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STY-BODIPY

(Synonyms: Styrene-BODIPY) 目录号 : GC45571

A fluorogenic probe for radical-trapping antioxidant activity

STY-BODIPY Chemical Structure

Cas No.:2383063-37-2

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500μg
¥1,696.00
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1mg
¥3,221.00
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5mg
¥10,175.00
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产品描述

STY-BODIPY is a styrene-conjugated fluorogenic probe for radical-trapping antioxidant (RTA) activity.1 Co-autoxidation of the STY-BODIPY signal carrier and a hydrocarbon co-substrate can be quantified by monitoring the loss of absorbance at 571 nm. STY-BODIPY has been used to measure the activity of RTAs, as well as the kinetics and stoichiometry of RTA reactions in cell-free assays.1,2,3

References
1. Haidasz, E.A., Van Kessel, A.T.M., and Pratt, D.A. A continuous visible light spectrophotometric approach to accurately determine the reactivity of radical-trapping antioxidants. J. Org. Chem. 81(3), 737-744 (2016).
2. Shah, R., Shchepinov, M.S., and Pratt, D.A. Resolving the role of lipoxygenases in the initiation and execution of ferroptosis. ACS Cent. Sci. 4(3), 387-396 (2018).
3. Chauvin, J.-P.R., Haidasz, E.A., Griesser, M., et al. Polysulfide-1-oxides react with peroxyl radicals as quickly as hindered phenolic antioxidants and do so by a surprising concerted homolytic substitution. Chem. Sci. 7(10), 6347-6356 (2016).

Chemical Properties

Cas No. 2383063-37-2 SDF
别名 Styrene-BODIPY
化学名 (T-4)-[2-[(3,5-dimethyl-2H-pyrrol-2-ylidene-κN)methyl]-5-[(1E)-2-phenylethenyl]-1H-pyrrolato-κN]difluoro-boron
Canonical SMILES CC(C=C1C)=[N+](C1=C2)[B-](F)(F)N3C2=CC=C3/C=C/C4=CC=CC=C4
分子式 C19H17BF2N2 分子量 322.2
溶解度 Benzene: 1 mg/ml 储存条件 Store at -20°C,protect from light
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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1 mg 5 mg 10 mg
1 mM 3.1037 mL 15.5183 mL 31.0366 mL
5 mM 0.6207 mL 3.1037 mL 6.2073 mL
10 mM 0.3104 mL 1.5518 mL 3.1037 mL
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Research Update

A Continuous Visible Light Spectrophotometric Approach To Accurately Determine the Reactivity of Radical-Trapping Antioxidants

J Org Chem 2016 Feb 5;81(3):737-44.PMID:26529543DOI:10.1021/acs.joc.5b02183.

Inhibited autoxidations-monitored either by O2 consumption or hydroperoxide formation-are the most reliable way to obtain kinetic and stoichiometric information on the activity of radical-trapping antioxidants (RTAs). While many comparatively simple "antioxidant assays" (e.g., the DPPH assay) have supplanted these in popularity, they are generally very poor substitutes since they often do not employ peroxyl radicals as the oxidant and do not account for both the kinetics and stoichiometry of the radical-trapping reaction(s). In an effort to make inhibited autoxidations as simple as the most popular "antioxidant assays", we have developed a spectrophotometric approach for monitoring reaction progress in inhibited autoxidations. The approach employs easily prepared 1-phenylbutadiene-conjugated or styrene-conjugated BODIPY chromophores (PBD-BODIPY or STY-BODIPY, respectively) as signal carriers that co-autoxidize along with a hydrocarbon substrate. We show that inhibition rate constants (kinh) are accurately determined for a range of phenolic and diarylamine RTAs using this approach and that mechanistic experiments, such as kinetic isotope effects and kinetic solvent effects, are equally easily carried out. Moreover, synergistic interactions between RTAs, as well as the unconventional activity of diarylamine RTAs, are captured using this methodology. Lastly, we show that the approach can be employed for monitoring reactions in aqueous solution.

General Approach to Identify, Assess, and Characterize Inhibitors of Lipid Peroxidation and Associated Cell Death

ACS Chem Biol 2023 Mar 17;18(3):561-571.PMID:36854078DOI:10.1021/acschembio.2c00897.

Lipid peroxidation (LPO) is associated with a variety of pathologies and drives a form of regulated necrosis called ferroptosis. There is much interest in small-molecule inhibitors of LPO as potential leads for therapeutic development for neurodegeneration, stroke, and acute organ failure, but this has been hampered by the lack of a universal high-throughput assay that can identify and assess candidates. Herein, we describe the development and validation of such an approach. Phosphatidylcholine liposomes loaded with ∼10% phospholipid hydroperoxide and STY-BODIPY, a fluorescent signal carrier that co-autoxidizes with polyunsaturated phospholipids, are shown to autoxidize at convenient and constant rates when subjected to an optimized Fe2+-based initiation cocktail. The use of this initiation system enables the identification of each of the various classes of LPO inhibitors which have been shown to rescue from cell death in ferroptosis: radical-trapping antioxidants (RTAs), peroxidase mimics, and iron chelators. Furthermore, a limited dose-response profile of inhibitors enables the resolution of RTA and non-RTA inhibitors─thereby providing not only relative efficacy but mechanistic information in the same microplate-based experiment. Despite this versatility, the approach can still be used to estimate rate constants for the reaction of RTAs with chain-propagating peroxyl radicals, as demonstrated for a representative panel of RTAs. To illustrate the utility of this assay, we carried out a preliminary investigation of the 'off-target' activity of several ferroptosis suppressors that have been proposed to act independently of inhibition of LPO, including lipoxygenase inhibitors, cannabinoids, and necrostatins, the archetype inhibitors of necroptosis.