Superoxide organic chemistry within the liposomal bilayer, part II: a correlation between location and chemistry

Free Radical Biology & Medicine
Michal AfriAryeh A Frimer

Abstract

Coumarin ester derivatives 1, substituted at C-4 and/or C-12 with alkyl chains, were synthesized and intercalated within DMPC liposomal bilayers. By correlating the 13C chemical shift with medium polarity [E(T)(30)], the relative location of these substrates within the liposomal bilayer was determined. The length of the alkyl chain substituents clearly influences the lipophilicity of the substrates and their location and orientation within the liposome: Superoxide readily saponifies the C-12 esteric linkage of 1, when this reaction site lies in a polar region of the liposome (E(T)(30) > 45 kcal/mol), to give the corresponding 7-hydroxy coumarin derivatives 2. However, when C-12 lies deeper and is hence less available to O(2)(*-), the lactonic carbon C-2, which lies in a shallower region (E(T)(30) = 43-49), is the preferred site for superoxide-mediated cleavage. When coumarin 1 is disubstituted with long chains at both C-12 and C-4, these derivatives lie deep within the bilayer and react only slowly with O(2)(*-). These results indicate there is indeed a correlation between location within the bilayer and substrate reactivity. Contrary to the suggestion of Dix and Aikens (Chem. Res. Toxicol.6:2-18; 1993) superoxide can penetrate...Continue Reading

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Citations

Mar 14, 2003·Free Radical Biology & Medicine·Leonard W VelsorEdward M Postlethwait
May 5, 2009·American Journal of Physiology. Lung Cellular and Molecular Physiology·Marco van der ToornDirk-Jan Slebos
Jan 30, 2008·Free Radical Biology & Medicine·Ayelet GamlielAryeh A Frimer
May 1, 2012·Journal of Chemical Theory and Computation·Markéta PaloncýováMichal Otyepka
Aug 9, 2008·Chemistry and Physics of Lipids·Yael CohenAryeh A Frimer
Jul 25, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Kazuo KobayashiMotonari Tsubaki
Jul 18, 2012·Journal of Liposome Research·Yael CohenAryeh A Frimer
Oct 8, 2013·Biochimica Et Biophysica Acta·Rodrigo M Cordeiro
Jun 3, 2016·Biological & Pharmaceutical Bulletin·Takahiro HorinouchiSoichi Miwa
May 7, 2010·Free Radical Biology & Medicine·Efrat BodnerAryeh A Frimer
Jan 15, 2014·The Journal of Physical Chemistry. B·Markéta PaloncýováMichal Otyepka
Jun 21, 2005·American Journal of Physiology. Heart and Circulatory Physiology·Anna K BrzezinskaWilliam M Chilian
Jul 13, 2018·Frontiers in Pharmacology·Dharmendra K YadavMi-Hyun Kim
Feb 12, 2019·Chemical Reviews·Kazuo Kobayashi

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