Biochemical aromatization of 2-methyleneandrostenedione: Stereochemistry of hydrogen removal at the C-1 position

Journal of Steroid Biochemistry and Molecular Biology

Volumn 101, Issue 4-5, 2006, Pages 239-245

  Numazawa, Mitsuteru ^a   Handa, Wakako ^a   Matsuzaki, Hisao ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

2 Methyleneandrostenedione; Androstenedione; Biochemical aromatization; C 1 hydrogen removal; Gas chromatography mass spectrometry; Stereochemistry

Indexed keywords

2 METHYLENE STEROID; 2 METHYLENEANDROSTENEDIONE; 2 METHYLESTRONE; ANDROSTENEDIONE DERIVATIVE; AROMATASE INHIBITOR; CARBONYL DERIVATIVE; DEUTERIUM; ESTRONE DERIVATIVE; HYDROGEN; STEROID; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYST; CHEMICAL BOND; CONFORMATION; ENZYME ACTIVITY; ENZYME SUBSTRATE; STEREOCHEMISTRY; STEREOISOMERISM; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; TANDEM MASS SPECTROMETRY;

ANDROSTENEDIONE; AROMATASE INHIBITORS; DEUTERIUM; HYDROGEN; ISOMERISM; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE;

EID: 33750001407     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2006.06.026     Document Type: Article

References (39)

