In order to identify a photoaffinity probe for 9-aminoacridine frameshift mutagenesis, 20 azido analogs of acridine were synthesized and tested in Ames' Salmonella tester strains, TA1535, TA1537, TA1538 and their corresponding excision-repair-proficient strains TA1975, TA1977, and TA1978, to determine their mutagenicity and toxicity relative to 9-aminoacridine. The substituent-mutagenicity patterns observed for these compounds agree very well with those obtained previously for non-azidoacridines. The results presented here show that the 2-azido-analog of 9-aminoacridine demonstrates biological activity similar to 9-aminoacridine prior to photolytic activation. With light activation, however, the 9-amino-2-azido derivative becomes more effective at producing frameshift mutations characteristics of 9-aminoacridine. Furthemore, this photolytic enhancement of mutagenesis appears to be due to the repairable lesion suggesting that covalent attachment of the drug occurs. © 1981.
Firth, W. J., Rock, S. G., Brown, B. R., & Yielding, L. W. (1981). Azido analogs of acridine: Photoaffinity probes for frameshift mutagenesis in Salmonella typhimurium. Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, 81(3), 295–309. https://doi.org/10.1016/0027-5107(81)90118-4