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Reaction mechanism in the photochemistry of the antileukaemic agents 2-chloro- and 2-bromo-2′-deoxyadenosine, studied by nanosecond laser flash photolysis

✍ Scribed by Barbara Czochralska; Lars Lindqvist

Publisher
Elsevier Science
Year
1999
Tongue
English
Weight
590 KB
Volume
50
Category
Article
ISSN
1011-1344

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✦ Synopsis

The reaction mechanism in the UV photochemistry of 2-chloro-2'-deoxyadenosine (Cladibrine) and 2-bromo-2'-deoxyadenosine in aqueous solution has been studied by laser photolysis at nanosecond time resolution. It is found that excitation at 266 nm wavelength produces heterolytic cleavage of the halogen-carbon bond by one-photon absorption and formation of the unstable 2-hydroxy tautomer of 2'-deoxyisoguanosine as predominant 'primary' product. The 2-hydroxy tautomer then transforms in 10-6-10-5 s into the stable 2-0~0 tautomer in an acid-base-catalysed reaction. A reaction mechanism is proposed and discussed in relation to previous UV low-intensity studies of these halogenodeoxyadenosines.

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