Structure-based design, synthesis, and biological evaluation of novel inhibitors of human cyclophilin A

Journal of Medicinal Chemistry

Volumn 49, Issue 3, 2006, Pages 900-910

  Guichou, Jean François ^a   Viaud, Julien ^a   Mettling, Clȩment ^b   Subra, Guy ^a   Lin, Yea Lih ^b   Chavanieu, Alain ^a  

^a CENTRE DE BIOCHIMIE STRUCTURALE   (France)

^b INSTITUTE OF HUMAN GENETICS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 BENZYLOXYPYRIDIN 2 YL) 3 (3 CHLOROPHENYL)UREA; 1 (3 BENZYLOXYPYRIDIN 2 YL) 3 (3 TRIFLUOROMETHYLPHENYL)UREA; ANTIRETROVIRUS AGENT; CIS TRANS ISOMERASE; CYCLOPHILIN A; CYCLOSPORIN A; ENZYME INHIBITOR; GAG PROTEIN; UNCLASSIFIED DRUG; ZIDOVUDINE;

ARTICLE; CELL IMMORTALIZATION; COMPUTER PROGRAM; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; HYDROGEN BOND; IN VITRO STUDY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PERIPHERAL BLOOD MONONUCLEAR CELL; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; VIRION; VIRUS INFECTIVITY; VIRUS REPLICATION; X RAY CRYSTALLOGRAPHY;

ANTI-HIV AGENTS; BINDING SITES; CELLS, CULTURED; CYCLOPHILIN A; DRUG DESIGN; HIV-1; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENYLUREA COMPOUNDS; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRION;

EID: 32344435310     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050716a     Document Type: Article

References (38)

