Equine cytochrome p450 aromatase exhibits an estrogen 2-hydroxylase activity in vitro

Journal of Steroid Biochemistry and Molecular Biology

Volumn 59, Issue 1, 1996, Pages 55-61

  Almadhidi, Jamal ^a   Moslemi, Safa ^a   Drosdowsky, Michel A ^a   Séralini, Gilles Eric ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

7ALPHA (4 AMINOPHENYLTHIO)ANDROSTENEDIONE; AROMATASE; AROMATASE INHIBITOR; CYTOCHROME P450; ESTRADIOL; FADROZOLE; FORMESTANE; MICONAZOLE; TESTOSTERONE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME INHIBITION; ENZYME PURIFICATION; FEMALE; HORSE; ISOTOPE LABELING; MALE; NONHUMAN; PLACENTA; STEROID HYDROXYLATION; TESTIS;

ANDROSTENEDIONE; ANIMALS; AROMATASE; AROMATASE INHIBITORS; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; ESTRADIOL; FADROZOLE; HORSES; IMMUNE SERA; KINETICS; MALE; MICONAZOLE; MICROSOMES; PLACENTA; STEROID HYDROXYLASES; SUBSTRATE SPECIFICITY; TESTIS; TESTOSTERONE;

ANIMALIA; EQUIDAE; EQUUS CABALLUS;

EID: 0030238877     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-0760(96)00085-4     Document Type: Article

References (46)

