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Contents Vol 66(8)

Temperature-Responsive Self-Assemblies of ‘Kinked’ Amphiphiles

Jennifer S. Squire A , Grégory Durand B C , Lynne Waddington D , Alessandra Sutti E and Luke C. Henderson A E F
+ Author Affiliations
- Author Affiliations

A Strategic Research Centre for Chemistry and Biotechnology, Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, Vic. 3216, Australia.

B Unité Mixte de Recherche 5247, Centre National de la Recherche Scientifique and Universités de Montpellier 1&2, Institut des Biomolécules Max Mousseron, Faculté de Pharmacie, 15 avenue Charles Flahault, F-34093 Montpellier Cedex 05, France.

C Université d'Avignon et des Pays de Vaucluse, Equipe Chimie Bioorganique et Systèmes Amphiphiles, 33 rue Louis Pasteur, F-84000 Avignon, France.

D CSIRO Materials Science and Engineering, Bayview Avenue, Clayton, Vic. 3168, Australia.

E Institute for Frontier Materials, Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, Vic. 3216, Australia.

F Corresponding author. Email: luke.henderson@deakin.edu.au

Australian Journal of Chemistry 66(8) 899-909 https://doi.org/10.1071/CH13278
Submitted: 31 May 2013  Accepted: 16 July 2013   Published: 7 August 2013

Abstract

The synthesis of novel norbornane-based amphiphiles and the thermal response of their corresponding colloids is presented. It was found that the hydrodynamic diameter (DH) expansion or contraction of 1–4 in response to increasing temperature was governed by the length of the hydrophobic region possessed by the amphiphile (a 12 or 16 carbon chain). These data were used as a starting point to extend into an active tumour targeting system whereby two amphiphiles were modified to incorporate the oestrogen receptor antagonist Tamoxifen at the polar head group. This was achieved by a triazole moiety while both the C12 (18) or C16 (19) hydrophobic chains were incorporated as the hydrophobic region in an attempt to retain the response to thermal stimuli observed in our preliminary findings. These functionalised novel amphiphiles possessed critical aggregation concentration values of 510 and 19 µM, while aqueous self-assemblies of 56 and 106 nm for 18 and 19 were observed. Imaging by cryogenic transmission electron microscopy showed 18 to possess liposomal morphology, while 19, bearing a C16 hydrophobic portion, formed non-defined amorphous aggregates. Finally, the response to temperature of these assemblies was investigated with only the C12 variant 18 displaying a temperature response in the 5–55°C thermal window investigated.


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