Mutagenic potency of some conjugated nitroaromatic compounds and its relationship to structure

Christopher Albert Mullin, Kamal A. Rashid, Ralph O. Mumma

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The mutagenicities of 12 conjugated non-fused nitroaromatic compounds and 1 amino analogue were determined in strains TA100 and TA98 of Salmonella typhimurium. Reversions by p-nitroaromatics increased in the order of the acetophenone, benzaldehyde, styrene, chalcone, cinnamic acid and stilbene indicating the importance for mutagenic potency of extended conjugation to the p-nitrophenyl substituent. Highest mutagenicity was found with α-substituted 4-nitrostyryl derivatives of which the phenyl derivative (31 revertants per nmole in TA100) was the most active. Generally, the TA100 strain was more sensitive than TA98 to these mutagens and S9 treatment was unnecessary for activity, although 4-nitrochalcone required S9 activation. Para-nitro isomers of the cinnamic acids and chalcones were much more active than the corresponding ortho and meta isomers. The 4-aminocinnamic acid analogue was inactive suggesting that complete reduction in Salmonella of 4-nitrocinnamic acid to an active amino derivative is not response for the high mutagenicity of the former. Mutagenicity of these p-nitrostyryl compounds may be explained by the covalent interaction of the electrophilic benzylic carbon with Salmonella DNA.

Original languageEnglish (US)
Pages (from-to)267-274
Number of pages8
JournalMutation Research/Genetic Toxicology
Volume188
Issue number4
DOIs
StatePublished - Jan 1 1987

Fingerprint

Salmonella
Chalcones
Derivatives
Chalcone
Stilbenes
Isomers
Acids
Styrene
Mutagens
Salmonella typhimurium
Carbon
DNA
Chemical activation
cinnamic acid
benzaldehyde
acetophenone

All Science Journal Classification (ASJC) codes

  • Genetics
  • Toxicology
  • Medicine(all)

Cite this

Mullin, Christopher Albert ; Rashid, Kamal A. ; Mumma, Ralph O. / Mutagenic potency of some conjugated nitroaromatic compounds and its relationship to structure. In: Mutation Research/Genetic Toxicology. 1987 ; Vol. 188, No. 4. pp. 267-274.
@article{d875da74cbcf41e3939a5836f8be3860,
title = "Mutagenic potency of some conjugated nitroaromatic compounds and its relationship to structure",
abstract = "The mutagenicities of 12 conjugated non-fused nitroaromatic compounds and 1 amino analogue were determined in strains TA100 and TA98 of Salmonella typhimurium. Reversions by p-nitroaromatics increased in the order of the acetophenone, benzaldehyde, styrene, chalcone, cinnamic acid and stilbene indicating the importance for mutagenic potency of extended conjugation to the p-nitrophenyl substituent. Highest mutagenicity was found with α-substituted 4-nitrostyryl derivatives of which the phenyl derivative (31 revertants per nmole in TA100) was the most active. Generally, the TA100 strain was more sensitive than TA98 to these mutagens and S9 treatment was unnecessary for activity, although 4-nitrochalcone required S9 activation. Para-nitro isomers of the cinnamic acids and chalcones were much more active than the corresponding ortho and meta isomers. The 4-aminocinnamic acid analogue was inactive suggesting that complete reduction in Salmonella of 4-nitrocinnamic acid to an active amino derivative is not response for the high mutagenicity of the former. Mutagenicity of these p-nitrostyryl compounds may be explained by the covalent interaction of the electrophilic benzylic carbon with Salmonella DNA.",
author = "Mullin, {Christopher Albert} and Rashid, {Kamal A.} and Mumma, {Ralph O.}",
year = "1987",
month = "1",
day = "1",
doi = "10.1016/0165-1218(87)90003-6",
language = "English (US)",
volume = "188",
pages = "267--274",
journal = "Mutation Research - Genetic Toxicology Testing and Biomonitoring of Environmental or Occupational Exposure",
issn = "0165-1218",
publisher = "Elsevier BV",
number = "4",

}

Mutagenic potency of some conjugated nitroaromatic compounds and its relationship to structure. / Mullin, Christopher Albert; Rashid, Kamal A.; Mumma, Ralph O.

In: Mutation Research/Genetic Toxicology, Vol. 188, No. 4, 01.01.1987, p. 267-274.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Mutagenic potency of some conjugated nitroaromatic compounds and its relationship to structure

AU - Mullin, Christopher Albert

AU - Rashid, Kamal A.

AU - Mumma, Ralph O.

PY - 1987/1/1

Y1 - 1987/1/1

N2 - The mutagenicities of 12 conjugated non-fused nitroaromatic compounds and 1 amino analogue were determined in strains TA100 and TA98 of Salmonella typhimurium. Reversions by p-nitroaromatics increased in the order of the acetophenone, benzaldehyde, styrene, chalcone, cinnamic acid and stilbene indicating the importance for mutagenic potency of extended conjugation to the p-nitrophenyl substituent. Highest mutagenicity was found with α-substituted 4-nitrostyryl derivatives of which the phenyl derivative (31 revertants per nmole in TA100) was the most active. Generally, the TA100 strain was more sensitive than TA98 to these mutagens and S9 treatment was unnecessary for activity, although 4-nitrochalcone required S9 activation. Para-nitro isomers of the cinnamic acids and chalcones were much more active than the corresponding ortho and meta isomers. The 4-aminocinnamic acid analogue was inactive suggesting that complete reduction in Salmonella of 4-nitrocinnamic acid to an active amino derivative is not response for the high mutagenicity of the former. Mutagenicity of these p-nitrostyryl compounds may be explained by the covalent interaction of the electrophilic benzylic carbon with Salmonella DNA.

AB - The mutagenicities of 12 conjugated non-fused nitroaromatic compounds and 1 amino analogue were determined in strains TA100 and TA98 of Salmonella typhimurium. Reversions by p-nitroaromatics increased in the order of the acetophenone, benzaldehyde, styrene, chalcone, cinnamic acid and stilbene indicating the importance for mutagenic potency of extended conjugation to the p-nitrophenyl substituent. Highest mutagenicity was found with α-substituted 4-nitrostyryl derivatives of which the phenyl derivative (31 revertants per nmole in TA100) was the most active. Generally, the TA100 strain was more sensitive than TA98 to these mutagens and S9 treatment was unnecessary for activity, although 4-nitrochalcone required S9 activation. Para-nitro isomers of the cinnamic acids and chalcones were much more active than the corresponding ortho and meta isomers. The 4-aminocinnamic acid analogue was inactive suggesting that complete reduction in Salmonella of 4-nitrocinnamic acid to an active amino derivative is not response for the high mutagenicity of the former. Mutagenicity of these p-nitrostyryl compounds may be explained by the covalent interaction of the electrophilic benzylic carbon with Salmonella DNA.

UR - http://www.scopus.com/inward/record.url?scp=0023179787&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023179787&partnerID=8YFLogxK

U2 - 10.1016/0165-1218(87)90003-6

DO - 10.1016/0165-1218(87)90003-6

M3 - Article

VL - 188

SP - 267

EP - 274

JO - Mutation Research - Genetic Toxicology Testing and Biomonitoring of Environmental or Occupational Exposure

JF - Mutation Research - Genetic Toxicology Testing and Biomonitoring of Environmental or Occupational Exposure

SN - 0165-1218

IS - 4

ER -