Poster Presentation RACI Biomolecular Division Conference 2013
Synthesis of water soluble mono and bis[60]fullerene based di and tetra cationic peptoids as potential anti-infective agents (#70)
An efficient synthesis of binaphthyl-based neutral, and mono- and di-cationic, peptoids has been described.1 Some of these compounds had antibacterial activities with MIC values of 1.9-3.9 μg/mL against Staphylococus aureus. Peptoid 1 had a MIC value of 4 μg/mL against a methicillin-resistant strain of S. aureus (MRSA) and a MIC value of 2 μg/mL against vancomycin-resistant strains of S. enterococci (VRE).
Our expertise in fullerenyl amino acids, encouraged us to replace the binaphthyl unit of (1) with a C60 unit since they are similar in size. [60]Fullerenyldihydropyrrole peptides have been prepared from the coupling of mono and bis [60]fullerenyldihydropyrrole carboxylic acids with glycine t-butyl ester and then deprotected to the acid and finally coupled with presynthesised L-lys-L-lys or L-lys-D-arg in an efficient manner.
Testing of these derivatives by broth microdilution against S. aureus NCTC 6571 and E. coli ATCC 10418 been done, the highest test concentrations ranged from 100 µg/ml to 340 µg/ml depending on each compound. The synthesis and biological results will be presented in the poster.