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Article: Antimicrobial resistance risk assessment in food safety

Claycamp, H.G / Hooberman, B.H

Journal of food protection. 2004 Sept., v. 67, no. 9

2004

Abstract: Microbiological risk assessments generally focus on estimating adverse human health risks from exposures to human pathogenic microbes. The assessment of potential human health risks posed by pathogens that have acquired resistance to antimicrobial drugs ... ...

Abstract	Microbiological risk assessments generally focus on estimating adverse human health risks from exposures to human pathogenic microbes. The assessment of potential human health risks posed by pathogens that have acquired resistance to antimicrobial drugs is a new application of risk assessment that is closely related to microbiological risk assessment. Antimicrobial resistance risk assessment is a risk analytical process that focuses on resistance determinants as hazardous agents that might lead to drug-resistant microbial infections in humans exposed to bacteria carrying the determinants. Antimicrobial-resistant infections could occur directly from actively invading or opportunistic pathogens or indirectly from the transfer of resistance genes to other bacteria. Here, we discuss risk assessment models that might be employed to estimate risks from drug-resistant bacteria in the animal food pathway and the types of models and data that may be used for microbiological risk assessments or antimicrobial resistance risk assessments.
Keywords	food safety ; public health ; risk assessment ; antibiotic resistance ; food contamination ; microbial contamination ; food pathogens ; serotypes ; risk communication ; risk management process ; Codex Alimentarius ; disease surveillance
Language	English
Dates of publication	2004-09
Size	p. 2063-2071.
Document type	Article
Note	Paper presented at the 1st International Conference on Microbiological Risk Assessment: Foodborne Hazards, July 26-26, 2002, Adelphi, Maryland.
ZDB-ID	243284-5
ISSN	1944-9097 ; 0362-028X
ISSN (online)	1944-9097
ISSN	0362-028X
Database	NAL-Catalogue (AGRICOLA)

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Article: Base-pair mutations caused by six aliphatic epoxides in Salmonella typhimurium TA100, TA104, TA4001, and TA4006.

Einistö, P / Hooberman, B H / Sinsheimer, J E

Environmental and molecular mutagenesis

1993 Volume 21, Issue 3, Page(s) 253–257

Abstract: Salmonella typhimurium strains TA100, TA104, TA4001, and TA4006 were used to detect the base-pair mutations caused by six aliphatic epoxides: chloropropylene oxide, glycidyl 1-naphthyl ether, glycidyl 4-nitrophenyl ether, 1-naphthyl-propylene oxide, ... ...

Abstract	Salmonella typhimurium strains TA100, TA104, TA4001, and TA4006 were used to detect the base-pair mutations caused by six aliphatic epoxides: chloropropylene oxide, glycidyl 1-naphthyl ether, glycidyl 4-nitrophenyl ether, 1-naphthyl-propylene oxide, styrene oxide, and trichloropropylene oxide. Dose-mutagenicity relationships could be established for all six epoxides in strains TA100 and TA104 but not in strains TA4001 and TA4006. These results, together with the lack of sensitivity of the TA100 revertants to DL-1,2,4-triazole-3-alanine, indicate CG-->TA transitions and/or CG-->AT transversions are of major importance for mutations induced by these epoxides in Salmonella TA100 and possibly TA104. In addition, since the reproducibility of the effect of the triazole on TA104 reversions was poor, TA-->AT transversions were not eliminated as also contributing to the mutagenicity of these epoxides in this Salmonella strain.
MeSH term(s)	Epoxy Compounds/chemistry ; Epoxy Compounds/toxicity ; Genes, Suppressor ; Mutagenesis ; Mutagenicity Tests ; Mutagens/chemistry ; Point Mutation ; Salmonella typhimurium/drug effects ; Salmonella typhimurium/genetics ; Structure-Activity Relationship ; Suppression, Genetic ; Trichloroepoxypropane/toxicity
Chemical Substances	Epoxy Compounds ; Mutagens ; glycidyl ethers ; Trichloroepoxypropane (3083-23-6) ; 1-naphthylpropylene oxide (68884-32-2) ; styrene oxide (9QH06NGT6O) ; propylene oxide (Y4Y7NYD4BK)
Language	English
Publishing date	1993
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	639145-x
ISSN	1098-2280 ; 0893-6692
ISSN (online)	1098-2280
ISSN	0893-6692
DOI	10.1002/em.2850210308
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Article: Quantitative structure-activity relationships for the mutagenicity of propylene oxides with Salmonella.

