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J Phys Chem Lett. 2014 Aug 21;5(16):2916-21. doi: 10.1021/jz501523s. Epub 2014 Aug 13.

Dissociative Electron Attachment to Anthralin to Model Its Biochemical Reactions.

The journal of physical chemistry letters

Stanislav A Pshenichnyuk, Alexei S Komolov

Affiliations

  1. †Institute of Molecule and Crystal Physics, Ufa Research Centre, Russian Academy of Sciences, Prospe?t Oktyabrya 151, 450075 Ufa, Russia.
  2. ‡Physics Faculty, St. Petersburg State University, Uljanovskaja 1, 198504 St. Petersburg, Russia.

PMID: 26278099 DOI: 10.1021/jz501523s

Abstract

The antipsoriatic drug anthralin (dithranol) is known to be extensively accumulated inside mitochondria of keratinocytes and to interact with the electron flow of the respiratory chain. Primary products of the one-electron reduction of polyphenolic anthralin observed in vivo are its dehydrogenated anions, which are formed by H-atom abstraction. The same species are mainly generated at low electron energies by dissociative electron attachment (DEA) to anthralin molecules in vacuo. A likely mechanism for the biochemical transformations of anthralin under reductive conditions in vivo is hypothesized on the basis of its DEA properties. The involvement of excited electronic states generated by ultraviolet irradiation of skin is discussed.

Keywords: electron transfer; low-energy electron-molecule interaction; mitochondrial respiration chain; molecular mechanisms; xenobiotics

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