Progress in the field of low molecular weight gelators (LMWGs) is motivated by the attractive self-assembling properties and associated mechanical strengths of the hydrogels that they form making them ideal for use in drug delivery. Many examples of gelators exist whose primary purpose is to act as a drug delivery vehicle; however there are no known examples of gelators that self-assemble in response to the non-covalent interactions provided by the drug itself. We have recently developed a series of low molecular weight gemcitabine prodrugs that we are able to formulate into a hydrogels using minimal external manipulation and that we propose could be used as an intra-tumoural drug delivery platform for gastric and pancreatic adenocarcinomas, eliminating the need for large systemic doses and reducing associated side effects.<br/>Here we present a series of amphiphilic gemcitabine pro-drugs generated <i>via</i> modification of the primary amine of the cytosine nucleobase. (Figure 1) Each of the enzyme/pH cleavable pro-drugs was evaluated for growth inhibition in MiaPaCa-2 and MKN-7 cell lines. Additionally the gelation of each pro-drug was evaluated and we noted that the hydrogels containing even a single amide functionality were able to form mechanically stable gels in a minimal amount of ethanol.

Gemcitabine pro-drugs as a self-assembling, intra-tumoural drug delivery platform for the treatment of gastric and pancreatic cancers

250th National Meeting (2015)

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