Potency ranking of triterpenoids as inducers of a cytoprotective enzyme and as inhibitors of a cellular inflammatory response via their electron affinity and their electrophilicity index

René V. Bensasson, Vincent Zoete, Gaston Berthier, Paul Talalay, Albena T. Dinkova-Kostova

Research output: Contribution to journalArticlepeer-review

Abstract

Electron affinity (EA) and electrophilicity index (ω) of 16 synthetic triterpenoids (TP), previously identified as inducers of cytoprotective enzymes and as inhibitors of cellular inflammatory responses, have been calculated by the molecular orbital method. Linear correlations were obtained by plotting the values of EA, as well as those of ω versus (i) the potencies of induction of NAD(P)H quinone reductase (NQO1, EC 1.6.99.2), a cytoprotective enzyme, expressed via the concentration of TP required to double the specific activity of NQO1 (CD value) and (ii) the values of their anti-inflammatory activity expressed via the IC-50 of TP for suppression of upregulation of inducible nitric oxide synthase (iNOS, EC 1.14.13.39), both previously experimentally determined. The observed correlations demonstrate quantitatively for a series of triterpenoids that their electrophilicity is a major factor determining their potency as inducers of the cytoprotective phase 2 response and as inhibitors of inflammatory processes.

Original languageEnglish (US)
Pages (from-to)118-126
Number of pages9
JournalChemico-Biological Interactions
Volume186
Issue number2
DOIs
StatePublished - Jul 2010

Keywords

  • Electron affinity
  • Inflammation
  • NAD(P)H-quinone oxidoreductase 1
  • Quantum chemical calculations
  • Structure-activity relationships

ASJC Scopus subject areas

  • Toxicology

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