Hooberman, B H / Chakraborty, P K / Sinsheimer, J E

Mutation research

1993 Volume 299, Issue 2, Page(s) 85–93

Abstract: A quantitative structure-activity relationship approach was used to investigate the mutagenicity of a series of seventeen-monosubstituted propylene oxides in Salmonella typhimurium strains TA100 and TA1535. Mutagenicity in strain TA100, using a liquid ... ...

Abstract	A quantitative structure-activity relationship approach was used to investigate the mutagenicity of a series of seventeen-monosubstituted propylene oxides in Salmonella typhimurium strains TA100 and TA1535. Mutagenicity in strain TA100, using a liquid suspension assay, was found to correlate with chemical reactivity, as measured by the rates of reaction with two model bionucleophiles, nicotinamide and 4-(4-nitrobenzyl)pyridine. However, since the reactivity of three of the epoxides did not correlate to their Taft sigma * values, as a measure of the electronic effects of substituent groups, neither was their mutagenicity predicted by this substituent constant. The relative mutagenicity for the propylene oxides was different in the liquid suspension assay than that determined by the standard plate incorporation assay and also differed between the two bacterial strains. The assay differences were attributed to epoxide stability. The differences between strains was observed to be due to the response of the error-prone repair system, found only in TA100, to the stronger alkylating agents.
MeSH term(s)	Alkylation ; DNA/chemistry ; DNA/drug effects ; DNA Damage ; Epoxy Compounds/chemistry ; Epoxy Compounds/toxicity ; Hydrolysis ; Mutagenicity Tests ; Mutagens/chemistry ; Regression Analysis ; Salmonella typhimurium/drug effects ; Salmonella typhimurium/genetics ; Structure-Activity Relationship
Chemical Substances	Epoxy Compounds ; Mutagens ; DNA (9007-49-2) ; propylene oxide (Y4Y7NYD4BK)
Language	English
Publishing date	1993-04
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	206607-5
ISSN	1873-135X ; 0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
ISSN (online)	1873-135X
ISSN	0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
DOI	10.1016/0165-1218(93)90085-r
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Article: Substituent effects on the in vitro and in vivo genotoxicity of 4-aminobiphenyl and 4-aminostilbene derivatives.

You, Z / Brezzell, M D / Das, S K / Hooberman, B H / Sinsheimer, J E

Mutation research

1994 Volume 320, Issue 1-2, Page(s) 45–58

Abstract: 4-Amino-4'-substituted biphenyls and 4-aminostilbenes substituted in the 3' or 4' position were studied for their in vitro and in vivo genotoxicity. The in vitro mutagenicity of the biphenyls with and without S9 activation was established with Salmonella ...

Abstract	4-Amino-4'-substituted biphenyls and 4-aminostilbenes substituted in the 3' or 4' position were studied for their in vitro and in vivo genotoxicity. The in vitro mutagenicity of the biphenyls with and without S9 activation was established with Salmonella strains TA98 and TA100 and that of the stilbenes with the same strains plus TA98/1,8-DNP6. The in vivo genotoxicity assay with both series of compounds was for chromosomal aberrations in the bone-marrow cells of mice following intraperitoneal administration of the chemicals. Hammett values of substituents, partition coefficients and frontier orbital energies (ELUMO and EHOMO) of the compounds were used for correlations with mutagenicity. The Salmonella mutagenicity in TA98 and TA98/1,8-DNP6 with S9 was correlated to Hammett sigma + values for the 4-aminostilbene substituents, showing a strong trend of increasing mutagenicity with an increase in the electron-withdrawing capability of the substituent. Hydrophobicity of the stilbenes, however, had little effect on their relative mutagenicity. The 4-aminobiphenyls showed a correlation between their mutagenicity and Hammett sigma + values of their 4'-substituents in stain TA98 with S9, although the trend was not as strong as for the stilbenes. But unlike the stilbenes, TA98 mutagenicity of the biphenyls could also be correlated to hydrophobicity, and structure-activity correlations for the biphenyls was substantially improved when both sigma + and hydrophobicity data were included. For strain TA100 with S9, little correlation was found between mutagenicity of the stilbenes and any of the parameters. However, a limited correlation did exist between the mutagenicity of the biphenyls and their hydrophobicity. There was also limited correlations of the mutagenicity for the stilbenes in TA98 and TA98/1,8-DNP6 with S9 to ELUMO or EHOMO. The in vivo genotoxicity results for the biphenyls and stilbenes could not be correlated to electronic effects as for the in vitro results, nor could they be explained by hydrophobicity. However, it is interesting to note that 3'-substituted 4-aminostilbenes were all substantially more genotoxic in vivo than their corresponding 4'-substituted counterparts. The most genotoxic compound in vivo in either series was 4-aminostilbene which would not have been predicted from the in vitro results.
MeSH term(s)	Aminobiphenyl Compounds/chemistry ; Aminobiphenyl Compounds/toxicity ; Animals ; Bone Marrow/drug effects ; Bone Marrow Cells ; Chromosome Aberrations ; Liver Extracts ; Mice ; Microsomes, Liver/enzymology ; Mutagenicity Tests ; Mutagens/chemistry ; Mutagens/toxicity ; Salmonella typhimurium/drug effects ; Salmonella typhimurium/genetics ; Stilbenes/chemistry ; Stilbenes/toxicity ; Structure-Activity Relationship
Chemical Substances	Aminobiphenyl Compounds ; Liver Extracts ; Mutagens ; Stilbenes ; 4-aminostilbene (834-24-2)
Language	English
Publishing date	1994-01
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	206607-5
ISSN	1873-135X ; 0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
ISSN (online)	1873-135X
ISSN	0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
DOI	10.1016/0165-1218(94)90058-2
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Article: Chromosomal aberrations in mouse lymphocytes exposed in vitro and in vivo to benzidine and 5 related aromatic amines.

