Chain length dependence of antimicrobial peptide–fatty acid conjugate activity

Chu-Kung, Alexander F.; Nguyen, Rose; Bozzelli, Kristen N.; Tirrell, Matthew

doi:10.1016/j.jcis.2009.11.057

Cited by 102 publications

(95 citation statements)

References 47 publications

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“…The literature also reports that long-chain unsaturated fatty acids, such as linoleic acid, show antibacterial activity and are considered the key ingredients of antimicrobial food additives and some antibacterial herbs. Other reports about the conjugate use of fatty acids and peptides or antibiotics were observed, all indicating a potentiation of antibiotic activity due the enhanced membrane permeability [40][41][42].…”

Section: Resultsmentioning

confidence: 91%

Synergistic action between Caryocar coriaceum Wittm. fixed oil with aminoglycosides in vitro

Saraiva

Matias

Coutinho

et al. 2011

Euro J Lipid Sci & Tech

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The oil obtained from the Caryocar coriaceum Wittm. ( pequi) fruit pulp (C. coriaceum fixed oil -CCFO), rich in fatty acids, has been secularly employed by traditional medicine in the treatment of respiratory affections, skin inflammation, and wounds. These observations encouraged us to investigate the antimicrobial activity of CCFO and to investigate its effect in combination with aminoglycosides. The minimum inhibitory concentration (MIC) of CCFO alone and associated with aminoglycosides against Escherichia coli and Staphylococcus aureus strains were determined using microdilution assay. CCFO alone had a MIC of 512 mg/mL against E. coli and S. aureus resistant strains. Combining the CCFO with aminoglycosides reduced the MIC of aminoglycosides against the resistant strains of E. coli and S. aureus. The results obtained indicate that CCFO displays a significant synergistic antibiotic effect when combined with aminoglycosides, demonstrating that the oil constituents (fatty acids) may act as potentiators of the antibiotic activity of aminoglycosides. These properties make CCFO oil an interesting alternative as a remedy or nutraceutical against multiresistant bacteria, preventing the development of resistance by these microorganisms.Practical applications: This article demonstrates the capacity of the C. coriaceum oil to enhance the antibiotic activity of aminoglycosides. This activity could represent a new way to combat the growing bacterial resistance to antibiotics, an important problem of public health.

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Section: Resultsmentioning

confidence: 91%

Synergistic action between Caryocar coriaceum Wittm. fixed oil with aminoglycosides in vitro

Saraiva

Matias

Coutinho

et al. 2011

Euro J Lipid Sci & Tech

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“…This may suggest that it is not the soluble peptide/nanofibers that prevent the growth of the bacteria on the agar plate and a different antimicrobial mechanism may be used by self-assembled nanofiber hydrogels. 48 We postulate that the antimicrobial activity displayed by hydrogels may be largely attributed to the surface chemistry of the supramolecular hydrogel nanofibers and their bulk rheological properties. Due to the formation of large quantities of elongated peptide nanofibers, excessive charge density is possible to trap the bacterial cell on the hydrogel surface and greatly reduces their motility.…”

Section: Resultsmentioning

confidence: 99%

Self-assembly of cationic multidomain peptide hydrogels: supramolecular nanostructure and rheological properties dictate antimicrobial activity

Jiang

Sellati

et al. 2015

Nanoscale

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Hydrogels are an important class of biomaterials that have been widely utilized for a variety of biomedical/medical applications. The biological performance of hydrogels, particularly those used as wound dressing could be greatly advanced if imbued with inherent antimicrobial activity capable of staving off colonization of the wound site by opportunistic bacterial pathogens. Possessing such antimicrobial properties would also protect the hydrogel itself from being adversely affected by microbial attachment to its surface. We have previously demonstrated the broad-spectrum antimicrobial activity of supramolecular assemblies of cationic multi-domain peptides (MDPs) in solution. Here, we extend the 1-D soluble supramolecular assembly to 3-D hydrogels to investigate the effect of the supramolecular nanostructure and its rheological properties on the antimicrobial activity of self-assembled hydrogels. Among designed MDPs, the bactericidal activity of peptide hydrogels was found to follow an opposite trend to that in solution. Improved antimicrobial activity of self-assembled peptide hydrogels is dictated by the combined effect of supramolecular surface chemistry and storage modulus of the bulk materials, rather than the ability of individual peptides/peptide assemblies to penetrate bacterial cell membrane as observed in solution. The structure–property–activity relationship developed through this study will provide important guidelines for designing biocompatible peptide hydrogels with built-in antimicrobial activity for various biomedical applications.

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“…These compounds have been gaining increased acceptance and attention because of the pressure for new antimicrobial agents against resistant pathogens. Different lipopeptide design strategies include peptide alkylation, acylation, and peptidomimetics, which are being studied preclinically (2,6,7,31,32). Clinically used lipopeptides include the antifungal agent caspofungin and the antimicrobial agent daptomycin.…”

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confidence: 99%

Ultrashort Peptide Bioconjugates Are Exclusively Antifungal Agents and Synergize with Cyclodextrin and Amphotericin B

Arnusch

Ulm

Josten

et al. 2012

Antimicrob Agents Chemother

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Many natural broad-spectrum cationic antimicrobial peptides (AMPs) possess a general mode of action that is dependent on lipophilicity and charge. Modulating the lipophilicity of AMPs by the addition of a fatty acid has been an effective strategy to increase the lytic activity and can further broaden the spectrum of AMPs. However, lipophilic modifications that narrow the spectrum of activity and exclusively direct peptides to fungi are less common. Here, we show that short peptide sequences can be targeted to fungi with structured lipophilic biomolecules, such as vitamin E and cholesterol. The conjugates were active against Aspergillus fumigatus, Cryptococcus neoformans, and Candida albicans but not against bacteria and were observed to cause membrane perturbation by transmission electron microscopy and in membrane permeability studies. However, for C. albicans, selected compounds were effective without the perturbation of the cell membrane, and synergism was seen with a vitamin E conjugate and amphotericin B. Moreover, in combination with ␤-cyclodextrin, antibacterial activity emerged in selected compounds. Biocompatibility for selected active compounds was tested in vitro and in vivo using toxicity assays on erythrocytes, macrophages, and mice. In vitro cytotoxicity experiments led to selective toxicity ratios (50% lethal concentration/MIC) of up to 64 for highly active antifungal compounds, and no in vivo murine toxicity was seen. Taken together, these results highlight the importance of the conjugated lipophilic structure and suggest that the modulation of other biologically relevant peptides with hydrophobic moieties, such as cholesterol and vitamin E, generate compounds with unique bioactivity.

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Chain length dependence of antimicrobial peptide–fatty acid conjugate activity

Cited by 102 publications

References 47 publications

Synergistic action between Caryocar coriaceum Wittm. fixed oil with aminoglycosides in vitro

Synergistic action between Caryocar coriaceum Wittm. fixed oil with aminoglycosides in vitro

Self-assembly of cationic multidomain peptide hydrogels: supramolecular nanostructure and rheological properties dictate antimicrobial activity

Ultrashort Peptide Bioconjugates Are Exclusively Antifungal Agents and Synergize with Cyclodextrin and Amphotericin B

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