Synthesis, micellisation and interaction of novel quaternary ammonium compounds derived from l-Phenylalanine with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine as model membrane in relation to their antibacterial activity, and their selectivity over human red blood cells

Joondan, Nausheen; Caumul, Prakashanand; Akerman, Matthew P.; Jhaumeer‐Laulloo, Sabina

doi:10.1016/j.bioorg.2015.01.001

Cited by 42 publications

(38 citation statements)

References 41 publications

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“…Recently, the selectivity of certain membrane-disrupting antibacterial agents has also been found to be dependent on their aggregation state, where monomers were the more selective species. 13 We believe these sharp differences in biological action between monomer and aggregates is directly related to the difference that we found for the action of monomers and aggregates of Triton X-100 on cholesterol-rich liposomes. 14 Specifically, whereas attack by monomers resulted in membrane leakage, attack by aggregates led to a catastrophic rupture of the membrane.…”

mentioning

confidence: 67%

Simple Strategy for Taming Membrane-Disrupting Antibiotics

Sabulski

Schell

et al. 2016

Bioconjugate Chem.

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A strategy has been devised for increasing the cellular selectivity of membrane-disrupting antibiotics based on the attachment of a facially amphiphilic sterol. Using Amphotericin B (AmB) as a prototype, covalent attachment of cholic acid bound to a series of α,ω-diamines has led to a dramatic reduction in hemolytic activity, a significant reduction in toxicity toward HEK293T cells, and significant retention of antifungal activity.

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mentioning

confidence: 67%

Simple Strategy for Taming Membrane-Disrupting Antibiotics

Sabulski

Schell

et al. 2016

Bioconjugate Chem.

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“…In this case the additional alkyl groups attached to the nitrogen moiety of steroidal amine screens the electrostatic head-group repulsion and strongly facilitates the surfactants self assembly, giving rise to a much lower CMC value compared to the hydrochloride salts of phenylalanine esters. The results indicated that an increase in the number of carbon atoms in the alkyl chain length of a surfactant increases its surface activity, causing a decrease in the CMC values [23,24].…”

Section: Characterization Of Aggregation Behaviormentioning

confidence: 99%

“…Studies also showed that an increase in hydrophobic interactions between the surfactant chain and those of the neighboring lipid molecule of the bacterial membrane, which in turn pulls the surfactant molecule further into the membrane, resulting in higher antibacterial activity with respect to chain length [23,24]. Once close contact is achieved by the hydrophilic end including the quaternary ammonium moiety of the surfactant, the hydrophobic end with the polar head of lipid proceeds to pass through the hydrophobic bilayer to result in cell leakage and lysis [27].…”

Section: Biological Activitymentioning

confidence: 99%

Cholic Acid‐Derived Facial Surfactants with Long Side‐Chain Quaternary Ammonium: Synthesis and Antimicrobial Activity Study

Zhou

et al. 2016

J Surfact & Detergents

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Four cholic acid cationic surfactants containing a flexible long aliphatic chain were synthesized efficiently. A long aliphatic chain was introduced first on the side‐chain carboxyl of cholic acid by one‐pot condensation reaction of cholic acid and C12–C18 amines using DCC (Dicyclohexylcarbodiimide) and HOBt (N‐hydroxybenzotrizole) as condensation agents for the formation of an amide framework. Then reduction of the amide and quaternization gave a cationic group for strengthening hydrophilicity. This strategy offered a very straightforward and efficient method for access to the designed surfactants in good overall yields. Preliminary results show that an increase both in the length of the hydrophobic tail and in the number of charged groups lowered the CMC of cholic acid‐derived cationic surfactants. Cholic acid‐based cationic surfactants containing a flexible longer aliphatic chain and a quaternary ammonium had the highest antimicrobial activity.

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“…Hemolytic activity was carried out according to our previously reported method [9]. Erythrocytes were suspended in saline buffer.…”

Section: Hemolytic Activitymentioning

confidence: 99%

“…From our previous studies, it was found that aromatic amino acid-based surfactants, namely phenylalanine and tyrosine possess good to excellent antimicrobial activities [8,9]. It was found that activity was governed by both the length of the hydrocarbon chain as well as the head group.…”

Section: Introductionmentioning

confidence: 99%

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

Joondan

Jhaumeer‐Laulloo

Caumul

2015

J Surfact & Detergents

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L-DOPA (L-3,4-dihydroxyphenylalanine) has been widely used as a drug in the clinical treatment of Parkinson's disease. In this report, the systematic study of the effect of chain length on the critical micelle concentration (CMC), antibacterial and antioxidant activity of esters derived from the aromatic amino acid L-3,4-dihydroxyphenylalanine as surfactants are accounted for the first time. The antibacterial activity displayed a cut-off effect at C 12 with respect to both gram positive and gram negative bacteria (except for Pseudomonas aeruginosa where the cut-off was displayed at C 10 ). Correlation of the CMC with the minimum inhibitory concentration (MIC) shows that the DOPA esters exist in micellar form at the MIC. An increase in chain length of the DOPA esters induces greater binding with phospholipid vesicles 1,2-dipalmitoyl-sn-glycero-3-phosphocholine. The C 12 ester possessed highest radical scavenging ability among the esters tested against both 2,2-diphenyl-1-picrylhydrazyl and 2,2 0 -azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) showing that antioxidant activity of the DOPA esters is also affected by chain length. This study showed that DOPA esters are promising candidates as antibacterial agents as well as good antioxidants.

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Synthesis, micellisation and interaction of novel quaternary ammonium compounds derived from l-Phenylalanine with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine as model membrane in relation to their antibacterial activity, and their selectivity over human red blood cells

Cited by 42 publications

References 41 publications

Simple Strategy for Taming Membrane-Disrupting Antibiotics

Simple Strategy for Taming Membrane-Disrupting Antibiotics

Cholic Acid‐Derived Facial Surfactants with Long Side‐Chain Quaternary Ammonium: Synthesis and Antimicrobial Activity Study

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

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