Exploring distal regions of the A3 adenosine receptor binding site: Sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 9, 2004, Pages 2021-2034

  Tchilibon, Susanna ^a   Kim, Soo Kyung ^a   Gao, Zhan Guo ^a   Harris, Brian A ^a   Blaustein, Joshua B ^a   Gross, Ariel S ^a   Duong, Heng T ^a   Melman, Neli ^a   Jacobson, Kenneth A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

Agonist; GPCR; Molecular modeling; Nucleoside; Purine receptor

Indexed keywords

2 (3 CHLOROPHENYL)CYCLOPROPYLADENOSINE; ADENOSINE A3 RECEPTOR; ADENOSINE A3 RECEPTOR AGONIST; ADENOSINE A3 RECEPTOR ANTAGONIST; ADENOSINE DERIVATIVE; N 6 (2 PHENYL 1 CYCLOPROPYL)ADENOSINE; N 6 (2,2 DIPHENYLCYCLOPROPYL)ADENOSINE; N 6 (CYCLOPROPYL)ADENOSINE; N 6 [2 (2 CHLOROPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (2 CYANOPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (2 METHYLPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 ACETAMIDOPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 AMINOPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 FLUOROPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 METHOXYPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 METHYLPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 NITROPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 THIENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3 TRIFLUOROMETHYLOXYPHENYL)CYCLOPROYL]ADENOSINE; N 6 [2 (3 TRIFLUOROMETHYLPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (3,5 DIFLUOROPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (4 CHLOROPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 (4 METHYLPHENYL)CYCLOPROPYL]ADENOSINE; N 6 [2 [3,5 BIS(TRIFLUOROMETHYL)PHENYL]CYCLOPROPYL]ADENOSINE; N 6 [2,2 BIS(PHENYLETHYL)CYCLOPROPYL]ADENOSINE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; DIASTEREOISOMER; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HYDROPHOBICITY; MOLECULAR MODEL; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOCHEMISTRY;

BINDING SITES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LIGANDS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, ADENOSINE A3; SPECTRUM ANALYSIS;

EID: 1842731069     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.02.037     Document Type: Article

References (40)

