Novel chiral naphthalimide-cycloalkanediamine conjugates: Design, synthesis and antitumor activity

A novel series of enantiopure naphthalimide-cycloalkanediamine conjugates were designed, synthetized and evaluated for in vitro cytotoxicity against human colon adenocarcinoma (LoVo), human lung adenocarcinoma (A549), human cervical carcinoma (Hela) and human promyelocytic leukemia cell lines (HL-60). The cytotoxicity of the compounds was highly dependent on size and relative stereochemistry of the cycloalkyl ring as well as length of the spacer. By contrast, any kind of enantioselection was observed for each pair of enantiomers. Flow cytometric analysis indicated that compounds 22 and 23 could effectively induce G2/M arrest in the four previous cell lines despite a mild apoptotic effect.

Automated summary

A novel series of enantiopure naphthalimide-cycloalkanediamine conjugates were designed, synthesized and evaluated for their in vitro cytotoxicity. The cytotoxicity of the compounds depended on the size of the cycloalkyl ring and length of the spacer, with no observed enantioselectivity. Compounds 22 and 23 were found to effectively induce G2/M arrest in the tested cell lines, despite a mild apoptotic effect.