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47989

Fura 2-AM

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

Synonym(s):

Fura-2 pentakis(acetoxymethyl) ester

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About This Item

Empirical Formula (Hill Notation):
C44H47N3O24
CAS Number:
108964-32-5
Molecular Weight:
1001.85
UNSPSC Code:
12171500
NACRES:
NA.32
PubChem Substance ID:
57651141
MDL number:
MFCD00036976
Beilstein/REAXYS Number:
8183748
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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

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

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8456
BCCJ0580
BCCF8185
BCCC0317
BCBV9098

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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
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)
Rubin Gulaboski et al.
Cell calcium, 43(6), 615-621 (2007-11-16)
Fura-2 is one of the most commonly used fluorescent dyes to analyze the cytosolic Ca(2+) concentration ([Ca(2+)](i)) of living cells. Fura-2-dependent measurements of [Ca(2+)](i) are susceptible to changes of pH, reactive oxygen species concentration and membrane potential. Fura-2 is often
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