DNA sequence-recognizing properties of minor groove alkylating agents - Effects of the replacement of N-methylpyrrole by an N-methylimidazole on tallimustine and its own homologue

The linkage of an heterocycle, like N-methylimidazole, to minor DNA groove binders containing two or three pyrroles lead to a new class of oligopeptid es with reduced antitumor activity both in vitro and in vivo if compared to tallimustine (CAS 115308-98-0) and its tetrapyrrole homologue 9. In the pr esent paper is reported the correlation between the cytoxicity of tallimust ine and its derivatives 9-11 with their ability to inhibit polymerase chain reaction (PCR) amplification of oestrogen receptor and Ha-ras gene sequenc es, containing A+T rich and G+C rich regions, respectively. Tallimustine an d its tetrapyrrole homologue 9 were found to have higher sequence selectivi ty for the human oestrogen receptor (ER) gene with respect to the relative imidazole-containing analogues.