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29222

Sigma-Aldrich

Thio-H

Synonym(s):

2-Amino-5-(5-phenyl-2-thienyl)phenol-N,N,O-triacetic acid tricesium salt

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About This Item

Empirical Formula (Hill Notation):
C22H16Cs3NO7S
Molecular Weight:
837.15
Beilstein/REAXYS Number:
9244017
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:

form

solid

fluorescence

λex 332 nm; λem 500 nm in 0.1 M Tris pH 8.0, 10 mM Ca2+

SMILES string

[Cs+].[Cs+].[Cs+].[O-]C(=O)COc1cc(ccc1N(CC([O-])=O)CC([O-])=O)-c2ccc(s2)-c3ccccc3

InChI

1S/C22H19NO7S.3Cs/c24-20(25)11-23(12-21(26)27)16-7-6-15(10-17(16)30-13-22(28)29)19-9-8-18(31-19)14-4-2-1-3-5-14;;;/h1-10H,11-13H2,(H,24,25)(H,26,27)(H,28,29);;;/q;3*+1/p-3

InChI key

GBQDXALAYDCKJB-UHFFFAOYSA-K

Features and Benefits

This is a new Calcium indicator with promising properties which provide an excellent addition to fluorescent Ca2+/Mg2+ indicators available already. It is a low-affinity Ca2+-indicators (Kd ca 55 μM). Such indicators are useful for determination of Ca2+ in intracellular compartments [or for monitoring steep increases in intracellular concentration of Ca2+ .
Compared to wellknown low-affinity Ca2+ indicators Thio-H is about three times brighter. This is based on strong molar absorption as well as high quantum yields. High fluorescent output allows low indicator concentrations to be used, which decreases the cation buffering effects of indicator. The indicator offers the interesting property of being both excitation and emission rationable, thus ratiomeric measurements are possible both in excitations as emission mode. Further spectroscopic data (0.1 M Tris, pH 8.0): low [Ca2+], Exc.max. 362 nm, Em.max. 500 nm; high [Ca2+], Exc.max. 332 nm, Em.max. 500 nm

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Intracellular, ratiomeric, fluorescent Ca2+/Mg2+ indicator with high brightness[1]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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E. Cielen et al. (N. Boens)
J. Chem. Soc. Perkin Trans. II, 1197-1197 (2002)

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