Synthesis and biological activity of progesterone derivatives as 5α-reductase inhibitors, and their effect on hamster prostate weight

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 25, Issue 3, 2010, Pages 306-311

  Bratoeff, Eugene ^a   Zambrano, Armando ^a   Heuze, Ivonne ^b   Palacios, Anay ^b   Ramríez, Daniela ^b   Cabeza, Marisa ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

Author keywords

5 reductase; Androgen receptor; Hamster prostate; Human prostate; Synthesis of 6 and 17 substituted progesterone derivatives

Indexed keywords

3,20 DIOXO 6,7 EPOXYPREGN 4 EN 7ALPHA YL ACETATE; 3,20 DIOXOPREGNA 4,6 DIEN 17ALPHA YL ACETATE; 6 CHLORO 3,20 DIOXOPREGNA 4,6 DIEN 17ALPHA YL ACETATE; ACETIC ACID ESTER; ANDROGEN RECEPTOR; FINASTERIDE; HYDROXYPROGESTERONE ACETATE; PROGESTERONE DERIVATIVE; STEROID 5ALPHA REDUCTASE; STEROID 5ALPHA REDUCTASE INHIBITOR; TESTOSTERONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; GONADECTOMY; HAMSTER; HUMAN; HUMAN TISSUE; IC 50; MALE; NONHUMAN; ORGAN WEIGHT; PRIORITY JOURNAL; PROSTATE; PROSTATE HYPERTROPHY; RADIOASSAY; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; CRICETINAE; HUMANS; INHIBITORY CONCENTRATION 50; MALE; ORGAN SIZE; PROGESTERONE; PROSTATE; STRUCTURE-ACTIVITY RELATIONSHIP; TESTOSTERONE; TESTOSTERONE 5-ALPHA-REDUCTASE;

ANIMALIA; CRICETINAE;

EID: 77951429785     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756360903179401     Document Type: Article

References (15)

1. Luu-The V, Bélanger A, Labrie F. Androgen biosynthetic pathways in human prostate. Best Pract Res Clin Endocrinol Metab 2008;22:207-221
2. Krieg M, Weiser H, Tunn S. Potential activities of androgen metabolizing enzymes in human prostate. J Steroid Biochem Mol Biol 1995;53:395-400.
3. Bratoeff E, Ramírez E, Flores E, Sánchez M, Heuze I, Cabeza M. New aromatic esters of progesterone as antiandrogens. J Enzyme Inhib Med Chem 2004;19:99-105. (Pubitemid 38744982)
4. Anderson KM, Liao S. Selective retention of dihydrotestosterone by prostatic nuclei. Nature 1968;219:277-279
5. Russell DW, Wilson JD. Steroid 5?-reductase: two genes/two enzymes. Annu Rev Biochem 1994;63:25-61. (Pubitemid 2109098)
6. Machetti F, Guarna A. Novel inhibitors of 5?-reductase. Expert Opin Ther Patents 2002;12:201-215
7. Flores E, Bratoeff E, Cabeza M, Ramírez E, Quiroz A, Heuze I. Steroid 5?-reductase inhibitors. Mini Rev Med Chem 2003;3:225-237
8. Bratoeff E, Carrillo E, Magaña M. Synthesis of 4 and 6-halopregnadiene derivatives with antiandrogenic activity. Mex Pharm Soc 1991;21:25-29
9. Hendry PWJ, Danzo BJ. Structural conversion of cytosolic steroid receptors by an age-dependent epididymal protease. J Steroid Biochem 1985;21:883-893
10. Liang T, Heiss EJ. Inhibition of 5?-reductase, receptor binding, and nuclear uptake of androgens in the prostate by a 4-methyl-4-aza-steroid. Biol Chem 1981;256:7998-8005. (Pubitemid 12232377)
11. Bradford MM. A rapid and sensitive method for the quantization of micrograms quantities of protein utilizing the principle of protein dye binding. Anal Biochem 1986;72:248-254
12. Hirosumi J, Nakayama O, Fagan T, Sawada K, Chida N, Inami M, et al. FK143, a novel non steroidal inhibition of steroid 5?-reductase: in vitro effects of human and animal prostatic enzymes. J Steroid Biochem Mol Biol 1995;52:357-363
13. Bratoeff E, Cabeza M, Pérez-Ornelas V, Recillas S, Heuze I. In vivo and in vitro effect of novel 4, 16-pregnadiene-6, 20 dione derivatives, as 5?-reductase inhibitors. J Steroid Biochem Mol Biol 2008;111:275-281
14. Cabeza M, Vilchis F, Lemus A, Díaz de León L, Pérez-Palacios G. Molecular interactions of levonorgestrel and its 5?-reduced derivative with androgen receptors in hamster flanking organs. Steroids 1995;60:630-635
15. Pérez-Ornbelas V, Cabeza M, Bratoeff E, Heuze I, Sánchez M, Ramírez E, et al. New 5?-reductase inhibitors: in vitro and in vivo effects. Steroids 2005;70:217-224 (Pubitemid 40342616)