Hydrogen Peroxide-Induced Deacetylation of Acetyl Resorufin as a Novel Indicator Reaction for Fluorometric Detection of Glucose Using Only Glucose Oxidase.

Maeda, Hatsuo; Matsu-Ura, Shinya; Nishida, Mari; Senba, Toshihisa; Yamauchi, Yuji; Ohmori, Hidenobu

doi:10.1248/cpb.49.294

Cited by 13 publications

(5 citation statements)

References 35 publications

(49 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(18). Possible reaction mechanism of probe 18 in the presence of 1 O2 [110] It was reported that deacetylation of non-fluorescent acetyl resorufin 21 to fluorescent resorufin can be induced by H 2 O 2 generated in glucose oxidase (GOD)-catalyzed oxidation of glucose [112,113]. This reaction mechanism has been used for the indirect fluorimetric determination of glucose by monitoring the formed H 2 O 2 (Fig.…”

Section: Spectroscopic Probes With Active Bonds Cleavable By Reactivementioning

confidence: 99%

Progress in Spectroscopic Probes with Cleavable Active Bonds

Chen¹,

Sun²,

2006

COC

View full text Add to dashboard Cite

Spectroscopic probes may be defined as the molecules that can react with analytes (targets) accompanying the changes of their spectroscopic (chromogenic, fluorescent, or chemiluminescent) properties; based on such changes the targets can thus be determined. Spectroscopic probes have been extensively investigated and used widely in many fields because of their powerful ability to improve analytical sensitivity and to offer greater temporal and spatial sampling capability. In this review, special interest is devoted to a new type of spectroscopic probe that is constructed with a cleavable active bond as a linker. This type of spectroscopic probe, developed greatly in the past few years, has opened a novel alternate route to the specific determination of analytes with high hydrolytic reactivity, e.g., from metal ions to enzyme activity, and enabled many biological processes to be monitored in situ and in real-time. Theoretically, various photophysical processes, such as photoinduced electron transfer, photoinduced proton transfer, and fluorescence resonance energy transfer, can be used to design spectroscopic probes with cleavable active bonds for selective detection of analytes. Herein we review the progress and application of this type of spectroscopic probe, including spectroscopic response mechanism and the probes with active bonds cleavable by enzyme, metal ion and reactive oxygen species.

show abstract

Section: Spectroscopic Probes With Active Bonds Cleavable By Reactivementioning

confidence: 99%

Progress in Spectroscopic Probes with Cleavable Active Bonds

Chen¹,

Sun²,

2006

COC

View full text Add to dashboard Cite

show abstract

“…[10] The method is based on simple deprotection, not on oxidation, thus allowing acyl derivatives of fluorescent compounds such as resorufin and fluorescein to work as probes for detecting cell-derived H 2 O 2 with higher selectively than that provided by DCFH and its analogues. Unfortunately, the competition between perhydrolysis and hydrolysis of acyl resorufins and fluoresceins in biological systems was not altered in a manner favorable towards H 2 O 2 -based deacylation.…”

mentioning

confidence: 99%

Fluorescent Probes for Hydrogen Peroxide Based on a Non‐Oxidative Mechanism

et al. 2004

Self Cite

View full text Add to dashboard Cite

Reactive oxygen species (ROS) such as superoxide (O 2 ÀC ), hydrogen peroxide (H 2 O 2 ), and the hydroxyl radical (HOC) are important mediators of pathological processes in various diseases.[1] Detection by fluorescent probes is one of the most useful methods for evaluating the roles of ROS in pathological processes. 2',7'-Dichlorofluorescin (DCFH) and its diacetyl derivative (DCFH-DA) [2] have been widely used as fluorescent probes for measuring cell-derived H 2 O 2 , [3] but these compounds suffer from the major drawback that they are poorly selective toward H 2 O 2 . Researchers have demonstrated that oxidation of DCFH to dichlorofluorescein is also induced by peroxidase [4] and other hemoproteins [5] as well as by hydroperoxides in the presence of peroxidase, [6] nitric oxide, [7] and peroxynitrite. [8] Therefore, the fluorescent response based on the oxidation of DCFH provides an index, not for cell-derived H 2 O 2 , but for the total oxidants present in biological systems. This limitation stems from its mechanism of fluorescence, which is based on oxidation. Dihydro derivatives of fluorescent compounds such as dihydrorhodamine 123 [3c,g] and N-acetyl-3,7-dihydroxyphenoxazine (Amplex Red) [9] have been shown to function as probes for detecting H 2 O 2 . However, their mechanism of action is similar to that of DCFH, which implies that low selectivity toward H 2 O 2 is a shortcoming that must be accepted when utilizing these probes. In fact, dihydrorhodamine 123 was shown to react with various ROS, [3c, 7b] and although Amplex Red seems to have high selectivity toward H 2 O 2 , peroxidase is essential for its fluorescence, similar to the case of DCFH. Thus, developing probes for H 2 O 2 based on a non-oxidative fluorescence mechanism, which would allow the highly specific and peroxidase-independent detection of H 2 O 2 under the complicated oxidative circumstances found in biological systems, is a worthwhile goal.Recently, we found that perhydrolysis of acyl resorufins is a useful reaction that acts as a fluorescent indicator for H 2 O 2 assays.[10] The method is based on simple deprotection, not on oxidation, thus allowing acyl derivatives of fluorescent compounds such as resorufin and fluorescein to work as probes for detecting cell-derived H 2 O 2 with higher selectively than that provided by DCFH and its analogues. Unfortunately, the competition between perhydrolysis and hydrolysis of acyl resorufins and fluoresceins in biological systems was not altered in a manner favorable towards H 2 O 2 -based deacylation.We thus designed pentafluorobenzenesulfonyl fluoresceins (1 a-c, Scheme 1) as selective fluorescent probes for H 2 O 2 but would eliminate, or at least significantly reduce, competition from hydrolysis reactions of the acetyl derivatives. These compounds were chosen for the following reasons: sulfonates are more stable to hydrolysis than are esters; fluoresceins have high fluorescence quantum yields in aqueous solution; and the pentafluorobenzene ring enhances the reactivity of the sulfonates tow...

show abstract

“…Resorufin is a water‐soluble fluorescent dye with a phenolic hydroxyl group, whereas its acyl derivatives exhibit no fluorescence. As expected, the fluorometry with acyl resorufins was useful for measurements of H 2 O 2 19,20 . Unfortunately, acyl resorufins could not find utility as intracellular H 2 O 2 probes, because these compounds are hydrolyzed easily by esterase, leading to high background responses within cells.…”

Section: Strategymentioning

confidence: 70%

“…As expected, the fluorometry with acyl resorufins was useful for measurements of H 2 O 2 . 19,20 Unfortunately, acyl resorufins could not find utility as intracellular H 2 O 2 probes, because these compounds are hydrolyzed easily by esterase, leading to high background responses within cells. And yet, the work on acyl resorufins enabled us to propose a working hypothesis, that is, a strategy for the design of fluorescent probes based on protection-deprotection chemistry (FIG.…”

Section: Strategymentioning

confidence: 99%

Which Are You Watching, an Individual Reactive Oxygen Species or Total Oxidative Stress?

Maeda

2008

Annals of the New York Academy of Sciences

Self Cite

View full text Add to dashboard Cite

The fluorometric measurement of an individual reactive oxygen species (ROS) provides useful biological and biochemical information on ROS as important mediators for the pathological conditions of various diseases and yet requires a highly specific probe toward the target ROS. To design such a specific ROS probe, this report proposes a new strategy based on protection-deprotection chemistry between fluoresceins and their derivatives protected with benzenesulfonyl groups. The strategy has allowed developing new fluorescent probes toward extra- and intracellular hydrogen peroxide or superoxide. Herein, I outline the strategy used for the design of these ROS probes and their probe performance with high selectivity toward hydrogen peroxide and superoxide, which could not be achieved until a simple deprotection, namely, a nonredox reaction, was used as a fluorescing process.

show abstract

Hydrogen Peroxide-Induced Deacetylation of Acetyl Resorufin as a Novel Indicator Reaction for Fluorometric Detection of Glucose Using Only Glucose Oxidase.

Cited by 13 publications

References 35 publications

Progress in Spectroscopic Probes with Cleavable Active Bonds

Progress in Spectroscopic Probes with Cleavable Active Bonds

Fluorescent Probes for Hydrogen Peroxide Based on a Non‐Oxidative Mechanism

Which Are You Watching, an Individual Reactive Oxygen Species or Total Oxidative Stress?

Contact Info

Product

Resources

About