Selective alkylation of carcinogenic 9-anthryloxirane at the N-3 position of adenine in DNA.

Abstract:

:Carcinogenic 9-anthryloxirane binds covalently to calf thymus DNA and poly(dA-dT). Application of the technique for DNA sequence determination shows that acid cleavage of the modified DNA frees approximately half of the anthryl groups from the DNA. HPLC analysis indicates that an adenine adduct and the glycol derived from 9-anthryloxirane are the major acid-labile products. Spectroscopic analyses establish that the adenine adduct is the N-3 adduct of 9-anthryloxirane to adenine. Similar analyses of modified poly(dA-dT) indicate that the binding of 9-anthryloxirane takes place selectively at the N-3 position of adenine. The significance of this finding is briefly discussed.

authors

Yang NC,Chang CW

doi

10.1073/pnas.82.16.5250

subject

Has Abstract

pub_date

1985-08-01 00:00:00

pages

5250-4

issue

16

eissn

0027-8424

issn

1091-6490

journal_volume

82

pub_type

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