Evaluation of microbial testing methods for the mutagenicity of quinoline and its derivatives
- 118 Downloads
- 21 Citations
Abstract
Using the “mutational enhancement” method and the Ames test, the mutagenicity and potential carcinogenicity of quinoline and its derivatives were determined and compared. Quinoline, 8-hydroxyquinoline, 5-hydroxyquinoline, 8-hydroxyquinoline sulfate, 6-nitroquinoline, 8-nitroquinoline, and 3-methylquinoline were mutagenic in the Ames direct plating test on TA 98 and TA 100 with activating system (S-9) from the rat liver. These compounds were not mutagenic in the “mutational enchancement” test onEscherichia coli HCR+ strain. 5,7-Dichloro-8-hydroxyquinoline, isoquinoline, and 2-chloroquinoline were nonmutagenic without or with S-9 in both the Ames and “mutational enhancement” test system. The compounds chloroquine, primaquine diphosphate, quinine hydrobromide, quinine hydrochloride, quinine lactate, quinine urea hydrochloride, quinine ethylcarbonate, quinine dihydrochloride, beta quinine quinine valerate, and quinine glycerophosphate were nonmutagenic with and without S-9 in the Ames test but mutagenic (20–60 μg/ml) in the “mutational enhancement” test method onEscherichia coli HCR+ strains. The observations reported here point out that the Ames test responds negatively to several quinoline derivatives that are positive in the “mutational enchancement” test method.
Keywords
Quinoline Chloroquine Quinine Isoquinoline GlycerophosphatePreview
Unable to display preview. Download preview PDF.
Literature Cited
- 1.Allison, J. L., O'Brien, R., Haun, F. E. 1965. DNA: reaction with chloroquine. Science149:111–113.Google Scholar
- 2.Ames, B. N., Durston, W. E., Yamasaki, E., Lee, F. D. 1974. Carcinogens are mutagens: a simple test system combining liver homogenates for activation and bacteria for detection. Proceedings of the National Academy of Sciences of the United States of America70:2281–2286.Google Scholar
- 3.Ames, B. N., McCann, J., Yamasaki, E. 1975. Methods for detecting carcinogens and mutagens with theSalmonella mammalian-microsome mutagenicity test. Mutation Research3:347–364.Google Scholar
- 4.Ames, B. N., Kammen, H. D., Yamasaki, E. 1975. Hair dyes are mutagenic: identification of a variety of mutagenic ingredients. Proceedings of the National Academy of the Sciences of the United States of America72:2423–2427.Google Scholar
- 5.Blodgett, L. W., Yielding, K. L. 1968. Comparison of chloroquine's bonding to DNA and polyadenylic and polyguanylic acids. Biochimica et Biophysica Acta169:451–456.PubMedGoogle Scholar
- 6.Bridges, B. A. 1972. Simple bacterial systems for detecting mutagenic agents. Lab. Pract.2:413–419.Google Scholar
- 7.Cleaver, J. E., Bootsma, D. 1975.Xeroderma pigmentosum: biochemical and genetic characteristics. Annual Review of Genetics9:19–35.PubMedGoogle Scholar
- 8.Cohen, S., Yielding, K. L. 1965. Spectrophotometric studies of the interaction of chloroquine with DNA. Journal of Bacteriology240:3123–3131.Google Scholar
- 9.Epler, J. L., Hardigree, A. A., Young, J. A., Rao, T. K. 1978. Feasibility of application of mutagenicity testing to aqueous environmental effluents. Mutation. Research53:88.Google Scholar
- 10.Epstein, W. L., Fukuyama, K., Epstein, J. H. 1971. Ultraviolet light, DNA repair and skin carcinogenesis in man. Federation Proceedings30:1766–1771.PubMedGoogle Scholar
- 11.Hirao, K., Shimohara, Y., Tsuda, H., Fukushina, S., Takahashi, M., Ito, N. 1976. Carcinogenic activity of quinoline on rat liver36:329–335.Google Scholar
- 12.Kier, L. D., Yamasaki, E., Ames, B. N. 1974. Detection of mutagenic activity in cigarette smoke condensates. Proceedings of the National Academy of Sciences of the United States of America71:4159–4163.PubMedGoogle Scholar
- 13.McCann, J., Choi, E., Yamasaki, E., Ames, B. N. 1975. Detection of carcinogens as mutagens inSalmonella-microsome test: assay of 300 chemicals. Proceedings of the National Academy of Sciences of the United States of America72:5135–5140.PubMedGoogle Scholar
- 14.Mohn, G., Ellenberger, J., McGregor, D. 1974. Development of mutagenicity tests usingEscherichia coli K-12 as indicator organisms. Mutation Research25:187–196.PubMedGoogle Scholar
- 15.Nagao, M., Yahagi, T., Seino, Y., Sugimura, T., Ito, N. 1977. Mutagenicities of quinoline and its derivatives. Mutation Research42:335–342.PubMedGoogle Scholar
- 16.O'Brien, R., Olenick, J., Haun, F. 1966. Reactions of quinine, chloquine and quinacrine with DNA and their effects on DNA and RNA polymerase reactions. Biochemistry55:1511–1516.Google Scholar
- 17.Rubin, I. B., Guerin, M. R., Hardigree, A. A., Epler, J. L. 1976. Fractionation of synthetic and crude oils from coal for biological testing. Environmental Research12:358–365.PubMedGoogle Scholar
- 18.Rupp, W. D., Wilde, III, C. E., Reno, D. L., Howard-Flanders, P. 1971. Exchange between DNA strands in ultraviolet-irradiatedEscherichia coli. Journal of Molecular Biology61:25–44.PubMedGoogle Scholar
- 19.Setlow, R. B., Carrier, W. L. 1964. The disappearance of thymine dimers from DNA: an error correcting mechanism. Proceedings of the National Academy of Sciences of the United States of America51:226–231.PubMedGoogle Scholar
- 20.Setlow, R. B., Carrier, W. L., Bollum, F. L. 1965. Pyrimidine dimers in ultraviolet-irradiated poly-deoxyinosine: deoxycytosine. Proceedings of the National Academy of Sciences of the United States of America53:1111–1118.PubMedGoogle Scholar
- 21.Sideropoulos, A. S., Shankel, D. M. 1968. Mechanism of caffeine enhancement of mutations induced by sublethal ultraviolet dosages. Journal of Bacteriology96:198–204.PubMedGoogle Scholar
- 22.Sideropoulos, A. S., Specht, S. M., Jones, M. T. 1980. Feasibility of testing DNA repair inhibitors for mutagenicity by a simple method. Mutation Research74:95–105.PubMedGoogle Scholar
- 23.Sideropoulos, A. S., Kacsuta, P., Betz, M. K. 1980. Mutations induced by substituted quinolines in ultravioletirradiated bacteria. Current Microbiology3:207–212.Google Scholar
- 24.Slater, E. E., Anderson, M. D., Rosenkranz, H. S. 1971. Rapid detection of mutagens and carcinogens. Cancer Research21:970–973.Google Scholar
- 25.Witkin, E. M. 1976. Ultraviolet mutagenesis and inducible DNA repair inEscherichia coli. Bacteriological Reviews40:869–907.PubMedGoogle Scholar
- 26.Yahagi, T., Degawa, M., Seito, Y., Matsushima, T., Nagao, N., Sugimura, T., Hashimoto, Y. 1975. Mutagenicity of carcinogenic azo dyes and their derivatives. Cancer Letters1:91–96.PubMedGoogle Scholar