PMID: 2493815Mar 24, 1989Paper

A new look at the rearrangement of adrenochrome under biomimetic conditions

Biochimica Et Biophysica Acta
A PalumboG Prota

Abstract

At physiological pH values, the rearrangement of adrenochrome leads, besides adrenolutin, to a major dimeric compound consisting of an adrenolutin moiety covalently linked to the angular 9-position of adrenochrome. When the reaction is carried out in air, the initially generated adrenolutin undergoes autoxidation to give 5,6-dihydroxy-1-methyl-isatin (DHMIs), which is smoothly oxidized to the 4,4'-dimer. Under an oxygen-depleted atmosphere, formation of these latter compounds is prevented, and the rearrangement of adrenochrome leads mainly to the adrenochrome dimer (about 50% yield) along with adrenolutin and 5,6-dihydroxy-1-methylindole (DHMI) in about 10% yield each. The product distribution is markedly dependent on the concentration of the aminochrome undergoing rearrangement, the nature of the buffer system used, and the pH of the medium. Heavy metal ions of common occurrence in biological systems, such as Cu2+, Zn2+, Co2+, significantly direct the reaction course towards the formation of adrenolutin, while Fe2+ and other cations with low redox potentials induce the almost exclusive formation of DHMI.

References

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Citations

Oct 1, 1992·Free Radical Biology & Medicine·A BindoliD J Deeble
Feb 18, 2016·Life Sciences·Thais Biondino Sardella GiornoPatricia Dias Fernandes
Feb 17, 2001·Nitric Oxide : Biology and Chemistry·M P RigobelloA Bindoli
Sep 23, 2016·International Journal of Molecular Sciences·Manickam Sugumaran
Oct 25, 2016·International Journal of Molecular Sciences·Manickam Sugumaran, Hanine Barek
Dec 13, 2012·Physical Chemistry Chemical Physics : PCCP·Bijan Kumar PaulNikhil Guchhait
Dec 2, 2000·Biochimica Et Biophysica Acta·K Polewski

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