New ester derivatives of dehydroepiandrosterone as 5α-reductase inhibitors

Steroids

Volumn 76, Issue 12, 2011, Pages 1241-1246

  Arellano, Yazmín ^a   Bratoeff, Eugene ^a   Garrido, Mariana ^a   Soriano, Juan ^c   Heuze, Yvonne ^b   Cabeza, Marisa ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

^c General Hospital of Mexico SS   (Mexico)

Author keywords

5 Reductase; Androgen receptor; Antiandrogens; Hamster prostate; Human prostate; Synthesis of ester derivatives of dehydroepiandrosterone

Indexed keywords

3BETA (3'OXAPENTANOYLOXY)ANDROST 5 EN 17 ONE; 3BETA BUTANOYLOXYANDROSTAN 17 ONE; 3BETA HEXANOYLOXYANDROST 5 EN 17 ONE; 3BETA PENTANOYLOXYANDROSTAN 17 ONE; 3BETA PROPANOYLOXYANDROSTAN 17 ONE; 5ALPHA,6BETA DIBROMO 3BETA (3' OXAPENTANOYLOXY)ANDROSTAN 17 ONE; 5ALPHA,6BETA DIBROMO 3BETA BUTANOYLOXYANDROSTAN 17 ONE; 5ALPHA,6BETA DIBROMO 3BETA PROPANOYLOXYANDROSTAN 17 ONE; ANDROGEN RECEPTOR; ANDROSTANEDIOL; ANDROSTANOLONE; FINASTERIDE; MIBOLERONE; PRASTERONE; PRASTERONE ACETATE; STEROID 5ALPHA REDUCTASE; STEROID 5ALPHA REDUCTASE INHIBITOR; TESTOSTERONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIANDROGEN THERAPY; ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOSOL; DRUG INHIBITION; DRUG SYNTHESIS; GONADECTOMY; HUMAN; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PROSTATE; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SEMINAL VESICLE; STRUCTURE ACTIVITY RELATION; TREATMENT OUTCOME;

5-ALPHA REDUCTASE INHIBITORS; ANDROGEN ANTAGONISTS; ANIMALS; CHOLESTENONE 5 ALPHA-REDUCTASE; CRICETINAE; DEHYDROEPIANDROSTERONE; HUMANS; MALE; MESOCRICETUS; RATS;

ANIMALIA; CRICETINAE; RATTUS;

EID: 80052781011     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.05.015     Document Type: Article

References (25)

