This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via Google Scholar Google Scholar Articles by Wood, M. L. Articles by Garner, R. C. Search for Related Content PubMed PubMed Citation Articles by Wood, M. L. Articles by Garner, R. C.

Structural Characterization of the Major Adducts Obtained after Reaction of an Ultimate Carcinogen Aflatoxin B₁-Dichloride with Calf Thymus DNA in Vitro

Department of Chemistry [M. L. W., J. R. L. S.], and Cancer Research Unit, [R. C. G.], University of York, Heslington, York Y01 5DD, United Kingdom

The major adduct formed on acid hydrolysis of calf thymus DNA which has been reacted with 8,9-dichloro-8,9-dihydroaflatoxin B₁, a chemical model of the ultimate carcinogen 8,9-dihydro-8,9-epoxyaflatoxin B₁ (AFB₁-epoxide), has been characterized by proton nuclear magnetic resonance and fast atom bombardment mass spectroscopy. This adduct has been identified as an N7-substituted guanine adduct analogous to that formed on reaction of AFB₁-8,9-epoxide with DNA in vivo and in vitro, namely trans-8,9-dihydro-8-(7-guanyl)-9-hydroxy AFB₁. This 8,9-dichloro-8,9-dihydroaflatoxin B₁ adduct in DNA, like its equivalent AFB₁-epoxide adduct, is prone to quantitative imidazole ring opening of the substituted guanine in mildly alkaline conditions and to substantial depurination under mildly acidic conditions.

¹ Current address: Department of Applied Biological Sciences, Massachusetts Institute of Technology, Cambridge, MA 02139.

² To whom requests for reprints should be addressed.

Received 3/19/87. Revised 2/ 8/88. Accepted 6/21/88.