Antibody-catalyzed oxidative degradation of nicotine using riboflavin

Bioorganic & Medicinal Chemistry
Tobin J DickersonKim D Janda

Abstract

Tobacco abuse remains a major cause of death worldwide despite ample evidence linking nicotine to various disease states. Consequently, immunopharmacotherapeutic approaches for the treatment of nicotine abuse have received increasing attention. Although a number of nicotine-binding antibodies have been disclosed, no antibody catalysts exist which efficiently degrade nicotine into pharmacologically inactive substances. Herein, we report the first catalytic antibodies which can oxidatively degrade nicotine. These biocatalysts use the micronutrient riboflavin and visible light as a source of singlet oxygen for the production of reactive oxygen species. Along with various known nicotine metabolites, antibody-catalyzed nicotine oxidations produce two novel nicotine oxidation products that were also detected in control ozonation reactions of nicotine. The reaction is efficient, with multiple turnovers of catalyst observed and total consumption of nicotine attained. These results demonstrate the potential of harnessing riboflavin as an endogenous sensitizer for antibody-catalyzed oxidations and demonstrate a new approach for the development of an active vaccine for the treatment of nicotine addiction using in vivo catalytically active...Continue Reading

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Citations

May 25, 2011·Drug Design, Development and Therapy·José Juan Escobar-ChávezIsabel Marlen Rodríguez-Cruz
Mar 22, 2014·Biotechnology Letters·Séverine Padiolleau-LefèvreBérangère Avalle
Mar 16, 2007·Proceedings of the National Academy of Sciences of the United States of America·Yang XuKim D Janda
Mar 1, 2008·Expert Review of Clinical Pharmacology·David A Gorelick
May 2, 2008·Expert Opinion on Investigational Drugs·Erich H Cerny, Thomas Cerny
Jun 6, 2006·Biophysical Journal·Jürgen BaierWolfgang Bäumler
Jul 22, 2016·Human Vaccines & Immunotherapeutics·Marco Pravetoni
Jun 27, 2014·ACS Applied Materials & Interfaces·Osvaldo N OliveiraLuciano Caseli
Mar 6, 2007·Journal of the American Chemical Society·Andrew P BroganKim D Janda

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