Formation and Excision of Covalent Deoxyribonucleic Acid Adducts of Benzo[A]Pyrene 4, 5-Epoxide and Benzo[A]Pyrenediol Epoxide I in Human Lung Cells A549

George Feldman; Joyce Remsen; Tzu chien V. Wang; Peter Cerutti

doi:10.1021/bi00547a008

Formation and Excision of Covalent Deoxyribonucleic Acid Adducts of Benzo[A]Pyrene 4, 5-Epoxide and Benzo[A]Pyrenediol Epoxide I in Human Lung Cells A549

George Feldman, Joyce Remsen, Tzu chien V. Wang, Peter Cerutti

University of Florida

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

43 Scopus citations

Abstract

The formation and repair of covalent DNA adducts induced by the two ultimate benzo[a]pyrene (BP) metabolites 4, 5-dihydro-4, 5-epoxybenzo[zz]pyrene (BPE) and 7β, 8α-dihydroxy-9a, 10a-epoxy-7, 8, 9, 10-tetrahydrobenzo [a] -pyrene (BPDE I) were studied in human epithelioid lung cells A549. The covalent DNA adducts of BPE were characterized by reacting native DNA specifically labeled in a single deoxynucleoside with racemic BPE in vitro. From the chromatographic analysis of enzymatic hydrolysates of BPE-treated DNA, it was concluded that adducts to deoxyguanosine (BPE-dG) and deoxyadenosine (BPE-dA) were formed. No adducts to the pyrimidine nucleotides were detected. DNA adducts with the same chromatographic properties were formed upon treatment of intact A549 cells with BPE. Treatment of A549 cells with racemic BPDE I mostly produced (7R)-N²-(7β, 8α, 9α-trihydroxy-7, 8, 9, 10-tetrahydrobenzo [tz]pyren-10-yl)deoxyguanosine (BPDE I-dG).

Original language	English
Pages (from-to)	1095-1101
Number of pages	7
Journal	Biochemistry
Volume	19
Issue number	6
DOIs	https://doi.org/10.1021/bi00547a008
State	Published - 1980
Externally published	Yes

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title = "Formation and Excision of Covalent Deoxyribonucleic Acid Adducts of Benzo[A]Pyrene 4, 5-Epoxide and Benzo[A]Pyrenediol Epoxide I in Human Lung Cells A549",

abstract = "The formation and repair of covalent DNA adducts induced by the two ultimate benzo[a]pyrene (BP) metabolites 4, 5-dihydro-4, 5-epoxybenzo[zz]pyrene (BPE) and 7β, 8α-dihydroxy-9a, 10a-epoxy-7, 8, 9, 10-tetrahydrobenzo [a] -pyrene (BPDE I) were studied in human epithelioid lung cells A549. The covalent DNA adducts of BPE were characterized by reacting native DNA specifically labeled in a single deoxynucleoside with racemic BPE in vitro. From the chromatographic analysis of enzymatic hydrolysates of BPE-treated DNA, it was concluded that adducts to deoxyguanosine (BPE-dG) and deoxyadenosine (BPE-dA) were formed. No adducts to the pyrimidine nucleotides were detected. DNA adducts with the same chromatographic properties were formed upon treatment of intact A549 cells with BPE. Treatment of A549 cells with racemic BPDE I mostly produced (7R)-N2-(7β, 8α, 9α-trihydroxy-7, 8, 9, 10-tetrahydrobenzo [tz]pyren-10-yl)deoxyguanosine (BPDE I-dG).",

author = "George Feldman and Joyce Remsen and Wang, {Tzu chien V.} and Peter Cerutti",

year = "1980",

doi = "10.1021/bi00547a008",

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volume = "19",

pages = "1095--1101",

journal = "Biochemistry",

issn = "0006-2960",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Formation and Excision of Covalent Deoxyribonucleic Acid Adducts of Benzo[A]Pyrene 4, 5-Epoxide and Benzo[A]Pyrenediol Epoxide I in Human Lung Cells A549

AU - Feldman, George

AU - Remsen, Joyce

AU - Wang, Tzu chien V.

AU - Cerutti, Peter

PY - 1980

Y1 - 1980

N2 - The formation and repair of covalent DNA adducts induced by the two ultimate benzo[a]pyrene (BP) metabolites 4, 5-dihydro-4, 5-epoxybenzo[zz]pyrene (BPE) and 7β, 8α-dihydroxy-9a, 10a-epoxy-7, 8, 9, 10-tetrahydrobenzo [a] -pyrene (BPDE I) were studied in human epithelioid lung cells A549. The covalent DNA adducts of BPE were characterized by reacting native DNA specifically labeled in a single deoxynucleoside with racemic BPE in vitro. From the chromatographic analysis of enzymatic hydrolysates of BPE-treated DNA, it was concluded that adducts to deoxyguanosine (BPE-dG) and deoxyadenosine (BPE-dA) were formed. No adducts to the pyrimidine nucleotides were detected. DNA adducts with the same chromatographic properties were formed upon treatment of intact A549 cells with BPE. Treatment of A549 cells with racemic BPDE I mostly produced (7R)-N2-(7β, 8α, 9α-trihydroxy-7, 8, 9, 10-tetrahydrobenzo [tz]pyren-10-yl)deoxyguanosine (BPDE I-dG).

AB - The formation and repair of covalent DNA adducts induced by the two ultimate benzo[a]pyrene (BP) metabolites 4, 5-dihydro-4, 5-epoxybenzo[zz]pyrene (BPE) and 7β, 8α-dihydroxy-9a, 10a-epoxy-7, 8, 9, 10-tetrahydrobenzo [a] -pyrene (BPDE I) were studied in human epithelioid lung cells A549. The covalent DNA adducts of BPE were characterized by reacting native DNA specifically labeled in a single deoxynucleoside with racemic BPE in vitro. From the chromatographic analysis of enzymatic hydrolysates of BPE-treated DNA, it was concluded that adducts to deoxyguanosine (BPE-dG) and deoxyadenosine (BPE-dA) were formed. No adducts to the pyrimidine nucleotides were detected. DNA adducts with the same chromatographic properties were formed upon treatment of intact A549 cells with BPE. Treatment of A549 cells with racemic BPDE I mostly produced (7R)-N2-(7β, 8α, 9α-trihydroxy-7, 8, 9, 10-tetrahydrobenzo [tz]pyren-10-yl)deoxyguanosine (BPDE I-dG).

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DO - 10.1021/bi00547a008

M3 - 文章

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AN - SCOPUS:0019306336

SN - 0006-2960

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ER -

Formation and Excision of Covalent Deoxyribonucleic Acid Adducts of Benzo[A]Pyrene 4, 5-Epoxide and Benzo[A]Pyrenediol Epoxide I in Human Lung Cells A549

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