Das, L / Das, S K / Hooberman, B H / Chu, E H / Sinsheimer, J E

Mutation research

1994 Volume 320, Issue 1-2, Page(s) 69–74

Abstract: Mouse lymphocytes were exposed in vitro for 2 h or in vivo for 24 h to benzidine and related aromatic amines to test for chromosome aberrations (CA) and mitotic indices. Uninduced mouse S9 was used to activate the amines for the in vitro tests to be ... ...

Abstract	Mouse lymphocytes were exposed in vitro for 2 h or in vivo for 24 h to benzidine and related aromatic amines to test for chromosome aberrations (CA) and mitotic indices. Uninduced mouse S9 was used to activate the amines for the in vitro tests to be consistent with the in vivo tests. Contrary to a previous report, no difference could be established in the genotoxicity of benzidine following activation with uninduced S9 compared to induced S9. There were concentration related increases in CA for benzidine and all the amines in vitro except for 4,4'-diaminostilbene which exhibited the greatest cellular toxicity towards cultured lymphocytes. Benzidine and its derivatives showed significant increases in CA in vivo compared to its negative control. The CA values for 4-aminostilbene were significantly higher than the other amines in both in vivo and in vitro studies. These genotoxicity results for 4-aminostilbene are consistent with our previous report of the pronounced CA effects in murine bone-marrow cells but would not be predicted from Salmonella mutagenicity tests.
MeSH term(s)	Aminobiphenyl Compounds/toxicity ; Animals ; Benzidines/toxicity ; Chromosome Aberrations ; Liver Extracts ; Lymphocytes/drug effects ; Lymphocytes/ultrastructure ; Male ; Mice ; Mice, Inbred C57BL ; Microsomes, Liver/enzymology ; Mutagenicity Tests ; Mutagens/toxicity ; Stilbenes/toxicity ; Structure-Activity Relationship
Chemical Substances	Aminobiphenyl Compounds ; Benzidines ; Liver Extracts ; Mutagens ; Stilbenes ; 4-aminostilbene (834-24-2)
Language	English
Publishing date	1994-01
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	206607-5
ISSN	1873-135X ; 0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
ISSN (online)	1873-135X
ISSN	0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
DOI	10.1016/0165-1218(94)90060-4
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Article: Substituent effects on the genotoxicity of 4-nitrostilbene derivatives.

Hooberman, B H / Brezzell, M D / Das, S K / You, Z / Sinsheimer, J E

Mutation research

1994 Volume 341, Issue 1, Page(s) 57–69

Abstract: 4-Nitrostilbene and twelve of its derivatives (eleven E-stilbenes and two Z-stilbenes) were examined for possible quantitative structure-activity relationships of their in vitro and in vivo genotoxicity. Relative mutagenicity was studied with and without ...

