The mechanism of guanine specific photooxidation in the presence of berberine and palmatine: activation of photosensitized singlet oxygen generation through DNA-binding interaction

Chemical Research in Toxicology
Kazutaka HirakawaToru Hirano

Abstract

The mechanism of DNA damage by photoexcited alkaloids, berberine and palmatine, was examined using 32P-labeled DNA fragments obtained from human genes. Berberine and palmatine easily bind to DNA, leading to the formation of strong fluorescent complexes. The binding constants of berberine and palmatine to DNA, estimated from an analysis of their fluorescence enhancements, indicate the formation of stable complexes. Photoexcited berberine and palmatine caused DNA cleavage, specifically at almost all guanine residues, under the aerobic condition after Escherichia coli formamidopyrimidine-DNA glycosylase or piperidine treatment, suggesting the formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodGuo), an oxidized product of 2'-deoxyguanosine, and further oxidized products. The formation of 8-oxodGuo was confirmed by HPLC measurement. The quantum yield of 8-oxodGuo formation by berberine was almost the same as that induced by palmatine. Berberine and palmatine did not cause DNA photodamage under anaerobic conditions. Scavengers of singlet oxygen (1O2), such as sodium azide and methional, inhibited DNA damage. These findings suggest that photoexcited berberine and palmatine give rise to 8-oxodGuo through 1O2 generation. The photos...Continue Reading

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Citations

Dec 6, 2008·Analytical and Bioanalytical Chemistry·Kazutaka Hirakawa
Dec 25, 2010·Photochemistry and Photobiology·Helmut GörnerLászló Biczók
Apr 7, 2011·Photochemistry and Photobiology·Kazutaka HirakawaYoshio Nosaka
May 16, 2007·Proceedings of the National Academy of Sciences of the United States of America·Gang ZhengBrian C Wilson
Apr 2, 2015·Luminescence : the Journal of Biological and Chemical Luminescence·Ran MiYan-Jun Hu
Nov 18, 2006·Phytochemistry·Lenka GrycováRadek Marek
Jan 16, 2010·Medicinal Research Reviews·Kakali Bhadra, Gopinatha Suresh Kumar
Sep 24, 2015·The Journal of Physical Chemistry. B·Kazutaka HirakawaShigetoshi Okazaki
Oct 1, 2008·Biochemical Pharmacology·Soo In BaeRobert M Snapka
Oct 3, 2006·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Sona JantovaSilvia Letasiova
Aug 15, 2006·Journal of Photochemistry and Photobiology. B, Biology·Sona JantováJuraj Lábaj
May 18, 2016·Photodiagnosis and Photodynamic Therapy·Juan WuQing-Juan Tang
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May 6, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Kazutaka Hirakawa, Hiroshi Segawa
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Feb 9, 2012·The Journal of Physical Chemistry. B·Kazutaka HirakawaYoshio Nosaka
Jun 1, 2007·Journal of Photochemistry and Photobiology. B, Biology·Kazutaka HirakawaHiroshi Segawa
Mar 1, 2014·Chemical Research in Toxicology·Kazutaka HirakawaShosuke Kawanishi
Oct 23, 2013·The Journal of Physical Chemistry. B·Kazutaka HirakawaShigetoshi Okazaki

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