A cell-permeable, low affinity fluorescent calcium indicator
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Fura-FF AM

Item No. 20416

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[6-[bis[2-[(acetyloxy)methoxy]-2-oxoethyl]amino]-5-[2-[6-[bis[2-[(acetyloxy)methoxy]-2-oxoethyl]amino]-2,3-difluorophenoxy]ethoxy]-2-benzofuranyl]-5-oxazolecarboxylic acid(acetyloxy)methyl ester
CAS Number
348079-12-9
Synonyms
  • Fura-FF Acetoxymethyl ester
Molecular Formula
C43H43F2N3O24
Formula Weight
1023.8
Purity
≥90%
Emission
514 nm (no Ca2+), 507 nm (high [Ca2+])
Excitation
365 nm (no Ca2+), 339 nm (high [Ca2+])
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=C(OCOC(C)=O)CN(C1=CC2=C(C=C(C3=NC=C(C(OCOC(C)=O)=O)O3)O2)C=C1OCCOC(C(F)=C(F)C=C4)=C4N(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O
InChi Code
InChI=1S/C43H43F2N3O24/c1-23(49)61-18-66-36(54)14-47(15-37(55)67-19-62-24(2)50)30-7-6-29(44)40(45)41(30)60-9-8-59-33-10-28-11-34(42-46-13-35(72-42)43(58)70-22-65-27(5)53)71-32(28)12-31(33)48(16-38(56)68-20-63-25(3)51)17-39(57)69-21-64-26(4)52/h6-7,10
InChi Key
FPUWXSBNYDMTRN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 µg

    $70

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    Product Description

    Fura-FF AM is a cell-permeable acetoxymethyl ester of the fluorescence calcium indicator fura-FF (potassium salt) (Item No. 20415). As fura-FF AM enters cells, it is hydrolyzed by intracellular esterases to produce fura-FF. Fura-FF is a difluorinated derivative of the calcium indicator fura-2 (Item Nos. 19531 | 20414). Unlike, fura-2, fura-FF has negligible magnesium sensitivity, thus reducing interference from this cation.1 Fura-FF also has a higher calcium dissociation constant than fura-2 (Kd(calcium) = 6 and 0.14 µM, respectively).1,2 However, the spectral properties of fura-FF and fura-2 are similar with fura-FF displaying excitation/emission spectra of 365/514 nm in the absence of calcium, with a shift to 339/507 nm in the presence of a high calcium concentration.3 Low affinity calcium dyes, including fura-FF, are preferred for studying compartments with high concentrations of calcium, such as mitochondria, or in cell systems that have relatively low calcium buffering capacities, such as neuronal dendrites and spines.4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hyrc, K.L., Bownik, J.M., and Goldberg, M.P. Ionic selectivity of low-affinity ratiometric calcium indicators: mag-Fura-2, Fura-2FF and BTC. Cell Calcium 27(2), 75-86 (2000).

    2. Grynkiewicz, G., Poenie, M., and Tsien, R.Y. A new generation of Ca2+ indicators with greatly improved fluorescence properties. The Journal of Biological Chemisty 260(6), 3440-3450 (1985).

    3. Ruggiu, A.A., Bannwarth, M., and Johnsson, K. Fura-2FF-based calcium indicator for protein labeling. Org. Biomol. Chem. 8(15), 3398-3401 (2010).

    4. Aponte, Y., Bischofberger, J., and Jonas, P. Efficient Ca2+ buffering in fast-spiking basket cells of rat hippocampus. J. Physiol. 586(8), 2061-2075 (2008).

    5. Canepari, M., Vogt, K., and Zecevic, D. Combining voltage and calcium imaging from neuronal dendrites. Cell. Mol. Neurobiol. 28(8), 1079-1093 (2008).

    6. Marcu, R., Neely, C.K., Karamanlidis, G., et al. Multi-parameter measurement of the permeability transition pore opening in isolated mouse heart mitochondria. J. Vis. Exp. 67:4131, (2012).