The Effect of Unsaturation on the Formation of Self-Assembled Gels from Fatty Acid l-Serine Amides and their Cytotoxicity Towards Caco-2 Cancer Cells

Li Yun Grace Lim; Yingying Su; Filip Braet; Pall Thordarson

doi:10.1071/CH09211

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The Effect of Unsaturation on the Formation of Self-Assembled Gels from Fatty Acid l-Serine Amides and their Cytotoxicity Towards Caco-2 Cancer Cells

Li Yun Grace Lim ^A , Yingying Su ^B , Filip Braet ^B and Pall Thordarson ^A ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.

^B Australian Key Centre for Microscopy and Microanalysis, The University of Sydney, NSW 2006, Australia.

^C Corresponding author. Email: p.thordarson@unsw.edu.au

Australian Journal of Chemistry 62(7) 653-656 https://doi.org/10.1071/CH09211
Submitted: 10 April 2009 Accepted: 27 May 2009 Published: 13 July 2009

Abstract

A series of saturated and unsaturated fatty acid l-serines 3 were synthesized and their ability to form self-assembled gels was investigated. The saturated (lauroyl 3a and steraoyl 3b) and monounsaturated (oleoyl 3c) fatty acid l-serines form gels in both water and organic solvent, whereas the diunsaturated linoleyl-l-serine 3d does not form gels in these solvents, indicating that unsaturation adversely affects the gelation process. Cytotoxicity studies on these compounds with Caco-2 cancer cells in vitro show that these gels are only moderately cytotoxic at concentrations up to 0.5 mM, making them a promising candidate for applications such as drug delivery.

Acknowledgements

The authors acknowledge the facilities as well as technical assistance from staff at the Australian Key Centre for Microscopy and Microanalysis (AKCMM) of the University of Sydney. We thank Dr Frankie Stevens of the AKCMM for excellent technical assistance with cell cultures and the cytotoxicity assays. We would also like to thank the Australian Research Council (ARC) for a Discovery Project Grant (DP0985059) to P.T. and F.B. and the University of New South Wales Centre for Nanomedicine initiative for financial support to P.T. for the present project. We also thank the ARC for an Australian Research Fellowship (DP0666325) to P.T.

References

The Effect of Unsaturation on the Formation of Self-Assembled Gels from Fatty Acid l-Serine Amides and their Cytotoxicity Towards Caco-2 Cancer Cells

Abstract

Acknowledgements

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