Self-Assembled Monolayers with Impact on Fluidity of Lipid Membranes

By: Joe Porwoll, Material Matters 2010, 5.3, 55.

Material Matters 2010, 5.3, 55.

Joe Porwoll, President Aldrich Chemical Co., Inc.

Do you have a compound that you wish Sigma-Aldrich® could list to help materials research? If it is needed to accelerate your research, it matters—please send your suggestion to and we will be happy to give it careful consideration.

Professor Nick Melosh of Stanford University kindly suggested that we offer cis-9-Octadecene-1-thiol (Aldrich Prod. No. 719692) as a product in our catalog. This molecule is designed to prepare disordered self-assembled monolayers that may have a significant influence on the fluidity of supported lipid membranes. A cisdouble bond introduces a kink in the hydrophobic alkyl chains, disrupting the packing behavior compared to saturated alkyl thiol molecules and leading to disordered monolayers that mimic fluid biological lipid membranes.1,2 Such monolayers can be used as supports for deposition of model lipid membranes on the monolayer-modified substrates.3 The terminal thiol group of the cis- 9-Octadecene-1-thiol allows for either assembly onto gold surfaces4 or functionalization with a wide variety of biological entities, for example using the thiol-ene chemistry or reactions with reactive double bonds of maleimide5 and acryloyl compounds.6

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  1. Rawicz, W.; Olbrich, K. C.; McIntosh, T.; Needham, D.; Evans, E. Biophys. J. 2000, 79, 328.
  2. Silvius. J. R. Thermotropic Phase Transitions of Pure Lipids in Model Membranes and Their Modifications by Membrane Proteins; John Wiley & Sons, Inc.: New York. 1982.
  3. Jans, K.; Van Meerbergen, B.; Reekmans, G.; Bonroy, K.; Annaert, W.; Maes, G.; Engelborghs, Y.; Borghs, G.; Bartic, C. Langmuir 2009, 25, 4564.
  4. Bain, C. D.; Troughton, E. B.; Tao, Y.-T.; Evall, J.; Whitesides, G. M.; Nuzzo, R. G. J. Am. Chem. Soc. 1989, 111, 321. 
  5. Kosif, I.; Park, E.-J.; Sanyal, R.; Sanyal, A. Macromolecules 2010, 43, 4140.
  6. Dondoni, A. Angew. Chem. Int. Ed. 2008, 47, 8995.

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