Literature DB >> 24380377

Unusual kinetic isotope effects of deuterium reinforced polyunsaturated fatty acids in tocopherol-mediated free radical chain oxidations.

Connor R Lamberson1, Libin Xu, Hubert Muchalski, J Rafael Montenegro-Burke, Vadim V Shmanai, Andrei V Bekish, John A McLean, Catherine F Clarke, Mikhail S Shchepinov, Ned A Porter.   

Abstract

Substitution of -CD2- at the reactive centers of linoleic and linolenic acids reduces the rate of abstraction of D by a tocopheryl radical by as much as 36-fold, compared to the abstraction of H from a corresponding -CH2- center. This H atom transfer reaction is the rate-determining step in the tocopherol-mediated peroxidation of lipids in human low-density lipoproteins, a process that has been linked to coronary artery disease. The unanticipated large kinetic isotope effects reported here for the tocopherol-mediated oxidation of linoleic and linolenic acids and esters suggests that tunneling makes this process favorable.

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Year:  2014        PMID: 24380377      PMCID: PMC4578730          DOI: 10.1021/ja410569g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  27 in total

1.  Temperature-dependent isotope effects in soybean lipoxygenase-1: correlating hydrogen tunneling with protein dynamics.

Authors:  Michael J Knapp; Keith Rickert; Judith P Klinman
Journal:  J Am Chem Soc       Date:  2002-04-17       Impact factor: 15.419

2.  Linking protein structure and dynamics to catalysis: the role of hydrogen tunnelling.

Authors:  Judith P Klinman
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2006-08-29       Impact factor: 6.237

Review 3.  Cholesterol, reactive oxygen species, and the formation of biologically active mediators.

Authors:  Robert C Murphy; Kyle M Johnson
Journal:  J Biol Chem       Date:  2008-02-19       Impact factor: 5.157

4.  Equivalent lipid oxidation profiles in advanced atherosclerotic lesions of carotid endarterectomy plaques obtained from symptomatic type 2 diabetic and nondiabetic subjects.

Authors:  Krishna Kathir; Joanne M Dennis; Kevin D Croft; Trevor A Mori; Antony K Lau; Mark R Adams; Roland Stocker
Journal:  Free Radic Biol Med       Date:  2010-05-15       Impact factor: 7.376

Review 5.  Free radical lipid peroxidation: mechanisms and analysis.

Authors:  Huiyong Yin; Libin Xu; Ned A Porter
Journal:  Chem Rev       Date:  2011-08-23       Impact factor: 60.622

Review 6.  Reactive oxygen species, isotope effect, essential nutrients, and enhanced longevity.

Authors:  Mikhail S Shchepinov
Journal:  Rejuvenation Res       Date:  2007-03       Impact factor: 4.663

Review 7.  Molecular action of vitamin E in lipoprotein oxidation: implications for atherosclerosis.

Authors:  S R Thomas; R Stocker
Journal:  Free Radic Biol Med       Date:  2000-06-15       Impact factor: 7.376

8.  Isotope-reinforced polyunsaturated fatty acids protect yeast cells from oxidative stress.

Authors:  Shauna Hill; Kathleen Hirano; Vadim V Shmanai; Beth N Marbois; Dragoslav Vidovic; Andrei V Bekish; Bradley Kay; Vincent Tse; Jonathan Fine; Catherine F Clarke; Mikhail S Shchepinov
Journal:  Free Radic Biol Med       Date:  2010-10-16       Impact factor: 7.376

9.  Nitroxyl radical plus hydroxylamine pseudo self-exchange reactions: tunneling in hydrogen atom transfer.

Authors:  Adam Wu; Elizabeth A Mader; Ayan Datta; David A Hrovat; Weston Thatcher Borden; James M Mayer
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

10.  Kinetic study of the phthalimide N-oxyl radical in acetic acid. Hydrogen abstraction from substituted toluenes, benzaldehydes, and benzyl alcohols.

Authors:  Nobuyoshi Koshino; Basudeb Saha; James H Espenson
Journal:  J Org Chem       Date:  2003-11-28       Impact factor: 4.354

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  11 in total

Review 1.  Emerging therapies in Friedreich's ataxia.

Authors:  Tanya V Aranca; Tracy M Jones; Jessica D Shaw; Joseph S Staffetti; Tetsuo Ashizawa; Sheng-Han Kuo; Brent L Fogel; George R Wilmot; Susan L Perlman; Chiadi U Onyike; Sarah H Ying; Theresa A Zesiewicz
Journal:  Neurodegener Dis Manag       Date:  2016

2.  Tunneling in tocopherol-mediated peroxidation of 7-dehydrocholesterol.

Authors:  H Muchalski; L Xu; N A Porter
Journal:  Org Biomol Chem       Date:  2014-12-01       Impact factor: 3.876

3.  Desmosterolosis and desmosterol homeostasis in the developing mouse brain.

Authors:  Luke B Allen; Thiago C Genaro-Mattos; Ned A Porter; Károly Mirnics; Zeljka Korade
Journal:  J Inherit Metab Dis       Date:  2019-04-08       Impact factor: 4.982

Review 4.  Free radical oxidation of cholesterol and its precursors: Implications in cholesterol biosynthesis disorders.

Authors:  L Xu; N A Porter
Journal:  Free Radic Res       Date:  2014-12-09

5.  Deuterium-Reinforced Polyunsaturated Fatty Acids Prevent Diet-Induced Nonalcoholic Steatohepatitis by Reducing Oxidative Stress.

Authors:  Haoran Li; Ouyang Zhang; Chenmin Hui; Yaxin Huang; Hengrong Shao; Menghui Song; Lingjia Gao; Shengnan Jin; Chunming Ding; Liang Xu
Journal:  Medicina (Kaunas)       Date:  2022-06-12       Impact factor: 2.948

6.  Deuterium-reinforced polyunsaturated fatty acids improve cognition in a mouse model of sporadic Alzheimer's disease.

Authors:  Ahmed Elharram; Nicole M Czegledy; Michael Golod; Ginger L Milne; Erik Pollock; Brian M Bennett; Mikhail S Shchepinov
Journal:  FEBS J       Date:  2017-10-27       Impact factor: 5.542

Review 7.  Possible Mechanisms of Biological Effects Observed in Living Systems during 2H/1H Isotope Fractionation and Deuterium Interactions with Other Biogenic Isotopes.

Authors:  Alexander Basov; Liliya Fedulova; Ekaterina Vasilevskaya; Stepan Dzhimak
Journal:  Molecules       Date:  2019-11-13       Impact factor: 4.411

8.  Is There an Optimal Combination of AREDS2 Antioxidants Zeaxanthin, Vitamin E and Vitamin C on Light-Induced Toxicity of Vitamin A Aldehyde to the Retina?

Authors:  Małgorzata B Różanowska; Barbara Czuba-Pełech; Bartosz Różanowski
Journal:  Antioxidants (Basel)       Date:  2022-06-09

9.  Reactivities and products of free radical oxidation of cholestadienols.

Authors:  Libin Xu; Ned A Porter
Journal:  J Am Chem Soc       Date:  2014-03-26       Impact factor: 15.419

10.  Resolving the Role of Lipoxygenases in the Initiation and Execution of Ferroptosis.

Authors:  Ron Shah; Mikhail S Shchepinov; Derek A Pratt
Journal:  ACS Cent Sci       Date:  2018-02-07       Impact factor: 14.553

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