Kinetics of hydrolysis to tetraols and binding of benzo(a)pyrene-7,8-dihydrodiol-9,10-oxide and its tetraol derivatives to DNA. Conformation of adducts

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

Research output: Contribution to journalArticle

Abstract

When the major reactive metabolite of benzo(a)pyrene, trans -7,8-dihydroxy - anti-9,10-epoxy -7,8,9,10-tetrahydrobenzo(a)pyrene (anti-BPDE) is incubated with DNA in aqueous solution at 25°C, both covalent binding and hydrolysis of anti-BPDE to its tetraols occur. Using fluorescence and absorption spectroscopy it is shown that hydrolysis of anti-BPDE is markedly accelerated by DNA. In the presence of 5A260 units of DNA per ml in cacodylate buffer solution, at an initial concentration of DNA phosphate/anti-BPDE ratio of 100, both the extent of covalent binding to DNA ( < 7% of the total anti-BPDE initially present) and hydrolysis of anti-BPDE reach their maximum levels within less than five minutes after mixing. Absorption and electric linear dichroism spectra indicate that the tetraols bind non-covalently to DNA by an intercalation mechanism, whereas the covalent product displays the characteristics of an externally bound complex.

Original languageEnglish (US)
Pages (from-to)1335-1342
Number of pages8
JournalBiochemical and Biophysical Research Communications
Volume92
Issue number4
DOIs
StatePublished - Feb 27 1980

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7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
Oxides
Conformations
Hydrolysis
Derivatives
Kinetics
DNA
Cacodylic Acid
Benzo(a)pyrene
Fluorescence spectroscopy
Intercalation
Metabolites
Absorption spectroscopy
Fluorescence Spectrometry
benzo(a)pyrene 7,8-dihydrodiol
7,8,9,10-tetrahydroxytetrahydrobenzo(a)pyrene
Buffers
Phosphates

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Kinetics of hydrolysis to tetraols and binding of benzo(a)pyrene-7,8-dihydrodiol-9,10-oxide and its tetraol derivatives to DNA. Conformation of adducts. / Geacintov, Nicholas; Ibanez, Victor; Gagliano, Antoine G.; Yoshida, Hiroko; Harvey, Ronald G.

In: Biochemical and Biophysical Research Communications, Vol. 92, No. 4, 27.02.1980, p. 1335-1342.

Research output: Contribution to journalArticle

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abstract = "When the major reactive metabolite of benzo(a)pyrene, trans -7,8-dihydroxy - anti-9,10-epoxy -7,8,9,10-tetrahydrobenzo(a)pyrene (anti-BPDE) is incubated with DNA in aqueous solution at 25°C, both covalent binding and hydrolysis of anti-BPDE to its tetraols occur. Using fluorescence and absorption spectroscopy it is shown that hydrolysis of anti-BPDE is markedly accelerated by DNA. In the presence of 5A260 units of DNA per ml in cacodylate buffer solution, at an initial concentration of DNA phosphate/anti-BPDE ratio of 100, both the extent of covalent binding to DNA ( < 7{\%} of the total anti-BPDE initially present) and hydrolysis of anti-BPDE reach their maximum levels within less than five minutes after mixing. Absorption and electric linear dichroism spectra indicate that the tetraols bind non-covalently to DNA by an intercalation mechanism, whereas the covalent product displays the characteristics of an externally bound complex.",
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AU - Ibanez, Victor

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AU - Yoshida, Hiroko

AU - Harvey, Ronald G.

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