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Title: Base sequence effects on interactions of aromatic mutagens with DNA

Abstract

Within this period, we have completed our investigations on the thermodynamic characteristics and base sequence dependence of duplex formation of benzo(a)pyrene diol epoxide (BPDE) DNA adducts. Different 11-mer oligonucleotides containing covalently bound BPDE moieties at the exocyclic amino group of a single guanine base were utilized in these studies. Last year, in the three-year progress report, some preliminary data were discussed. A final account is provided here. New techniques were developed for assessing the preferred orientations of the enantiomers of (+)-BPDE and ({minus})-BPDE relative to the 5in {r arrow} 3in polarity of DNA strands; these investigations were prompted by predictions derived from our computer modeling studies. Significant progress was made towards synthesizing BPDE-adenine adducts in base sequence-specific oligonucleotides. We failed, on the other hand, to synthesize nitrosopyrene-oligonucleotide adducts because of intrinsic low reactivities of the nitrenium derivative ions with oligonucleotides. Nature was against us in this effort. Therefore, this particular goal to be abandoned. 14 refs., 8 figs., 4 tabs.

Authors:
Publication Date:
Research Org.:
New York Univ., NY (United States)
Sponsoring Org.:
USDOE; USDOE, Washington, DC (United States)
OSTI Identifier:
5047004
Report Number(s):
DOE/ER/60674-4
ON: DE92002476
DOE Contract Number:  
FG02-88ER60674
Resource Type:
Technical Report
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.; DNA ADDUCTS; COMPUTERIZED SIMULATION; MOLECULAR STRUCTURE; POLYCYCLIC AROMATIC HYDROCARBONS; BIOLOGICAL EFFECTS; METABOLITES; ABSORPTION SPECTROSCOPY; ADENINES; BENZOPYRENE; BIOCHEMICAL REACTION KINETICS; DNA; DNA MISMATCH; EPOXIDES; GUANINE; MUTAGENS; NUCLEIC ACID DENATURATION; OLIGONUCLEOTIDES; PROGRESS REPORT; STEREOCHEMISTRY; THERMODYNAMIC PROPERTIES; TOXICITY; ADDUCTS; AMINES; ANTIMETABOLITES; AROMATICS; AZAARENES; CONDENSED AROMATICS; DOCUMENT TYPES; DRUGS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; HYDROXY COMPOUNDS; KINETICS; NUCLEIC ACIDS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; ORGANIC OXYGEN COMPOUNDS; PHYSICAL PROPERTIES; PURINES; REACTION KINETICS; SIMULATION; SPECTROSCOPY; 550200* - Biochemistry; 550400 - Genetics; 560300 - Chemicals Metabolism & Toxicology

Citation Formats

Geacintov, N E. Base sequence effects on interactions of aromatic mutagens with DNA. United States: N. p., 1991. Web. doi:10.2172/5047004.
Geacintov, N E. Base sequence effects on interactions of aromatic mutagens with DNA. United States. https://doi.org/10.2172/5047004
Geacintov, N E. 1991. "Base sequence effects on interactions of aromatic mutagens with DNA". United States. https://doi.org/10.2172/5047004. https://www.osti.gov/servlets/purl/5047004.
@article{osti_5047004,
title = {Base sequence effects on interactions of aromatic mutagens with DNA},
author = {Geacintov, N E},
abstractNote = {Within this period, we have completed our investigations on the thermodynamic characteristics and base sequence dependence of duplex formation of benzo(a)pyrene diol epoxide (BPDE) DNA adducts. Different 11-mer oligonucleotides containing covalently bound BPDE moieties at the exocyclic amino group of a single guanine base were utilized in these studies. Last year, in the three-year progress report, some preliminary data were discussed. A final account is provided here. New techniques were developed for assessing the preferred orientations of the enantiomers of (+)-BPDE and ({minus})-BPDE relative to the 5in {r arrow} 3in polarity of DNA strands; these investigations were prompted by predictions derived from our computer modeling studies. Significant progress was made towards synthesizing BPDE-adenine adducts in base sequence-specific oligonucleotides. We failed, on the other hand, to synthesize nitrosopyrene-oligonucleotide adducts because of intrinsic low reactivities of the nitrenium derivative ions with oligonucleotides. Nature was against us in this effort. Therefore, this particular goal to be abandoned. 14 refs., 8 figs., 4 tabs.},
doi = {10.2172/5047004},
url = {https://www.osti.gov/biblio/5047004}, journal = {},
number = ,
volume = ,
place = {United States},
year = {Thu Sep 19 00:00:00 EDT 1991},
month = {Thu Sep 19 00:00:00 EDT 1991}
}