Steroidogenic cytochrome P450 (CYP) enzymes as drug targets: Combining substructures of known CYP inhibitors leads to compounds with different inhibitory profile

Comptes Rendus Chimie

Volumn 12, Issue 10-11, 2009, Pages 1117-1126

  Hille, Ulrike E ^a   Hu, Qingzhong ^a   Pinto Bazurco Mendieta, Mariano A E ^a   Bartels, Marc ^a   Vock, Carsten A ^a   Lauterbach, Thomas ^b   Hartmann, Rolf W ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b Schwarz Pharma AG   (Germany)

Author keywords

Approche de combinaison substructures; Breast cancer; Cancer de la prostate; Cancer du sein; Congestive heart failure; Drug targets; Enzymes st ro dog niques CYP; Inhibiteurs; Inhibitors; Insuffisance cardiaque congestive; M dicaments cibles; Prostate cancer; Steroidogenic CYP enzymes; Substructure combination approach

Indexed keywords

EID: 71849117108     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2009.03.007     Document Type: Article

References (41)

1. Brodie A.M., Schwarzel W.C., Shaikh A.A., and Brodie H.J. Endocrinology 100 (1977) 1684
2. Huggins C., and Hodges C.V. Cancer Res. 1 (1941) 293
3. Huggins C., Stevens R.E., and Hodges C.V. Arch. Surg. 43 (1941) 209
4. Labrie F., Belanger A., Luu-The V., Labrie C., Simard J., Cusan L., Gomez J., and Candas B. Endocr. Rev. 26 (2005) 361
5. Reissmann T., Schally A.V., Bouchard P., Riethmiiller H., and Engel J. Hum. Reprod. Update 6 (2000) 322
6. Harris K.A., Weinberg V., Bok R.A., Kakefuda M., and Small E.J. J. Urol. 168 (2002) 542
7. Eklund J., Kozloff M., Vlamakis J., Starr A., Mariott M., Gallot L., Jovanovic B., Schilder L., Robin E., Pins M., and Bergan R.C. Cancer 106 (2006) 2459
8. Small E.J., Halabi S., Ratain M.J., Rosner G., Stadler W., Palchak D., Marshall E., Rago R., Hars V., Wilding G., Petrylak D., and Vogelzang N.J. J. Clin. Oncol. 20 (2002) 3369
9. De Coster R., Wouters W., Bruynseels J., and Steroid J. Biochem. Mol. Biol. 56 (1996) 133
10. Madan R.A., and Arlen P.M. Drugs 9 (2006) 49
11. Pitt B., Remme W., Zannad F., Neaton J., Martinez F., Roniker B., Bittman R., Hurley S., Kleiman J., and Gatlin M. N. Engl. J. Med. 348 (2003) 1309
12. Pitt B., Zannad F., Remme W.J., Cody R., Castaigne A., Perez A., Palensky J., and Wittes J. N. Engl. J. Med. 341 (1999) 709
13. Demers L.M., Melby J.C., Wilson T.E., Lipton A., Harvey H.A., and Santen R.J. J. Clin. Endocrinol. Metab. 70 (1990) 1162
14. Bureik M., Hubel K., Dragan C.A., Scher J., Becker H., Lenz N., and Bernhardt R. Mol. Cell. Endocrinol. 217 (2004) 249
15. Heim R., Lucas S., Grombein C.M., Ries C., Schewe K.E., Negri M., Müller-Vieira U., Birk B., and Hartmann R.W. J. Med. Chem. 51 (2008) 5064
