TY - JOUR
T1 - Conformations of adducts and kinetics of binding to DNA of the optically pure enantiomers of anti-benzo(a)pyrene diol epoxide
AU - Geacintov, Nicholas E.
AU - Yoshida, Hiroko
AU - Ibanez, Victor
AU - Jacobs, Stephen A.
AU - Harvey, Ronald G.
N1 - Funding Information:
We thank Dr. Y. Mnyukh for performing the linear dichroism This research was supported by the Department of Energy (Contract 78EVO4959 and in part by Contract E(ll-1) 23661, and in part Public Health Service, Grant No. CA20851 awarded by the National tute, Department of Health and Human Services. The preparation tiomers of anti BaPDE at the University of Chicago was supported American Cancer Society (Grant BC-132), by the Public Health Grants No. CA09183 and CA14599 awarded by the Cancer Department Health and Human Services.
PY - 1984/7/18
Y1 - 1984/7/18
N2 - Kinetic flow dichroism studies indicate that the (+) enantiomer of 7β, 8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene physically bound at intercalative-type sites in double-stranded DNA undergoes covalent binding reactions to form adducts at external binding sites. The conformation of the non-covalent complex derived from the (-) stereoisomer is also intercalative in nature, but the conformations of the covalent adducts are heterogeneous and are characterized by both intercalative-type and external conformations. It is suggested that the distinctly higher biological activity of the (+) enantiomer relative to the activity of the (-) enantiomer may be related to the preponderance of 7,8,9-triol benzo(a)pyrene residues covalently linked to deoxyguanine and located at external binding sites in the DNA adducts.
AB - Kinetic flow dichroism studies indicate that the (+) enantiomer of 7β, 8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene physically bound at intercalative-type sites in double-stranded DNA undergoes covalent binding reactions to form adducts at external binding sites. The conformation of the non-covalent complex derived from the (-) stereoisomer is also intercalative in nature, but the conformations of the covalent adducts are heterogeneous and are characterized by both intercalative-type and external conformations. It is suggested that the distinctly higher biological activity of the (+) enantiomer relative to the activity of the (-) enantiomer may be related to the preponderance of 7,8,9-triol benzo(a)pyrene residues covalently linked to deoxyguanine and located at external binding sites in the DNA adducts.
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U2 - 10.1016/0006-291X(84)90435-2
DO - 10.1016/0006-291X(84)90435-2
M3 - Article
C2 - 6430294
AN - SCOPUS:0021281074
SN - 0006-291X
VL - 122
SP - 33
EP - 39
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
IS - 1
ER -