An unusual solvatochromic effect was found in a newly developed fluorophore dihydroquinolinimine (DQI), which considerably diminishes fluorescence quantum yield from 62% in dichloromethane to 6% in methanol, as well as a significant red-shift of the fluorescence emission from 478 nm in n-hexane to 573 nm in methanol. The density functional theory (DFT) calculation rationalized this environment-sensitive fluorescent response with a considerable change of dipolar moment between excited and ground state. The novel environment-sensitive property makes DQI an ideal fluorescent turn-on biosensor for selective biomolecular recognition. An aryl sulfonamide-conjugated DQI (SA-DQI) molecule was successfully used to detect human carbonic anhydrase II (hCAII) with a fifteen-fold enhancement of fluorescence intensity. Remarkably, the SA-DQI is a background-free fluorescent probe that can recognize membrane-bound hCAII on 293T cells without removal of unbound SA-DQIs. Finally, a more water soluble fluorophore, SA-TEG-DQI, was synthesized, and track a specific protein, carbonic anhydrase which located around the inner ear in early development, in zebrafish. This binding-directed fluorescence turn-on platform would be a powerful tool to a real-time study of biomolecular interactions.

<i>In vivo</i> monitoring of carbonic anhydrases expression with fluorescence turn-on enrichment

2019 Fall National Meeting

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In vivo monitoring of carbonic anhydrases expression with fluorescence turn-on enrichment