Caprolactone Based Biodegradable Polymeric Fluorescence Probe for Selective and Sensitive Detection of Carbon Monoxide and Hypoxia in Environmental and Biological Samples

Bhutia, Sonam Pintso (2023) Caprolactone Based Biodegradable Polymeric Fluorescence Probe for Selective and Sensitive Detection of Carbon Monoxide and Hypoxia in Environmental and Biological Samples. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Sonam Pintso Bhutia (18MS036)) Thesis_18MS036.pdf - Submitted Version Restricted to Repository staff only Download (4MB)

Abstract

A Polymeric biodegradable fluorescent probe containing a Nitro group with Caprolactone and polyethylene glycol (PEG) as the backbone for sensitive and selective detection of carbon monoxide and hypoxia was proposed. The polymeric fluorescent probe is synthesized in 2 parts. Firstly, Monomer 1 is prepared which consist a propargyl unit attached with an oxygen atom of the phenol, which is further attached to a naphthalic anhydride moiety. Secondly, a caprolactone moiety containing an azide group is polymerised with polyethylene glycol to give a polymeric chain of PCl(N3)-PEG-PCl(N3). (PCl=polycaprolactone). The PEG unit of the polymeric chain helps in enhancing the water solubility and also helps in inhibiting bacterial growth and providing biocompatibility effect to the polymer. The caprolactone is biodegradable and can be easily degraded by lipases and esterase of various microorganisms. The Monomer and the polymeric backbone are later polymerized together using Click reaction where the azide(N³) from the polymeric backbone and the alkyne unit from the propargyl part of the monomer forms a triazole ring. The triazole ring has an antimicrobial effect and is widely used in drugs due to its antifungal abilities. The Nitro unit of the fluorescent probe converts to an Amine in presence of Carbon Monoxide or in Hypoxic environment. The probe is based on ‘turn on fluorescence’ where initially the probe has no fluorescence but starts to show fluorescence later due to some changes in their functional groups. The synthesized compounds were all characterized by ¹H and 1³C NMR spectroscopy. The reported fluorescence probe can sensitively and selectively determine carbon monoxide and hypoxic environment and its potential application for detection in biological samples and medical application remains unexplored

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