Cited by 1,283Pharmacogenetics and Drug MetabolismMetal-Catalyzed Oxygenation MechanismsMicrobial metabolism and enzyme function

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Enzymatic O-Methylation of Epinephrine and Other Catechols

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Axelrod, Julius, Tomchick, Robert·1958·Journal of Biological Chemistry

DOI 10.1016/s0021-9258(18)64731-3

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ON TYROSINE AND TRYPTOPHANE DETERMINATIONS IN PROTEINS
Folin, O., & Ciocalteu, V. (1927) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)84277-6 · Cited by 2,990
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O-Methylation of Epinephrine and Other Catechols in vitro and in vivo
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3-Methoxy-4-hydroxy-D-mandelic acid, a urinary metabolite of norepinephrine
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O-Methylation of Catechol Amines in Vivo
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METHYLATION OF NICOTINAMIDE WITH A SOLUBLE ENZYME SYSTEM FROM RAT LIVER
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O-methylation, the principal pathway for the metabolism of epinephrine and norepinephrine in the rat
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“The enzyme is expressed in a variety of animal tissues and in cultured fibroblasts (Axelrod and Tomchick 1958; Jacobowitz 1972).”
Background
Substrate stereospecificity and selectivity of catechol-O-methyltransferase for DOPA, DOPA derivatives and α-substituted catecholamines
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“Catechol-O-methyltransferase catalyzes the O-methylation of catechols by transferring the methyl group of S-adenosylmethionine (SAM) to a hydroxyl group on the catechol substrate [1].”
Background
Stereoselective enzymatic O-methylation of tetrahydropapaveroline and tetrahydroxyberbine alkaloids
Meyerson, L. R., Cashaw, J. L., McMurtrey, K. D., & Davis, V. E. (1979) · Biochemical Pharmacology · doi:10.1016/0006-2952(79)90535-5 · Cited by 28
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Determination of plasma catecholamines by means of radioenzymatic labelling and high pressure liquid chromatographic separation
Appel, E., Bayer, P., Hajd�, P., Palm, D., Schofer, J. J., & Uihlein, M. (1981) · Naunyn-Schmiedeberg s Archives of Pharmacology · doi:10.1007/bf00499840 · Cited by 28
Optical specificity of monoamine oxidase
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Developmental Patterns of Catechol‐O‐Methyltransferase in Genetically Different Rat Strains: Enzymatic and Immunochemical Studies
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Untersuchungen zum Vorkommen zweier O-Methyltransferasen in Tulipa-Antheren
Sütfeld, R., & Wiermann, R. (1978) · Biochemie und Physiologie der Pflanzen · doi:10.1016/s0015-3796(17)30366-9 · Cited by 28
Detection of catechol-O-methyltransferase Val158Met polymorphism by a simple one-step tetra-primer amplification refractory mutation system-PCR
Ruiz-Sanz, J. I., Aurrekoetxea, I., del Agua, A. R., & Ruiz‐Larrea, M. B. (2007) · Molecular and Cellular Probes · doi:10.1016/j.mcp.2006.12.001 · Cited by 27
Association study of catechol-O-methyltransferase gene polymorphisms with schizophrenia and psychopathological symptoms in Han Chinese
Chen, C., Lu, R., Yeh, Y., Shih, M.-C., & Huang, S. (2011) · Genes Brain & Behavior · doi:10.1111/j.1601-183x.2010.00670.x · Cited by 27
“dopamine (Axelrod and Tomchick 1958), and dysfunction of central dopamine neurotransmission plays a key role in the pathogenesis of schizophrenia (Davis et al.”
Background
A simplified characterization of S-adenosyl- l -methionine-consuming enzymes with 1-Step EZ-MTase: a universal and straightforward coupled-assay for in vitro and in vivo setting
Burgos, E. S., Walters, R. O., Huffman, D. M., & Shechter, D. (2017) · Chemical Science · doi:10.1039/c7sc02830j · Cited by 26
Tyrosine hydroxylase in human adrenal glands and human pheochromocytoma
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CATECHOL-O-METHYL TRANSFERASE AND MONOAMINE OXIDASE ACTIVITY IN THE OCULAR TISSUES OF ALBINO RABBITS.
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Selective Para- or Meta-O-Methylation with Catechol O-Methyl Transferase from Rat Liver
Masri, M. S., ROBBINS, D. J., Emerson, O. H., & DeEds, F. (1964) · Nature · doi:10.1038/202878a0 · Cited by 27
THE CATECHOL ESTROGEN, 2‐HYDROXYESTRADIOL, INHIBITS CATECHOL‐O‐METHYLTRANSFERASE ACTIVITY IN NEUROBLASTOMA CELLS
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Catechol O-methyltransferase The para- and meta-O-methylations of noradrenaline
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“Catechol-O-methyl transference (COMT) encodes a catabolic enzyme involved in the degradation of dopamine [3].”
Background
Fragment-Based Calculations of Enzymatic Thermochemistry Require Dielectric Boundary Conditions
