Long-wavelength fluorescent boronate probes for the detection and intracellular imaging of peroxynitrite

Abstract

Two boronate fluorescent probes have been developed for the detection of peroxynitrite (TCFB1 and TCFB2). TCFB1 was shown to have a low sensitvity towards peroxynitrite and have a poor solubility in aqueous solution whereas TCFB2 demonstrated high sensitivity towards peroxynitrite and mitochondria localisation with the ability to detect exogenous and endogenous peroxynitrite in live cells (Hep-G2, RAW 264.7, HeLa and A459).

ESIPT-based ratiometric fluorescence probe for the intracellular imaging of peroxynitrite

“…Within our research, we are particularly interested in the development of small molecule fluorescent probes for the detection of biologically relevant analytes in vivo owing to their high sensitivity, selectivity, high spatial and temporal resolution. [8][9][10][11][12] Currently, there are several targeted fluorescence probes for the detection of biologically relevant analytes. However, to the best of our knowledge, there are no ONOO À fluorescence probes that localize at the ER so we set out to develop an ER-targeting ONOO À fluorescence probe.…”

“…Due to boronates/ boronic acids having a greater reactivity towards ONOO À over HClO/ClO À (min) and H 2 O 2 (hours), this unit would therefore allow the selective detection of ONOO À . 8,10,11,22 Furthermore, the functionalization of the amino group of ABAH with a thiolreactive chloroacetamide functional group enables the covalent attachment of ABAH-LW to biomacromolecules located at the ER enabling targeted visualization of the ER in the presence of ONOO À . 23 ABAH-LW was synthesized over four steps.…”

Monitoring NAD(P)H by an ultrasensitive fluorescent probe to reveal reductive stress induced by natural antioxidants in HepG2 cells under hypoxia

“…33,34 TCF-based uorophores typically have a donor-p-acceptor (D-p-A) structure with long emission wavelengths, and many uorescent probes have been developed. 35 Here, we designed and synthesized a TCF-based uorescent probe (TCF-MQ) for the detection of NAD(P)H (Scheme 1). TCF-MQ and all intermediate structures were fully characterized by 1 H NMR, 13 C NMR, and HRMS (see the Experimental section and the ESI †).…”

Boronate‐Based Fluorescence Probes for the Detection of Hydrogen Peroxide

“…For this reason, researchers are actively seeking new and effective approaches for H 2 O 2 detection. With our research, we are particularly interested in the development of small‐molecule fluorescent probes, as they are well suited to meet the need of tools to map the spatial and temporal distribution of H 2 O 2 in living cells. However, the major challenge for practical H 2 O 2 sensing in biological environments is creating water‐soluble systems that respond to H 2 O 2 .…”