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Related Experiment Videos

Agmatine oxidation by copper amine oxidase.

Paolo Ascenzi1, Mauro Fasano, Maria Marino

  • 1Department of Biology, University Roma Tre, Rome, Italy. ascenzi@uniroma3.it

European Journal of Biochemistry
|February 16, 2002
PubMed
Summary

A novel compound, N-amidino-2-hydroxypyrrolidine, derived from agmatine oxidation, inhibits nitric oxide synthase (NOS) and trypsin. This agmatine derivative exhibits higher affinity for these enzymes than agmatine or clonidine.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Pharmacology

Background:

  • Agmatine is an endogenous amine with diverse physiological roles.
  • Copper amine oxidases catalyze the oxidation of various substrates, including agmatine.
  • Nitric oxide synthases (NOS) and trypsin are crucial enzymes in physiological processes.

Purpose of the Study:

  • To identify the oxidation product of agmatine catalyzed by Pisum sativum L. copper amine oxidase.
  • To investigate the inhibitory effects of the identified compound on NOS and trypsin.
  • To compare the binding affinity of the novel compound with agmatine and clonidine.

Main Methods:

  • Agmatine oxidation catalyzed by Pisum sativum L. copper amine oxidase.
  • Identification of the oxidation product using one- and two-dimensional (1)H-NMR spectroscopy.

Related Experiment Videos

  • Enzyme inhibition assays to determine inhibition constants (Ki) for NOS-I, NOS-II, and trypsin.
  • Radioligand binding assays to compare the displacement of [(3)H]clonidine from rat heart membranes.

    • Main Results:

    • N-amidino-2-hydroxypyrrolidine was identified as the oxidation product of agmatine.
    • N-amidino-2-hydroxypyrrolidine competitively inhibited NOS-I, NOS-II, and trypsin with Ki values in the micromolar range.
    • The novel compound demonstrated significantly higher affinity for NOS-I, NOS-II, and trypsin compared to agmatine and clonidine.
    • N-amidino-2-hydroxypyrrolidine and agmatine were more potent than clonidine in displacing [(3)H]clonidine from rat heart membranes.

    Conclusions:

    • N-amidino-2-hydroxypyrrolidine is a potent inhibitor of nitric oxide synthase and trypsin.
    • The study reveals a novel biologically active metabolite of agmatine.
    • These findings suggest potential therapeutic applications for N-amidino-2-hydroxypyrrolidine in conditions involving NOS or trypsin activity.