Abstract
A group of bis-cationic imidazo[1,2-a]pyridinium salts and related compounds, some of which exhibit in vivo trypanocidal activity, have been investigated for induction of petite mutagenesis in Saccharomyces cerevisiae. All of the compounds which are active trypanocides induce mutagenesis. There appears to be a correlation between trypanocidal activity and mutagenic activity which may have its structural origin in the spatial separation of the cationic centers.
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- Braithwaite A. W., Baguley B. C. Existence of an extended series of antitumor compounds which bind to deoxyribonucleic acid by nonintercalative means. Biochemistry. 1980 Mar 18;19(6):1101–1106. doi: 10.1021/bi00547a009. [DOI] [PubMed] [Google Scholar]
- Cain B. F., Atwell G. J., Seelye R. N. Potential antitumour agents. X. Bisquaternary salts. J Med Chem. 1969 Mar;12(2):199–206. doi: 10.1021/jm00302a001. [DOI] [PubMed] [Google Scholar]
- Carrondo M. A., Coll M., Aymami J., Wang A. H., van der Marel G. A., van Boom J. H., Rich A. Binding of a Hoechst dye to d(CGCGATATCGCG) and its influence on the conformation of the DNA fragment. Biochemistry. 1989 Sep 19;28(19):7849–7859. doi: 10.1021/bi00445a047. [DOI] [PubMed] [Google Scholar]
- Das B. P., Boykin D. W. Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles. J Med Chem. 1977 Sep;20(9):1219–1221. doi: 10.1021/jm00219a023. [DOI] [PubMed] [Google Scholar]
- Feigon J., Denny W. A., Leupin W., Kearns D. R. Interactions of antitumor drugs with natural DNA: 1H NMR study of binding mode and kinetics. J Med Chem. 1984 Apr;27(4):450–465. doi: 10.1021/jm00370a007. [DOI] [PubMed] [Google Scholar]
- Ferguson L. R. Apparent changes in structure-activity relationships for antimitochondrial effects of 9-anilinoacridines according to Saccharomyces cerevisiae strain and methodology. Mutat Res. 1984 Jun;136(3):223–231. doi: 10.1016/0165-1218(84)90056-9. [DOI] [PubMed] [Google Scholar]
- Ferguson L. R., Turner P. M. Mitotic crossing-over by anticancer drugs in Saccharomyces cerevisiae strain D5. Mutat Res. 1988 Feb;204(2):239–249. doi: 10.1016/0165-1218(88)90095-x. [DOI] [PubMed] [Google Scholar]
- Hall R. M., Trembath M. K., Linnane A. W., Wheelis L., Criddle R. S. Factors affecting petite induction and the recovery of respiratory competence in yeast cells exposed to ethidium bromide. Mol Gen Genet. 1976 Mar 30;144(3):253–262. doi: 10.1007/BF00341723. [DOI] [PubMed] [Google Scholar]
- Hervé P., Philip T., Flesch M., Rozenbaum A., Plouvier E., Cahn J. Y., Noir A., Peters A., Leconte des Floris R. Intensive cytoreductive regimen and autologous bone marrow transplantation in leukemia. Present status and the future. A review. Eur J Cancer Clin Oncol. 1983 Aug;19(8):1043–1052. doi: 10.1016/0277-5379(83)90027-5. [DOI] [PubMed] [Google Scholar]
- Larsen T. A., Goodsell D. S., Cascio D., Grzeskowiak K., Dickerson R. E. The structure of DAPI bound to DNA. J Biomol Struct Dyn. 1989 Dec;7(3):477–491. doi: 10.1080/07391102.1989.10508505. [DOI] [PubMed] [Google Scholar]
