Synthesis and Characterization of SAMs and Tethered Bilayer Membranes from Unsymmetrically Substituted 1,2-Dithianes

Christopher J. Burns; Leslie D. Field; Brian J. Petteys; Damon D. Ridley

doi:10.1071/CH05175

RESEARCH ARTICLE

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Synthesis and Characterization of SAMs and Tethered Bilayer Membranes from Unsymmetrically Substituted 1,2-Dithianes

Christopher J. Burns ^A ^B ^C , Leslie D. Field ^A , Brian J. Petteys ^A and Damon D. Ridley ^A

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Cooperative Research Centre for Molecular Engineering and Technology, University of Sydney, Sydney NSW 2006, Australia.

^B Current address: Cytopia Pty Ltd, Baker Medical Research Institute, PO Box 6492, St Kilda Rd Central, Melbourne VIC 8008, Australia.

^C Corresponding author. Email: chris.burns@cytopia.com.au

Australian Journal of Chemistry 58(10) 738-748 https://doi.org/10.1071/CH05175
Submitted: 25 July 2005 Accepted: 7 October 2005 Published: 8 November 2005

Abstract

The synthesis of a series of new membrane-forming compounds, based on previously established components used in an ion-channel switch (ICS) biosensor (Nature 1997, 387, 580) is described. All new compounds are derived from 4,5-dihydroxy-1,2-dithiane, and contain a hydrophilic reservoir section (based on ethylene glycol units) and a lypophilic section (based on the natural lipid phytanol). Ellipsometry and contact angle measurements indicate that self-assembled monolayers (SAMs) formed from the new materials possess thicknesses and membrane packing comparable to previously reported biosensor components. Tethered bilayer lipid membranes (t-BLMs) incorporating the novel materials were studied using impedance spectroscopy with the ion-carrier valinomycin. The electrical behavior and calculated membrane thickness of the t-BLMs are comparable to those derived from the standard ICS components and this demonstrates that the novel membrane-forming compounds form stable membranes that are sufficiently fluid to transport potassium ions in the presence of valinomycin.

Acknowledgment

We thank the Australian Government through the Cooperative Research Centre for Molecular Engineering and Technology for financial support, and Pacific Dunlop Ltd for the award of a Pacific Dunlop Scholarship (B.J.P.). We thank Mr Mohammed Islam (Ambri Ltd) for performing the contact angle and ellipsometry measurements.

References

Synthesis and Characterization of SAMs and Tethered Bilayer Membranes from Unsymmetrically Substituted 1,2-Dithianes

Abstract

Acknowledgment

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