Recruitment of SH-Containing Peptides to Lipid and Biological Membranes through the Use of a Palmitic Acid Functionalized with a Maleimide Group

• Published in: Angewandte Chemie International Edition Vol. 54; no. 1; pp. 323 - 326
• Main Authors: Haralampiev, Ivan, Mertens, Monique, Schwarzer, Roland, Herrmann, Andreas, Volkmer, Rudolf, Wessig, Pablo, Müller, Peter
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 02-01-2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Biological; Biological activity; Biological membranes; Biomolecules; Cell Membrane - metabolism; Cell membranes; Derivatives; Fluorescence; Fluorescence spectroscopy; Lipids; Liposomes; Liposomes - chemistry; Liposomes - metabolism; Macrophages - cytology; Macrophages - metabolism; maleimide; Maleimides - chemistry; Maleimides - metabolism; Membranes; Microscopy, Confocal; Palmitic acid; Palmitic Acid - chemistry; Palmitic Acid - metabolism; palmitoylation; Peptides; Peptides - chemistry; Peptides - metabolism; Rhodamine; Spectrometry, Fluorescence; Strategy; Sulfhydryl Compounds - analysis; Sulfhydryl Compounds - metabolism; membranes; peptides; maleimide; liposomes; palmitic acid; palmitoylation
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201408089

This study presents a novel and easily applicable approach to recruit sulfhydryl‐containing biomolecules to membranes by using a palmitic acid which is functionalized with a maleimide group. Notably, this strategy can also be employed with preformed (biological) membranes. The applicability of the assay is demonstrated by characterizing the binding of a Rhodamine‐labeled peptide to lipid and cellular membranes using methods of fluorescence spectroscopy, lifetime measurement, and microscopy. Our approach offers new possibilities for preparing biologically active liposomes and manipulating living cells.
A lure for biomolecules: A palmitic acid derivative functionalized with a maleimide group serves to recruit sulfhydryl‐containing biomolecules to membranes (see picture). The approach offers new possibilities for the preparation of biologically active liposomes and the manipulation of living cells.