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Synthesis and characterization of a new Bifunctionalized, Fluorescent, and Amphiphilic molecule for recruiting SH-Containing molecules to membranes

  • 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 severalThis 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.show moreshow less

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Author details:Monique MertensGND, Malte Hilsch, Ivan HaralampievGND, Rudolf Volkmer, Pablo WessigORCiDGND, Peter Müller
DOI:https://doi.org/10.1002/cbic.201800268
ISSN:1439-4227
ISSN:1439-7633
Pubmed ID:https://pubmed.ncbi.nlm.nih.gov/29785742
Title of parent work (English):ChemBioChem
Publisher:Wiley-VCH
Place of publishing:Weinheim
Publication type:Article
Language:English
Date of first publication:2018/05/22
Publication year:2018
Release date:2021/10/18
Tag:DBD dyes; fatty acids; liposomes; maleimide; membranes; palmitoylation
Volume:19
Issue:15
Number of pages:5
First page:1643
Last Page:1647
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer review:Referiert
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