Synthesis, DNA Interactions and Anticancer Evaluation of Novel Diamidine Derivatives of 3,4-Ethylenedioxythiophene

Abstract

Abstract. Eight novel diamidino 3,4-ethylenedioxythiophene-2,5-dicarboxanilides (5a-h), obtained by condensation reaction of 3,4-ethylenedioxythiophene-2,5-dicarbonyl chloride and corresponding 3-or 4-aminobenzamidines, were evaluated for interactions with double-stranded DNA and RNA, and their cytotoxicity was assayed against the panel of human cancer cell lines. All compounds preferentially bind into the minor groove of DNA and had higher affinity for DNA than for RNA. Compounds 5a-h showed a moderate antiproliferative effect toward the panel of seven carcinoma cells line, whereby the highest inhibitory potential was displayed by compound 5a with unsubstituted amidino moieties in para position.

Synthesis and structure–activity relationship of amidine derivatives of 3,4-ethylenedioxythiophene as novel antibacterial agents

“…The synthesis and characterization of compounds 18-35 have been described in our previous reports [26][27][28]. In this study we extended our investigations towards evaluation of the antibacterial activity.…”

“…These findings prompted our investigation of diamidine derivatives of 3,4-ethylenedioxythiophene, synthesized in our laboratory, as potential antibacterial agents [26][27][28]. Here we report the antibacterial activities of compounds with 3,4-ethylenedioxythiophene central unit combined with benzimidazole, phenyl, carboxamidophenyl and amidine building blocks employed as already known pharmacophores.…”

“…The compounds 18-35 have been described previously [26][27][28]. The synthesis and physical properties of novel compounds are given as follows.…”

“…IC 50 values for all compounds and for both cell lines were >95 µM. New derivatives 9-17, in general, affected eukaryotic cells to a lesser extent than previously synthesized compounds bis-benzimidazoles 18-20[26], bis-phenyls 21-26[27] and carboxamid-amidines 27-34[28] that showed cytotoxic activity against several different human cell lines. Out of the subsets of previously synthesized molecules, compounds 25 and 27 were more cytotoxic than their counterparts displaying cytotoxic effect in the low across all the tested cell lines, while compound 19, although being the most effective in its subset, was not as potent and consistent against all the cell lines.…”

Synthesis, Crystal Structure and in vitro DNA Binding Studies of Combretastatin A-4 Analogue

“…Since DNA is considered to be a primary target of most of the anticancer compounds and essentially based on the idea that compounds with planar aromatic rings are known to be its intercalators [14] an investigation of DNA binding propensity of synthesized compound was evaluated using different biophysical methods. [15] Even though DNA binding ability of a vast number of compounds has been reported, [16,17] the point of interest in this study is metal free DNA binding ability of a natural product analogue synthesized from two bioactive constituents.…”