Issue 11, 2002
From the journal:

Photochemical & Photobiological Sciences

Naphthoquinolizinium derivatives as a novel platform for DNA-binding and DNA-photodamaging chromophores

Giampietro Viola,*a   Milena Bressanini,ac   Nadia Gabellini,b   Daniela Vedaldi,a   Francesco Dall‘Acquaa  and  Heiko Ihmels*c  

* Corresponding authors

a Department of Pharmaceutical Sciences, via Marzolo 5, University of Padova, Italy
E-mail: giampietro.viola.1@unipd.it
Fax: (+39) 0498275366
Tel: (+39) 0498275705

b Department of Biological Chemistry, via G. Colombo 3, University of Padova, Italy

c Institute of Organic Chemistry, University of Würzburg, Am Hubland, Würzburg, Germany

Abstract

The association of the naphtho[1,2-b]quinolizinium bromide (5a) and naphtho[2,1-b]quinolizinium bromide (5b) with DNA and the propensity of these cationic arenes to damage DNA after UV-A irradiation have been studied. Spectrophotometric and fluorimetric titrations show that the two isomers 5a and 5b bind to DNA (K ≈ 105 M−1). The highest affinity was observed for GC base pairs. The mode of binding was investigated by CD and LD spectroscopy. Whereas quinolizinium 5a exclusively intercalates in DNA, the isomer 5b exhibits a deviation from perfect intercalation into the double helix. Moreover, efficient DNA damage was observed on UV-A irradiation in the presence of the quinolizinium salts. Primer extension analysis indicates that the photocleavage takes place preferentially at guanine-rich regions.

Graphical abstract: Naphthoquinolizinium derivatives as a novel platform for DNA-binding and DNA-photodamaging chromophores

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Article information

DOI
https://doi.org/10.1039/B204275D
Article type
Paper
Submitted
03 May 2002
Accepted
16 Sep 2002
First published
15 Oct 2002

Photochem. Photobiol. Sci., 2002,1, 882-889

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Naphthoquinolizinium derivatives as a novel platform for DNA-binding and DNA-photodamaging chromophores

G. Viola, M. Bressanini, N. Gabellini, D. Vedaldi, F. Dall‘Acqua and H. Ihmels, Photochem. Photobiol. Sci., 2002, 1, 882 DOI: 10.1039/B204275D

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