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47989

Sigma-Aldrich

Fura 2-AM

BioReagent, suitable for fluorescence, ≥95.0% (HPLC)

Sinónimos:

Fura-2 pentakis(acetoxymethyl) ester

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About This Item

Fórmula empírica (notación de Hill):
C44H47N3O24
Número de CAS:
108964-32-5
Peso molecular:
1001.85
Beilstein/REAXYS Number:
8183748
MDL number:
MFCD00036976
UNSPSC Code:
12171500
PubChem Substance ID:
57651141
NACRES:
NA.32

product line

BioReagent

Quality Level

100

assay

≥95.0% (HPLC)

form

solid

solubility

DMSO: soluble

fluorescence

λex 355 nm; λem 495 nm in 0.1 M Tris pH 8.0, esterase; 10 mM Ca2+

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)c1ccc(C)cc1OCCOc2cc3cc(oc3cc2N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O)-c4ncc(o4)C(=O)OCOC(C)=O

InChI

1S/C44H47N3O24/c1-25-7-8-32(46(16-39(53)65-20-60-26(2)48)17-40(54)66-21-61-27(3)49)35(11-25)58-9-10-59-36-12-31-13-37(43-45-15-38(71-43)44(57)69-24-64-30(6)52)70-34(31)14-33(36)47(18-41(55)67-22-62-28(4)50)19-42(56)68-23-63-29(5)51/h7-8,11-15H,9-10,16-24H2,1-6H3

InChI key

VPSRLGDRGCKUTK-UHFFFAOYSA-N

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General description

Fura 2-AM (Fura 2), also known as acetoxy-methyl-ester, is a calcium-specific ratio-metric fluorescent dye. In response to calcium ions, ratio metric dyes like Fura 2 changes their respective excitation or emission spectra. The intracellular calcium concentration is determined by the fluorescence emission ratio or excitation at distinct wavelengths. Fura 2 has an emission peak at 505nm, and the excitation peak ranges between 340-380nm and is the preferred calcium indicator.

Application

Fura 2-AM is a popular probe used to determine dynamic changes in cytosolic free calcium in intact living cells.

Features and Benefits

The major benefits of using the ester form of Fura 2 as Fura 2-AM are:

  • It is cell-permeable.
  • It can be loaded into cells easily.
Other advantages of using Fura 2-AM over single wavelength dyes is that the ratio signal is independent of :
  • The dye concentration.
  • Illumination intensity, and
  • Optical path length.

Other Notes

Membrane-permeable derivative of Fura-2. Used to load the chelator into cells. Hydrolysed enzymatically in the cell to yield Fura-2 which remains within the cell

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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M Poenie et al.
Nature, 315(6015), 147-149 (1985-05-09)
Although the regulation of events in the cell division cycle by calcium or other cations has been the subject of much interest and speculation, experimental studies have been hampered by the difficulty of measuring submicromolar intracellular free calcium concentrations ([Ca2+]i)
The use of microinjection and video microscopy for the study of calmodulin and calcium in living cells.
M Shelanski et al.
Methods in enzymology, 139, 824-834 (1987-01-01)
W Almers et al.
FEBS letters, 192(1), 13-18 (1985-11-11)
The Ca concentration ([Ca2+]i) in single rat peritoneal mast cells was measured by means of the new fluorescent Ca-indicator dye fura-2. Dye-loaded cells were made to degranulate with either antigen or compound 48/80. In cells loaded with extracellularly applied, membrane-permeant
Robin R Hodges et al.
Experimental eye research, 103, 99-113 (2012-09-15)
The purpose of this study was to identify the signaling pathways that epidermal growth factor (EGF) uses to stimulate mucin secretion from cultured rat conjunctival goblet cells and to compare the pathways used by EGF with those used by the
G Grynkiewicz et al.
The Journal of biological chemistry, 260(6), 3440-3450 (1985-03-25)
A new family of highly fluorescent indicators has been synthesized for biochemical studies of the physiological role of cytosolic free Ca2+. The compounds combine an 8-coordinate tetracarboxylate chelating site with stilbene chromophores. Incorporation of the ethylenic linkage of the stilbene
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