Synthesis and antimicrobial activity of symmetrical two-tailed dendritic tricarboxylato amphiphiles

Sugandhi, Eko W.; Falkinham, Joseph O.; Gandour, Richard D.

doi:10.1016/j.bmc.2007.03.017

Cited by 17 publications

(13 citation statements)

References 28 publications

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“…H NMR (400 MHz, CDCl 3 ) δ 2.73 -2.59 (m, 1H), 1.48 -1.10 (m, 42H), 0.87 (t, J = 6.7 Hz, 6H); 13 C NMR (101 MHz, CDCl 3 ) δ 51.2, 38.2, 31.9, 29.8, 29.7 -29.6 (m), 29.3, 26.2, 22. 7, 14.1.Spectroscopic data is in agreement with published data 4. …”

supporting

confidence: 90%

Peptide catalysis in aqueous emulsions

2014

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confidence: 90%

Peptide catalysis in aqueous emulsions

2014

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“…Long-chain secondary alcohols, which may be active ingredients in cosmetic formulations 34,35 , performance additives in oleochemicals or building blocks in natural product synthesis 36 and for organic photosensitisers 37 , are currently not accessible from natural fatty acids. Established synthetic routes almost exclusively build on Grignard-type reactions of halide-derived nucleophiles with aldehydes or formic acid esters 37 , thereby necessitating multistep syntheses, leading to racemic products and generating significant amounts of salt wastes.…”

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confidence: 99%

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

et al. 2020

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En route to a bio-based chemical industry, the conversion of fatty acids into building blocks is of particular interest. Enzymatic routes, occurring under mild conditions and excelling by intrinsic selectivity, are particularly attractive. Here we report photoenzymatic cascade reactions to transform unsaturated fatty acids into enantiomerically pure secondary fatty alcohols. In a first step the C=C-double bond is stereoselectively hydrated using oleate hydratases from Lactobacillus reuteri or Stenotrophomonas maltophilia. Also, dihydroxylation mediated by the 5,8-diol synthase from Aspergillus nidulans is demonstrated. The second step comprises decarboxylation of the intermediate hydroxy acids by the photoactivated decarboxylase from Chlorella variabilis NC64A. A broad range of (poly)unsaturated fatty acids can be transformed into enantiomerically pure fatty alcohols in a simple one-pot approach.

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“…The MIC then increases for amphiphiles with tail lengths exceeding this optimal length. [14][15][16][17][18][19][20][21] Variations in spacing between head groups can also impact the MIC. For example, studies conducted by our labs show that amphiphiles with a 5-carbon spacer between two cationic head groups are the most biologically active.…”

Section: Introductionmentioning

confidence: 99%

“…13 A large variety of novel amphiphiles has been synthesized in an effort to increase effectiveness and specificity. [14][15][16][17][18][19][20][21][22][23][24] Amphiphile structure, including size and relative number of hydrophobic tails and hydrophilic head groups, governs colloidal characteristics including the critical aggregation concentration (CAC) and thermodynamic properties. 25 At concentrations below the CAC, amphiphiles tend to align at the air-water interface in equilibrium with dissolved monomers in solution.…”

Section: Introductionmentioning

confidence: 99%

Colloidal and antibacterial properties of novel triple-headed, double-tailed amphiphiles: Exploring structure–activity relationships and synergistic mixtures

Marafino

Gallagher

Barragan

et al. 2015

Bioorganic & Medicinal Chemistry

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Two novel series of tris-cationic, tripled-headed, double-tailed amphiphiles were synthesized and the effects of tail length and head group composition on the critical aggregation concentration (CAC), thermodynamic parameters, and minimum inhibitory concentration (MIC) against six bacterial strains were investigated. Synergistic antibacterial combinations of these amphiphiles were also identified. Amphiphiles in this study are composed of a benzene core with three benzylic ammonium bromide groups, two of which have alkyl chains, each 8-16 carbons in length. The third head group is a trimethylammonium or pyridinium. Log of critical aggregation concentration (log[CAC]) and heat of aggregation (ΔHagg) were both inversely proportional to the length of the linear hydrocarbon chains. Antibacterial activity increases with tail length until an optimal tail length of 12 carbons per chain, above which, activity decreased. The derivatives with two 12 carbon chains had the best antibacterial activity, killing all tested strains at concentrations of 1-2μM for Gram-positive and 4-16μM for Gram-negative bacteria. The identity of the third head group (trimethylammonium or pyridinium) had minimal effect on colloidal and antibacterial activity. The antibacterial activity of several binary combinations of amphiphiles from this study was higher than activity of individual amphiphiles, indicating that these combinations are synergistic. These amphiphiles show promise as novel antibacterial agents that could be used in a variety of applications.

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Synthesis and antimicrobial activity of symmetrical two-tailed dendritic tricarboxylato amphiphiles

Cited by 17 publications

References 28 publications

Peptide catalysis in aqueous emulsions

Peptide catalysis in aqueous emulsions

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

Colloidal and antibacterial properties of novel triple-headed, double-tailed amphiphiles: Exploring structure–activity relationships and synergistic mixtures

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