1. Thompson Jr. E.A., and Siiteri P.K. The involvement of human placental microsomal cytochrome P-450 in aromatization. J. Biol. Chem. 249 (1974) 5373-5378
2. Kellis Jr. J.T., and Vickery L.E. Purification and characterization of human placental aromatase P-450. J. Biol. Chem. 262 (1987) 4413-4420
3. Yoshida N., and Osawa Y. Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization. Biochemistry 30 (1991) 3003-3010
4. Thompson Jr. E.A., and Siiteri P.K. Utilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione. J. Biol. Chem. 249 (1974) 5364-5372
5. 4-androstene-3,17-dione oestrone by endocrine tissue. Biochem. Biophys. Acta 17 (1955) 441-442
6. 4-androstene-3,17-dione by placental microsomes. Endocrinology 71 (1962) 723-728
7. Skinner S.J.M., and Akhtar M. The stereospecific removal of a C-19 hydrogen atom in oestrogen biosynthesis. Biochem. J. 114 (1969) 75-81
8. Osawa Y., Shibata K., Rohrer D., Weeks C., and Duax W.L. Reassignment of the absolute configuration of estrogen biosynthesis. J. Am. Chem. Soc. 97 (1975) 4400-4402
9. Akhtar M., Calder M.R., Corina D.L., and Wright J.N. Mechanistic studies on C-19 dimethylation on oestrogen biosynthesis. Biochem. J. 201 (1982) 569-580
10. Covey D.F. Aromatase inhibitors: specific inhibitors of estrogen biosynthesis. In: Berg D., and Plemel M. (Eds). Steroid Biosynthesis Inhibitors: Pharmaceutical and Agrochemical Aspects. (1988), Eliss Horwood Ltd., Chichester 534-571
11. Oh S.S., and Robinson C.H. Mechanism of human placental aromatase: a new active site model. J. Steroid Biochem. Mol. Biol. 44 (1993) 389-397
12. Akhtar M., Lee-Robichaud P., Akhtar M.E., and Wright J.N. The impact of aromatase mechanism on other P450s. J. Steroid Biochem. Mol. Biol. 61 (1997) 127-132
13. 2. J. Chem. Soc., Chem. Commun. (1976) 854-856
14. Cole P.A., and Robinson C.H. Peroxide model reaction for placental aromatase. J. Am. Chem. Soc. 110 (1988) 1284-1285
15. Korzekwa K.R., Tragen W.F., Smith S.J., Osawa Y., and Gillette J.R. Theoretical studies on the mechanism of conversion of androgens to estrogens by aromatase. Biochemistry 30 (1991) 6155-6162
16. Oh S.S., and Robinson C.H. Synthesis of and chemical model reaction studies with 3-deoxyandrogens: evidence supporting a 2,3-enolizations hypothesis in human placental aromatase catalysis. J. Chem. Soc., Perkin Trans 1 (1994) 2237-2243
17. Kao Y.-C., Korzekwa K.R., Laughton C.A., and Chen S. Evaluation of the mechanism of aromatase cytochrome P-450. Eur. J. Biochem. 268 (2001) 243-251
18. Hackett J.C., Brueggemeier R.W., and Hadad C.M. The final step of cytochrome P-450 aromatase: a density functional theory study. J. Am. Chem. Soc. 127 (2005) 5224-5237
19. 19 bond by human placental aromatase. Biochemistry 44 (2005) 10839-10845
20. Vanden Bossche H. Inhibitors of P450-dependent steroid biosynthesis: from research to mediate treatment. J. Steroid Biochem. Mol. Biol. 43 (1992) 1003-1021
21. Brodie A.M., and Santen R.J. Aromatase inhibitors in breast cancer treatment-overview and perspective. Breast Cancer Res. Treat. 30 (1994) 1-6
22. Johnston J.O. Aromatase inhibitors. Crit. Rev. Biochem. Mol. Biol. 33 (1998) 375-405
23. Harper-Wynne C., and Dowsett M. Recent advances in the clinical application of aromatase inhibitors. J. Steroid Biochem. Mol. Biol. 76 (2001) 179-186
24. Numazawa M., Yoshimura A., and Oshibe M. Enzymic aromatization of 16-alkyl-substituted androgens, potent competitive and mechanism-based inhibitors of aromatase. Biochem J. 329 (1998) 151-156
25. Numazawa M., Nagaoka M., Morio M., and Kamiyama T. 19-Oxygenations of 3-deoxy androgens, potent competitive inhibitors of estrogen biosynthesis, with human placental aromatase. J. Steroid Biochem. Mol. Biol. 71 (1999) 173-179
26. Numazawa M., Ando M., and Zennyoji R. Studies on the catalytic function of aromatase: aromatization of 6-alkoxy-substituted androgens. J. Steroid Biochem. Mol. Biol. 82 (2002) 65-73
27. Numazawa M., Watari Y., Yamada K., Umemura N., and Handa W. Probing the active site of aromatase with 2-methyl-substituted androstenedione analogs. Steroids 68 (2003) 503-513
28. Numazawa M., Handa W., Hasegawa C., and Takahashi M. Structure-activity relationships of 2α-substituted androstenedione analogs as aromatase inhibitors and their aromatization reactions. J. Steroid. Biochem. Mol. Biol. 97 (2005) 353-359
29. 4: stereospecific deuterium-labeling at the C-1α position of a 4-en-3-one steroid. Chem. Pharm. Bull. 54 (2006) 554-556
30. Brodie H.J., Hayano M., and Gut M. The stereochemical course of the catalytic hydrogenation of ring a unsaturated steroids. J. Am. Chem. Soc. 84 (1962) 3766-3767
31. Hosoda H., Yamashita K., Sagae H., and Nambara T. Studies on dimethyl-tert-butyl ethers of steroid. Chem. Pharm. Bull. 23 (1975) 2118-2122
32. Ringold H.J., Hayano M., and Stefavonovic V. Concerning the stereochemistry and mechanism of the bacterial C-1,2 dehydrogenation of steroids. J. Biol. Chem. 238 (1963) 1960-1965
33. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montogomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Frarkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Oritiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, B. Revision 05 (2003), Gaussian Inc., Pittsburgh, PA
34. Ryan K.J. Placental synthesis of steroid hormone. In: Tulchinsky D., and Ryan K.J. (Eds). Material-Fetal Endocrinology (1980), W.B. Sanders, Philadelphia 3-16
35. Busetta B., Conberton G., Courseille C., and Hospital M. Cryst. Struct. Commun. 1 (1972) 129-133
36. 18 steroids. Biochemistry 7 (1968) 33-40
37. Brodie H.J., Possanza C., and Townsley J.D. Studies on the mechanism of estrogen biosynthesis. V. Stereochemistry comparison of aromatization in placental and microbiological systems. Biochem. Biophys. Acta. 152 (1968) 770-777
38. Numazawa M., and Mutsumi A. 6α,7α-cyclopropan derivative of androst-4-ene: a novel class of competitive aromatase inhibitors. Biochem. Biophys. Res. Commun. 177 (1991) 401-406
39. Numazawa M., Mutsumi A., Hoshi K., Oshibe M., Ishikawa E., and Kigawa H. Synthesis and biochemical studies of 16- or 19-substituted androst-4-enes as aromatase inhibitors. J. Med. Chem. 34 (1991) 2496-2504