Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides

Vyas, Sandhya M.; Tuřánek, Jaroslav; Knotigová, Pavlína Turánek; Kašná, Andrea; Kvardová, Veronika; Koganti, Venkat R.; Rankin, Stephen E.; Knutson, Barbara L.; Lehmler, Hans‐Joachim

doi:10.1039/b516039a

Cited by 33 publications

(39 citation statements)

References 31 publications

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“…Regarding the surfactants with the charge in the same position (MKM and PKM), concentration-dependent hemolytic activity decreased with increasing length of the hydrophobic tail. Likewise, several authors have reported similar results for the hemolysis of hydrogels of amino acid-based cationic amphiphiles (Roy and Das 2008) and of partially fluorinated pyridinium bromides (Vyas et al 2006). This behavior contrasts with the typically hemolytic activity described for cationic 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 surfactants, where longer alkyl chains are associated with higher membrane lytic activity (Rasia et al 2007;Benavides et al 2004).…”

Section: Hemolysis Assaysupporting

confidence: 55%

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

et al. 2011

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Section: Hemolysis Assaysupporting

confidence: 55%

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

et al. 2011

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“…In the case of the LALM, LAKM and the Gemini C 6 (LL) 2 , the titration curve showed two inflection points, this indicates that the two amino groups do not have identical acidic character. 2 3 2 2 ± 0.9 1.9 ± 0.7 6.9 ± 0.1…”

Section: Physicochemical Studiesmentioning

confidence: 99%

“…It is noteworthy the Langmuir 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 low pKa of the Gemini C 6 (LK) 2 …”

Section: Physicochemical Studiesmentioning

confidence: 99%

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pH-Sensitive Surfactants from Lysine: Assessment of Their Cytotoxicity and Environmental Behavior

et al. 2012

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The toxicity and environmental behavior of new pH-sensitive surfactants from lysine are presented. Three different chemical structures are studied: surfactants with one amino acid and one alkyl chain, surfactants with two amino acids on the polar head and one alkyl chain, and gemini surfactants. The pH sensitivity of these compounds can be tuned by modifying their chemical structures. Cytotoxicity has been evaluated using erythrocytes and fibroblast cells. The toxic effects against these cells depend on the hydrophobicity of the molecules as well as their cationic charge density. The effect of hydrophobicity and cationic charge density on toxicity is different for each type of cells. For erythrocytes, the toxicity increases as hydrophobicity and charge density increases. Nevertheless, for fibroblasts cationic charge density affects cytotoxicity in the opposite way: the higher charge density, the lower the toxicity. The effect of the pH on hemolysis has been evaluated in detail. The aquatic toxicity was established using Daphnia magna. All surfactants yielded EC50 values considerably higher than that reported for cationic surfactants based on quaternary ammonium groups. Finally, their biodegradability was evaluated using the CO2 headspace test (ISO 14593). These lysine derivatives showed high levels of biodegradation under aerobic conditions and can be classified as “readily biodegradable compounds”.

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“…Cationic surfactants with this architecture exhibit a much higher surface activity than their monomeric counterparts, can easily be adsorbed at interfaces, and can interact with the cellular membranes of microorganisms, giving them high antimicrobial activity. Owing to their special ability to selfassemble, they show great promise in various areas, such as gene transfection [8][9][10][11], drug entrapment and release [12][13][14], and vitamin solubilization [15], and as components of body care products [16] and antibacterial and antifungal formulations [17,18]. Conventional cationic surfactants are highly chemically stable, but have poor chemical and biological degradability, which limits their use.…”

Section: Introductionmentioning

confidence: 99%

Gemini ester quat surfactants and their biological activity

Łuczyński

Frąckowiak

Włoch

et al. 2013

Cellular and Molecular Biology Letters

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Cationic gemini surfactants are an important class of surface-active compounds that exhibit much higher surface activity than their monomeric counterparts. This type of compound architecture lends itself to the compound being easily adsorbed at interfaces and interacting with the cellular membranes of microorganisms. Conventional cationic surfactants have high chemical stability but poor chemical and biological degradability. One of the main approaches to the design of readily biodegradable and environmentally friendly surfactants involves inserting a bond with limited stability into the surfactant molecule to give a cleavable surfactant. The best-known example of such a compound is the family of ester quats, which are cationic surfactants with a labile ester bond inserted into the molecule. As part of this study, a series of gemini ester quat surfactants were synthesized and assayed for their biological activity. Their hemolytic activity and changes in the fluidity and packing order of the lipid polar heads were used as the measures of their biological activity. A clear correlation between the hemolytic activity of the tested compounds and their alkyl chain length was established. It was found that the compounds with a long hydrocarbon chain showed higher activity. Moreover, the compounds with greater spacing between their alkyl chains were more active. This proves that they incorporate more easily into the lipid bilayer of the erythrocyte membrane and affect its properties to a greater extent. A better understanding of the process of cell lysis by surfactants and of their biological activity may assist in developing surfactants with enhanced selectivity and in widening their range of application.

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Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides

Cited by 33 publications

References 31 publications

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

pH-Sensitive Surfactants from Lysine: Assessment of Their Cytotoxicity and Environmental Behavior

Gemini ester quat surfactants and their biological activity

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