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Development and evaluation of cationic amphiphilic antimicrobial 2,5-diketopiperazines
UiT Arctic Univ Norway, Norway;Univ Aberdeen, UK.
University of Gothenburg.
RISE Res Inst Sweden.
UiT Arctic Univ Norway, Norway.
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2018 (English)In: Journal of Peptide Science, ISSN 1075-2617, E-ISSN 1099-1387, Vol. 24, no 7, article id UNSP e3090Article in journal (Refereed) Published
Abstract [en]

Both pathogenic bacteria and fungi are developing resistance to common antimicrobial treatment at an alarming rate. To counteract this development, it is of essence to develop new classes of antimicrobial agents. One such class is antimicrobial peptides, most of which are derived from the innate immune system. In this study, a series of novel 2,5-diketopiperazines were designed, synthesized, and evaluated for their antimicrobial abilities. The compounds were designed to probe the pharmacophore dictated for short linear mimics of antimicrobial cationic peptides, and as such, the compounds contain a range of cationic and hydrophobic functionalities. Several of the prepared compounds displayed high antimicrobial activities toward bacteria and also against human pathogenic fungi. Of particular interest was the high activity toward fungal strains with an inherent increased resistance toward conventional antifungal agents. The most effective compounds displayed inhibition of Candida glabrata and Candida krusei growth at concentrations between 4 and 8 mu g/mL, which is comparable to commercial antifungal agents in use. Structure activity relationship studies revealed a similar dependence on cationic charge and the volume of the hydrophobic bulk as for linear cationic antimicrobial peptides. Finally, the hemolytic activity of selected compounds was evaluated, which revealed a potential to produce active compounds with attenuation of unwanted hemolysis. The findings highlight the potential of cyclic cationic amphiphilic peptidomimetics as a class of promising compounds for the treatment of infections caused by microorganisms with an increased resistance to conventional antimicrobial agents.

Place, publisher, year, edition, pages
John Wiley & Sons, 2018. Vol. 24, no 7, article id UNSP e3090
Keywords [en]
2, 5-diketopiperazine, antifungal agents, antimicrobial, Candida krusei, MRSA, structure-activity relationship
National Category
Biochemistry and Molecular Biology
Research subject
Natural Science, Biomedical Sciences
Identifiers
URN: urn:nbn:se:lnu:diva-77499DOI: 10.1002/psc.3090ISI: 000440144700005PubMedID: 29845683Scopus ID: 2-s2.0-85047664224OAI: oai:DiVA.org:lnu-77499DiVA, id: diva2:1243969
Conference
7th International Meeting on Antimicrobial Peptides, AUG 25-27, 2017, Univ Copenhagen, Copenhagen, DENMARK
Available from: 2018-08-31 Created: 2018-08-31 Last updated: 2019-08-29Bibliographically approved

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Sandholm, KerstinNilsson Ekdahl, Kristina

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