1. 1. Almadhidi J., Séralini G.-E., Fresnel J., Silberzahn P. and Gaillard J.-L.: Immunohistochemical localization of cytochrome P450 aromatase in equine gonads. J. Histochem. Cytochem. 43 (1995) 571-577.
2. AROM), and their use in its purification. Arch. Biochem. Biophys. 243 (1985) 480-491.
3. 3. Simpson E. R., Mahendroo M. S., Means G. D., Kilgore M. W., Hinshelwood M. M., Graham-Lorence S., Amarneh B., Ito Y., Fisher C. R., Dodson Michael M., Mendelson C. R. and Bulun S. E.: Aromatase cytochrome P450, the enzyme responsible for estrogen biosynthesis. Endocr. Rev. 15 (1994) 342-355.
4. 4. Brodie A. M. H. and Santen R. J.: Aromatase and its inhibitors in breast cancer treatment - overview and perspective. Breast Cancer Res. Treat. 30 (1994) 1-6.
5. 5. Reed M. J.: The role of aromatase in breast tumors. Breast Cancer Res. Treat. 30 (1994) 7-17.
6. 6. Bulun S. E., Economos K., Miller D. and Simpson E. R.: CYP19 (aromatase cytochrome P450) gene expression in human malignant endometrial tumors. J. Clin. Endocr. Metab. 79 (1994) 1831-1834.
7. 7. Matzkin H. and Soloway M. S.: Immunohistochemical evidence of the existence and localization of aromatase in human prostatic tissues. Prostate 21 (1992) 309-314.
8. 8. Elbrecht A. and Smith R. G.: Aromatase enzyme activity and sex determination in chickens. Science 255 (1992) 467-470.
9. 9. Pieau C., Girondot M., Richard-Mercier N., Desvages G., Dorizzi M. and Zaborski P.: Temperature sensitivity of sexual differentiation of gonads in the european pond turtle: Hormonal involvement. J. Exp. Zool. 270 (1994) 86-94.
10. 10. Balthazart J. and Foidart A.: Brain aromatase and the control of male sexual behavior. J. Steroid Biochem. Molec. Biol. 44 (1993) 521-540.
11. 11. Ito Y., Fisher C. R., Conte F. A., Grumbach M. M. and Simpson E. R.: Molecular basis of aromatase deficiency in an adult female with sexual infantilism and polycystic ovaries. Proc. Natn. Acad. Sci. U.S.A. 90 (1993) 11673-11677.
12. 12. Ball P. and Knuppen R.: Catecholoestrogens (2-and 4-hydroxy-oestrogens): chemistry, biogenesis, metabolism, occurrence and physiological significance. Acta Endocr. Copenh. 93 suppl. 232 (1980) 1-128.
13. 13. Spink D. C., Eugster H.-P., Lincoln II D. W., Schuetz J. D., Schuetz E. G., Johnson J. A., Kaminsky L. S. and Gierthy J. F.: 17β-Estradiol hydroxylation catalyzed by human cytochrome P450 1A1: a comparison of the activities induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in MCF-7 cells with those from heterologous expression of the cDNA. Arch. Biochem. Biophys. 293 (1992) 342-348.
14. 14. Osawa Y., Higashiyama T., Shimizu Y. and Yarborough C.: Multiple functions of aromatase and the active site structure; aromatase is the placental estrogen 2-hydroxylase. J. Steroid Biochem. Molec. Biol. 44 (1993) 469-480.
15. 15. Short R. V.: Steroid concentrations in the follicular fluid of mares at various stages of the reproductive cycle. J. Endocr. 22 (1961) 153-163.
16. 16. Silberzahn P., Almahbobi G., Dehennin L. and Merouane A.: Estrogen metabolites in equine ovarian follicles: gas chromatographic-mass spectrometric determinations in relation to follicular ultrastructure and progestin content. J. Steroid Biochem. 22 (1985) 501-505.
17. 17. Fishman J. and Dixon D.: 2-Hydroxylation of estradiol by human placental microsomes. Biochemistry 6 (1967) 1683-1687.
18. 18. Kono S., Brandon D., Merriam G. R., Loriaux L. and Lipsett M. B.: Low plasma levels of 2-hydroxyestrone are consistent with its rapid metabolic clearance. Steroids 36 (1980) 463-472.
19. 19. Gaillard J.-L.: Equine testicular aromatase: substrates specificity and kinetic characteristics. Camp. Biochem. Physiol. 100B (1991) 107-115.
20. 20. Gaillard J.-L. and Silberzahn P.: Aromatization of 19-norandrogens by equine testicular microsomes. J. Biol. Chem. 262 (1987) 5717-5722.
21. 21. Al-Timimi I., Gaillard J.-L., Amri H. and Silberzahn P.: Androgen synthesis and aromatization by equine corpus luteum microsomes. J. Biol. Chem. 264 (1989) 7161-7168.
22. 22. Dintinger T., Gaillard J.-L., Moslemi S., Zwain I. and Silberzahn P.: Androgen and 19-norandrogen aromatization by equine and human placental microsomes. J. Steroid Biochem. 33 (1989) 949-954.
23. 23. Bradford M. M.: A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analyt. Biochem. 72 (1976) 248-254.
