ArticleBioorganic & medicinal chemistry letters2015
Chemical conjugation of 2-hexadecynoic acid to C5-curcumin enhances its antibacterial activity against multi-drug resistant bacteria.
Article in Bioorganic & medicinal chemistry letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 23 citations in OpenAlex.
- Dual Mechanisms of Action of a Halogenated Allyl Fatty Acid against Methicillin-ResistantACS omega · 2025Article
- Protein-Protein Interactions as Promising Molecular Targets for Novel Antimicrobials Aimed at Gram-Negative Bacteria.International journal of molecular sciences · 2025Review
- Anti-staphylococcal fatty acids: mode of action, bacterial resistance and implications for therapeutic application.Microbiology (Reading, England) · 2025Review
- Synthesis of the NovelACS omega · 2024Article
- Vinyl halogenated fatty acids display antibacterial activity against clinical isolates of methicillin-resistantMedical research archives · 2022Article
- Antibacterial fatty acids: An update of possible mechanisms of action and implications in the development of the next-generation of antibacterial agents.Progress in lipid research · 2021Review
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- Article
- Biological activities of curcuminoids, other biomolecules from turmeric and their derivatives - A review.Journal of traditional and complementary medicine · 2017Review
- Type IV traffic ATPase TrwD as molecular target to inhibit bacterial conjugation.Molecular microbiology · 2016Article
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Authors and funding
10 authors at 3 institutions in 1 country.
Funding
Abstract
The first total synthesis of a C5-curcumin-2-hexadecynoic acid (C5-Curc-2-HDA, 6) conjugate was successfully performed. Through a three-step synthetic route, conjugate 6 was obtained in 13% overall yield and tested for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains. Our results revealed that 6 was active against eight MRSA strains at MICs that range between 31.3 and 62.5 μg/mL. It was found that the presence of 2-hexadecynoic acid (2-HDA, 4) in conjugate 6 increased 4-8-fold its antibacterial activity against MRSA strains supporting our hypothesis that the chemical connection of 4 to C5-curcumin (2) increases the antibacterial activity of 2 against Gram-positive bacteria. Combinational index (CIn) values that range between 1.6 and 2.3 were obtained when eight MRSA strains were treated with an equimolar mixture of 2 and 4. These results demonstrated that an antagonistic effect is taking place. Finally, it was investigated whether conjugate 6 can affect the replication process of S. aureus, since this compound inhibited the supercoiling activity of the S. aureus DNA gyrase at minimum inhibitory concentrations (MIC) of 250 μg/mL (IC50=100.2±13.9 μg/mL). Moreover, it was observed that the presence of 4 in conjugate 6 improves the anti-topoisomerase activity of 2 towards S. aureus DNA gyrase, which is in agreement with results obtained from antibacterial susceptibility tests involving MRSA strains.
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