Development of highly selective and sensitive probes for hydrogen peroxideElectronic supplementary information (ESI) available: general methods. See http://www.rsc.org/suppdata/cc/b3/b309393j/

Abstract

Probes that react specifically with hydrogen peroxide to release chromophoric or fluorescent reporter groups were designed and synthesized.

Design Strategies for Water-Soluble Small Molecular Chromogenic and Fluorogenic Probes

“…The first example of such probes is compound 213, in which aminocoumarin is masked by a p-dihydroxyborylbenzyloxycarbonyl group. 552 Chang's group synthesized a series of H 2 O 2 probes based on the diboronate-and monoboronate-masked xanthene, resorufin, and other structures. Figure 39 shows some of the typical structures (214−218).…”

Development of a sensitive long-wavelength fluorogenic probe for nitroreductase: A new fluorimetric indictor for analyte determination by dehydrogenase-coupled biosensors

“…Recently, we reported the generation of a new long-wavelength latent fluorophore for use in monitoring salicylate hydroxylase activities with a fluorogenic coumarin-releasing mechanism based on the 1,6-rearrangementelimination reaction (Huang et al, 2010). The latter reaction has been utilized to release drugs from prodrugs (Haba et al, 2005;Flader et al, 2000), in the selective cleavage of peptides from an enzyme-labile linker during solid phase synthesis (Sauerbrei et al, 1998), and off-on fluorescence mechanism of a hydrogen peroxidesensitive latent fluorophore (Lo and Chu, 2003). We hypothesized that the same fluorescence releasing mechanism could be adapted to the design a latent fluorophore for monitoring NTR activity.…”

Ionic Transport through Chemically Functionalized Hydrogen Peroxide-Sensitive Asymmetric Nanopores

“…20 The resulting phenolic compound further undergoes decarboxylation and 1,6-elimination reactions, leading to the generation of amine groups. 21 H 2 O 2 acts as a triggering agent which generates the amine groups on the backbone of the boronic ester carbamate chains. 21 Figure 2b shows the I-V curves of the BEC-modified pore when exposed to a H 2 O 2 solution for different times.…”

“…21 H 2 O 2 acts as a triggering agent which generates the amine groups on the backbone of the boronic ester carbamate chains. 21 Figure 2b shows the I-V curves of the BEC-modified pore when exposed to a H 2 O 2 solution for different times. As expected, an inversion of the ionic current rectification 18,19 with respect to that of Figure 2a was observed due to the amine moieties on the pore surface (in our experimental conditions, the amine groups are protonated, imparting positive charge to the pore surface).…”