Stereoselective Inhibition of Aromatase by Enantiomers of Aminoglutethimide*
Abstract
The dextrorotatory enantiomer of aminoglutethimide is 38 times more potent than the levoenantiomer in inhibiting aromatization of testosterone by human placental microsomes. The spectral affinity constant for microsomal cytochrome P-450 is 36 times greater for the d-enantiomer. Enzymatic inhibition and affinity are highly correlated for each of the isomers as well as for the racemic mixture. Spectral analysis of the interactions of the inhibitors with the substrate supports the evidence for participation of cytochrome P-450 in aromatization.
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Naturally occurring plant flavones are potent inhibitors of aromatase.
“Kellis and Vickery have reported that naturally occurring plant flavones are potent in- hibitors of aromatase (21).”
From Nicotine, cotinine, and anabasine inhibit aromatase in human trophoblast in vitro. (1986) · cites this paper as [21]
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Nicotine, cotinine, and anabasine inhibit aromatase in human trophoblast in vitro.
Barbieri, R. L., Gochberg, J., & Ryan, K. J. (1986) · Journal of Clinical Investigation · doi:10.1172/jci112494 · Cited by 197 · see citing works
Simultaneous High-Purity Enantiomeric Resolution of Conglomerates Using Magnetic Substrates
Bhowmick, D., Sang, Y., Santra, K., Halbauer, M., Capua, E., Paltiel, Y., Naaman, R., & Tassinari, F. (2021) · Crystal Growth & Design · doi:10.1021/acs.cgd.1c00093 · Cited by 24 · see citing works
- Authors
- GRAVES, P. E., & SALHANICK, H. A.
- Affiliations
- Harvard University (US)
- Venue
- Endocrinology
- Publisher
- The Endocrine Society
- Published
- 1979-07
- Volume
- 105
- Issue
- 1
- Pages
- 52-57
- ISSN
- 0013-7227 (ISSN-L)
- 1945-7170
- OpenAlex
- W2049190772
- Cited by
- 146
- References
- 0
- Citations by year
- 2021: 1 · 2020: 1 · 2019: 1 · 2018: 1 · 2017: 1 · 2015: 1 · 2014: 2 · 2013: 3 · 2012: 3
- FWCI
- 4.39
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Endocrinology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Estrogen and related hormone effects
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Keywords
- aminoglutethimide, enantiomers, stereoselective inhibition, aromatase inhibition, testosterone aromatization, human placental microsomes, cytochrome P450, enzyme inhibition
- MeSH terms
- Aminoglutethimide, Cytochrome P-450 Enzyme System, Female, Humans, Kinetics, Microsomes, Oxidoreductases, Placenta, Pregnancy, Spectrum Analysis, Stereoisomerism, Testosterone, Aromatase Inhibitors
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