1. Harding, M. W.; Handschumacher, R. E.; Speicher, D. W. Isolation and amino acid sequence of cyclophilin. J. Biol. Chem. 1986, 261, 8547-8555.
2. Hunter, T. Prolyl isomerases and nuclear function. Cell 1998, 92, 141-143.
3. Galat, A. Peptidylproline cis-trans-isomerases: Immunophilins. Eur. J. Biochem. 1993, 216, 689-707.
4. Schreiber, S. L. Chemistry and biology of the immunophilins and their immunosuppressive ligands. Science 1991, 251, 283-287.
5. Gothel, S. F.; Marahiel, M. A. Peptidyl-prolyl cis-trans isomerases, a superfamily of ubiquitous folding catalysts. Cell. Mol. Life Sci. 1999, 55, 423-436.
6. Marks, A. R. Cellular functions of immunophilins. Physiol. Rev. 1996, 76, 631-649.
7. Pratt, W. B.; Toft, D. O. Steroid receptor interactions with heat shock protein and immunophilin chaperones. Endocr. Rev. 1997, 18, 306-360.
8. Chen, Y. G.; Liu, F.; Massague, J. Mechanism of TGFbeta receptor inhibition by FKBP12. EMBO J. 1997, 16, 3866-3876.
9. Galat, A. Peptidylprolyl cis/trans isomerases (immunophilins): Biological diversity-targets-functions. Curr. Top. Med. Chem. 2003, 3, 1315-1347.
10. Fischer, G.; Wittmann-Liebold, B.; Lang, K.; Kiefhaber, T.; Schmid, F. X. Cyclophilin and peptidyl-prolyl cis-trans isomerase are probably identical proteins. Nature 1989, 337, 476-478.
11. Liu, J.; Farmer, J. D., Jr.; Lane, W. S.; Friedman, J.; Weissman, I.; et al. Calcineurin is a common target of cyclophilin-cyclosporin A and FKBP-FK506 complexes. Cell 1991, 66, 807-815.
12. Luban, J. Absconding with the chaperone: Essential cyclophilin-Gag interaction in HIV-1 virions. Cell 1996, 87, 1157-1159.
13. Mlynar, E.; Bevec, D.; Billich, A.; Rosenwirth, B.; Steinkasserer, A. The nonimmunosuppressive cyclosporin A analogue SDZ NIM 811 inhibits cyclophilin A incorporation into virions and virus replication in human immunodeficiency virus type 1-infected primary and growth-arrested T cells. J. Gen. Virol. 1997, 78, 825-835.
14. Hansson, M. J.; Mattiasson, G.; Mansson, R.; Karlsson, J.; Keep, M. F.; et al. The nonimmunosuppressive cyclosporin analogues NIM811 and UNIL025 display nanomolar potencies on permeability transition in brain-derived mitochondria. J. Bioenerg. Biomembr. 2004, 36, 407-413.
15. Sosa, I.; Reyes, O.; Kuffler, D. P. Immunosuppressants: Neuroprotection and promoting neurological recovery following peripheral nerve and spinal cord lesions. Exp. Neurol. 2005, 31, 31.
16. Wu, Y. Q.; Belyakov, S.; Choi, C.; Limburg, D.; Thomas, I. B.; et al. Synthesis and biological evaluation of nonpeptidic cyclophilin ligands. J. Med. Chem. 2003, 46, 1112-1115.
17. Kallen, J.; Spitzfaden, C.; Zurini, M. G.; Wider, G.; Widmer, H.; et al. Structure of human cyclophilin and its binding site for cyclosporin A determined by X-ray crystallography and NMR spectroscopy. Nature 1991, 353, 276-279.
18. Mikol, V.; Kallen, J.; Pflugl, G.; Walkinshaw, M. D. X-ray structure of a monomeric cyclophilin A-cyclosporin A crystal complex at 2.1 A resolution. J. Mol. Biol. 1993, 234, 1119-1130.
19. Zhao, Y.; Ke, H. Mechanistic implication of crystal structures of the cyclophilin-dipeptide complexes. Biochemistry 1996, 35, 7362-7368.
20. Zydowsky, L. D.; Etzkorn, F. A.; Chang, H. Y.; Ferguson, S. B.; Stolz, L. A.; et al. Active site mutants of human cyclophilin A separate peptidyl-prolyl isomerase activity from cyclosporin A binding and calcineurin inhibition. Protein Sci. 1992, 1, 1092-1099.
21. Mikol, V.; Papageorgiou, C.; Borer, X. The role of water molecules in the structure-based design of (5-hydroxynorvaline)-2-cyclosporin: Synthesis, biological activity, and crystallographic analysis with cyclophilin A. J Med. Chem. 1995, 38, 3361-3367.
22. Rarey, M.; Wefing, S.; Lengauer, T. Placement of medium-sized molecular fragments into active sites of proteins. J. Comput.-Aided Mol. Des. 1996, 10, 41-54.
23. Wang, R.; Lai, L.; Wang, S. Further development and validation of empirical scoring functions for structure-based binding affinity prediction. J. Comput. Aided Mol. Des. 2002, 16, 11-26.
24. Jain, A. N. Surflex: Fully automatic flexible molecular docking using a molecular similarity-based search engine. J. Med. Chem. 46, 499-511, 2003.
25. Leban, J.; Pegoraro, S.; Dormeyer, M.; Lanzer, M.; Aschenbrenner, A.; Kramer, B. Sulfonyl-phenyl-ureido benzamidines: A novel structural class of potent antimalarial agents. Bioorg. Med. Chem. Lett. 2004, 14, 1979-1982.
26. 11C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents. J. Med. Chem. 2003, 46, 2740-2754.
27. Laudien, R.; Mitzner, R. Phenylureas. Part 1. Mechanism of the basic hydrolysis of phenylureas. J. Chem. Soc., Perkin Trans. 2 2001, 11, 2226-2229.
28. Kabalka, G. W.; Deshpande, S. M.; Wadgaonkar, P. P.; Chatla, N. The transformation of nitriles into amides using sodium percarbonate. Synth. Commun. 1990, 20 (10), 1445-1451.
29. Kofron, J. L.; Kuzmic, P.; Kishore, V.; Colon-Bonilla, E.; Rich, D. H. Determination of kinetic constants for peptidyl prolyl cis-trans isomerases by an improved spectrophotometric assay. Biochemistry 1991, 30, 6127-6134.
30. Saphire, A. C.; Bobardt, M. D.; Gallay, P. A. Cyclophilin a plays distinct roles in human immunodeficiency virus type 1 entry and postentry events, as revealed by spinoculation. J. Virol. 2002, 76, 4671-4677.
31. Thali, M.; Bukovsky, A.; Kondo, E.; Rosenwirth, B.; Walsh, C. T.; et al. Functional association of cyclophilin A with HIV-1 virions. Nature 1994, 372, 363-365.
32. Braaten, D.; Franke, E. K.; Luban, J. Cyclophilin A is required for the replication of group M human immunodeficiency virus type 1 (HIV-1) and simian immunodeficiency virus SIV(CPZ)GAB but not group O HIV-1 or other primate immunodeficiency viruses. J. Virol. 1996, 70, 4220-4227.
33. Saphire, A. C.; Bobardt, M. D.; Gallay, P. A. trans-Complementation rescue of cyclophilin A-deficient viruses reveals that the requirement for cyclophilin A in human immunodeficiency virus type 1 replication is independent of its isomerase activity. J. Virol. 2002, 76, 2255-2262.
34. Sokolskaja, E.; Sayah, D. M.; Luban, J. Target cell cyclophilin A modulates human immunodeficiency virus type 1 infectivity. J. Virol. 2004, 78, 12800-12808.
35. Clipstone, N. A.; Crabtree, G. R. Identification of calcineurin as a key signaling enzyme in T-lymphocyte activation. Nature 1992, 357, 695-697.
36. Towers, G. J.; Hatziioannou, T.; Cowan, S.; Goff, S. P.; Luban, J.; et al. Cyclophilin A modulates the sensitivity of HIV-1 to host restriction factors. Nat. Med. 2003, 9, 1138-1143.
37. Douguet, D.; Munier-Lehmann, H.; Labesse, G.; Pochet, S. LEA3D: A computer-aided ligand design for structure-based drug design. J. Med. Chem. 2005, 48, 2457-68.
38. Tuffery, P. XmMol: An x11 and motif program for macromolecular visualization and modeling. J. Mol. Graph. 1995, 13, 67-72, 62.