A biocompatible hydrogel as a template for oxidative decomposition reactions: a chemodosimetric analysis and in vitro imaging of hypochlorite |
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Authors: | Dipen Biswakarma Nilanjan Dey Santanu Bhattacharya |
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Institution: | Department of Organic Chemistry, Indian Institute of Science, Bangalore Karnataka 560012 India ; School of Applied & Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata 700032 India, +91 8022932664 ; Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bengaluru 560064 Karnataka India ; Department of Chemistry, BITS Pilani, Hyderabad Campus, Jawahar Nagar, Shameerpet Mandal, Hyderabad-500078 India |
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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.The self-assembly properties of new biocompatible, thermoreversible fluorescent hydrogels, composed of amino acid residues have been reported. A unique gel-to-sol transition is triggered by chemodosimetric interaction in the presence of hypochlorite. |
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