1. Fredholm B.B., IJzerman A.P., Jacobson K.A., Klotz K.-N., Linden J. Pharm. Rev. 53:2001;527.
2. von Lubitz D.K.J.E., Lin R.C.-S., Popik P., Carter M.F., Jacobson K.A. Eur. J. Pharmacol. 263:1994;59.
3. Ohta A., Sitkovsky M. Nature. 414:2001;916.
4. Stambaugh K., Jacobson K.A., Jiang J.-l., Liang B.T. Am. J. Physiol. 273:1997;H501-H505.
5. Fishman P., Madi L., Bar-Yehuda S., Barer F., Del Valle L., Khalili K. Oncogene. 21:2002;4060.
6. Gao Z.-G., Kim S.-K., Biadatti T., Chen W., Lee K., Barak D., Kim S.G., Johnson C.R., Jacobson K.A. J. Med. Chem. 45:2002;4471.
7. Gao Z.-G., Blaustein J., Gross A.S., Melman N., Jacobson K.A. Biochem. Pharmacol. 65:2003;1675.
8. Kim S.-K., Gao Z.-G., Van Rompaey P., Gross A.S., Chen A., Van Calenbergh S., Jacobson K.A. J. Med. Chem. 46:2003;4847.
9. Gao Z.-G., Jeong L.S., Moon H.R., Kim H.O., Choi W.J., Shin D.H., Elhalem E., Comin M.J., Melman N., Mamedova L., Gross A.S., Rodriguez J.B., Jacobson K.A. Biochem. Pharmacol. 67:2004;892-901.
10. Zablocki, J.A.; Wu, L.; Shryock, J.; Belardinelli, L. Curr. Top. Med. Chem. 2003, in press
11. Williams M., Risley E.A. Proc. Nat. Acad. Sci. USA. 77:1980;6892.
12. Vallgårda J., Appelberg U., Arvidsson L.-E., Hjorth S., Svensson B.E., Hacksell U. J. Med. Chem. 39:1996;1485.
13. Trivedi B.K., Blankley C.J., Bristol J.A., Hamilton H.W., Patt W.C., Kramer W.J., Johnson S.A., Bruns R.F., Cohen D.M., Ryan M.J. J. Med. Chem. 34:1991;1043.
14. Daly J.W., Padgett W., Thompson R.D., Kusachi S., Bungi W.J., Olsson R.A. Biochem. Pharmacol. 35:1986;2467.
15. Knutsen L.J., Lau J., Petersen H., Thomsen C., Weis J.U., Shalmi M., Judge M.E., Hansen A.J., Sheardown M.J. J. Med. Chem. 42:1999;3463.
16. Gallo-Rodriguez C., Ji X.-D., Melman N., Siegman B.D., Sanders L.H., Orlina J., Fischer B., Pu Q.-L., Olah M.E., van Galen P.J.M., Stiles G.L., Jacobson K.A. J. Med. Chem. 37:1994;636.
17. Palczewski K., Kumasaka T., Hori T., Behnke C.A., Motoshima H., Fox B.A., Le Trong I., Teller D.C., Okada T., Stenkamp T.E., Yamamoto M., Miyano M. Science. 289:2000;739.
18. Fossetta J., Jackson J., Deno G., Fan X., Du X.K., Bober L., Soude-Bermejo A., de Bouteiller O., Caux C., Lunn C., Lundell D., Palmer R.K. Mol. Pharmacol. 63:2003;342.
19. Cheng Y.-C., Prusoff W.H. Biochem. Pharmacol. 22:1973;3099.
20. Sybyl Molecular Modeling System, version 6.9; Tripos Inc., St. Louis, Missouri 63144, USA
21. Blatchford J.K., Orchin M. J. Org. Chem. 29:1964;839.
22. Parsons M., Young L., Lee J.-E., Jacobson K.A., Liang B.T. FASEB J. 14:2000;1423.
23. van Galen P.J.M., van Bergen A.H., Gallo-Rodriguez C., Melman N., Olah M.E., IJzerman A.P., Stiles G.L., Jacobson K.A. Mol. Pharmacol. 45:1994;1101.
24. Jacobson K.A., Kim H.S., Ravi G., Kim S.K., Lee K., Chen A., Chen W., Kim S.G., Barak D., Liang B.T., Gao Z.-G. Drug Devel. Res. 58:2003;330.
25. Klotz K.N., Hessling J., Hegler J., Owman C., Kull B., Fredholm B.B., Lohse M.J. Naunyn Schmiedeberg's Arch. Pharmacol. 357:1998;1.
26. Nordstedt C., Fredholm B.B. Anal. Biochem. 189:1990;231.
27. Halgren T.A. J. Comput. Chem. 20:1999;730.
28. Stewart J.J.P. J. Comput. Aided Mol. Des. 4:1990;1.
29. Cornell W.D., Cieplak P., Bayly C.I., Gould I.R., Merz K.M. Jr., Ferguson D.M., Spellmeyer D.C., Fox T., Caldwell J.W., Kollman P.A. J. Am. Chem. Soc. 117:1995;5179.
30. Gao Z.-G., Kim S.-K., Gross A.S., Chen A., Blaustein J.B., Jacobson K.A. Mol. Pharmacol. 63:2003;1021.
31. Jacobson K.A., Gao Z.-G., Chen A., Barak D., Kim S.-A., Lee K., Link A., Van Rompaey P.V., Van Calenbergh S., Liang B.T. J. Med. Chem. 44:2001;4125.
32. 1 angles was within 3 kcal/mol.
33. A series of various energetically favorable bound conformations for model 1 and similar bound conformations for model 2 were aligned in 3D-Cartesian space without RMS fitting of all molecules, because the alignment result obtained using RMS fitting of the ribose ring was not in close agreement with the 3D-QSAR.
34. Cramer R.D. III, Patterson D.E., Bunce J.D. J. Am. Chem. Soc. 110:1988;5959.
35. Cramer R.D. III, DePriest S.A., Patterson D.E., Hecht P. Kubinyi H. 3D QSAR in Drug Design: Theory, Methods and Applications: The Developing Practice of Comparative Molecular Field Analysis. 1993;443 ESCOM, Leiden, The Netherlands.
36. Klebe G., Abraham U., Mietzner T. J. Med. Chem. 37:1994;4130.
37. Klebe G., Abraham U. J. Comput. Aided Mol. Des. 13:1999;1.
38. Viswanadhan V.N., Ghose A.K., Revankar G.R., Robins R.K. J. Chem. Inf. Comput. Sci. 29:1989;163.
39. Wold S., Albano C., Dunn W.J. III, Edlund U., Esbensen K., Geladi P., Hellberg S., Johansson E., Lindberg W., Sjostrom M. Wold Kowalski B. Chemometrics: Mathematics and Statistics in Chemistry: Multivatiate Data Analysis in Chemistry. 1984;17 Reidel, Dordrecht, Netherlands.
40. Bush B.L., Nachbar R.B. Jr. J. Comput. Aided Mol. Des. 7:1993;587.