Mass spectrometric sequencing of site-specific carcinogen-modified oligodeoxyribonucleotides containing bulky benzo[a]pyrene diol epoxide- deoxyguanosyl adducts

Jinsong Ni, Tongming Liu, Alexander Kolbanovskiy, Jacek Krzeminski, Shantu Amin, Nicholas Geacintov

Research output: Contribution to journalArticle

Abstract

Site-specific carcinogen-modified oligonucleotides are often used in site-directed mutagenesis and other biological and biochemical studies of structure-function relationships. Postsynthetic analysis and confirmation of the sites of carcinogen binding in such oligonucleotides is an important step in the characterization of these site-specific carcinogen-DNA adducts. It is shown here that negative ion mode electrospray tandem mass spectrometry methods and collision-induced dissociation offer a rapid and convenient approach for the sequencing of products derived from the reaction of the carcinogenic and mutagenic metabolite of benzo[a]pyrene, the diol epoxide r7,t8-dihydroxy-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (anti-BPDE), with the 11-mer oligonucleotide d(CATGCGGCCTAC). The site of reaction of anti-BPDE with either one of the three dG residues in this oligonucleotide can be accurately established by comparing the mass/charge ratios of the observed collision-induced dissociation fragments with calculated values.

Original languageEnglish (US)
Pages (from-to)222-229
Number of pages8
JournalAnalytical Biochemistry
Volume264
Issue number2
DOIs
StatePublished - Nov 15 1998

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Oligodeoxyribonucleotides
Benzo(a)pyrene
Epoxy Compounds
Oligonucleotides
Carcinogens
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
Mutagenesis
DNA Adducts
Metabolites
Tandem Mass Spectrometry
Site-Directed Mutagenesis
Mass spectrometry
Negative ions
Binding Sites
Ions

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Mass spectrometric sequencing of site-specific carcinogen-modified oligodeoxyribonucleotides containing bulky benzo[a]pyrene diol epoxide- deoxyguanosyl adducts. / Ni, Jinsong; Liu, Tongming; Kolbanovskiy, Alexander; Krzeminski, Jacek; Amin, Shantu; Geacintov, Nicholas.

In: Analytical Biochemistry, Vol. 264, No. 2, 15.11.1998, p. 222-229.

Research output: Contribution to journalArticle

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abstract = "Site-specific carcinogen-modified oligonucleotides are often used in site-directed mutagenesis and other biological and biochemical studies of structure-function relationships. Postsynthetic analysis and confirmation of the sites of carcinogen binding in such oligonucleotides is an important step in the characterization of these site-specific carcinogen-DNA adducts. It is shown here that negative ion mode electrospray tandem mass spectrometry methods and collision-induced dissociation offer a rapid and convenient approach for the sequencing of products derived from the reaction of the carcinogenic and mutagenic metabolite of benzo[a]pyrene, the diol epoxide r7,t8-dihydroxy-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (anti-BPDE), with the 11-mer oligonucleotide d(CATGCGGCCTAC). The site of reaction of anti-BPDE with either one of the three dG residues in this oligonucleotide can be accurately established by comparing the mass/charge ratios of the observed collision-induced dissociation fragments with calculated values.",
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AU - Geacintov, Nicholas

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