期刊
MOLECULES
卷 27, 期 18, 页码 -出版社
MDPI
DOI: 10.3390/molecules27185913
关键词
diketopiperazine; cyclo(Trp-Arg); natural product; synthesis; structure revision; antimicrobial; antibiotic enhancement
资金
- Catalyst: Seeding Dumont d'Urville NZ-France Science & Technology Support Programme by the New Zealand Ministry of Business, Innovation and Employment [19-UOA-057-DDU]
Two diketopiperazine natural products were found to have antibacterial activity and enhance the action of antibiotics. However, the synthesized diastereomers did not exhibit the same properties, indicating that these compounds are not suitable templates for new treatments for microbial infections.
New therapeutic options to combat the growing incidence of antimicrobial resistance are urgently needed. A 2015 publication reported the isolation and biological evaluation of two diketopiperazine natural products, cyclo(l-Trp-l-Arg) (CDP 2) and cyclo(d-Trp-d-Arg) (CDP 3), from an Achromobacter sp. bacterium, finding that the latter metabolite in particular exhibited strong antibacterial activity towards a range of wound-related microorganisms and could synergize the action of ampicillin. Intrigued by these biological activities and noting inconsistencies in the structural characterization of the natural products, we synthesized the four diastereomers of cyclo(Trp-Arg) and evaluated them for antimicrobial and antibiotic enhancement properties. The detailed comparison of spectroscopic data raises uncertainty regarding the structure of CDP 2 and disproves the structure of CDP 3. In our hands, none of the four stereoisomers of cyclo(Trp-Arg) exhibited detectable intrinsic antimicrobial properties towards a range of Gram-positive and Gram-negative bacteria or fungi nor could they potentiate the action of antibiotics. These discrepancies in biological properties, compared with the activities reported in the literature, reveal that these specific cyclic dipeptides do not represent viable templates for the development of new treatments for microbial infections.
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