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Issue 36, 2015
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Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies

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Abstract

Novel, cyclic peptidomimetics were synthesized by facile acylation reactions using benzotriazole chemistry. Microbiological testing of the synthesized compounds revealed an exceptionally high activity against Candida albicans with a minimum inhibitory concentration (MIC) two orders of magnitude lower than the MIC of the antifungal reference drug amphotericin B. A strikingly high activity was also observed against three Gram-negative bacterial strains (Pseudomonas aeruginosa, Klebsiella pneumoniae and Proteus vulgaris), two of which are known human pathogens. Thus the discovered chemotype is a potential polypharmacological agent. The toxicity against mammalian tumor cells was found to be low, as demonstrated in five different human cell lines (HeLa, cervical; PC-3, prostate; MCF-7, breast; HepG2, liver; and HCT-116, colon). The internal consistency of the experimental data was studied using 3D-pharmacophore and 2D-QSAR.

Graphical abstract: Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies

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Publication details

The article was received on 09 Jul 2015, accepted on 31 Jul 2015 and first published on 31 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01400J
Citation: Org. Biomol. Chem., 2015,13, 9492-9503

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    Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies

    M. A. Ibrahim, S. S. Panda, A. A. Oliferenko, P. V. Oliferenko, A. S. Girgis, M. Elagawany, F. Z. Küçükbay, C. S. Panda, G. G. Pillai, A. Samir, K. Tämm, C. D. Hall and A. R. Katritzky, Org. Biomol. Chem., 2015, 13, 9492
    DOI: 10.1039/C5OB01400J

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