Abstract	4-Nitrostilbene and twelve of its derivatives (eleven E-stilbenes and two Z-stilbenes) were examined for possible quantitative structure-activity relationships of their in vitro and in vivo genotoxicity. Relative mutagenicity was studied with and without S9 activation in Salmonella strains TA98 and TA100, as well as in the nitroreductase deficient strains TA98/NR and TA100/NR. Chromosomal aberrations in the bone-marrow cells of mice following intraperitoneal administration of the nitrostilbenes were observed as an indicator of in vivo genotoxicity. All of the compounds were active in TA98 and TA100 without S9 activation, with the exception of 4-amino-4'-nitrostilbene in TA100. Mutagenic activity was greatly reduced or eliminated in the NR strains, which is consistent with metabolic activation of the compounds by bacterial reductase. The presence of S9 lowered the activity of most of the nitrostilbenes presumedly by enzymatic detoxication. Hammet values of substituents, partition coefficients and frontier orbital energies (ELUMO and EHOMO) were studied for correlations with mutagenicity of the eleven E-stilbenes. Correlations could be established between mutagenicity in TA98 without S9 activation and the Hammet values. The same mutagenicity could also be correlated to ELUMO. Rationales for these correlations include the concept that electron-withdrawing groups which lower ELUMO should facilitate the reduction of the nitro group, leading to the proximate mutagen hydroxylamine. The correlations are also explained by the concept that electron-withdrawing groups should help stabilize the hydroxylamine intermediate and make the ultimate mutagenic species, the nitrenium ions, more reactive toward DNA. The relationship between mutagenicity and electronic effects of substituent groups found in vitro could not be extended to the in vivo results. However, except for the dinitrostilbenes, where insolubility prevented their testing, all the nitrostilbenes produced a statistically significant increase in chromosomal aberrations compared to the negative solvent control.
MeSH term(s)	Animals ; Biotransformation ; Chromosome Aberrations ; Male ; Mice ; Mutagenicity Tests ; Mutation ; Salmonella typhi/drug effects ; Stilbenes/chemistry ; Stilbenes/toxicity ; Structure-Activity Relationship
Chemical Substances	Stilbenes
Language	English
Publishing date	1994-11
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	206607-5
ISSN	1873-135X ; 0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
ISSN (online)	1873-135X
ISSN	0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
DOI	10.1016/0165-1218(94)90024-8
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: The genotoxicity of enantiomeric aliphatic epoxides.

Sinsheimer, J E / Chen, R / Das, S K / Hooberman, B H / Osorio, S / You, Z

Mutation research

1993 Volume 298, Issue 3, Page(s) 197–206

Abstract: The (R)- and (S)-optical isomers of 9 epoxides, benzyloxymethyloxirane, epichlorohydrin, glycidol, glycidyl 3-nitrobenzenesulfonate, glycidyl 4-nitrobenzoate, glycidyl tosylate, styrene oxide, glycidyl 1-naphthyl ether and glycidyl 4-nitrophenyl ether, ... ...

Abstract	The (R)- and (S)-optical isomers of 9 epoxides, benzyloxymethyloxirane, epichlorohydrin, glycidol, glycidyl 3-nitrobenzenesulfonate, glycidyl 4-nitrobenzoate, glycidyl tosylate, styrene oxide, glycidyl 1-naphthyl ether and glycidyl 4-nitrophenyl ether, have been compared for their in vivo and in vitro genotoxicity. The in vitro short-term test employed was the Ames mutagenicity assay with Salmonella strain TA100. The in vivo tests were chromosomal aberrations (CA) as well as sister-chromatid exchange (SCE) in bone-marrow cells of mice following intraperitoneal administration of these epoxides. Differences in mutagenicity between isomers were established with TA100 for all the compounds. While 13 of the isomers were genotoxic compared to a negative control by CA measurements, only in the case of glycidyl 4-nitrobenzoate could a significant difference be found between isomers by this test. However, with SCE evaluations, differences were detected between the (R)- and (S)-isomers for all the pairs of compounds with the exception of those for benzyloxymethyloxirane and glycidyl 4-nitrophenyl ether. At least in part, differences in the patterns of genotoxicity among compounds can be related to their differences in reaction pathways.
MeSH term(s)	Animals ; Bone Marrow/drug effects ; Chromosome Aberrations ; Dose-Response Relationship, Drug ; Epoxy Compounds/chemistry ; Epoxy Compounds/toxicity ; Male ; Mice ; Mutagenesis/drug effects ; Mutagenicity Tests ; Mutagens ; Nitrobenzoates/chemistry ; Nitrobenzoates/toxicity ; Salmonella typhimurium/drug effects ; Sister Chromatid Exchange/drug effects ; Stereoisomerism ; Structure-Activity Relationship
Chemical Substances	Epoxy Compounds ; Mutagens ; Nitrobenzoates ; glycidyl 4-nitrobenzoate
Language	English
Publishing date	1993-01
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	206607-5
ISSN	1873-135X ; 0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
ISSN (online)	1873-135X
ISSN	0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
DOI	10.1016/0165-1218(93)90041-b
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Article: Reactivity of mutagenic propylene oxides with deoxynucleosides and DNA.