- Leupin W., Chazin W. J., Hyberts S., Denny W. A., Wüthrich K. NMR studies of the complex between the decadeoxynucleotide d-(GCATTAATGC)2 and a minor-groove-binding drug. Biochemistry. 1986 Oct 7;25(20):5902–5910. doi: 10.1021/bi00368a010. [DOI] [PubMed] [Google Scholar]
- Luck G., Reinert K. E., Baguley B., Zimmer C. Interaction of the nonintercalative antitumour drugs SN-6999 and SN-18071 with DNA: influence of ligand structure on the binding specificity. J Biomol Struct Dyn. 1987 Jun;4(6):1079–1094. doi: 10.1080/07391102.1987.10507699. [DOI] [PubMed] [Google Scholar]
- Mahler H. R., Perlman P. S. Induction of respiration deficient mutants in Saccharomyces cerevisiae by berenil. I. Berenil, a novel, non-intercalating mutagen. Mol Gen Genet. 1973 Mar 19;121(4):285–294. doi: 10.1007/BF00433228. [DOI] [PubMed] [Google Scholar]
- NAGAI S. Induction of the respiration-deficient mutation in yeast by various synthetic dyes. Science. 1959 Oct 30;130(3383):1188–1189. doi: 10.1126/science.130.3383.1188-a. [DOI] [PubMed] [Google Scholar]
- Nagley P., Mattick J. S., Hall R. M., Linnane A. W. Biogenesis of mitochondria. 43. A comparative study of petite induction and inhibition of mitochondrial DNA replication in yeast by ethidium bromide and berenil. Mol Gen Genet. 1975 Dec 9;141(4):291–304. doi: 10.1007/BF00331451. [DOI] [PubMed] [Google Scholar]
- Nathan H. C., Bacchi C. J., Nichol C. A., Duch D. S., Mullaney E. A., Hutner S. H. Antitumor phthalanilides active in acute and chronic Trypanosoma brucei brucei murine infections. Am J Trop Med Hyg. 1984 Sep;33(5):845–850. doi: 10.4269/ajtmh.1984.33.845. [DOI] [PubMed] [Google Scholar]
- Pjura P. E., Grzeskowiak K., Dickerson R. E. Binding of Hoechst 33258 to the minor groove of B-DNA. J Mol Biol. 1987 Sep 20;197(2):257–271. doi: 10.1016/0022-2836(87)90123-9. [DOI] [PubMed] [Google Scholar]
- Shapiro T. A., Englund P. T. Selective cleavage of kinetoplast DNA minicircles promoted by antitrypanosomal drugs. Proc Natl Acad Sci U S A. 1990 Feb;87(3):950–954. doi: 10.1073/pnas.87.3.950. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Slonimski P. P., Perrodin G., Croft J. H. Ethidium bromide induced mutation of yeast mitochondria: complete transformation of cells into respiratory deficient non-chromosomal "petites". Biochem Biophys Res Commun. 1968 Feb 15;30(3):232–239. doi: 10.1016/0006-291x(68)90440-3. [DOI] [PubMed] [Google Scholar]
- Sundberg R. J., Dahlhausen D. J., Manikumar G., Mavunkel B., Biswas A., Srinivasan V., Musallam H. A., Reid W. A., Jr, Ager A. L. Cationic antiprotozoal drugs. Trypanocidal activity of 2-(4'-formylphenyl)imidazo[1,2-a]pyridinium guanylhydrazones and related derivatives of quaternary heteroaromatic compounds. J Med Chem. 1990 Jan;33(1):298–307. doi: 10.1021/jm00163a049. [DOI] [PubMed] [Google Scholar]
- Teng M. K., Usman N., Frederick C. A., Wang A. H. The molecular structure of the complex of Hoechst 33258 and the DNA dodecamer d(CGCGAATTCGCG). Nucleic Acids Res. 1988 Mar 25;16(6):2671–2690. doi: 10.1093/nar/16.6.2671. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Zimmermann F. K. A yeast strain for visual screening for the two reciprocal products of mitotic crossing over. Mutat Res. 1973 Oct;21(5):263–269. [PubMed] [Google Scholar]