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“Co(II) and Mn(II), on the other hand, are most effective in catalysis [3].”
BackgroundInfluential
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Eagon, P. K., Willett, J. E., Seguiti, S. M., Appler, M. L., Gavaler, J. S., & Thiel, D. H. V. (1987) · Gastroenterology · doi:10.1016/0016-5085(87)90240-x · Cited by 26
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“The principle of the method and detailed procedures are described by Peuler and Johnson (29), Axelrod and Tomchick (30), and Michaels et al. (31).”
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“The enzyme, which metabolizes catecholamines and catechol-estrogens in the CNS and periphery, was discovered by Julius Axelrod in the late 1950s, contributing to his share of the 1970 Nobel Prize for Physiology or Medicine (Axelrod and Tomchick, 1958). COMT soon captured the attention of pioneering biological psychiat…”
Influential
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“…no activity on 5-hydroxy anthranilic acid could be observed (Figure 1), likely because the missing second hydroxy group in the ortho position is essential for the reaction, as also described for OMTs in the catechol metabolism (Axelrod and Tomchick, 1958, 1958; Mannisto and Kaakkola, 1999).”
Background
Systems Pharmacogenomics – Gene, Disease, Drug and Placebo Interactions: A Case Study in COMT
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“The endogenous substrates of COMT include the catecholamine neurotransmitters and the hormones dopamine, norepinephrine, and epinephrine (Table 1) [2].”
Background
Development of a PC12 Cell Based Assay for Screening Catechol- O -methyltransferase Inhibitors
Zhang, G., Buchler, I. P., Depasquale, M. J., Wormald, M., Liao, G., Wei, H., Barrow, J. C., & Carr, G. V. (2019) · ACS Chemical Neuroscience · doi:10.1021/acschemneuro.9b00395 · Cited by 26
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“COMT enzyme catalyzes the inactivation of catecholamines, including adrenaline, noradrenaline and dopamine (Axelrod and Tomchick, 1958).”
Background
Induction of emesis inSuncus murinusby pyrogallol, a generator of free radicals
Torii, Y., Saitō, H., & Matsuki, N. (1994) · British Journal of Pharmacology · doi:10.1111/j.1476-5381.1994.tb14753.x · Cited by 25
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“The superior in vivo efficacy, coupled with high recovery (81% within 6 h) of the drug in the urine of mice (unpublished data), suggests that BO-1341 may not be appreciably metabolized by an enzyme such as catechol 0-methyl transferase (1).”
Background
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Hagan, R. M., Raxworthy, M. J., & Gulliver, P. A. (1980) · Biochemical Pharmacology · doi:10.1016/0006-2952(80)90574-2 · Cited by 25
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Urine of Children with Sympathetic Tumors
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Catechol‐O‐methyltransferaseVal158Metpolymorphism and clinical characteristics in first episode non‐affective psychosis
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“2. and its enzyme is directly involved in the catabolism of dopamine [Axelrod and Tomchick, 1958].”
Background
Analytical methodologies for sensing catechol-O-methyltransferase activity and their applications
Wang, F., Wang, P., Zhao, D., Gonzalez, F. J., Fan, Y., Xia, Y., Ge, G., & Yang, L. (2020) · Journal of Pharmaceutical Analysis · doi:10.1016/j.jpha.2020.03.012 · Cited by 24
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“studies have shown that ZDHHC8 polymorphisms might directly affect the susceptibility of schizophrenia in a gender-specific manner [Axelrod and Tomchick, 1958; Mukai et al., 2004].”
Background
Kinetics of Rat Brain and Liver Solubilized Membrane-Bound Catechol-O-Methyltransferase
Bonifácio, M. J., Vieira‐Coelho, M. A., Borges, N., & Soares-da-Silva, P. (2000) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.2000.2105 · Cited by 24
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Dacre, J. C., & Williams, R. T. (1968) · Journal of Pharmacy and Pharmacology · doi:10.1111/j.2042-7158.1968.tb09822.x · Cited by 24
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Caldwell, J., & Marsh, M. V. (1982) · Elsevier eBooks · doi:10.1016/b978-0-407-02322-2.50007-2 · Cited by 24
Human erythrocyte histamine N-methyltransferase: radiochemical microassay and biochemical properties
Loon, J. A. V., Pazmiño, P. A., & Weinshilboum, R. M. (1985) · Clinica Chimica Acta · doi:10.1016/0009-8981(85)90337-7 · Cited by 24
Assay of catechol O-methyltransferase by determination of the m- and p-O-methylated products using high-performance liquid chromatography
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The Metabolism of the Catecholamines (Clinical Implications)
COHEN, R. A., BRIDGERS, W. F., Axelrod, J., WEIL-MALHERBE, H., LABROSSE, E. H., Bunney, W. E., CARDON, P. V., & KETY, S. S. (1962) · Annals of Internal Medicine · doi:10.7326/0003-4819-56-6-960 · Cited by 24
