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Synthesis and Characterization of a New Bifunctionalized, Fluorescent, and Amphiphilic Molecule for Recruiting SH‐Containing Molecules to Membranes
Author(s) -
Mertens Monique,
Hilsch Malte,
Haralampiev Ivan,
Volkmer Rudolf,
Wessig Pablo,
Müller Peter
Publication year - 2018
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800268
Subject(s) - moiety , membrane , fluorophore , maleimide , chemistry , amphiphile , fluorescence , molecule , biological membrane , fluorescence in the life sciences , vesicle , combinatorial chemistry , polymer chemistry , organic chemistry , biochemistry , copolymer , polymer , physics , quantum mechanics
This study describes the synthesis and characterization of an amphiphilic construct intended to recruit SH‐containing molecules to membranes. The construct consists of 1) an aliphatic chain to enable anchoring within membranes, 2) a maleimide moiety to react with the sulfhydryl group of a soluble (bio)molecule, and 3) a fluorescence moiety to allow the construct to be followed by fluorescence spectroscopy and microscopy. It is shown that the construct can be incorporated into preformed membranes, thus allowing application of the approach with biological membranes. The close proximity between the fluorophore and the maleimide moiety within the construct causes fluorescence quenching. This allows monitoring of the reaction with SH‐containing molecules by measurement of increases in fluorescence intensity and lifetime. Notably, the construct distributes into laterally ordered membrane domains of lipid vesicles, which is probably triggered by the length of its membrane anchor. The advantages of the new construct can be employed for several biological, biotechnological, and medicinal applications.