PMID: 9448752Feb 4, 1998Paper

Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models

Chemico-biological Interactions
J L BoltonJ A Thompson

Abstract

Quinone methides (QMs) are electrophiles formed in several biological processes including direct oxidations of 4-alkylphenols by cytochromes P450. These species may be responsible for the adverse effects of certain phenolic compounds through protein alkylation, but little information is available concerning specific targets or the resulting mechanisms of cell injury. The present goal was to determine the most likely sites of adduct formation among competing protein nucleophiles utilizing QMs of varying electrophilicity. Reactions of poorly reactive, moderately reactive, and highly reactive QMs, 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadienone (BHT-QM), 6-tert-butyl-2-(2'-hydroxyl-1',1'-dimethylethyl)-4-methylene- 2,5-cyclohexadienone (BHTOH-QM), and 2-tert-butyl-6-methyl-4-methylene-2,5-cyclohexadienone (BDMP-QM), respectively, were investigated in aqueous solutions with nucleophilic amino acids. Each QM rapidly formed a thioether derivative of cysteine with little or no competition from the addition of water (hydration). The alpha-amino groups were the primary sites of alkylation for all other amino acids examined including lysine, histidine, tyrosine, and serine, and the pseudo-first order rates were 5 to 8-fold greater tha...Continue Reading

References

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Citations

May 24, 2008·Glycobiology·Brian P Rempel, Stephen G Withers
Sep 4, 2012·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Chitra SridarPaul F Hollenberg
Apr 1, 2014·Journal of Controlled Release : Official Journal of the Controlled Release Society·Nadine HammerAchim M Goepferich
Dec 15, 2015·Evidence-based Complementary and Alternative Medicine : ECAM·Charu SharmaShreesh Ojha
Oct 31, 2009·Chemistry & Biology·Alvin R KingDaniele Piomelli
May 25, 2016·Journal of the American Chemical Society·Andrea K SteigerMichael D Pluth
Jun 22, 2016·Annals of the New York Academy of Sciences·Qinggeng ZhuangChristopher M Hadad
Nov 26, 2009·European Journal of Medicinal Chemistry·Sébastien MadonnaJean-Louis Kraus
Apr 25, 2014·The Journal of Organic Chemistry·Đani ŠkalameraNikola Basarić
Apr 26, 2014·Chemical Science·Selvanathan ArumugamVladimir V Popik
Jul 13, 2016·Angewandte Chemie·Tomohiro DouraYasuteru Urano
Sep 21, 2000·FEBS Letters·R H van den HeuvelW J van Berkel
Nov 16, 2007·Organic & Biomolecular Chemistry·Frank Brotzel, Herbert Mayr
Apr 20, 2010·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Jianyao WangRasmy Talaat
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Jun 20, 2003·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Donglu ZhangJames Mitroka
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Jan 18, 2020·Chemistry : a European Journal·Matthew M CerdaMichael D Pluth
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May 18, 2021·Chemical Communications : Chem Comm·Hiroki KashimaYasuteru Urano
Mar 16, 2011·Chemical Reviews·Johannes A H SchwöbelMark T D Cronin
Oct 31, 2018·Chemical Research in Toxicology·Amanda DegnerMargareta Törnqvist
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Mar 19, 2019·Chemical Research in Toxicology·Shane R ByrneSteven E Rokita
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