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New amino acid and peptide derivatives of 5H-indolo[2,3-b]quinoline and their biological activity.

Katarzyna Sidoryk 1Wojciech J. Szczepek 1Łukasz S. Kaczmarek 1Joanna Wietrzyk 2Marta Świtalska 2Wanda Peczyńska-Czoch 3Joanna Stefańska 4

1. Pharmaceutical Research Institute (IF), Rydygiera 8, Warszawa 01-793, Poland
2. Polish Academy of Sciences, Institute of Immunology and Experimental Therapy (IITD), Rudolfa Weigla 12, Wrocław 53-114, Poland
3. Wrocław University of Technology, Department of Organic Chemistry, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland
4. Medical University of Warsaw, Department of Pharmaceutical Microbiology, Oczki, Warsaw 02-007, Poland


   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).


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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Submitted: 2010-01-27 06:46
Revised:   2010-03-07 16:02