A fluorescent indicator for estimating intracellular pH
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BCECF AM

Item No. 15922

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3',6'-bis[(acetyloxy)methoxy]-5(or 6)-[[(acetyloxy)methoxy]carbonyl]-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-2',7'-dipropanoic acid, 2',7'-bis[(acetyloxy)methyl] ester
Synonyms
  • BCECF Acetoxymethyl ester
Molecular Formula
C42H40O21
Formula Weight
880.7
Purity
≥95%
Emission
535 nm
Excitation
440, 490 nm
Formulation (Request formulation change)
An oil
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleDMF: SolubleDMSO: Soluble
SMILES
O=C(C)OCOC1=C(CCC(OCOC(C)=O)=O)C=C(C2(C(C=CC(C(OCOC(C)=O)=O)=C3)=C3C(O2)=O)C(C(O4)=C5)=CC(CCC(OCOC(C)=O)=O)=C5OCOC(C)=O)C4=C1.O=C(C)OCOC6=C(CCC(OCOC(C)=O)=O)C=C(C7(C(C=C(C(OCOC(C)=O)=O)C=C8)=C8C(O7)=O)C(C(O9)=C%10)=CC(CCC(OCOC(C)=O)=O)=C%10OCOC(C)=O)C9=C6
InChi Code
InChI=1S/2C42H40O21/c1-22(43)52-17-57-34-15-36-32(13-27(34)7-10-38(48)59-19-54-24(3)45)42(31-9-6-29(12-30(31)41(51)63-42)40(50)61-21-56-26(5)47)33-14-28(8-11-39(49)60-20-55-25(4)46)35(16-37(33)62-36)58-18-53-23(2)44;1-22(43)52-17-57-34-15-36-32(12-27(34)7-10-38(48)59-19-54-24(3)45)42(31-14-29(6-9-30(31)41(51)63-42)40(50)61-21-56-26(5)47)33-13-28(8-11-39(49)60-20-55-25(4)46)35(16-37(33)62-36)58-18-53-23(2)44/h2*6,9,12-16H,7-8,10-11,17-21H2,1-5H3
InChi Key
JBGGWLORWOIHKM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $171

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    5 mg

    $810

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    Product Description

    BCECF AM ester is a widely-used fluorescent indicator for estimating intracellular pH.1,2 This membrane-permeant compound is modified by intracellular esterases to produce BCECF, a polar fluorescein derivative that is retained by cells. Intracellular BCECF is stable and has an efflux half-life of greater than two hours.3 Intracellular pH measurements are made by ratio imaging, which involves determining the pH-dependent ratio of emission intensity (detected at 535 nm) when the dye is excited at 490 nm vs. the emission intensity when excited at 440 nm.2,4 This approach is amenable to either spectrofluorometry or flow cytometry.2,5 BCECF AM can also be used to investigate intracellular changes in other ions, including potassium.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rink, T.J., Tsien, R.Y., and Pozzan, T. Cytoplasmic pH and free Mg2+ in lymphocytes. J. Cell Biol. 95(1), 189-196 (1982).

    2. Ozkan, P., and Mutharasan, R. A rapid method for measuring intracellular pH using BCECF-AM. Biochim. Biophys. Acta 1572(1), 143-148 (2002).

    3. Dive, C., Cox, H., Watson, J.V., et al. Polar fluorescein derivatives as improved substrate probes for flow cytoenzymological assay of cellular esterases. Mol.Cell Probe 2(2), 131-145 (1988).

    4. O'Connor, N., and Silver, R.B. Ratio imaging: Practical considerations for measuring intracellular Ca2+ and pH in living cells. Methods Cell Biol. 81, 415-433 (2007).

    5. Chow, S., Hedley, D., and Tannock, I. Flow cytometric calibration of intracellular pH measurements in viable cells using mixtures of weak acids and bases. Cytometry 24(4), 360-367 (1996).

    6. Balkay, L., Márián, T., Emri, M., et al. Flow cytometric determination of intracellular free potassium concentration. Cytometry 28(1), 42-49 (1997).