Effect of Chain Length on the Micellization, Antibacterial, DPPC Interaction and Antioxidant Activities of <scp>l</scp>‐3,4‐Dihydroxyphenylalanine (<scp>l</scp>‐DOPA) Esters

Joondan, Nausheen; Jhaumeer‐Laulloo, Sabina; Caumul, Prakashanand

doi:10.1007/s11743-015-1720-8

Cited by 8 publications

(2 citation statements)

References 30 publications

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“…Lipophilicity is also known to influence the biological activity of various compounds [11,12]. Turos et al reported that increasing alkyl chain length from methyl to butyl in alkylaryl disulfide system enhances the anti-bacterial properties of these compounds [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates

et al. 2017

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A series of dialkyl 2,2'-disulfanediyldibenzoates with alkyl chain length C8 to C12 were synthesized and characterized by spectral studies. The structure of compound 3 was also confirmed by X-ray crystallography. The compounds were found to possess good antibacterial activity, especially with respect to Gram positive bacteria, and the activity was found to increase with concomitant increase in chain length. Binding studies of compound 3 with the synthetic phospholipid 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) showed that the compound interacts with biological membrane mainly via hydrophobic interactions.

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Section: Introductionmentioning

confidence: 99%

Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates

et al. 2017

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“…Our group has been dealing with the synthesis, physicochemical and biological properties of O-alkyl esters of aromatic and cyclic amino acids [14][15][16][17][18]. In this study, a series of O-alkyl ester of methionine and their hydrochloride derivatives were synthesised and their physicochemical properties were investigated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and physicochemical properties of non-ionic and cationic surfactants derived from methionine

Joondan

Radhan

Laulloo

et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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Amino acid based surfactants have been widely used as alternative to classical surfactants due to their interesting physicochemical properties, biological activities, biodegradability and low toxicity. The study of the physicochemical properties of surfactants such as critical micelle concentration (CMC) and Krafft temperature is an important aspect in determining their use in detergents or pharmaceutical compositions. In this study, a series of non-ionic and cationic surfactants with varying chain lengths (C8-C12), namely the O-alkyl esters of methionine and their hydrochloride derivatives respectively were synthesized and characterized by spectral data.In view of systematically studying the effect of the head group and chain length on the physicochemical properties, the critical micelle concentrations of both series were evaluated using conductivity measurements and pyrene fluorescence spectroscopy. The Krafft temperatures of selected synthesized methionine-based surfactants were also evaluated. The methionine surfactants were synthesized in good to moderate yield (54 -81%). For both ester and the hydrochloride series, the CMC of the surfactants were found to decrease with chain length, as commonly observed for all surfactants. The non-ionic O-alkyl esters of methionine displayed relatively lower CMC values compared to their ester hydrochloride derivatives for all the chain length studied. The ester hydrochloride derivatives showed an increase in the Krafft temperature with increasing chain length showing that the surfactants with longer chain length has a tendency to micellise at a much higher temperature.

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Vibrational studies of saccharide-induced lipid film reorganization at aqueous/air interfaces

et al. 2018

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Effect of Chain Length on the Micellization, Antibacterial, DPPC Interaction and Antioxidant Activities of l‐3,4‐Dihydroxyphenylalanine (l‐DOPA) Esters

Cited by 8 publications

References 30 publications

Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates

Synthesis, antibacterial activities and phospholipid membrane interactions of novel dialkyl 2,2’-disulfanediyldibenzoates

Synthesis and physicochemical properties of non-ionic and cationic surfactants derived from methionine

Vibrational studies of saccharide-induced lipid film reorganization at aqueous/air interfaces

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