Cell and microsome mediated binding of 7, 12-dimethylbenz(a)anthracene to DNA studied by fluorescence spectroscopy

V. Ivanovic; N. E. Geacintov; A. M. Jeffrey; P. P. Fu; R. G. Harvey; I. B. Weinstein

doi:10.1016/S0304-3835(78)93962-9

Cell and microsome mediated binding of 7, 12-dimethylbenz(a)anthracene to DNA studied by fluorescence spectroscopy

V. Ivanovic, N. E. Geacintov, A. M. Jeffrey, P. P. Fu, R. G. Harvey, I. B. Weinstein

Chemistry

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

Abstract

Fluorescence spectra of DNA isolated from hamster embryo cells incubated with 7, 12-dimethylbenz(a)anthracene, or DNA modified in a microsomal system by reaction with this carcinogen or its 7-hydroxymethyl derivative, were compared to various model compounds. The spectra indicate that the DMBA derivative bound to DNA, in all 3 cases, has a 9, 10-dimethylanthracene-like chromophore. They also provide the first evidence of the similarity in structure of the DNA-bound products between 7, 12-dimethylbenz(a)anthracene and its 7-hydroxymethyl derivative. Our results are consistent with an activation mechanism that involves saturation of the 1, 2, 3, 4-ring positions.

Original language	English (US)
Pages (from-to)	131-140
Number of pages	10
Journal	Cancer Letters
Volume	4
Issue number	C
DOIs	https://doi.org/10.1016/S0304-3835(78)93962-9
State	Published - 1978

ASJC Scopus subject areas

Oncology
Cancer Research

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10.1016/S0304-3835(78)93962-9

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@article{29859725a7124ca9bbaa767dcaab60cc,

title = "Cell and microsome mediated binding of 7, 12-dimethylbenz(a)anthracene to DNA studied by fluorescence spectroscopy",

abstract = "Fluorescence spectra of DNA isolated from hamster embryo cells incubated with 7, 12-dimethylbenz(a)anthracene, or DNA modified in a microsomal system by reaction with this carcinogen or its 7-hydroxymethyl derivative, were compared to various model compounds. The spectra indicate that the DMBA derivative bound to DNA, in all 3 cases, has a 9, 10-dimethylanthracene-like chromophore. They also provide the first evidence of the similarity in structure of the DNA-bound products between 7, 12-dimethylbenz(a)anthracene and its 7-hydroxymethyl derivative. Our results are consistent with an activation mechanism that involves saturation of the 1, 2, 3, 4-ring positions.",

author = "V. Ivanovic and Geacintov, {N. E.} and Jeffrey, {A. M.} and Fu, {P. P.} and Harvey, {R. G.} and Weinstein, {I. B.}",

note = "Funding Information: The authors wish to thank Drs. P. Vigny, M. Duquesne and P.L. Grover, as well as R.C. Moschel, W.M. Baird and A. Dipple for sharing their unpublished fluorescence data with us. We are grateful to Dr. J.W. Flesher for a sample of 7-OHM--12MBA and to Mr. Douglas Eisenberg for preparing the hamster embryo cell cultures. This research was supported by NCI Grant CA2-1111 and Contract CP2-3234 to I.B.W,; by ERDA Contract E(11-1)2386 to N.E.G.; and by ACS Grant BC-132B and NCI Grant 19448 to R.G.H.",

year = "1978",

doi = "10.1016/S0304-3835(78)93962-9",

language = "English (US)",

volume = "4",

pages = "131--140",

journal = "Cancer Letters",

issn = "0304-3835",

publisher = "Elsevier Ireland Ltd",

number = "C",

}

TY - JOUR

T1 - Cell and microsome mediated binding of 7, 12-dimethylbenz(a)anthracene to DNA studied by fluorescence spectroscopy

AU - Ivanovic, V.

AU - Geacintov, N. E.

AU - Jeffrey, A. M.

AU - Fu, P. P.

AU - Harvey, R. G.

AU - Weinstein, I. B.

N1 - Funding Information: The authors wish to thank Drs. P. Vigny, M. Duquesne and P.L. Grover, as well as R.C. Moschel, W.M. Baird and A. Dipple for sharing their unpublished fluorescence data with us. We are grateful to Dr. J.W. Flesher for a sample of 7-OHM--12MBA and to Mr. Douglas Eisenberg for preparing the hamster embryo cell cultures. This research was supported by NCI Grant CA2-1111 and Contract CP2-3234 to I.B.W,; by ERDA Contract E(11-1)2386 to N.E.G.; and by ACS Grant BC-132B and NCI Grant 19448 to R.G.H.

PY - 1978

Y1 - 1978

N2 - Fluorescence spectra of DNA isolated from hamster embryo cells incubated with 7, 12-dimethylbenz(a)anthracene, or DNA modified in a microsomal system by reaction with this carcinogen or its 7-hydroxymethyl derivative, were compared to various model compounds. The spectra indicate that the DMBA derivative bound to DNA, in all 3 cases, has a 9, 10-dimethylanthracene-like chromophore. They also provide the first evidence of the similarity in structure of the DNA-bound products between 7, 12-dimethylbenz(a)anthracene and its 7-hydroxymethyl derivative. Our results are consistent with an activation mechanism that involves saturation of the 1, 2, 3, 4-ring positions.

AB - Fluorescence spectra of DNA isolated from hamster embryo cells incubated with 7, 12-dimethylbenz(a)anthracene, or DNA modified in a microsomal system by reaction with this carcinogen or its 7-hydroxymethyl derivative, were compared to various model compounds. The spectra indicate that the DMBA derivative bound to DNA, in all 3 cases, has a 9, 10-dimethylanthracene-like chromophore. They also provide the first evidence of the similarity in structure of the DNA-bound products between 7, 12-dimethylbenz(a)anthracene and its 7-hydroxymethyl derivative. Our results are consistent with an activation mechanism that involves saturation of the 1, 2, 3, 4-ring positions.

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U2 - 10.1016/S0304-3835(78)93962-9

DO - 10.1016/S0304-3835(78)93962-9

M3 - Article

C2 - 417802

AN - SCOPUS:0018148126

SN - 0304-3835

VL - 4

SP - 131

EP - 140

JO - Cancer Letters

JF - Cancer Letters

IS - C

ER -

Cell and microsome mediated binding of 7, 12-dimethylbenz(a)anthracene to DNA studied by fluorescence spectroscopy

Abstract

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