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

Content Provider	Springer Nature Link
Author	gueira, Daniele Rubert Mitjans, Montserrat Morán, M. Carmen Pérez, Lourdes Vinardell, M. Pilar
Copyright Year	2011
Abstract	Many strategies for treating diseases require the delivery of drugs into the cell cytoplasm following internalization within endosomal vesicles. Thus, compounds triggered by low pH to disrupt membranes and release endosomal contents into the cytosol are of particular interest. Here, we report novel cationic lysine-based surfactants (hydrochloride salts of Nε- and Nα-acyl lysine methyl ester) that differ in the position of the positive charge and the length of the alkyl chain. Amino acid-based surfactants could be promising novel biomaterials in drug delivery systems, given their biocompatible properties and low cytotoxic potential. We examined their ability to disrupt the cell membrane in a range of pH values, concentrations and incubation times, using a standard hemolysis assay as a model of endosomal membranes. Furthermore, we addressed the mechanism of surfactant-mediated membrane destabilization, including the effects of each surfactant on erythrocyte morphology as a function of pH. We found that only surfactants with the positive charge on the α-amino group of lysine showed pH-sensitive hemolytic activity and improved kinetics within the endosomal pH range, indicating that the positive charge position is critical for pH-responsive behavior. Moreover, our results showed that an increase in the alkyl chain length from 14 to 16 carbon atoms was associated with a lower ability to disrupt cell membranes. Knowledge on modulating surfactant-lipid bilayer interactions may help us to develop more efficient biocompatible amino acid-based drug delivery devices.
Starting Page	1203
Ending Page	1215
Page Count	13
File Format	PDF
ISSN	09394451
Journal	Amino Acids
Volume Number	43
Issue Number	3
e-ISSN	14382199
Language	English
Publisher	Springer Vienna
Publisher Date	2011-12-02
Publisher Place	Vienna
Access Restriction	Subscribed
Subject Keyword	Lysine-based surfactants Hemolysis pH-sensitivity Membrane disruption Drug delivery Life Sciences Analytical Chemistry Biochemistry Proteomics Neurobiology Biochemical Engineering
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Clinical Biochemistry

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