Djuric, Z / Hooberman, B H / Rosman, L / Sinsheimer, J E

Environmental mutagenesis

1986 Volume 8, Issue 3, Page(s) 369–383

Abstract: In an extension of previous studies with deoxycytidine and thymidine reactivities, propylene oxide, glycidol, epichlorohydrin, and trichloropropylene oxide were reacted with deoxyguanosine as well as deoxyadenosine and, except for the trichloro compound, ...

Abstract	In an extension of previous studies with deoxycytidine and thymidine reactivities, propylene oxide, glycidol, epichlorohydrin, and trichloropropylene oxide were reacted with deoxyguanosine as well as deoxyadenosine and, except for the trichloro compound, with DNA. Reactivity with the purine deoxynucleosides as well as the four deoxynucleosides in DNA were quantitated by HPLC methods. Correlations were found for the reactivity with individual deoxynucleosides in solution to Taft sigma electron-withdrawing values of the substituents on the epoxides and for reaction with model nucleophiles. In general, these correlations were not as pronounced for the reactivities of the propylene oxides with the nucleosides in DNA. Correlations for reactivity of the propylene oxides with the individual deoxynucleosides in solution and in DNA, except for dThd, were indicated for mutagenicity in TA100 in the liquid-preincubation Ames test. However, this was not the case for mutagenicities determined with the plate incorporation procedure nor with TA1535, where the relative mutagenicity of trichloropropylene oxide was the outstanding difference. Trichloropropylene oxide appeared to depend upon the error-prone system in TA100 for full expression of its mutagenicity.
MeSH term(s)	Alkylation ; Chromatography, High Pressure Liquid ; Chromatography, Thin Layer ; DNA/metabolism ; Deoxyadenosines/metabolism ; Deoxyguanosine/metabolism ; Deoxyribonucleosides/metabolism ; Epoxy Compounds/analogs & derivatives ; Epoxy Compounds/metabolism ; Epoxy Compounds/pharmacology ; Ethers, Cyclic/metabolism ; Mutagenicity Tests ; Salmonella typhimurium/drug effects ; Structure-Activity Relationship
Chemical Substances	Deoxyadenosines ; Deoxyribonucleosides ; Epoxy Compounds ; Ethers, Cyclic ; DNA (9007-49-2) ; Deoxyguanosine (G9481N71RO) ; propylene oxide (Y4Y7NYD4BK)
Language	English
Publishing date	1986
Publishing country	United States
Document type	Comparative Study ; Journal Article ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	392053-7
ISSN	0192-2521
ISSN	0192-2521
DOI	10.1002/em.2860080306
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Article: Genotoxicity of chryseno[4,5-bcd]thiophene and its sulfone derivative.

Sinsheimer, J E / Hooberman, B H / Das, S K / Savla, P M / Ashe, A J

Environmental and molecular mutagenesis

1992 Volume 19, Issue 3, Page(s) 259–264

Abstract: Our recent syntheses of chryseno[4,5-bcd]thiophene together with its potential sulfone metabolite, chryseno[4,5-bcd]thiophene-4,4-dioxide, have made these compounds available for genotoxicity testing. Such toxicity testing is of interest as this ... ...

