Bolaamphiphilic Bis-Dehydropeptide Hydrogels as Potential Drug Release Systems

23 March 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The self-assembly of nanometric structures from molecular building blocks is an effective
way to make new functional materials for biological and technological applications. In this work
four symmetrical bolaamphiphiles based on dehydrodipeptides
(phenylalanyldehydrophenylalanine and tyrosyldehydrophenylalanine) linked through phenyl
or naphthyl linkers (terephthalic acid and 2,6-naphthalenedicarboxylic acid) were prepared and
their self-assembly properties studied. The results showed that all compounds with the exception
of the bolaamphiphile of tyrosyldehydrophenylalanine and 2,6-naphthalene dicarboxylic acid
gave self-standing hydrogels with critical gelation concentrations of 0.3 and 0.4 wt% using a pH
trigger. The self-assembly of these hydrogelators was investigated using STEM microscopy,
which revealed a network of entangled fibres. According to rheology the dehydrodipeptide
bolaamphiphile hydrogelators are viscoelastic materials with an elastic modulus G’ that falls in
the range of native tissue (0.37 kPa brain – 4.5 kPa cartilage). In viability and proliferation studies,
it was found that these compounds were non-toxic towards the human keratinocyte cell line,
HaCaT. In sustained release assays, we studied the effects of the charge present on the model
drug compound on the rate of cargo release from the hydrogel networks. Methylene blue (MB),
methyl orange (MO) and ciprofloxacin were chosen as cationic, anionic and overall neutral cargo,
respectively. These studies have shown that the hydrogels provide a sustained release of methyl
orange and ciprofloxacin, while the methylene blue is retained by the hydrogel network.


Supramolecular Hydrogels
Drug delivery


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