A biocompatible hydrogel as a template for oxidative decomposition reactions: a chemodosimetric analysis and in vitro imaging of hypochlorite

Abstract

The self-assembly properties of new biocompatible, thermoreversible fluorescent hydrogels, composed of amino acid residues, e.g., L-phenylalanine (PyL-PheOx) and L-tyrosine (PyL-TyrOx), have been reported. Spectroscopic investigations indicate that PyL-PheOx forms π-stacked ‘compact’ aggregates, while ‘loose’ aggregates with stronger CT characteristics are observed for PyL-TyrOx. Both the compounds showed the presence of fibrous networks in the self-assembled state. Circular dichroism spectral studies indicate the formation of M-helical and P-helical structures for PyL-PheOx and PyL-TyrOx, respectively. A striking gel-to-sol transition, caused by oxidative decomposition, is explicitly noticed in the presence of hypochlorite. A mechanistic investigation reveals the oxidation of the acyl aroyl hydrazine core of the gelators in the presence of ClO−. In addition to this, change in the fluorescence emission intensity of the hydrogel in the presence of ClO− is utilized for the analysis of commercial bleach samples. Gel-coated paper strips are also developed for the on-site detection of ClO−. Furthermore, the system is utilized for imaging hypochlorite in live mammalian cells.