Comparison of the mutagenicity of quinoline and all monohydroxyquinolines with a series of arene oxide, trans-dihydrodiol, diol epoxide, N-oxide and arene hydrate derivatives of quinoline in the Ames/Salmonella microsome test

Willems, M.I.; Dubois, Garrett C.; Boyd, Derek R.; Davies, R. Jeremy H.; Hamilton, Lynne; McCullough, John J.; Bladeren, P.J. van

doi:10.1016/s0165-1218(10)80002-3

Cited by 34 publications

(17 citation statements)

References 15 publications

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“…3-FQ was mainly metabolized to 5,6-dihydro-5,6-dihydroxy derivatives, 23) likely through hydrolysis of the corresponding 5,6-epoxides, and 5,6-dihydroquinoline 5,6-epoxide was shown to be much less mutagenic than quinoline in Salmonella typhimurium TA100. 23,24) Similarly, 3FQ showed less clastogenicity and cytotoxicity than quinoline in the in vitro CA and MN tests.…”

Section: Discussionmentioning

confidence: 92%

Clastogenicity of Quinoline and Monofluorinated Quinolines in Chinese Hamster Lung Cells

Suzuki

Takeshita²,

Saeki

et al. 2007

JOURNAL OF HEALTH SCIENCE

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Quinoline and four monofluorinated derivatives of quinoline (FQ's) were tested for their clastogenicity in a Chinese hamster lung (CHL) cell line using chromosomal aberration (CA) and micronucleus (MN) tests. Quinoline and all the fluoroquinolines, 3-, 5-, 6-, and 8-FQ, induced CA in the presence of the metabolic activation system. However, the clastogenic property was altered by fluorine-substitution. 3-FQ showed reduced cytotoxicity and clastogenicity. It was positive only at a higher dose than the other compounds. 6-FQ was as cytotoxic and clastogenic as quinoline when tested in the lower dose range (less than 0.075 mg/ml). 5-FQ and 8-FQ were only moderately clastogenic in the CA test although their toxicity was similar to that of quinoline. The MN test showed almost the same tendency in clastogenicity as the CA test, except that 8-FQ showed a negative result. These results demonstrate that fluorinesubstitution can modify the clastogenicity of quinoline, probably through interference of the metabolic activation.

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Section: Discussionmentioning

confidence: 92%

Clastogenicity of Quinoline and Monofluorinated Quinolines in Chinese Hamster Lung Cells

Suzuki

Takeshita²,

Saeki

et al. 2007

JOURNAL OF HEALTH SCIENCE

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“…The induction of esthesioneuroepitheliomas and sarcomas NOS in the nasal cavity of male rats in the present study may be attributed to circulatory or exhalatory influence of quinoline or its metabolites on nasal tissue after gastrointestinal absorption. Quinoline has significant mutagenic activity in Salmonella Typhimurium (TA98 and TA100) and Escherichia coli (WP2uvrA) after metabolic activation by the rat liver S9 fraction (Nagao et al, 1977;Takahashi et al, 1988;LaVoie et al, 1991;Willems et al, 1992;JETOC, 1996) and induces unscheduled DNA synthesis in rat hepatocytes in vitro (LaVoie et al, 1991). Positive mammalian clastogenicity of quinoline on cultured Chinese hamster lung cells after metabolic activation by the rat liver S9 fraction has also been reported (JETOC, 1996).…”

Section: Discussionmentioning

confidence: 99%

Carcinogenicity of quinoline by drinking-water administration in rats and mice

Matsumoto¹,

Kano²,

Suzuki³

et al. 2018

J. Toxicol. Sci.

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-The carcinogenicity of quinoline was examined by administrating quinoline in the drinking water to groups of 50 F344/DuCrj rats and 50 Crj: BDF1 mice of each sex. In rats, the doses of quinoline were 0, 200, 400, and 800 ppm for males and 0, 150, 300, and 600 ppm for females. In male rats, administration of quinoline was terminated at week 96 due to high mortality caused by tumors. There were significant increases of hepatocellular adenomas, hepatocellular carcinomas, hepatocellular adenomas and/or carcinomas (combined), and liver hemangiomas, hemangiosarcomas, hemangiomas and/ or hemangiosarcomas (combined) in both male and female rats, and nasal esthesioneuroepitheliomas and sarcoma NOS (not otherwise specified) in males. In mice, doses of quinoline were 0, 150, 300 and 600 ppm for both males and females. Administration of quinoline was terminated at week 65 in males and at week 50 in females due to high mortality caused by tumors. There were marked increases of hemangiomas, hemangiosarcomas, and hemangiomas and/or hemangiosarcomas (combined) in the retroperitoneum, mesenterium, and liver in males, and in the retroperitoneum, mesenterium, peritoneum, and subcutis in females. Additionally, histiocytic sarcomas were statistically increased in the livers of female mice. Thus the present studies provided clear evidence of carcinogenic activity of quinoline administered in the drinking water in both rats and mice.

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“…The chemical 8HQ is not genotoxic unless metabolically activated, e.g., by rodent liver or by S9-mix (Hollstein et al, 1978;Willems et al, 1992); mutagenic activity of 8HQ was correlated to the formation of water-soluble quinoline intermediate metabolites, which constitute epoxide derivatives that could form DNA adducts (Tada et al, 1980).…”

Section: Sensitivity To 8hqmentioning

confidence: 99%

Further phenotypic characterization of pso mutants of Saccharomyces cerevisiae with respect to DNA repair and response to oxidative stress

Pungartnik¹,

Picada²,

Brendel³

et al. 2002

Genet. Mol. Res.

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cox11-∆ exhibited additivity of 8HQ and NDEA sensitivities of the single mutants, indicating that two different repair/recovery systems are involved in survival. DEO sensitivity of the double mutant was equal or less than that of the single snm1-∆ mutant. In order to determine if there was oxidative damage to nucleotide bases by these drugs we employed an established bacterial test with and without metabolic activation. After S9-mix biotransformation, NDEA and to a lesser extent 8HQ, lead to significantly higher mutagenesis in an Escherichia coli tester strain WP2-IC203 as compared to WP2, whereas DEO-induced mutagenicity remained unchanged.

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Comparison of the mutagenicity of quinoline and all monohydroxyquinolines with a series of arene oxide, trans-dihydrodiol, diol epoxide, N-oxide and arene hydrate derivatives of quinoline in the Ames/Salmonella microsome test

Cited by 34 publications

References 15 publications

Clastogenicity of Quinoline and Monofluorinated Quinolines in Chinese Hamster Lung Cells

Clastogenicity of Quinoline and Monofluorinated Quinolines in Chinese Hamster Lung Cells

Carcinogenicity of quinoline by drinking-water administration in rats and mice

Further phenotypic characterization of pso mutants of Saccharomyces cerevisiae with respect to DNA repair and response to oxidative stress

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