Melatonin: Free Radicals and Metabolites Resulting by Emission and Consumption of Solvated Electrons (eaq-): Reaction Mechanisms

In Vivo. 2015 Sep-Oct;29(5):605-9.

Abstract

Background/aim: Melatonin not only regulates circadian rhythm, but also induces apoptosis in tumor cells. Hence, elucidation of the basic reaction mechanisms of melatonin and its metabolites is a matter of interest.

Material and methods: Melatonin dissolved in a mixture of water/ethanol=40/60 form associates (unstable complexes). For simulation of biological processes, melatonin was excited by UV light into the singlet state.

Results: By using monochromatic UV light (λ=254 nm) melatonin ejects solvated electrons (eaq (-)), a part of which is scavenged by melatonin in ground state contained in the associates. Consequently, with increase of melatonin concentration a decrease of the determined quantum yield of emitted eaq (-), Q(eaq (-)), is obtained. The complex molecular structure of melatonin contains functional groups which can emit eaq (-), as well such consuming eaq (-). As a succession of these processes various types of metabolites are generated, as well as degradation products, with lower molecular weight, are formed.

Conclusion: Not melatonin per se, but the ejected eaq (-) and thereby resulting various metabolites are responsible for different biological properties of melatonin.

Keywords: Melatonin; free radicals; metabolites; solvated electrons.

MeSH terms

  • Algorithms
  • Antioxidants / chemistry*
  • Electrons
  • Free Radicals / chemistry
  • Melatonin / chemistry*
  • Models, Chemical
  • Molecular Structure

Substances

  • Antioxidants
  • Free Radicals
  • Melatonin