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目录号 : GC61587

Sel-green是一种选择性的硒醇荧光探针,用于定量硒酶硫氧蛋白还原酶中的Sec含量,并对活细胞中的Sec进行荧光呈像。

Sel-green Chemical Structure

Cas No.:1574299-37-8

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5 mg
¥3,150.00
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10 mg
¥5,220.00
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产品描述

Sel-green, a selective selenol fluorescent probe, is applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells[1].

Sel-green displays >20-fold selectivity of Sec over DTT[1]. Sel-green is suitable for identifying the selenol species metabolized from various selenocompounds in cells, which helps to clarify the mechanism underlying the cytotoxicity of different selenocompounds[1].

[1]. Baoxin Zhang, et al. Selective selenol fluorescent probes: design, synthesis, structural determinants, and biological applications. J Am Chem Soc. 2015 Jan 21;137(2):757-69.

Chemical Properties

Cas No. 1574299-37-8 SDF
Canonical SMILES O=S(C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O)(NC2=CC3=CC=C(N(CC)CC)C=C3OC2=O)=O
分子式 C19H18N4O8S 分子量 462.43
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1 mg 5 mg 10 mg
1 mM 2.1625 mL 10.8124 mL 21.6249 mL
5 mM 0.4325 mL 2.1625 mL 4.325 mL
10 mM 0.2162 mL 1.0812 mL 2.1625 mL
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Research Update

Assay of selenol species in biological samples by the fluorescent probe Sel-green

Methods Enzymol 2022;662:259-273.PMID:35101214DOI:10.1016/bs.mie.2021.10.021.

Selenium (Se) is an essential trace element for diverse cellular functions. The biological significance of Se is predominantly dependent on its incorporation into the selenocysteine (Sec) for synthesis of selenoproteins (SePs), such as thioredoxin reductase family enzymes and glutathione peroxidase family enzymes. In general, the hyperactivity of the selenol group in Sec confers the Sec residue critical for functions of SePs. The Sec is much less abundant than its sulfur analog cysteine (Cys), and it remains a high challenge to detect Sec, especially in complex biological samples. We recently reported a selective fluorescent probe Sel-green for selenols and summarized the principles for design of selenol (and thiophenol) probes. Sel-green discriminates selenols from other biological species, especially thiols, under physiological conditions, and has been applied to detect both endogenous and exogenous selenol species in live cells. In this chapter, we describe a protocol and guideline for the selective detection of Sec by applying the Sel-green. This protocol is also suitable for detection of other selenol species. This practical and convenient assay would assist scientists to better understand the pivotal roles of Sec as well as SePs.

Selective selenol fluorescent probes: design, synthesis, structural determinants, and biological applications

J Am Chem Soc 2015 Jan 21;137(2):757-69.PMID:25562612DOI:10.1021/ja5099676.

Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo.