Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators

Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators

A new bolaamphiphile analog featuring carbamate moieties was synthesized in six steps starting from thymidine. The amphiphile structure exhibits nucleoside-sugar polar heads attached to a hydrophobic spacer via carbamate (urethane) functions. This molecular structure, which possesses additional H-bo...

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Bibliographic Details
Main Authors: Laurent Latxague, Alexandra Gaubert, David Maleville, Julie Baillet, Michael A. Ramin, Philippe Barthélémy
Format: Article
Language:English
Published: MDPI AG 2016-09-01
Series:Gels
Subjects:
nucleolipid
nucleoside
glycosyl
bolaamphiphiles
low-molecular-weight gels (LMWG)
carbamate
hydrogels
supramolecular assemblies
thixotropy
Online Access:http://www.mdpi.com/2310-2861/2/4/25
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spelling doaj-6f4dc0603f8947d691fada316b51dedb2020-11-25T00:38:56ZengMDPI AGGels2310-28612016-09-01242510.3390/gels2040025gels2040025Carbamate-Based Bolaamphiphile as Low-Molecular-Weight HydrogelatorsLaurent Latxague0Alexandra Gaubert1David Maleville2Julie Baillet3Michael A. Ramin4Philippe Barthélémy5ARNA laboratory, Univ. Bordeaux, ChemBioPharm, INSERM, U1212, CNRS UMR 5320, F-33000 Bordeaux, FranceARNA laboratory, Univ. Bordeaux, ChemBioPharm, INSERM, U1212, CNRS UMR 5320, F-33000 Bordeaux, FranceARNA laboratory, Univ. Bordeaux, ChemBioPharm, INSERM, U1212, CNRS UMR 5320, F-33000 Bordeaux, FranceARNA laboratory, Univ. Bordeaux, ChemBioPharm, INSERM, U1212, CNRS UMR 5320, F-33000 Bordeaux, FranceARNA laboratory, Univ. Bordeaux, ChemBioPharm, INSERM, U1212, CNRS UMR 5320, F-33000 Bordeaux, FranceARNA laboratory, Univ. Bordeaux, ChemBioPharm, INSERM, U1212, CNRS UMR 5320, F-33000 Bordeaux, FranceA new bolaamphiphile analog featuring carbamate moieties was synthesized in six steps starting from thymidine. The amphiphile structure exhibits nucleoside-sugar polar heads attached to a hydrophobic spacer via carbamate (urethane) functions. This molecular structure, which possesses additional H-bonding capabilities, induces the stabilization of low-molecular-weight gels (LMWGs) in water. The rheological studies revealed that the new bolaamphiphile 7 stabilizes thixotropic hydrogels with a high elastic modulus (G′ > 50 kPa).http://www.mdpi.com/2310-2861/2/4/25nucleolipidnucleosideglycosylbolaamphiphileslow-molecular-weight gels (LMWG)carbamatehydrogelssupramolecular assembliesthixotropy
collection DOAJ
language English
format Article
sources DOAJ
author Laurent Latxague
Alexandra Gaubert
David Maleville
Julie Baillet
Michael A. Ramin
Philippe Barthélémy
spellingShingle Laurent Latxague
Alexandra Gaubert
David Maleville
Julie Baillet
Michael A. Ramin
Philippe Barthélémy
Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators
Gels
nucleolipid
nucleoside
glycosyl
bolaamphiphiles
low-molecular-weight gels (LMWG)
carbamate
hydrogels
supramolecular assemblies
thixotropy
author_facet Laurent Latxague
Alexandra Gaubert
David Maleville
Julie Baillet
Michael A. Ramin
Philippe Barthélémy
author_sort Laurent Latxague
title Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators
title_short Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators
title_full Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators
title_fullStr Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators
title_full_unstemmed Carbamate-Based Bolaamphiphile as Low-Molecular-Weight Hydrogelators
title_sort carbamate-based bolaamphiphile as low-molecular-weight hydrogelators
publisher MDPI AG
series Gels
issn 2310-2861
publishDate 2016-09-01
description A new bolaamphiphile analog featuring carbamate moieties was synthesized in six steps starting from thymidine. The amphiphile structure exhibits nucleoside-sugar polar heads attached to a hydrophobic spacer via carbamate (urethane) functions. This molecular structure, which possesses additional H-bonding capabilities, induces the stabilization of low-molecular-weight gels (LMWGs) in water. The rheological studies revealed that the new bolaamphiphile 7 stabilizes thixotropic hydrogels with a high elastic modulus (G′ > 50 kPa).
topic nucleolipid
nucleoside
glycosyl
bolaamphiphiles
low-molecular-weight gels (LMWG)
carbamate
hydrogels
supramolecular assemblies
thixotropy
url http://www.mdpi.com/2310-2861/2/4/25
work_keys_str_mv AT laurentlatxague carbamatebasedbolaamphiphileaslowmolecularweighthydrogelators
AT alexandragaubert carbamatebasedbolaamphiphileaslowmolecularweighthydrogelators
AT davidmaleville carbamatebasedbolaamphiphileaslowmolecularweighthydrogelators
AT juliebaillet carbamatebasedbolaamphiphileaslowmolecularweighthydrogelators
AT michaelaramin carbamatebasedbolaamphiphileaslowmolecularweighthydrogelators
AT philippebarthelemy carbamatebasedbolaamphiphileaslowmolecularweighthydrogelators
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