Chemodex

Fluorescein-5-thiosemicarbazide

Product Code:
 
CDX-F0005
Product Group:
 
Dyes, Stains, and Probes
Supplier:
 
Chemodex
Regulatory Status:
 
RUO
Shipping:
 
Ambient
Storage:
 
-20 °C
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Chemical Structure
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Chemical Structure

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CodeSizePrice
CDX-F0005-M05050 mg£126.00
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CDX-F0005-M100100 mg£218.00
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CDX-F0005-M500500 mg£863.00
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This product comes from: Switzerland.
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Further Information

Alternate Names/Synonyms:
5-FTSC; FTSC, FTZ; N-(3',6'-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)-hydrazinecarbothioamide
Appearance:
Orange to brown powder.
CAS:
76863-28-0
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Protect from light and moisture.
InChi:
InChI=1S/C21H15N3O5S/c22-24-20(30)23-10-1-4-14-13(7-10)19(27)29-21(14)15-5-2-11(25)8-17(15)28-18-9-12(26)3-6-16(18)21/h1-9,25-26H,22H2,(H2,23,24,30)
InChiKey:
OIMMDIXLTJAVTF-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 76863-28-0. Formula: C21H15N3O5S. MW: 421.43. Synthetic. Labeling of cell-surface functional groups (glycophorins). Detection of protein carbonyls in aging tissues.
MDL:
MFCD04221432
Molecular Formula:
C21H15N3O5S
Molecular Weight:
421.43
Package Type:
Vial
Product Description:
Hydrazide derivative of fluorescein. An amine-containing cell impermeant fluorescent probe that can be reversibly coupled to aldehydes and ketones on diverse molecules. This forms a Schiff base - which can be further reduced to generate stable amine derivatives by treatment with reducing agents such as sodium borohydride (NaBH4) or sodium cyanoborohydride (NaCNH3). Carboxylic acids of proteins and other water-soluble biopolymers can also be coupled to this fluorescein derivative in aqueous solution using water-soluble carbodiimides such as EDAC. Fluorescent tag for labeling of cell-surface functional groups (glycophorins) and many other diverse molecules, including DNA, RNA, polysaccharides, sialylated glycoproteins, carbonylated proteins, carbonyl derivatives, and N-acetylneuraminic acid. Useful for determining protein and peptide topology on the cell surface. This probe has been used for directly imaging of mucin-type O-linked glycoproteins within living cells, for imaging polysaccharides transported in living cells and for fluorescence labeling of short RNA by oxidation at the 3?-End. Spectral data: lambdaex=492nm; lambdaem=516nm (in 0.1 M Tris pH9.0).
Purity:
>97% (NMR)
SMILES:
NNC(=S)NC1=CC2=C(C=C1)C1(OC2=O)C2=C(OC3=C1C=CC(O)=C3)C=C(O)C=C2
Solubility Chemicals:
Soluble in water or DMF.
Source / Host:
Synthetic.
Transportation:
Non-hazardous
UNSPSC Category:
Fluorescent Reagents
UNSPSC Number:
41105331
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

(1) D.H. Atha, et al.; Biochim. Biophys. Acta 785, 1 (1984) | (2) B. Ahn, et al.; Anal. Biochem. 161, 245 (1987) | (3) W.A. Duijndam, et al.; J. Immunol. Methods 109, 289 (1988) | (4) J.D. Corbett, et al.; Biophys. J. 66, 25 (1994) | (5) T.P. Wu, et al.; Nucleic Acids Res. 24, 3472 (1996) | (6) X. Gao, et al.; Bioorg. Chem. 25, 163 (1997) | (7) N. Tamilarasu, et al.; Bioconjug. Chem. 12, 135 (2001) | (8) A.R. Chauduri, et al.; Mech. Ageing Developm. 127, 849 (2006) | (9) Y. Zhang, et al.; Carbohydr. Res. 346, 2156 (2011) | (10) Y. Zhang, et al.; Glycoconj. J. 29, 445 (2012) | (11) Y. Zhang, et al.; Eurp. Food. Res. Technol. 239, 867 (2014) | (12) M. Have, et al.; Plant Biol. 17, 973 (2015) | (13) C. Qiu, et al.; Methods Mol. Biol. 1297, 113 (2015) | (14) R.W. Sabnis; Handbook of Fluorescent Dyes and Probes p224 (2015) | Oral absorption characteristics and mechanisms of a pectin-type polysaccharide from Smilax china L. across the intestinal epithelium: Y. Zhang, et al.; Carbohydr. Polym. 270, 118383 (2021)