An ESIPT based naphthalimide chemosensor for visualizing endogenous ONOO^- in living cells.

ABSTRACT: Based on ESIPT, we designed and synthesized a naphthalimide chemosensor N-CBT for selectively visualizing endo/exogenous peroxynitrite (ONOO^-) in living cells. The incorporation of 2-benzothiazoleacetonitrile offers N-CBT a rare pre-existing eight-membered ring hydrogen bonding configuration, which is able to generate two types of emission of naphthalimide. Confirmed by calculation results, fast proton transfer from the hydroxyl group to the carbonyl group occurs along with excited-state energy transfer via the intramolecular H-bond, leading to a tautomeric transformation from the excited enol form to the excited keto form. In aqueous solution, the formation of intermolecular hydrogen bonding with water perturbs ESIPT and destroys the stable planar construction. By breaki

SUBMITTER: Fu Y 

PROVIDER: S-EPMC9077266 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature