Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1988 Dec 15;256(3):911–915. doi: 10.1042/bj2560911

Oxidation of 3-amino-1-phenylprop-1-enes by monoamine oxidase and their use in a continuous assay of the enzyme.

C H Williams 1, J Lawson 1, F R Backwell 1
PMCID: PMC1135502  PMID: 3223960

Abstract

3-Amino-1-phenylprop-1-ene (cinnamylamine) and some derivatives were examined as substrates for monoamine oxidases A and B in mitochondria. All of the amines examined were readily oxidized by monoamine oxidase B but much less readily by monoamine oxidase A. E-Cinnamylamine was found to have Km 0.025 mM and Vmax. 3.9 nmol/min per mg of mitochondrial protein. Corresponding values with monoamine oxidase A were 0.026 mM and 0.85 nmol/min per mg respectively. Despite their different stereochemistry, E- and Z-N-methylcinnamylamines were almost equally effective as substrates for monoamine oxidase B. The characteristic u.v. absorbance and high absorption coefficient of cinnamaldehyde, the product produced by enzymic oxidation of cinnamylamine, is utilized in a sensitive continuous spectrophotometric assay for both enzymes in the rat and for the assay of a purified monoamine oxidase B from bovine liver.

Full text

PDF
911

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BELLEAU B., MORAN J. Deuterium isotope effects in relation to the chemical mechanism of monoamine oxidase. Ann N Y Acad Sci. 1963 Jul 8;107:822–839. doi: 10.1111/j.1749-6632.1963.tb13326.x. [DOI] [PubMed] [Google Scholar]
  2. CIGNARELLA G., OCCELLI E., TESTA E. BICYCLIC HOMOLOGS OF PIPERAZINE. VII. SYNTHESIS AND ANALGESIC ACTIVITY OF 3-ARALKENYL-8-PROPIONYL-3,8-DIAZABICYCLO(3.2.1)OCTANES. J Med Chem. 1965 May;8:326–331. doi: 10.1021/jm00327a010. [DOI] [PubMed] [Google Scholar]
  3. Fowler C. J., Tipton K. F. Deamination of 5-hydroxytryptamine by both forms of monoamine oxidase in the rat brain. J Neurochem. 1982 Mar;38(3):733–736. doi: 10.1111/j.1471-4159.1982.tb08692.x. [DOI] [PubMed] [Google Scholar]
  4. Hiebert C. K., Silverman R. B. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogues. Inactivation of monoamine oxidase by conformationally rigid analogues of N,N-dimethylcinnamylamine. J Med Chem. 1988 Aug;31(8):1566–1570. doi: 10.1021/jm00403a013. [DOI] [PubMed] [Google Scholar]
  5. Houslay M. D., Tipton K. F. A kinetic evaluation of monoamine oxidase activity in rat liver mitochondrial outer membranes. Biochem J. 1974 Jun;139(3):645–652. doi: 10.1042/bj1390645. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Houslay M. D., Tipton K. F. The nature of the electrophoretically separable multiple forms of rat liver monoamine oxidase. Biochem J. 1973 Sep;135(1):173–186. doi: 10.1042/bj1350173. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Johnston J. P. Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem Pharmacol. 1968 Jul;17(7):1285–1297. doi: 10.1016/0006-2952(68)90066-x. [DOI] [PubMed] [Google Scholar]
  8. Knoll J., Magyar K. Some puzzling pharmacological effects of monoamine oxidase inhibitors. Adv Biochem Psychopharmacol. 1972;5:393–408. [PubMed] [Google Scholar]
  9. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  10. Salach J. I. Monoamine oxidase from beef liver mitochondria: simplified isolation procedure, properties, and determination of its cysteinyl flavin content. Arch Biochem Biophys. 1979 Jan;192(1):128–137. doi: 10.1016/0003-9861(79)90078-x. [DOI] [PubMed] [Google Scholar]
  11. Severina I. S. On the substrate-binding sites of the active centre of mitochondrial monoamine oxidase. Eur J Biochem. 1973 Oct 5;38(2):239–246. doi: 10.1111/j.1432-1033.1973.tb03055.x. [DOI] [PubMed] [Google Scholar]
  12. Simon D. Z., Salvador R. L., Champagne G. Acetylenics. 1. Aromatic amines containing the acetylenic triple bond. J Med Chem. 1970 Nov;13(6):1249–1250. doi: 10.1021/jm00300a068. [DOI] [PubMed] [Google Scholar]
  13. Squires R. F. Additional evidence for the existence of several forms of mitochondrial monoamine oxidase in the mouse. Biochem Pharmacol. 1968 Jul;17(7):1401–1409. doi: 10.1016/0006-2952(68)90076-2. [DOI] [PubMed] [Google Scholar]
  14. TABOR C. W., TABOR H., ROSENTHAL S. M. Purification of amine oxidase from beef plasma. J Biol Chem. 1954 Jun;208(2):645–661. [PubMed] [Google Scholar]
  15. WEISSBACH H., SMITH T. E., DALY J. W., WITKOP B., UDENFRIEND S. A rapid spectrophotometric assay of mono-amine oxidase based on the rate of disappearance of kynuramine. J Biol Chem. 1960 Apr;235:1160–1163. [PubMed] [Google Scholar]
  16. Williams C. H. A new specific inhibitor of monoamine oxidase A. Biochem Pharmacol. 1982 Jul 1;31(13):2305–2307. doi: 10.1016/0006-2952(82)90121-6. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES