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Cited by 85Molecular Sensors and Ion DetectionRedox biology and oxidative stressAdvanced Fluorescence Microscopy Techniques

Design of a practical fluorescent probe for superoxide based on protection–deprotection chemistry of fluoresceins with benzenesulfonyl protecting groups

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Maeda, Hatsuo, Yamamoto, Kayoko, Kohno, Iho, Hafsi, Leila, Itoh, Norio, Nakagawa, Shinsaku, Kanagawa, Naoko, Suzuki, Keiichiro +1 more·2007·Chemistry – A European Journal
DOI 10.1002/chem.200600522
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Abstract

A strategy for designing probes based on protection–deprotection chemistry involving fluoresceins and their benzenesulfonyl (BES) derivatives has led to the development of a much more practical superoxide (O 2−.) probe than the previously reported bis(2,4‐dinitro‐BES) tetrafluorofluorescein (6 a). Examination of various BES derivatives, developed from the starting point of the prototype probe 6 a, yielded 4,5‐dimethoxy‐2‐nitro‐BES tetrafluorofluorescein (BESSo; 7 j) as the optimal reagent. A microtiter plate assay with BESSo showed a tenfold improved detection limit for O 2−. compared with such an assay based on 6 a. BESSo showed markedly better specificity for O 2−. than for GSH or other reactive oxygen species, and this specificity was significantly higher than that of Fe 2+ and some reducing enzymes. These features have resulted in the development of an assay based on BESSo that is capable of providing more unambiguous results for O 2−. release from neutrophils, with or without stimulation by phorbol myristate acetate, as compared with an assay based on 6 a. Intracellular generation of O 2−. in human Jurkat T cells stimulated by butyric acid has been measured by using flow cytometry and fluorescence microscopy utilizing the acetoxymethyl derivative of BESSo.

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  • Maeda et al., 2007, demonstrated that probe (b) serves as an optimal sensor for detection of O2•− in aqueous solutions at pH 7.4, with a detection limit 10 times higher than probe (a).

    “Additionally, based on a strategy of deprotection of the benzenesulfonyl group, Maeda et al., 2007, demonstrated that probe (b) serves as an optimal sensor for the detection of O2•− in aqueous solutions and pH 7.4, the detection limit of this probe for O2•− is 10 times higher than that of probe (a).”

    From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as Maeda et al., 2007

  • Probe (b) shows high selectivity towards O2•− over glutathione and other ROS such as hydrogen peroxide, hypochlorite, tert-butyl peroxide, singlet oxygen, •NO and peroxynitrite.

    “In addition, probe (b) shows a high selectivity towards O2•− over glutathione and other ROS, such as hydrogen peroxide, hypochlorite, tert-butyl peroxide, singlet oxygen, •NO and peroxynitrite [165].”

    From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [165]

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Authors
Maeda, H., Yamamoto, K., Kohno, I., Hafsi, L., Itoh, N., Nakagawa, S., Kanagawa, N., Suzuki, K., & Uno, T.
Affiliations
  • The University of Osaka (JP)
  • Hyogo Medical University (JP)
ORCID
Venue
Chemistry – A European Journal
Publisher
Wiley
Published
2007-02-08
Volume
13
Issue
7
Pages
1946-1954
ISSN
  • 0947-6539 (ISSN-L)
  • 1521-3765
DOI
10.1002/chem.200600522
OpenAlex
W2092966266
Cited by
85
References
49
Citations by year
2024: 2 · 2023: 2 · 2022: 2 · 2021: 7 · 2020: 3 · 2019: 12 · 2018: 5 · 2017: 5 · 2016: 4 · 2015: 8 · 2014: 6 · 2013: 4 · 2012: 5
FWCI
1.27
Type
journal article
Language
en
Open access
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations
  • Chemistry - A European Journal (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • Ministry of Education, Culture, Sports, Science and Technology
  • Mochida Memorial Foundation for Medical and Pharmaceutical Research
Topics
  • Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › Advanced Fluorescence Microscopy Techniques
Keywords
superoxide detection, fluorescent probes, fluorescein, Jurkat cells, acetoxymethyl ester, phorbol myristate acetate stimulation
MeSH terms
Cells, Cultured, Chemistry, Organic, Fluoresceins, Fluorescent Dyes, Humans, Kinetics, Neutrophils, Sulfonic Acids, Superoxides, T-Lymphocytes, Tetradecanoylphorbol Acetate

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