Biological activity of novel progesterone derivatives having a bulky ester side chains at C-3

Steroids

Volumn 73, Issue 8, 2008, Pages 838-843

  Cabeza, Marisa ^a   Bratoeff, Eugene ^b   Ramírez, Elena ^b   Heuze, Ivonne ^a   Recillas, Sergio ^a   Berrios, Hilda ^a   Cruz, Angel ^b   Cabrera, Olmo ^b   Perez, Victor ^b  

^a DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Androgen receptor; Bulky ester side chains steroids; Hamster prostate; Mibolerone

Indexed keywords

3BETA CYCLOBUTYLCARBONYLOXY 4,16 PREGNADIENE 6,20 DIONE; 3BETA CYCLOHEXYLCARBONYLOXY 4,16 PREGNADIENE 6,20 DIONE; 3BETA CYCLOPENTYLCARBONYLOXY 4,16 PREGNADIENE 6,20 DIONE; 3BETA CYCLOPROPYLCARBONYLOXY 4,16 PREGNADIENE 6,20-DIONE; ANDROGEN RECEPTOR; ANDROSTANOLONE; ANTIANDROGEN; MIBOLERONE; PROGESTERONE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CYTOSOL; DRUG EFFECT; HAMSTER; IC 50; IN VIVO STUDY; LIPOPHILICITY; MALE; NONHUMAN; ORGAN WEIGHT; PARTITION COEFFICIENT; PROSTATE HYPERTROPHY; SEMINAL VESICLE;

ANIMALS; CRICETINAE; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MESOCRICETUS; ORGAN SIZE; PROGESTERONE; PROSTATE; SEMINAL VESICLES; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

CRICETINAE; RATTUS;

EID: 44249125940     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.03.006     Document Type: Article

References (16)

1. Quigley C.A., Debellis A., Marschke K.B., Elawady M.K., Wilson E.M., and French F.S. Androgen receptor defects: historical, clinical, and molecular perspectives. Endocr Rev 16 (1995) 271-321
2. McKenna N.J., Lanz R.B., and O'Malley B.W. Nuclear receptors coregulators: cellular and molecular biology. Endocr Rev 20 (1999) 321-344
3. Lee H.J., and Chang C. Recent advances in androgen receptor action. Cell Mol Life Sci 60 8 (2003) 1613-1622
4. Gobinet J., Poujol N., and Sultan Ch. Molecular action of androgens. Mol Cell Endocrinol 198 (2002) 15-24
5. O'Leary M.P., Roehrborn C., Andriole G., Nockel C., Boyle P., and Hofner K. Improvements in benign prostatic hyperplasia-specific quality of life with dutasteride, the novel dual 5α-reductase inhibitor. BJU Int 92 3 (2003) 262-266
6. Santos A.F., Huang H., and Tindall D.J. The androgen receptor: a potential for therapy of prostate cancer. Steroids 69 (2004) 79-85
7. Bratoeff E., Cabeza M., Ramírez E., Heuze I., and Flores E. Recent advances in Chemistry and pharmacological activity of new steroidal antiandrogens and 5α- reductase inhibitors. Curr Med Chem 12 (2005) 927-943
8. Perez V., Cabeza M., Bratoeff E., Heuze I., Sánchez M., Ramírez E., and Naranjo E. New 5α-reductase inhibitors: in vitro and in vivo effects. Steroids 70 (2005) 217-224
9. Hendry W.J., and Danzo B.J. Structural conversion of cytosolic steroids receptors by an age-dependent epididymal protease. J Steroid Biochem 23 (1985) 883-893
10. Cabeza M., Vilchis F., Lemus A.E., Diaz de León L., and Pérez-Palacios G. Molecular interactions of levonorgestrel and its 5α-reduced derivative with androgen receptors in hamster flanking organs. Steroids 60 (1995) 630-635
11. Bradford M.M. 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
12. Liang T., and Heiss E. Inhibition of 5α-reductase, receptor binding and nuclear uptake of androgens in the prostate by 4-methyl-4-aza-steroid. J Biol Chem 256 (1981) 7998-8005
13. Cabeza M., Flores E., Heuze I., Sánchez M., Bratoeff E., Ramírez E., and Francolugo V.A. Novel 17 substituted pregnadiene derivatives as 5α-reductase inhibitors and their binding affinity for the andogen receptors. Chem Pharm Bull 52 (2004) 535-539
14. Cabeza M., Bratoeff E., Flores E., Ramírez E., Calleros J., Montes D., Quiróz A., and Heuze I. 5α-reductase inhibitors and antiandrogenic activities of novel steroids in hamster seminal vesicles. Chem Pharm Bull 50 (2002) 1447-1452
15. Lipinski C., Lombardo F., Dominy W., and Finley P. Experimental and computational approach to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 23 (1997) 3-25
16. Fujita T., Iwassa J., and Hansch C. Substituent constant, Π, derived from partition coefficients. J Am Chem Soc 86 (1964) 5175-5179