Mutagenicity of benzylic acetates, sulfates and bromides of polycyclic aromatic hydrocarbons

Eleanor G Rogan, Ercole Cavalieri, Betty A. Walker, Ramadas Balasubramanian, Peter G. Wislocki, Robert W. Roth, Richard K. Saugier

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Abstract

Studies were performed to determine the direct mutagenicity of the acetates and some bromides and sulfates of hydroxymethyl polycyclic aromatic hydrocarbons in S. typhimurium strains TA98 and TA100. Benzylic acetates, bromides and sulfates were synthesized and characterized. The compounds tested were benzyl alcohol, 5-hydroxymethylchrysene, 1-hydroxymethylpyrene, 6-hydroxymethylbenzo[a] pyrene, 6-(2-hydroxyethyl)benzo[a]pyrene, 6-hydroxymethylanthanthrene, 9-hydroxymethylanthracene, 9-hydroxymethyl-10-methylanthracene, 7-hydroxymethylbenz[a]anthracene, 7-(2-hydroxyethyl)benz[a] anthracene, 12-hydroxymethylbenz[a] anthracene, 7-hydroxymethyl-12-methylbenz [a] anthracene, 12-hydroxymethyl-7-methylbenz [a] anthracene, 1-hydroxy-3-methylcholanthrene, 2-hydroxy-3-methylcholanthrene, 3-hydroxy-3,4-dihydrocyclopenta[cd]pyrene and 4-hydroxy-3,4-dihydrocyclopenta[cd] pyrene. The benzylic sulfate esters of 6-hydroxymethylbenzo [a] pyrene and 7-hydroxymethylbenz [a] anthracene were the most mutagenic compounds, whereas the aliphatic sulfate ester of 7-hydroxyethylbenz[a] anthracene did not cause an increase in mutations above background. All meso-anthracenic benzylic acetate esters were mutagenic in both strains with various degrees of activity, whereas the corresponding non-benzylic esters were inactive, as expected. Of the non-mesobenzylic acetate esters, only the 3-acetoxy-3,4-dihydrocyclopenta[cd]pyrene was mutagenic. In the benzylic bromide series, only the eight mesoanthracenic were mutagenic, whereas benzyl bromide and 5-bromomethylchrysene were inactive. The aliphatic bromides, 6-(2-bromoethyl)benzo[a]-pyrene and 7-(2-bromoethyl)benz[a]anthracene did not display significant activity. The potencies of the acetate esters more accurately reflect the mutagenicity because the rate of solvolysis did not compete with the reactivity of the esters with bacterial DNA. In the case of benzylic sulfates and bromides, the rate of solvolysis was very rapid and could have diminished the level of mutagenicity, depending on the assay conditions. These results demonstrate that meso-anthracenic benzylic acetates, sulfates and bromides are mutagenic, whereas benzylic acetate esters attached to other carbon atoms are inactive.

Original languageEnglish (US)
Pages (from-to)253-275
Number of pages23
JournalChemico-Biological Interactions
Volume58
Issue numberC
DOIs
StatePublished - Jan 1 1986

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Polycyclic Aromatic Hydrocarbons
Bromides
Sulfates
Esters
Acetates
Benzo(a)pyrene
Benzyl Alcohol
Bacterial DNA
Anthracene
Pyrene
Assays
Carbon
Atoms
Mutation

Keywords

  • Benzylic acetates
  • Benzylic bromides
  • Benzylic sulfates
  • Mutagenicity: Polycyclic aromatic hydrocarbons

ASJC Scopus subject areas

  • Toxicology

Cite this

Mutagenicity of benzylic acetates, sulfates and bromides of polycyclic aromatic hydrocarbons. / Rogan, Eleanor G; Cavalieri, Ercole; Walker, Betty A.; Balasubramanian, Ramadas; Wislocki, Peter G.; Roth, Robert W.; Saugier, Richard K.

In: Chemico-Biological Interactions, Vol. 58, No. C, 01.01.1986, p. 253-275.

Research output: Contribution to journalArticle

Rogan, Eleanor G ; Cavalieri, Ercole ; Walker, Betty A. ; Balasubramanian, Ramadas ; Wislocki, Peter G. ; Roth, Robert W. ; Saugier, Richard K. / Mutagenicity of benzylic acetates, sulfates and bromides of polycyclic aromatic hydrocarbons. In: Chemico-Biological Interactions. 1986 ; Vol. 58, No. C. pp. 253-275.
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T1 - Mutagenicity of benzylic acetates, sulfates and bromides of polycyclic aromatic hydrocarbons

AU - Rogan, Eleanor G

AU - Cavalieri, Ercole

AU - Walker, Betty A.

AU - Balasubramanian, Ramadas

AU - Wislocki, Peter G.

AU - Roth, Robert W.

AU - Saugier, Richard K.