16. Ulmschneider S., Müller-Vieira U., Mitrenga M., Hartmann R.W., Oberwinkler-Marchais S., Klein C.D., Bureik M., Bernhardt R., Antes I., and Lengauer T. J. Med. Chem. 48 (2005) 1796
17. Ulmschneider S., Müller-Vieira U., Klein C.D., Antes I., Lengauer T., and Hartmann R.W. J. Med. Chem. 48 (2005) 1563
18. Q.Y. Hu, G.M. Ksander Novartis AG, Switzerland, WO 2008076860; 2008.
19. Bayer H., Batzl C., Hartmann R.W., and Mannschreck A. J. Med. Chem. 34 (1991) 2685
20. Bayer H., and Hartmann R.W. Arch. Pharm. (Weinheim) 324 (1991) 815
21. Hartmann R.W., Bayer H., and Grün G. J. Med. Chem. 37 (1994) 1275
22. Hartmann R.W., Bayer H., Grün G., Sergejew T., Bartz U., and Mitrenga M. J. Med. Chem. 38 (1995) 2103
23. Wachall B.G., Hector M., Zhuang Y., and Hartmann R.W. Bioorg. Med. Chem. 7 (1999) 1913
24. Zhuang Y., Wachall B.G., and Hartmann R.W. Bioorg. Med. Chem. 8 (2000) 1245
25. Jagusch C., Negri M., Hille U.E., Hu Q., Bartels M., Jahn-Hoffmann K., Pinto-Bazurco Mendieta M.A., Rodenwaldt B., Müller-Vieira U., Schmidt D., Lauterbach T., Recanatini M., Cavalli A., and Hartmann R.W. Bioorg. Med. Chem. 16 (2008) 1992
26. U.E. Hille, Q. Hu, M. Bartels, U. Müller-Vieira, D. Schmidt, T. Lauterbach, R.W. Hartmann, Europ. J. Med. Chem., in press, doi:10.1016/j.ejmech.2009.01.002.
27. Voets M., Antes I., Scherer C., Müller-Vieira U., Biemel K., Barassin C., Marchais-Oberwinkler S., and Hartmann R.W. J. Med. Chem. 48 (2005) 6632
28. Weinstock J., Gaitanopoulos D.E., Oh H.J., Pfeiffer F.R., Karash C.B., Venslavsky J.W., Sarau H.M., Flaim K.E., Hieble J.P., and Kaiser C. J. Med. Chem. 29 (1986) 1615
29. Bravo F., McDonald F.E., Neiwert W.A., Do B., and Hardcastle K.I. Org. Lett. 5 (2003) 2123
30. Sergejew T., and Hartmann R.W. J. Enzym Inhib. 8 (1994) 113
31. Ehmer P.B., Jose J., and Hartmann R.W. J. Steroid Biochem. Mol. Biol. 75 (2000) 57
32. Ehmer P.B., Bureik M., Bernhardt R., Müller U., Hartmann R.W., and Steroid J. Biochem. Mol. Biol. 81 (2002) 173
33. Denner K., and Bernhardt R. In: Ishimura Y., Shimada H., and Suematsu M. (Eds). Oxygen Homeostasis and Its Dynamics. 1st ed. (1998), Springer-Verlag, Tokyo, Berlin, Heidelberg, New York 231
34. Denner K., Doehmer J., and Bernhardt R. Endocr. Res. 21 (1995) 443
35. Böttner B., Denner K., and Bernhardt R. Eur. J. Biochem. 252 (1998) 458
36. Thompson Jr. E.A., and Siiteri P.K. J. Biol. Chem. 249 (1974) 5373
37. Graves P.E., and Salhanick H.A. Endocrinology 105 (1979) 52
38. Foster A.B., Jarman M., Leung C.S., Rowlands M.G., and Taylor G.N. J. Med. Chem. 26 (1983) 50
39. Lézé M.P., Le Borgne M., Pinson P., Palusczak A., Duflos M., Le Baut G., and Hartmann R.W. Bioorg. Med. Chem. Lett. 16 (2006) 1134
40. Wächter G.A., Hartmann R.W., Sergejew T., Grün G.L., and Ledergerber D. J. Med. Chem. 39 (1996) 834
41. Hartmann R.W., and Batzl C. J. Med. Chem. 29 (1986) 1362