1. E.P. Jenkins, S. Anderson, J. Imperato-McGinley, J.D. Wilson, and D.W. Russell Genetic and pharmacological evidence for more than one human steroid 5 alpha-reductase J Clin Invest 89 1992 293 300
2. M. Marberger Drug insight: 5alpha-reductase inhibitors for the treatment of benign prostatic hyperplasia Nat Clin Pract Urol 3 2006 495 503 (Pubitemid 44377540)
3. K.M. Anderson, and S. Liao Selective retention of dihydrotestosterone by prostatic nuclei Nature 219 1968 277 279
4. L.N. Thomas, C.B. Lazier, R. Gupta, R.W. Norman, D.A. Troyer, S.P. O'Brien, and R.S. Rittmaster Differential alterations in 5alpha-reductase type 1 and type 2 levels during development and progression of prostate cancer Prostate 6 2005 231 239 (Pubitemid 40571057)
5. D.W. Russell, and J.D. Wilson Steroid 5α-reductase: two genes/two enzymes Annu Rev Biochem 63 1994 25 61
6. A.E. Thigpen, K.M. Cala, and D.W. Russell Characterization of Chinese hamster ovary cell lines expressing human 5-alpha reductase isozymes J Biol Chem 268 1993 17404 17412 (Pubitemid 23236981)
7. H. Bonkhoff, U. Stein, G. Aumuller, and K. Remberger Differential expression of 5-alpha reductase isozymes in the human prostate and prostatic carcinomas Prostate 291 1996 261 267 (Pubitemid 26365292)
8. V.D. Handratta, T.S. Vasaitis, V.C.O. Njar, L.J. Gediya, G.H. Katria, P. Chopra, D. Newman, R. Farquar, Z. Guo, Y. Qiu, and A.M.H. Brodie Novel C-17-heteroaryl steroidal CYP 17 inhibitors/antiandrogens: synthesis, in vitro biological activity, pharmacokinetics, and antitumor activity in LAPC4 human prostate cancer xenograft model J Med Chem 48 2005 2972 2984 (Pubitemid 40552912)
9. V.C.O. Njar, and A.M.H. Brodie Inhibitors of 17α-hydroxylase-C17, 20-lyase (CYP17): Potential agents for the treatment of prostate cancer Curr Pharm Des 5 1999 163 180 (Pubitemid 29159609)
10. B.J. Long, D.N. Grigoryev, I.P. Nnane, Y.Z. Liu, and A.M. Brodie Antiandrogenic effect of novel androgen synthesis inhibitors on hormone-dependent prostate cancer Cancer Res 60 2000 6630 6640
11. K.C. Nicolaou, J.A. Pfefferkrn, J.A. Roecker, G.Q. Cao, S. Barluenga, and H.J. Mitchel Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans J Am Chem Soc 122 2000 9939 9953
12. 19-Steroids as androgen receptor modulators: design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists Biorgan Med Chem 14 2006 5933 5947 (Pubitemid 44080586)
13. V. Pérez-Ornelas, M. Cabeza, E. Bratoeff, I. Heuze, M. Sánchez, E. Ramírez, and E. Naranjo New 5α-reductase inhibitors: in vitro and in vivo effects Steroids 70 2005 217 224 (Pubitemid 40342616)
14. M. Cabeza, E. Gutiérrez, R. Miranda, Y. Heuze, E. Bratoeff, G. Flores, and E. Ramírez Androgenic and antiandrogenic effect of progesterone derivatives with different halogen as substituents at C-6 position Steroids 64 1999 413 421 (Pubitemid 29340523)
15. M. Cabeza, Y. Heuze, H. Quintana, and E. Bratoeff Comparison between two different hamster models used for the determination of testosterone and finasteride activity Asian J Anim Vet Adv 5 2010 202 209
16. C.M. Gaubert, R.R. Trembla, and Y.Y. Bubé Effect of sodium molibdate on cytosolic androgen receptor in rat prostate J Steroid Biochem 13 1980 931 937 (Pubitemid 10013375)
17. P. Davies, P. Thomas, and K. Griffiths Measurement of free and occupied cytoplasmic and nuclear androgen receptor sites in rat prostate ventral prostate gland J Endocr 74 1977 393 404 (Pubitemid 8185879)
18. P.W.J. Hendry, and B.J. Danzo Structural conversion of cytosolic steroid receptors by an age-dependent epididymal protease J Steroid Biochem 21 1985 883 893 (Pubitemid 16152406)
19. T. Liang, and E.J. Heiss Inhibition of 5α-reductase, receptor binding, and nuclear uptake of androgens in the prostate by a 4-methyl-4-aza-steroid Biol Chem 256 1981 7998 8005 (Pubitemid 12232377)
20. M.M. Bradford A rapid and sensitive method for the quantization of micrograms quantities of protein utilizing the principle of protein dye binding Anal Biochem 72 1986 248 254
21. M. Cabeza, F. Vilchis, A. Lemus, L. Díaz de León, and G. Pérez-Palacios Molecular interactions of levonorgestrel and its 5α-reduced derivative with androgen receptors in hamster flanking organs Steroids 60 1995 630 635
22. G.H. Rasmusson, G.F. Reynolds, N.G. Steinberg, E. Walton, G.F. Patel, and T. Liang Azasteroids: structure-activity relationships for inhibition of 5-alpha reductase and of androgen receptor binding J Med Chem 29 1986 2298 2315 (Pubitemid 17182310)
23. J. Hirosumi, O. Nakayama, T. Fagan, K. Sawada, N. Chida, and M. Inami FK143, a novel non steroidal inhibition of steroid 5α-reductase: in vitro effects of human and animal prostatic enzymes J Steroid Biochem Mol Biol 52 1995 357 363
24. E. Bratoeff, M. Cabeza, V. Pérez-Ornelas, S. Recillas, and I. Heuze In vivo and in vitro effect of novel 4, 16-pregnadiene-6, 20 dione derivatives, as 5α-reductase inhibitors J Steroid Biochem Mol Biol 111 2008 275 281
25. N. Bruchovsky, and J.D. Wilson The conversion of testosterone to 5-alpha-androstan-17-beta-ol-3-one by rat prostate in vivo and in vitro J Biol Chem 243 1968 2012 2022