In our earlier studies on chemical and biological properties of indolo[2,3-b]quinoline derivatives we have found that amino acid conjugates of 2-amino- and 9-amino-11-methyl-6H-indolo[2,3-b]quinoline display cytotoxic activity [1] and solubility in water contrary to inactive and non soluble in water unsubstituted 11-methyl-6H-indolo[2,3-b]quinoline.

   Continuing our search of more active cytotoxic compounds we decided to synthesize selected amino acid and peptide conjugates with 2-amino and 9-amino-5,11-dimethyl-5H-indolo[2,3-b]quinoline. We designed and obtained a series of novel Gly-, L-Pro-, D-Pro-, L-His-, D-His- as well as Gly-Gly-, L-Pro-Gly-, L-His-Gly-, Gly-L-Pro-, L-Pro-L-Pro- derivatives. Amino acid derivatives were obtained in coupling reactions using TBTU method and peptide derivatives were synthesized through a "step by step" method.

         DiMIQ                       R= Gly-, L-Pro-, D-Pro-,L-His-, D-His-,

                                           Gly-L-Pro-, L-Pro-L-Pro-, L-Pro-Gly-,

                                          Gly-Gly-, L-His-Gly-.

   New compounds were evaluated for their cototoxic activity againts KB cell line and antimicrobial activity in vitro, according to a routine procedures. The biological tests showed that all amino acid derivatives of 5,11-dimethyl-5H-indolo[2,3-b]quinoline display significant biological activity. The peptide derivatives of 5,11-dimethyl-5H-indolo[2,3-b]quinoline exhibit similar cytotoxic activity againts KB cells compared to 5,11-dimethyl-5H-indolo[2,3-b]quinoline (DiMIQ).

References

1. K.Sidoryk, Ł.Kaczmarek, W.J.Szczepek, J.Wietrzyk, M. Świtalska and W.Peczyńska-Czoch, Polish J. Chem., 82, 2095, 2008.

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