24. 24. Moslemi S., Dintinger T., Dehennin L., Silberzahn P. and Gaillard J.-L.: Different in vitro metabolism of 7 α-methyl-19-nortestosterone by human and equine aromatases. Eur. J. Biochem. 214 (1993) 569-576.
25. 25. Vibet A., Dintinger T., Maboundou J. C., Gaillard J.-L., Divoux D. and Silberzahn P.: Estrogen synthetase in the horse. Comparison of equine placental and rat liver NADPH-cytochrome c (P-450) reductase activities. FEBS Lett. 261 (1990) 31-34.
26. 26. Laemmli U. K.: Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227 (1970) 680-685.
27. 27. Thompson E.A. Jr. and Siiteri P. K.: Utilization of oxygen and reduced nicotinamide adenine dinuucleotide phosphate by human placental microsomes during aromatization of androstenedione. J. Biol. Chem. 249 (1974) 5364-5372.
28. 28. Numazawa M. and Satoh S.: Kinetic studies of inhibition of estradiol 2-and 16α-hydroxylases in rat liver microsomes with various cytochrome P-450 inhibitors. J. Steroid Biochem. 29 (1988) 221-226.
29. 29. Kellis J. T. and Vickery L. E.: Purification and characterization of human placental aromatase cytochrome P-450. J. Biol. Chem. 262 (1987) 4413-4420.
30. 30. Bunyagidj C. and McLachlan J. A.: Determination of estradiol 2-and 4-hydroxylase activities in mouse liver microsomes by liquid chromatography/electrochemistry. J. Chromatogr. Sci. 26 (1988) 24-28.
31. 31. Shimizu Y., Yarborough C. and Osawa Y.: Competitive product inhibition of aromatase by natural estrogens. J. Steroid Biochem. Molec. Biol. 44 (1993) 651-656.
32. 32. Balthazart J., Stoop R., Foidart A., Granneman J. C. M. and Lambert J. G. D.: Distribution and regulation of estrogen-2-hydroxylase in the quail brain. Brain Res. Bull 35 (1994) 339-345.
33. 33. Longcope C., Layne D. S. and Tait J. F.: Metabolic clearance rates and interconversions of estrone and 17β-estradiol in normal males and females. J. Clin. Invest. 47 (1968) 93-106.
34. 34. Naftolin F., Morishita H., Davies I. J., Todd R. and Ryan K. J.: 2-Hydroxyestrone induced rise in serum luteinizing hormone in the immature male rat. Biochem. Biophys. Res. Commun. 64 (1975) 905-910.
35. 35. Spicer L. J. and Hammond J. M.: Regulation of ovarian function by catecholestrogens: current concepts. J. Steroid Biochem. 33 (1989) 489-501.
36. 36. Paria B. C., Chakraborty C. and Dey S. K.: Catechol estrogen formation in the mouse uterus and its role in implantation. Molec. Cell. Endocr. 69 (1990) 25-32.
37. 37. Vandewalle B. and Lefebvre J.: Opposite effects of estrogen and catecholestrogen on hormone-sensitive breast cancer cell growth and differentiation. Molec. Cell. Endocr. 61 (1989) 239-246.
38. 38. Zhu B. T., Roy D. and Liehr J. G.: The carcinogenic activity of ethinyl estrogens is determined by both their hormonal characteristics and their conversion to catechol metabolites. Endocrinology 132 (1993) 577-583.
39. 39. Merriam G. R., MacLusky N. J., Pickard M. K. and Naftolin F.: Comparative properties of catechol estrogens. 1. Methylation by catechol-O-methyltransferase and binding to cytosol estrogen receptors. Steroids 31 (1980) 1-11.
40. 40. Lloyd T. and Weisz J.: Direct inhibition of tyrosine hydroxylase activity by catecholestrogens. J. Biol. Chem. 263 (1978) 4841-4843.
41. 41. Blackburn J. R., Pfaus J. G. and Phillips A. G.: Dopamine functions in appetitive and defensive behaviours. Progr. Neurobiol. 39 (1992) 247-279.
42. 42. Merriam G. R., Pfeiffer D. G., Loriaux D. L. and Lipsett M. B.: Catechol estrogen and the control of gonadotropin and prolactin secretion in man. J. Steroid Biochem. 19 (1983) 619-625.
43. 43. Kogo H., Johnson D. C., Dey S. K. and Takeo S.: A comparison of the effects of estradiol and 2-and 4-hydroxyestradiol on uterine ornithine decarboxylase activity in immature rats. Japan. J. Pharmacol. 61 (1993) 65-67.
44. 44. Biswas A., Chaudhury A., Chattoraj S. C. and Dale S. L.: Do catechol estrogen participate in the initiation of labor?. Am. J. Obstet. Gynecol. 165 (1991) 984-987.
45. 45. Zhang Z. and Davis D. L.: Cell-type specific responses in prostaglandin secretion by glandular and stromal cells from pig endometrium treated with catecholestrogen, methoxyestrogens and progesterone. Prostaglandins 44 (1992) 53-64.
46. 2+-catalyzed oxidation of low or high density lipoprotein: antioxidative effects of steroid on lipoproteins. Endocr. J. 41 (1994) 605-611.