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Influence of Long-Tailed Alcohols on the Solubilisation of Cationic DHAB Bilayers
Physical Organic Chemistry Unit, Stratingh Institute University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
* Author to whom correspondence should be addressed.
Received: 17 February 2004 / Accepted: 19 March 2004 / Published: 31 January 2005
Abstract: The effects of n-decanol and cetyl alcohol incorporated into cationic di-n-hexadecyldimethylammonium bromide (DHAB) bilayers on the packing and the resistance against solubilisation by Triton X-100 have been investigated. Solubilisation experiments revealed that the mismatch between the C10-tail of n-decanol with the DHAB-tails does not affect the structural integrity of the vesicles. On the contrary, upon increasing amounts of cetyl alcohol, of which the tail matches in size with the DHAB-tails, breakdown of the vesicles is promoted, whereas complete solubilisation is strongly hampered. The system is further investigated by DSC and cryo-EM experiments. In addition, the effects of n-decanol and cetyl alcohol embedded into DHAB bilayers on the vesicular rate constants for the decarboxylation of 6-nitrobenzisoxazole-3-carboxylate (6-NBIC) suggest that both alcohols affect the structure of the Stern region in an equal manner, leading to a decrease in the catalysis. Therefore, it is concluded that addition of the alcohols leads to changes in properties of the interior of the bilayer, rather than the polar-apolar interface.
Keywords: n-Decanol; cetyl alcohol; TritonX-100; bilayers; vesicles; bilayer fragments; decarboxylation; 6-NBIC; solubilisation; DSC; cryo-EM
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Linthorst, J.A.; Klijn, J.E.; Engberts, J.B. Influence of Long-Tailed Alcohols on the Solubilisation of Cationic DHAB Bilayers. Int. J. Mol. Sci. 2005, 6, 104-118.
Linthorst JA, Klijn JE, Engberts JB. Influence of Long-Tailed Alcohols on the Solubilisation of Cationic DHAB Bilayers. International Journal of Molecular Sciences. 2005; 6(1):104-118.
Linthorst, Johan A.; Klijn, Jaap E.; Engberts, Jan B. 2005. "Influence of Long-Tailed Alcohols on the Solubilisation of Cationic DHAB Bilayers." Int. J. Mol. Sci. 6, no. 1: 104-118.