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N2 - Studies were performed to determine the direct mutagenicity of the acetates and some bromides and sulfates of hydroxymethyl polycyclic aromatic hydrocarbons in S. typhimurium strains TA98 and TA100. Benzylic acetates, bromides and sulfates were synthesized and characterized. The compounds tested were benzyl alcohol, 5-hydroxymethylchrysene, 1-hydroxymethylpyrene, 6-hydroxymethylbenzo[a] pyrene, 6-(2-hydroxyethyl)benzo[a]pyrene, 6-hydroxymethylanthanthrene, 9-hydroxymethylanthracene, 9-hydroxymethyl-10-methylanthracene, 7-hydroxymethylbenz[a]anthracene, 7-(2-hydroxyethyl)benz[a] anthracene, 12-hydroxymethylbenz[a] anthracene, 7-hydroxymethyl-12-methylbenz [a] anthracene, 12-hydroxymethyl-7-methylbenz [a] anthracene, 1-hydroxy-3-methylcholanthrene, 2-hydroxy-3-methylcholanthrene, 3-hydroxy-3,4-dihydrocyclopenta[cd]pyrene and 4-hydroxy-3,4-dihydrocyclopenta[cd] pyrene. The benzylic sulfate esters of 6-hydroxymethylbenzo [a] pyrene and 7-hydroxymethylbenz [a] anthracene were the most mutagenic compounds, whereas the aliphatic sulfate ester of 7-hydroxyethylbenz[a] anthracene did not cause an increase in mutations above background. All meso-anthracenic benzylic acetate esters were mutagenic in both strains with various degrees of activity, whereas the corresponding non-benzylic esters were inactive, as expected. Of the non-mesobenzylic acetate esters, only the 3-acetoxy-3,4-dihydrocyclopenta[cd]pyrene was mutagenic. In the benzylic bromide series, only the eight mesoanthracenic were mutagenic, whereas benzyl bromide and 5-bromomethylchrysene were inactive. The aliphatic bromides, 6-(2-bromoethyl)benzo[a]-pyrene and 7-(2-bromoethyl)benz[a]anthracene did not display significant activity. The potencies of the acetate esters more accurately reflect the mutagenicity because the rate of solvolysis did not compete with the reactivity of the esters with bacterial DNA. In the case of benzylic sulfates and bromides, the rate of solvolysis was very rapid and could have diminished the level of mutagenicity, depending on the assay conditions. These results demonstrate that meso-anthracenic benzylic acetates, sulfates and bromides are mutagenic, whereas benzylic acetate esters attached to other carbon atoms are inactive.

AB - Studies were performed to determine the direct mutagenicity of the acetates and some bromides and sulfates of hydroxymethyl polycyclic aromatic hydrocarbons in S. typhimurium strains TA98 and TA100. Benzylic acetates, bromides and sulfates were synthesized and characterized. The compounds tested were benzyl alcohol, 5-hydroxymethylchrysene, 1-hydroxymethylpyrene, 6-hydroxymethylbenzo[a] pyrene, 6-(2-hydroxyethyl)benzo[a]pyrene, 6-hydroxymethylanthanthrene, 9-hydroxymethylanthracene, 9-hydroxymethyl-10-methylanthracene, 7-hydroxymethylbenz[a]anthracene, 7-(2-hydroxyethyl)benz[a] anthracene, 12-hydroxymethylbenz[a] anthracene, 7-hydroxymethyl-12-methylbenz [a] anthracene, 12-hydroxymethyl-7-methylbenz [a] anthracene, 1-hydroxy-3-methylcholanthrene, 2-hydroxy-3-methylcholanthrene, 3-hydroxy-3,4-dihydrocyclopenta[cd]pyrene and 4-hydroxy-3,4-dihydrocyclopenta[cd] pyrene. The benzylic sulfate esters of 6-hydroxymethylbenzo [a] pyrene and 7-hydroxymethylbenz [a] anthracene were the most mutagenic compounds, whereas the aliphatic sulfate ester of 7-hydroxyethylbenz[a] anthracene did not cause an increase in mutations above background. All meso-anthracenic benzylic acetate esters were mutagenic in both strains with various degrees of activity, whereas the corresponding non-benzylic esters were inactive, as expected. Of the non-mesobenzylic acetate esters, only the 3-acetoxy-3,4-dihydrocyclopenta[cd]pyrene was mutagenic. In the benzylic bromide series, only the eight mesoanthracenic were mutagenic, whereas benzyl bromide and 5-bromomethylchrysene were inactive. The aliphatic bromides, 6-(2-bromoethyl)benzo[a]-pyrene and 7-(2-bromoethyl)benz[a]anthracene did not display significant activity. The potencies of the acetate esters more accurately reflect the mutagenicity because the rate of solvolysis did not compete with the reactivity of the esters with bacterial DNA. In the case of benzylic sulfates and bromides, the rate of solvolysis was very rapid and could have diminished the level of mutagenicity, depending on the assay conditions. These results demonstrate that meso-anthracenic benzylic acetates, sulfates and bromides are mutagenic, whereas benzylic acetate esters attached to other carbon atoms are inactive.

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KW - Benzylic bromides

KW - Benzylic sulfates

KW - Mutagenicity: Polycyclic aromatic hydrocarbons

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