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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.zeige mehrzeige weniger

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Metadaten
Verfasserangaben: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
Titel des übergeordneten Werks (Englisch):ChemBioChem
Verlag:Wiley-VCH
Verlagsort:Weinheim
Publikationstyp:Wissenschaftlicher Artikel
Sprache:Englisch
Datum der Erstveröffentlichung:22.05.2018
Erscheinungsjahr:2018
Datum der Freischaltung:18.10.2021
Freies Schlagwort / Tag:DBD dyes; fatty acids; liposomes; maleimide; membranes; palmitoylation
Band:19
Ausgabe:15
Seitenanzahl:5
Erste Seite:1643
Letzte Seite:1647
Organisationseinheiten:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC-Klassifikation:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer Review:Referiert
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