Non-covalent intercalative binding of 7,8-dihydroxy-9,10-epoxybenzo(a)pyrene to DNA

Nicholas Geacintov, Hiroko Yoshida, Victor Ibanez, Ronald G. Harvey

Research output: Contribution to journalArticle

Abstract

When the benzo(a)pyrene diol epoxide (±)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BPDE) is mixed into a DNA solution, a 10nm red shift in the absorption maximum of BPDE appears at 354nm which is due to a non-covalent intercalation complex. The major reaction pathway at this intercalation site is the hydrolysis of BPDE to its tetraol which is accompanied by a decrease in the absorbance and a shift from 354 to 353nm (the latter is due to intercalated tetraol). The non-covalent binding constants are approximately 8200M-1 for BPDE and 3300M-1 for the tetraol at 25°C, pH 7.0. Covalent adduct formation between BPDE and DNA occurs either at another, external binding site, or after some rearrangement of the intercalated BPDE, since covalent adducts display a 345nm absorption maximum (2nm red shift only).

Original languageEnglish (US)
Pages (from-to)1569-1577
Number of pages9
JournalBiochemical and Biophysical Research Communications
Volume100
Issue number4
DOIs
StatePublished - Jun 30 1981

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7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
DNA
Intercalation
Benzo(a)pyrene
Epoxy Compounds
pyrene
Hydrolysis
Binding Sites

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Non-covalent intercalative binding of 7,8-dihydroxy-9,10-epoxybenzo(a)pyrene to DNA. / Geacintov, Nicholas; Yoshida, Hiroko; Ibanez, Victor; Harvey, Ronald G.

In: Biochemical and Biophysical Research Communications, Vol. 100, No. 4, 30.06.1981, p. 1569-1577.

Research output: Contribution to journalArticle

Geacintov, Nicholas ; Yoshida, Hiroko ; Ibanez, Victor ; Harvey, Ronald G. / Non-covalent intercalative binding of 7,8-dihydroxy-9,10-epoxybenzo(a)pyrene to DNA. In: Biochemical and Biophysical Research Communications. 1981 ; Vol. 100, No. 4. pp. 1569-1577.
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AU - Harvey, Ronald G.

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AB - When the benzo(a)pyrene diol epoxide (±)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BPDE) is mixed into a DNA solution, a 10nm red shift in the absorption maximum of BPDE appears at 354nm which is due to a non-covalent intercalation complex. The major reaction pathway at this intercalation site is the hydrolysis of BPDE to its tetraol which is accompanied by a decrease in the absorbance and a shift from 354 to 353nm (the latter is due to intercalated tetraol). The non-covalent binding constants are approximately 8200M-1 for BPDE and 3300M-1 for the tetraol at 25°C, pH 7.0. Covalent adduct formation between BPDE and DNA occurs either at another, external binding site, or after some rearrangement of the intercalated BPDE, since covalent adducts display a 345nm absorption maximum (2nm red shift only).

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