Abstract	Our recent syntheses of chryseno[4,5-bcd]thiophene together with its potential sulfone metabolite, chryseno[4,5-bcd]thiophene-4,4-dioxide, have made these compounds available for genotoxicity testing. Such toxicity testing is of interest as this thiophene is an isoster of the established carcinogen benzo[a]pyrene and is one of the thiaarenes which are potential environmental contaminants found in fossil fuels. Although the thiophene was less mutagenic than benzo[a]pyrene in Salmonella strains TA98 and TA100 after S9 activation, it exhibited in vivo chromosomal aberration activity equal to that of benzo[a]pyrene in the bone-marrow cells of mice. A reduced activity with Salmonella as well as in the bone-marrow cell assay for the sulfone does not support its role as the key active metabolic intermediate for the genotoxicity of the thiophene. Our molecular orbital calculations would be consistent with the concept of activation through a diol-epoxide mechanism and offers an explanation for the reduced genotoxicity of the sulfone via this mechanism. These genotoxicity studies support the concern that sulfur isosters of established carcinogenic polycyclic aromatic hydrocarbons could themselves be toxic.
MeSH term(s)	Animals ; Benzo(a)pyrene/toxicity ; Bone Marrow/drug effects ; Chromosome Aberrations ; Chrysenes/metabolism ; Chrysenes/pharmacology ; Chrysenes/toxicity ; Male ; Mice ; Molecular Structure ; Mutagenicity Tests ; Mutagens/toxicity ; Salmonella/drug effects ; Thiophenes/metabolism ; Thiophenes/pharmacology ; Thiophenes/toxicity
Chemical Substances	Chrysenes ; Mutagens ; Thiophenes ; chrysene (084HCM49PT) ; chryseno(4,5-bcd)thiophene-4,4-dioxide (142022-84-2) ; Benzo(a)pyrene (3417WMA06D) ; chryseno(4,5-bcd)thiophene (72076-98-3)
Language	English
Publishing date	1992
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	639145-x
ISSN	1098-2280 ; 0893-6692
ISSN (online)	1098-2280
ISSN	0893-6692
DOI	10.1002/em.2850190311
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Article: The in vivo and in vitro genotoxicity of aromatic amines in relationship to the genotoxicity of benzidine.

Sinsheimer, J E / Hooberman, B H / Das, S K / Brezzell, M D / You, Z

Mutation research

1992 Volume 268, Issue 2, Page(s) 255–264

Abstract: Benzidine and 12 related aromatic amines have been studied for the effects of substituent groups and pi orbital conjugation on their genotoxicity as measured by their mutagenicity in vitro with Salmonella and by chromosomal aberrations (CA) in vivo in ... ...

Abstract	Benzidine and 12 related aromatic amines have been studied for the effects of substituent groups and pi orbital conjugation on their genotoxicity as measured by their mutagenicity in vitro with Salmonella and by chromosomal aberrations (CA) in vivo in the bone-marrow cells of mice. The in vitro studies indicated increases in mutagenicity with increases in the electron withdrawing ability of para' substituents. Mutagenicity also increases with increased conjugation as shown by the degree of planarity of the biphenyl compounds and by comparing the mutagenicities of biphenyl amines to stilbenes as well as to ethylene bridged diphenyl compounds. The relative in vitro mutagenicity results were not predictive of relative in vivo CA results. The 3 most genotoxic compounds in vivo were the conjugated amines without substituents in the para' position. The CA values for 4-aminostilbene were exceptionally high. These in vivo results indicate increased genotoxicity for benzidine analogs without substitution in the para' position.
MeSH term(s)	Aminobiphenyl Compounds/chemistry ; Aminobiphenyl Compounds/toxicity ; Animals ; Benzidines/toxicity ; Bone Marrow/drug effects ; Chromosome Aberrations ; Magnetic Resonance Spectroscopy ; Male ; Mice ; Mutagenesis ; Mutagenicity Tests ; Rats ; Rats, Inbred Strains ; Salmonella typhimurium ; Stilbenes/chemistry ; Stilbenes/toxicity ; Structure-Activity Relationship
Chemical Substances	Aminobiphenyl Compounds ; Benzidines ; Stilbenes ; benzidine (2X02101HVF) ; 4-aminostilbene (834-24-2)
Language	English
Publishing date	1992-08
Publishing country	Netherlands
Document type	Comparative Study ; Journal Article ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	206607-5
ISSN	1873-135X ; 0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
ISSN (online)	1873-135X
ISSN	0027-5107 ; 1383-5718 ; 0165-1110 ; 0165-1161 ; 0165-7992 ; 0921-8777 ; 0165-1218 ; 1383-5726 ; 0167-8817 ; 0921-8734 ; 1383-5742
DOI	10.1016/0027-5107(92)90232-q
Database	MEDical Literature Analysis and Retrieval System OnLINE

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