Organogelation and cytotoxic evolution of phosphonate ester functionalised hydrophobic alkanediamide motifs

Abstract

Here we report various rigid alkanediamide derivatives, with three different substitution patterns of phosphonate ester for investigation of organogelation properties. The gelation properties of these compounds can be tuned by altering the number and position of the phosphonate esters. It was found that supramolecular self-assembly of the bisphosphonate esters (1a, 1d, 1h and 2a–b) resulted gel formation, whereas that of the tetraphosphonate esters (3a, 3d, 3h) resulted in construction of nanospheres and microspheres. The diverse morphology of the gel formation appears to depend predominantly on the substituted phenyl ring of the phosphonate ester functionality. Subsequent in vitro cytotoxic screening against four human tumour cell lines (A549, MDA-MB-231, MCF-7 and HeLa) using MTT assays revealed that derivatives 1f–h and 3a show cytotoxic potencies at concentrations less than 5 μM (IC₅₀ values). Compounds 1f–h exhibited promising activity against A549 cell line, 1g–h were highly effective against MDA-MB-231, 1f and 3a show potential against MCF-7 and 1f–g were active against the HeLa cell line.

Keywords::

• organogelation
• self-assembly
• alkanediamides
• phosphonate ester
• scanning electron microscopy

Acknowledgement

We thank Vijay S. Patil for his assistance with sample analysis.

Additional information

Funding

Sid. V.B. wishes to thank the DAE-BRNS, Mumbai, India for financial support under project no. 2009/37/39/BRNS. She. V.B. acknowledges the Australian Research Council, under a Future Fellowship Scheme (FT110100152).