Interactions Between Estrogens and Catechol Amines III. Studies on the Methylation of Catechol Estrogens, Catechol Amines and other Catechols by the Catechol-O-Methyltransferase1 of Human Liver
Abstract
The substrate specificity of the catechol-O-methyltransferase, purified from human liver 380-fold, has been tested with a variety of compounds. Catechol estrogens, as well as catechol amines are methylated to their corresponding monomethyl ethers. The relation of the rates of methylation of catechol estrogens and catechol amines depended on enzyme and substrate concentration; under standard assay conditions, 2-hydroxy-17β-estradiol was the preferred substrate for the enzyme, as compared with epinephrine and other catechols tested. Km-values for 2-hydroxy-17β-estradiol were 15 μm, for 2-hydroxy-estrone 20 μm, for 2-hydroxy-estriol 25 μm and for-hydroxy-estrone 20 μm. For epinephrine and norepinephrine, Km-values of 300 μm and 200 μm, respectively, were obtained. The ratio of formation of the isomeric monomethyl ethers of catechol estrogens varied between 1.3 and 95, depending on the substrate incubated. On the basis of kinetic studies with different enzyme preparations, different inhibitors and different concentrations of the substrates, it is concluded that both catechol estrogens and catechol amines are methylated by the same Catechol-O-methyltransferase. The enzymic methylation of epinephrine was inhibited competitively by 2- and 4-hydroxylated estrogens; the Ki-values were 7.0 μm for 2-hydroxy-17β-estradiol, 8.5 μm for 2-hydroxy-estrone, 12.2 μm for 2-hydroxy-estriol, 50 μm for 4-hydroxy-estrone and, for comparison, 154 μm for the addition of norepinephrine. A non-competitive inhibition was observed with the corresponding isomeric monomethyl ethers. The extent of inhibition not only depended on the relative concentrations of substrates and inhibitors, but also on the concentrations of MgCl2S-adenosylmethionine and enzyme. The results reported here indicate that the enzymic methylation and biological inactivation of neurotransmitters is strongly inhibited by 2-hydroxy-estrogens. These findings are of possible clinical relevance with respect to the regulation of blood pressure under normal and pathological conditions.
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COMT methylates 2- and 4-hydroxyestrogens, producing methoxyestrogens.
“COMT methylates 2- and 4-hydroxyestrogens, thereby producing the so-called methoxyestrogens [180].”
From Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: a comprehensive review (2019) · cites this paper as [180]
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Claustre, J., Peyrin, L., Fitoussi, R., & Mornex, R. (1980) · Psychopharmacology · doi:10.1007/bf00431970 · Cited by 35 · see citing works
“Estrogens may, however, interact with catecholamine metabolism since they are able to inhibit competitively the enzyme catechol O-methyl transferase (COMT) (Ball et al., 1972), and catecholamine uptake 2 (Iversen, 1973).”
BackgroundSoluble and membrane-bound catechol-O-methyltransferase in normal and malignant mammary gland
Tenhunen, J., Heikkilä, P., Alanko, A., Heinonen, E., Akkila, J., & Ulmanen, I. (1999) · Cancer Letters · doi:10.1016/s0304-3835(99)00197-4 · Cited by 35 · see citing works
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A radioimmunoassay method for urinary catechol estrogens
Chattoraj, S. C. (1978) · Steroids · doi:10.1016/0039-128x(78)90051-x · Cited by 34 · see citing works
Estrogen modulates inhibition of return in healthy human females
Colzato, L. S., Pratt, J., & Hommel, B. (2011) · Neuropsychologia · doi:10.1016/j.neuropsychologia.2011.11.003 · Cited by 33 · see citing works
- Authors
- BALL, P., KNUPPEN, R., HAUPT, M., & BREUER, H.
- Affiliations
- University of Bonn (DE)
- Venue
- The Journal of Clinical Endocrinology & Metabolism
- Publisher
- The Endocrine Society
- Published
- 1972-04
- Volume
- 34
- Issue
- 4
- Pages
- 736-746
- ISSN
- 0021-972X (ISSN-L)
- 1945-7197
- OpenAlex
- W2010928336
- Cited by
- 280
- References
- 0
- Citations by year
- 2025: 1 · 2023: 2 · 2022: 1 · 2021: 1 · 2020: 1 · 2019: 2 · 2018: 3 · 2017: 2 · 2016: 1 · 2015: 1 · 2014: 3 · 2013: 2 · 2012: 2
- FWCI
- 6.20
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Clinical Endocrinology & Metabolism (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Cancer Institute
- Topics
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Estrogen and related hormone effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Keywords
- catechol estrogens, epinephrine, norepinephrine, methylation, 2-hydroxyestrone, 4-hydroxyestrone, monomethyl ether, substrate specificity, enzyme kinetics, competitive inhibition, non-competitive inhibition, human liver
- MeSH terms
- Adult, Carbon Isotopes, Catecholamines, Catechols, Chemistry, Chlorides, Cysteine, Dopamine, Epinephrine, Estradiol, Estriol, Estrogens, Estrone, Humans, Kinetics, Liver, Magnesium, Male, Mandelic Acids, Methylation, Methyltransferases, Norepinephrine, S-Adenosylmethionine, Time Factors, Chemical Phenomena
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