Design and synthesis of a new fluorescent probe for cytochrome P450 3A4 (CYP 3A4)

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 21, 2003, Pages 3643-3645

  Chougnet, Antoinette ^a   Stoessel, Catherine ^a   Woggon, Wolf D ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 3A4; FLUORESCENT DYE; PROTEIN INHIBITOR; TESTOSTERONE;

ARTICLE; BINDING AFFINITY; CATALYSIS; DRUG BINDING; DRUG BINDING SITE; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SYNTHESIS; DRUG TOXICITY; ENZYME ACTIVE SITE; ENZYME BINDING; HYDROXYLATION;

EID: 0141545137     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.08.027     Document Type: Article

References (19)

1. Guengerich F.P. Cytochrome P450: Structure, Mechanism, and Biochemistry. Ortiz de Montellano P.R. Biochemistry. 1995;473-525 Plenum Press, New York.
2. (a) Lilja, J.; Kivisto, K.; Neuvonen, P. Clin. Pharmacol. Ther. 2000,68,384.
3. (b) Lin J.H., Lu A.Y.H. Pharmacol. Rev. 49:1997;403.
4. (c) Guengerich F.P. Ann. Rev. Pharmacol. Tox. 1999;1.
5. Wang R.W., Newton D.J., Liu N., Atkins W.M., lu A.Y.H. Drug Metab. Dispos. 28:2000;360.
6. (a) Hosea N.A., Miller G.P., Guengerich F.P. Biochemistry. 39:2000;5929.
7. (b) Dabrowski M.J., Schrag M.L., Wienkers L.C., Atkins W.M. J. Am. Chem. Soc. 124:2002;11866.
8. Kenworthy K.E., Clarke S.E., Andrews J., Houston J.B. Drug Metab. Dispos. 29:2001;1644.
9. Sun M., Song P.-S. Biochemistry. 12:1973;4663.
10. Collins D.J., Jackson W.R., Timms R.N. Aust. J. Chem. 30:1977;2167.
11. 1H NMR, most significant is the shift difference of H at C-4: 5.80 ppm (β) and 5.51 ppm (α): Collins D.J., Jackson W.R., Timms R.N. Tetrahedron Lett. 6:1976;495.
12. Jones C.D., Mason N.R. Steroids. 23:1975;323.
13. Carell T., Schmid H., Reinhard M. J. Org. Chem. 63:1998;8741.
14. 50 values that are within experimental error indistuingishable from 100% 6β-4.
15. Wandel C., Kim R.B., Guengerich F.P., Wood A.J.J. Drug Metab. Dispos. 28:2000;895.
16. Jefcoate C.R. Methods Enzymol. 52:1978;258.
17. Stresser D.M., Blanchard A.P., Turner S.D., Erve J.C.L., Dandeneau A.A., Miller V.P., Crespi C.L. Drug Metab. Dispos. 28:2000;1440.
18. 50=240 μM for testosterone 1 as a substrate.
19. Stoessel, C.; Chougnet, A.; Woggon, W.-D.; In preparation.