Role of Neurochemicals in Schizophrenia
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Haplotype analysis of the COMT‐ARVCF gene region in Israeli anorexia nervosa family trios
Michaelovsky, E., Frisch, A., Leor, S., Stein, D. J., Danziger, Y., Carel, C. A., Fennig, S., Mimouni, M., Klauck, S. M., Benner, A., et al. (2005) · American Journal of Medical Genetics Part B Neuropsychiatric Genetics · doi:10.1002/ajmg.b.30230 · Cited by 23
“The COMT gene (OMIM #116790; GDB: 119795) encodes an enzyme (catechol-O-methyltransferase, EC 2.1.1.6) that participates in the catabolism of brain catecholamine neurotransmitters such as dopamine and norepinephrine [Axelrod and Tomchick, 1958].”
BackgroundInfluential
Semisynthetic .BETA.-lactam antibiotics. II. Effect on antibacterial activity of ureido N-substituents in the 6-((R)-2-(3-(3,4-dihydroxybenzoyl)-1-ureido)-2-phenylacetamido)penicillanic acids.
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Catecholamines
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Radioenzymatic assay of plasma adrenaline and noradrenaline: evidence for a catechol-O-methyltransferase (COMT) inhibiting factor associated with essential hypertension
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The metabolism of bufuralol: Urinary metabolite profiles in rat, dog and man
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COMT Val158Met modulates subjective responses to intravenous nicotine and cognitive performance in abstinent smokers
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Evaluation of COMT Gene rs4680 Polymorphism as a Risk Factor for Endometrial Cancer
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“Methylation process increases the concentrations of 4-methoxyestradiol (4-MeOE2) and 2-methoxyestradiol (2-MeO-E2),out of which 2-MeO-E2 possess anti-proliferative, cytotoxic and apoptotic activity therefore decreasing the potential for DNA damage and tumorogenesis [8, 48].”
Background
The role of methionine in regulating folate-dependent reactions in isolated rat hepatocytes
Billings, R. E., Noker, P. E., & Tephly, T. R. (1981) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(81)90129-6 · Cited by 22
Dopamine–glutamate abnormalities in the frontal cortex associated with the catechol-O-methyltransferase (COMT) in schizophrenia
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Sympathoadrenal and adrenal hormonal responses of newborn calves to hypothermia.
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Effect of training on hormonal responses to exercise in competitive swimmers
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“Catechol-o-methyl transferase was isolated from rat liver by the method of Axelrod and Tomchick [2].”
Method
Opossum kidney (OK) cells in culture synthesize and degrade the natriuretic hormone dopamine: A comparison with rat renal tubular cells
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Increase in response and number of α-adrenoceptors of rat vas deferens on brief pretreatment with an α-agonist
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Assay for catechol-o-methyltransferase in erythrocytes using a new fluorogenic substrate, 2-(3,4-dihydroxyphenyl)naphtho[1,2-d]thiazole
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N- and O-Methylation
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The Basic Constituents of Toad Venoms
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Assay for catechol-o-methyltransferase by high-performance liquid chromatography with fluorescence detection
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Radiometric Micromethods for the Study of Some Amino Acid Decarboxylases
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INHIBITION OF MONOAMINE OXIDASE BY 2‐METHYL‐3‐PIPERIDINOPYRAZINE
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Authors: Axelrod, J., & Tomchick, R.
Affiliations: United States Public Health Service (US)
Venue: Journal of Biological Chemistry
Publisher: Elsevier BV
Published: 1958-09
Volume: 233
Issue: 3
Pages: 702-705
ISSN: 0021-9258 (ISSN-L)
DOI: 10.1016/s0021-9258(18)64731-3
OpenAlex: W1543624067
Cited by: 1,283
References: 16
Citations by year: 2026: 6 · 2025: 8 · 2024: 8 · 2023: 12 · 2022: 14 · 2021: 19 · 2020: 11 · 2019: 16 · 2018: 13 · 2017: 15 · 2016: 28 · 2015: 12 · 2014: 14 · 2013: 19 · 2012: 21
FWCI: 55.85
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
creativecommons.org/licenses/by/4.0/ (vor, 22705 d)
Locations: Journal of Biological Chemistry (publishedVersion, cc-by)
PubMed (publishedVersion)
Topics: Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Microbial metabolism and enzyme function
Keywords: epinephrine, catechol, O-methylation, enzymatic methylation, catecholamine metabolism
MeSH terms: Catechols, Epinephrine, Methylation, Norepinephrine, Transferases

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Enzymatic O-Methylation of Epinephrine and Other Catechols

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