W., and Ernst O.P. Nature 454 (2008) 183
31. Rasmussen S.G., Choi H.J., Rosenbaum D.M., Kobilka T.S., Thian F.S., Edwards P.C., Burghammer M., Ratnala V.R., Sanishvili R., Fischetti R.F., Schertler G.F., Weis W.I., and Kobilka B.K. Nature 450 (2007) 383
32. Rosenbaum D.M., Cherezov V., Hanson M.A., Rasmussen S.G., Thian F.S., Kobilka T.S., Choi H.-J., Yao X.-J., Weis W.I., Stevens R.C., and Kobilka B.K. Science 318 (2007) 1266
33. Cherezov V., Rosenbaum D.M., Hanson M.A., Rasmussen S.G., Thian F.S., Kobilka T.S., Choi H.-J., Kuhn P., Weis W.I., Kobilka B.K., and Stevens R.C. Science 318 (2007) 1258
34. Hanson M.A., Cherezov V., Griffith M.T., Roth C.B., Jaakola V.P., Chien E.Y., Velasquez J., Kuhn P., and Stevens R.C. Structure 16 (2008) 897
35. Warne, T.; Serrano-Vega, M. J.; Baker, J. G.; Moukhametzianov, R.; Edwards, P. C.; Henderson, R.; Leslie, A. G.; Tate, C. G.; Schertler, G. F. Nature, 2008 June 25 (Epub ahead of print).
36. Patny A., Desai P.V., and Avery M.A. Curr. Med. Chem. 13 (2006) 1667
37. Ballesteros J.A., Shi L., and Javitch J.A. Mol. Pharmacol. 60 (2001) 1
38. Becker O.M., Shacham S., Marantz Y., and Noiman S. Curr. Opin. Drug. Discov. Dev. 63 (2003) 353
39. Moro S., Spalluto G., and Jacobson K.A. Trends Pharmacol. Sci. 261 (2005) 44
40. Nowak M., Kolaczkowski M., Pawlowski M., and Bojarski A.J. J. Med. Chem. 491 (2006) 205
41. McLean T.H., Chambers J.J., Parrish J.C., Braden M.R., Marona-Lewicka D., Kurrasch-Orbaugh D., and Nichols D.E. J. Med. Chem. 4914 (2006) 4269
42. Hobrath J.V., and Wang S. J. Med. Chem 4915 (2006) 4470
43. Singh S., Malik B.K., and Sharma D.K. Chem. Biol. Drug. Des. 693 (2007) 191
44. Patny A., Desai P.V., and Avery M.A. Proteins. 654 (2006) 824
45. Lu Z.L., Saldanha J.W., and Hulme E.C. Trends Pharmacol. Sci. 233 (2002) 140
46. Zhang Y., Sham Y.Y., Rajamani R., Gao J.L., and Portoghese P.S. ChemBioChem 6 (2005) 859
47. Lattanzi R., Spetea M., Schullner F., Rief S.B., Krassnig R., Negri L., and Schmidhammer H. J. Med. Chem. 48 (2005) 3372
48. Spetea M., Schüllne F., Moisa R.C., Berzetei-Gurske I.P., Schraml B., Dorfler C., Aceto M.D., Harris L.S., Coop A., and Schmidhammer H. J. Med. Chem. 47 (2004) 3242
49. Greiner E., Spetea M., Krassnig R., Schullne F., Aceto M., Harris L.S., Traynor J.R., Woods J.H., Coop A., and Schmidhammer H. J. Med. Chem. 46 (2003) 1758
50. Rennison D., Moynihan H., Traynor J.R., Lewis J.W., and Husbands S.M. J. Med. Chem 49 (2006) 6104
51. Nieland N.P., Moynihan H.A., Carrington S., Broadbear J., Woods J.H., Traynor J.R., Husbands S.M., and Lewis J.W. J. Med. Chem. 4917 (2006) 5333
52. Grundt P., Jales A.R., Traynor J.R., Lewis J.W., and Husbands S.M. J. Med. Chem. 46 (2003) 1563