A modular trigger for the development of selective superoxide probes

Abstract

We report here a new bioinspired copper-based strategy of superoxide sensing and the development of sensitive (>90-fold fluorescence turn-on) and selective superoxide probes for imaging variations in the endogenous superoxide level in various live mammalian cells (HEK293T, HeLa and A431).

Selective catecholamine detection in living cells by a copper-mediated oxidative bond cleavage

“…A correct combination of the ligand donors (in both the first and second coordination sphere), terminal oxidant and substrate is therefore critical for useful copper-based oxidations. Different from the bioinorganic model studies or previous ROS/metal sensing in which the metal-oxygen oxidant is generated directly from oxygenation or ROS coordination,39,41–43 CAP488 is not reactive towards O 2 until being activated by catecholamines, therefore representing a new way to activate copper-based, O 2 -dependent oxidation.…”

“…S12†). The reaction of CAP488 with the catecholamines also produced no detectable amount of ROS as revealed by LCMS analysis of the CAP488 /catecholamine reaction mixtures in the presence of a H 2 O 2 probe,66 an O 2 – probe39 or a general ROS probe (Fig. S20–S22†).…”

“…In particular, we are inspired by the oxidative reactivity of dopamine β-hydroxylase (DβH), which is a copper oxygenase featuring a His/His/Met coordination, and reason that a similar catecholamine-triggered, copper-based oxidation can be harnessed for the selective release of a caged fluorescent reporter (Scheme 1). 39–43 Here we report the design and development of a prototypical catecholamine probe (CAP) that is based on a copper-based oxidative reaction and demonstrate that it can successfully detect changes in catecholamine levels in PC12 models of neuronal differentiation and Parkinson's disease. Combined with morphological assessment of the cells in the same imaging experiment, an integrative study of important neuronal processes by morphology and molecular imaging is demonstrated for the first time.…”

Activity‐Based Sensing: A Synthetic Methods Approach for Selective Molecular Imaging and Beyond

“…For example, Kodera and co‐workers utilized the H 2 O 2 ‐mediated uncaging of resorufin fluorescent scaffolds of iron complexes . Magnetic resonance imaging (MRI) probes from the Que group utilized H 2 O 2 ‐mediated cobalt oxidation, with detection shown through magnetic anisotropy changes in the 19 F signal, while Au‐Yeung and co‐workers have developed copper‐fluorophore ABS probes for superoxide …”

Aktivitätsbasierte Sensorik: ein synthetisch‐methodischer Ansatz für die selektive molekulare Bildgebung und darüber hinaus.

“…[221] Au-Yeung et al haben analog Kupferfluorophorsonden fürden ABS-Nachweis von Superoxid entwickelt. [222] Im Bereich metallorganischer Verbindungen entwickelte unser Labor die Kohlenmonoxidsonde 1( COP-1), der eine palladiumkatalysierte Carbonylierung zum selektiven Nachweis von Kohlenmonoxid (CO) zugrundeliegt;e in Pd-Fluoreszenzlçscher wird dabei unter gleichzeitiger Bildung einer C-C-Bindung von einem Fluorophor freigesetzt (Tabelle 9). [223] Da in biologischen Systemen viele zweiatomige Verbindungen vergleichbarer Grçße(z.…”