Interactions of surfactants with living cells.

Perani, A.; Gérardin, Christine; Stacey, G. J.; Infante, M. R.; Vinardell, M. Pilar; Rodehüser, L.; Selve, C.; Maugras, M.

doi:10.1007/s007260170025

Cited by 18 publications

(9 citation statements)

References 13 publications

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“…It has been proposed that high concentrations of surfactants cause necrosis whereas low concentrations induce apoptosis [53]. Enomoto and co-workers [54] demonstrated that some cationic surfactants, such as benzalkonium chloride, induce apoptosis at very low concentration (below CMC) by causing structural changes on the plasma membrane, such as phosphatidylserine translocation, but anionic and amphoteric surfactants could not induce apoptotic cell death.…”

Section: Discussionmentioning

confidence: 99%

In Vitro Surfactant Structure-Toxicity Relationships: Implications for Surfactant Use in Sexually Transmitted Infection Prophylaxis and Contraception

et al. 2011

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BackgroundThe need for woman-controlled, cheap, safe, effective, easy-to-use and easy-to-store topical applications for prophylaxis against sexually transmitted infections (STIs) makes surfactant-containing formulations an interesting option that requires a more fundamental knowledge concerning surfactant toxicology and structure-activity relationships.Methodology/Principal FindingsWe report in vitro effects of surfactant concentration, exposure time and structure on the viability of mammalian cell types typically encountered in the vagina, namely, fully polarized and confluent epithelial cells, confluent but non-polarized epithelial-like cells, dendritic cells, and human sperm. Representatives of the different families of commercially available surfactants – nonionic (Triton X-100 and monolaurin), zwitterionic (DDPS), anionic (SDS), and cationic (CnTAB (n = 10 to 16), C12PB, and C12BZK) – were examined. Triton X-100, monolaurin, DDPS and SDS were toxic to all cell types at concentrations around their critical micelle concentration (CMC) suggesting a non-selective mode of action involving cell membrane destabilization and/or destruction. All cationic surfactants were toxic at concentrations far below their CMC and showed significant differences in their toxicity toward polarized as compared with non-polarized cells. Their toxicity was also dependent on the chemical nature of the polar head group. Our results suggest an intracellular locus of action for cationic surfactants and show that their structure-activity relationships could be profitably exploited for STI prophylaxis in vaginal gel formulations. The therapeutic indices comparing polarized epithelial cell toxicity to sperm toxicity for all surfactants examined, except C12PB and C12BZK, does not justify their use as contraceptive agents. C12PB and C12BZK are shown to have a narrow therapeutic index recommending caution in their use in contraceptive formulations.Conclusions/SignificanceOur results contribute to understanding the mechanisms involved in surfactant toxicity, have a predictive value with regard to their safety, and may be used to design more effective and less harmful surfactants for use in topical applications for STI prophylaxis.

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Section: Discussionmentioning

confidence: 99%

In Vitro Surfactant Structure-Toxicity Relationships: Implications for Surfactant Use in Sexually Transmitted Infection Prophylaxis and Contraception

et al. 2011

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“…Toxic surfactant molecules can induce cell apoptosis or necrosis depending on the concentration of the surfactant [52,53]. The surfactant molecules at a high concentration (near or above CMC) may form mixed micelles with membrane lipids, which may solubilize cell membranes.…”

Section: Mechanisms Of Surfactant Effects On Biodegradation Of Pahsmentioning

confidence: 99%

Surfactant-mediated Biodegradation of Polycyclic Aromatic Hydrocarbons

Chen

2009

Materials

129

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Polycyclic aromatic hydrocarbons (PAHs) are toxic environmental pollutants that are known or suspected carcinogens or mutagens. Bioremediation has been used as a general way to eliminate them from the contaminated sites or aquifers, but their biodegradation is rather limited due to their low bioavailability because of their sparingly soluble nature. Surfactant-mediated biodegradation is a promising alternative. The presence of surfactants can increase the solubility of PAHs and hence potentially increase their bioavailability. However, inconclusive results have been reported on the effects of surfactant on the biodegradation of PAHs. In this work, surfactant-mediated biodegradation of PAHs is reviewed.

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“…Since the latter do not possess any metabolic activity that could induce apoptosis, when a compound shows haemolytic activity it can be considered as a chaotropic agent, able to alter and cause disorder in the membrane of erythrocytes. Compounds with a chaotropic impact on erythrocyte membranes could exert a similar effect also on the membranes of other cell types [11].…”

Section: Haemolysis Assaymentioning

confidence: 99%

“…*Address correspondence to this author at the Dipartimento di Scienze Farmaceutiche, Città Universitaria, viale A. Doria, 6; I-95125 Catania, Italy; E-mail: r.pignatello@unict.it Similarly, N-acyl lipoamino acids have been widely studied also for their effects on erythrocytes and cell membranes, and potential toxicity [10][11][12]. Like lipopolysaccharides, some natural conjugates of lipids and amino acids present in bacterial sources can act as endotoxins for the human body [13].…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of Cell Tolerability of a Series of Lipoamino Acids Using Biological Membranes and a Biomembrane Model.

Pignatello

Noce²,

Campisi³

et al. 2007

CDD

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The interaction of a series of amphiphilic 2-alkyl aminoacids (lipoamino acids, LAAs) with different cell cultures and biomembrane models was investigated. LAAs can be useful promoieties to modify the physico-chemical properties of many drugs, and in particular their lipophilicity. Tests were performed in vitro on mammalian cells (murine astrocytes) and human red blood cells (haemolysis), and in vivo on rabbit eye as alternative models to assess the tolerability or the potential damaging effects of these compounds on different biological systems. The mode of interaction of LAAs with pure phospholipid multilamellar liposomes, taken as a biomembrane model, was also analysed by differential scanning calorimetry experiments. Different tolerability/toxicity patterns were obtained in the various models; in particular, the most lipophilic terms of the series, methyl 2-aminohexadecanoate (LAA16), displayed haemolytic activity and toxicity for mouse astrocyte cultures. A specific assay confirmed that LAA16 acted at level of cell membranes, while neither any damaging effects on nucleus or apoptotic induction were observed. The shorter-chain LAAs and the tetradecyl homologue (LAA14) showed the best compatibility with the various cell models.

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Interactions of surfactants with living cells.

Cited by 18 publications

References 13 publications

In Vitro Surfactant Structure-Toxicity Relationships: Implications for Surfactant Use in Sexually Transmitted Infection Prophylaxis and Contraception

In Vitro Surfactant Structure-Toxicity Relationships: Implications for Surfactant Use in Sexually Transmitted Infection Prophylaxis and Contraception

Surfactant-mediated Biodegradation of Polycyclic Aromatic Hydrocarbons

Evaluation of Cell Tolerability of a Series of Lipoamino Acids Using Biological Membranes and a Biomembrane Model.

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