Synthesis and biophysical characterization of an odd-numbered 1,3-diamidophospholipid

Neuhaus, Frederik; Mueller, Dennis; Tanasescu, Radu; Balog, Sandor; Takashi Ishikawa; Brezesinski, Gerald; Zumbuehl, Andreas

doi:10.1021/acs.langmuir.7b04227

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Synthesis and biophysical characterization of an odd-numbered 1,3-diamidophospholipid

Neuhaus, Frederik Department of Chemistry, University of Fribourg, Switzerland - National Centre of Competence in Research in Chemical Biology, Geneva, Switzerland
Mueller, Dennis Department of Chemistry, University of Fribourg, Switzerland
Tanasescu, Radu Department of Chemistry, University of Fribourg, Switzerland
Balog, Sandor Adolphe Merkle Institute, University of Fribourg, Switzerland
Takashi Ishikawa Paul Scherrer Institute (PSI), OFLB/010, Villigen PSI, Switzerland
Brezesinski, Gerald Max Planck Institute of Colloids and Interfaces, Research Campus, Potsdam, Germany
Zumbuehl, Andreas Department of Chemistry, University of Fribourg, Switzerland - National Centre of Competence in Research in Chemical Biology, Geneva, Switzerland

13.03.2018

Published in:

Langmuir. - 2018, vol. 34, no. 10, p. 3215–3220

English Nanomedicine suffers from low drug delivery efficiencies. Mechanoresponsive vesicles could provide an alternative way to release active compounds triggered by the basic physics of the human body. 1,3-Diamidophospholipids with C16 tails proved to be an effective building block for mechanoresponsive vesicles, but their low main phase transition temperature prevents an effective application in humans. As the main phase transition temperature of a membrane depends on the fatty acyl chain length, we synthesized a C17 homologue of a 1,3-diamidophospholipid: Rad-PC-Rad. The elevated main phase transition temperature of Rad-PC-Rad allows mechanoresponsive drug delivery at body temperature. Herein, we report the biophysical properties of Rad-PC-Rad monolayer and bilayer membranes. Rad-PC- Rad is an ideal candidate for advancing the concept of physically triggered drug release.

Faculty

Faculté des sciences et de médecine

Department

Département de Chimie

Language