Synthesis of DNA interstrand cross-links using a photocaged nucleobase |
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Authors: | Hentschel Sarah Alzeer Jawad Angelov Todor Schärer Orlando D Luedtke Nathan W |
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Affiliation: | Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zürich (Switzerland) http://www.bioorganic-chemistry.com/ |
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Abstract: | The missing linking: BCNU is a chemotherapy drug that generates an ethylene bridge between N(1) of deoxyguanosine and N(3) of deoxycytidine. No synthesis of a DNA containing this moiety has been reported until now. A new strategy uses a photocaged nucleobase that, when released, generates a highly reactive intermediate which cross-links the opposing DNA strand in a manner analogous to BCNU (see scheme, NBOC=ortho-nitrobenzyloxycarbonyl). |
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Keywords: | alkylation DNA nitrosourea photocage |
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