Reaction of the 7,8-diol 9,10-epoxide of benzo[a]pyrene with guanine in DNA. Ab initio calculations and proposed reaction mechanism

Lin, J.; Lebreton, Pierre; Shipman, Lester L.

doi:10.1021/j100443a016

Cited by 16 publications

(9 citation statements)

References 3 publications

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“…Slight welectron density increase is found at C2, the para position, only for the 4-hydroxy tautomers studied. Our results agree in general with those of Lin [26]. Nucleophilic attack would be directed by the LUMO which has its largest coefficient at C6 and electrophilic attack would be directed by the HOMO which has its largest coefficient at C5 for the neutral species reported here.…”

Section: Resultssupporting

confidence: 91%

STO‐3G study of uracil, thymine, 5‐fluorouracil, 5‐methoxyuracil, and their 4‐hydroxytautomeric forms

Zielinski

1982

Int J of Quantum Chemistry

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Section: Resultssupporting

confidence: 91%

STO‐3G study of uracil, thymine, 5‐fluorouracil, 5‐methoxyuracil, and their 4‐hydroxytautomeric forms

Zielinski

1982

Int J of Quantum Chemistry

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“…In addition, physical intercalation has been proposed as a prerequisite for covalent binding of activated PAH to DNA (Meehan & Straub, 1979;Meehan & Bond, 1984;Lin et al, 1980). It is believed that DNA alkylation is responsible for the mutagenicity and tumorigenicity of PAH.…”

Section: Discussionmentioning

confidence: 99%

Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA

Wolfe¹,

Shimer²,

Meehan³

1987

Biochemistry

1,937

806

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We have investigated the physical binding of pyrene and benzo[a]pyrene derivatives to denatured DNA. These compounds exhibit a red shift in their absorbance spectra of 9 nm when bound to denatured calf thymus DNA, compared to a shift of 10 nm when binding occurs to native DNA. Fluorescence from the hydrocarbons is severely quenched when bound to both native and denatured DNA. Increasing sodium ion concentration decreases binding of neutral polycyclic aromatic hydrocarbons to native DNA and increases binding to denatured DNA. The direct relationship between binding to denatured DNA and salt concentration appears to be a general property of neutral polycyclic aromatic hydrocarbons. Absorption measurements at 260 nm were used to determine the duplex content of denatured DNA. When calculated on the basis of duplex binding sites, equilibrium constants for binding of 7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydro-benzo[a]pyrene to denatured DNA are an order of magnitude larger than for binding to native DNA. The effect of salt on the binding constant was used to calculate the sodium ion release per bound ligand, which was 0.36 for both native and denatured DNA. Increasing salt concentration increases the duplex content of denatured DNA, and it appears that physical binding of polycyclic aromatic hydrocarbons consists of intercalation into these sites.

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“…[17][18][19][20][21][22][23]. These studies while providing useful information on the different possible mechanisms and structures did not permit to make a clear cut choice between them and did not thus permit in particular to solve the dilemma about the pre-eminence of exteriorly bound or intercalative covalent association.…”

Section: Ohmentioning

confidence: 99%

Sequence Selectivity, a Test of the Nature of the Covalent Adduct Formed Between Benzo[a]pyrene and DNA

Zakrzewska¹,

Pullman²

1987

Journal of Biomolecular Structure and Dynamics

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A theoretical study is presented of the energetic and structural properties of covalent adducts of benzo[a]pyrene and a DNA fragment. Energy optimisation is performed with the use of minimiser with constraints and an advanced semiempirical energy formula. Three types of adducts are studied: an external complex with the benzopyrene located in the DNA minor groove and two types of intercalative complexes with the carcinogen situated on the 3' side and 5' side of the covalently bound guanine. For each of the adducts the effects of DNA base sequence are examined. It is shown that the results for the intercalative complex with the carcinogen situated on the 5' side of the modified guanine correlate with the experimentally determined sequence preference.

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Reaction of the 7,8-diol 9,10-epoxide of benzo[a]pyrene with guanine in DNA. Ab initio calculations and proposed reaction mechanism

Cited by 16 publications

References 3 publications

STO‐3G study of uracil, thymine, 5‐fluorouracil, 5‐methoxyuracil, and their 4‐hydroxytautomeric forms

STO‐3G study of uracil, thymine, 5‐fluorouracil, 5‐methoxyuracil, and their 4‐hydroxytautomeric forms

Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA

Sequence Selectivity, a Test of the Nature of the Covalent Adduct Formed Between Benzo[a]pyrene and DNA

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