Total Synthesis, Mass Spectrometric Sequencing, and Stabilities of Oligonucleotide Duplexes with Single trans-anti-BPDE-N6-dA Lesions in the N-ras codon 61 and Other Sequence Contexts

Jacek Krzeminski, Jinsong Ni, Ping Zhuang, Natalia Luneva, Shantu Amin, Nicholas E. Geacintov

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Three different oligonucleotides (one of them comprising a portion of the N-ras protooncogene) with single bay region anti-BPDE-modified adenine residues (anti-BPDE = 7r,8t-dihydroxy-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene) were prepared by total synthesis methods, characterized, and sequenced by electrospray tandem mass spectrometry techniques. While all of the BPDE-modified duplexes are destabilized relative to the unmodified double-stranded oligonucleotides, the thermodynamic stabilities of duplexes containing 105 (+)-trans-lesions are consistently lower than those of duplexes containing the stereoisomeric 10R (-)-trans adducts. In contrast, similar duplexes, but with fjord region BcPhDE-N6-dA adducts are not thermodynamically destabilized by these bulky lesions (anti-BcPhDE: 4r,3t-dihydroxy-t1,2-epoxy-1,2,3,4-tetrahydrobenzo[c]phenanthrene).

Original languageEnglish (US)
Pages (from-to)1-10
Number of pages10
JournalPolycyclic Aromatic Compounds
Volume17
Issue number1-4
DOIs
StatePublished - Jan 1 1999

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7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
Oligonucleotides
Pyrene
Mass spectrometry
Thermodynamic stability
Adenine

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

@article{0d9c79ce3efb482fa66676d1744c080c,
title = "Total Synthesis, Mass Spectrometric Sequencing, and Stabilities of Oligonucleotide Duplexes with Single trans-anti-BPDE-N6-dA Lesions in the N-ras codon 61 and Other Sequence Contexts",
abstract = "Three different oligonucleotides (one of them comprising a portion of the N-ras protooncogene) with single bay region anti-BPDE-modified adenine residues (anti-BPDE = 7r,8t-dihydroxy-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene) were prepared by total synthesis methods, characterized, and sequenced by electrospray tandem mass spectrometry techniques. While all of the BPDE-modified duplexes are destabilized relative to the unmodified double-stranded oligonucleotides, the thermodynamic stabilities of duplexes containing 105 (+)-trans-lesions are consistently lower than those of duplexes containing the stereoisomeric 10R (-)-trans adducts. In contrast, similar duplexes, but with fjord region BcPhDE-N6-dA adducts are not thermodynamically destabilized by these bulky lesions (anti-BcPhDE: 4r,3t-dihydroxy-t1,2-epoxy-1,2,3,4-tetrahydrobenzo[c]phenanthrene).",
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Total Synthesis, Mass Spectrometric Sequencing, and Stabilities of Oligonucleotide Duplexes with Single trans-anti-BPDE-N6-dA Lesions in the N-ras codon 61 and Other Sequence Contexts. / Krzeminski, Jacek; Ni, Jinsong; Zhuang, Ping; Luneva, Natalia; Amin, Shantu; Geacintov, Nicholas E.

In: Polycyclic Aromatic Compounds, Vol. 17, No. 1-4, 01.01.1999, p. 1-10.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Total Synthesis, Mass Spectrometric Sequencing, and Stabilities of Oligonucleotide Duplexes with Single trans-anti-BPDE-N6-dA Lesions in the N-ras codon 61 and Other Sequence Contexts

AU - Krzeminski, Jacek

AU - Ni, Jinsong

AU - Zhuang, Ping

AU - Luneva, Natalia

AU - Amin, Shantu

AU - Geacintov, Nicholas E.

PY - 1999/1/1

Y1 - 1999/1/1

N2 - Three different oligonucleotides (one of them comprising a portion of the N-ras protooncogene) with single bay region anti-BPDE-modified adenine residues (anti-BPDE = 7r,8t-dihydroxy-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene) were prepared by total synthesis methods, characterized, and sequenced by electrospray tandem mass spectrometry techniques. While all of the BPDE-modified duplexes are destabilized relative to the unmodified double-stranded oligonucleotides, the thermodynamic stabilities of duplexes containing 105 (+)-trans-lesions are consistently lower than those of duplexes containing the stereoisomeric 10R (-)-trans adducts. In contrast, similar duplexes, but with fjord region BcPhDE-N6-dA adducts are not thermodynamically destabilized by these bulky lesions (anti-BcPhDE: 4r,3t-dihydroxy-t1,2-epoxy-1,2,3,4-tetrahydrobenzo[c]phenanthrene).

AB - Three different oligonucleotides (one of them comprising a portion of the N-ras protooncogene) with single bay region anti-BPDE-modified adenine residues (anti-BPDE = 7r,8t-dihydroxy-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene) were prepared by total synthesis methods, characterized, and sequenced by electrospray tandem mass spectrometry techniques. While all of the BPDE-modified duplexes are destabilized relative to the unmodified double-stranded oligonucleotides, the thermodynamic stabilities of duplexes containing 105 (+)-trans-lesions are consistently lower than those of duplexes containing the stereoisomeric 10R (-)-trans adducts. In contrast, similar duplexes, but with fjord region BcPhDE-N6-dA adducts are not thermodynamically destabilized by these bulky lesions (anti-BcPhDE: 4r,3t-dihydroxy-t1,2-epoxy-1,2,3,4-tetrahydrobenzo[c]phenanthrene).

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