Adduct formation between the carcinogen N-acetoxy-2-acetylaminofluorene and synthetic polydeoxyribonucleotides

Donald J. Harvan; J. Ronald Hass; Michael W. Lieberman

doi:10.1016/0009-2797(77)90085-0

Adduct formation between the carcinogen N-acetoxy-2-acetylaminofluorene and synthetic polydeoxyribonucleotides

Donald J. Harvan, J. Ronald Hass, Michael W. Lieberman

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The chemical carcinogen N-acetoxy-2-acetylaminofluorene (NA-AAF) was reacted with poly(dG-dC) · poly(dG-dC); poly dG · poly dC; poly(dA-dT) · poly(dA-dT); and poly dA · poly dT under a variety of conditions. Poly(dG-dC) · poly(dG-dC) was found to be 1.5-3 times more reactive than the homo GC polymer and 10-20 more reactive than the A + T polymers. Lowering the ionic strength increased the extent of reaction, while pH change (8.9 vs. 5.5) had only a small effect. If ionic strength was adjusted so that the two guanine-containing polymers showed equal thermal stability (as judged by T_m) then the alternating copolymer was 7 times as reactive as the homopolymer. In agreement with previous investigators, the major product was found to be 8-(N-2-fluorenylacetamido) deoxyguanosine.

Original language	English (US)
Pages (from-to)	203-210
Number of pages	8
Journal	Chemico-Biological Interactions
Volume	17
Issue number	2
DOIs	https://doi.org/10.1016/0009-2797(77)90085-0
State	Published - May 1977

ASJC Scopus subject areas

Toxicology

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@article{58bf3932c5c3420e920bb1abd6273741,

title = "Adduct formation between the carcinogen N-acetoxy-2-acetylaminofluorene and synthetic polydeoxyribonucleotides",

abstract = "The chemical carcinogen N-acetoxy-2-acetylaminofluorene (NA-AAF) was reacted with poly(dG-dC) · poly(dG-dC); poly dG · poly dC; poly(dA-dT) · poly(dA-dT); and poly dA · poly dT under a variety of conditions. Poly(dG-dC) · poly(dG-dC) was found to be 1.5-3 times more reactive than the homo GC polymer and 10-20 more reactive than the A + T polymers. Lowering the ionic strength increased the extent of reaction, while pH change (8.9 vs. 5.5) had only a small effect. If ionic strength was adjusted so that the two guanine-containing polymers showed equal thermal stability (as judged by Tm) then the alternating copolymer was 7 times as reactive as the homopolymer. In agreement with previous investigators, the major product was found to be 8-(N-2-fluorenylacetamido) deoxyguanosine.",

author = "Harvan, {Donald J.} and Hass, {J. Ronald} and Lieberman, {Michael W.}",

note = "Funding Information: National Institutes of Health, National Institute of Environmental Health Sciences, P,O. Box 12233, Research Triangle Park, N.C. 27709 (U.S.A.) Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",

year = "1977",

month = may,

doi = "10.1016/0009-2797(77)90085-0",

language = "English (US)",

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journal = "Chemico-Biological Interactions",

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AU - Hass, J. Ronald

AU - Lieberman, Michael W.

N1 - Funding Information: National Institutes of Health, National Institute of Environmental Health Sciences, P,O. Box 12233, Research Triangle Park, N.C. 27709 (U.S.A.) Copyright: Copyright 2014 Elsevier B.V., All rights reserved.

PY - 1977/5

Y1 - 1977/5

N2 - The chemical carcinogen N-acetoxy-2-acetylaminofluorene (NA-AAF) was reacted with poly(dG-dC) · poly(dG-dC); poly dG · poly dC; poly(dA-dT) · poly(dA-dT); and poly dA · poly dT under a variety of conditions. Poly(dG-dC) · poly(dG-dC) was found to be 1.5-3 times more reactive than the homo GC polymer and 10-20 more reactive than the A + T polymers. Lowering the ionic strength increased the extent of reaction, while pH change (8.9 vs. 5.5) had only a small effect. If ionic strength was adjusted so that the two guanine-containing polymers showed equal thermal stability (as judged by Tm) then the alternating copolymer was 7 times as reactive as the homopolymer. In agreement with previous investigators, the major product was found to be 8-(N-2-fluorenylacetamido) deoxyguanosine.

AB - The chemical carcinogen N-acetoxy-2-acetylaminofluorene (NA-AAF) was reacted with poly(dG-dC) · poly(dG-dC); poly dG · poly dC; poly(dA-dT) · poly(dA-dT); and poly dA · poly dT under a variety of conditions. Poly(dG-dC) · poly(dG-dC) was found to be 1.5-3 times more reactive than the homo GC polymer and 10-20 more reactive than the A + T polymers. Lowering the ionic strength increased the extent of reaction, while pH change (8.9 vs. 5.5) had only a small effect. If ionic strength was adjusted so that the two guanine-containing polymers showed equal thermal stability (as judged by Tm) then the alternating copolymer was 7 times as reactive as the homopolymer. In agreement with previous investigators, the major product was found to be 8-(N-2-fluorenylacetamido) deoxyguanosine.

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Adduct formation between the carcinogen N-acetoxy-2-acetylaminofluorene and synthetic polydeoxyribonucleotides

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