ChemicalBook CAS DataBase List 117464-70-7

117464-70-7

Name	BCECF-AM
CAS	117464-70-7
Molecular Formula	C42H40O21
MDL Number	MFCD00036969
Molecular Weight	880.75
MOL File	117464-70-7.mol

Synonyms

2,7-BIS(2-CARBOXYETHYL)-5,6-CARBOXYFLUORESCEIN 2',7'-BIS(2-CARBOXYETHYL)-5(6)-CARBOXYFLUORESCEIN ACETOXYMETHYL ESTER 2',7'-BIS-(2-CARBOXYETHYL)-5-(AND-6)-CARBOXYFLUORESCEIN, ACETOXYMETHYL ESTER 2',7'-BIS-(CARBOXYETHYL)-5(6')-CARBOXYFLUORESCEIN ACETOXYMETHYL ESTER BCECF-AM SPIRO(ISOBENZOFURAN-1(3H),9'-(9H)XANTHENE)-2',7'-DIPROPANOIC ACID 2',7'-bis(2-carboxyethyl)-5(6)-*carboxyfluorescei BCECF.AM ESTER, 1 MG/ML IN*ANHYDROUS DMSO Bcecf-AmSolution 2',7'-bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester mixed isomers bcecf-acetoxymethyl 2',7'-bis(2-carboxyethyl)-5(6)-carboxyfluorescein AM ester BCECF-AM solution, Spiro(isobenzofuran-1(3H),9μ-(9H)xanthene)-2μ,7μ-dipropanoic acid 2',7'-Bis(2-acetoxymethoxycarbonylethyl)-3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acid acetoxymethyl ester 2,7-Bis[2-(acetoxymethoxycarbonyl)ethyl]-3,6-dihydroxy-3'-oxospiro[9H-xanthene-9,1'(3'H)-isobenzofuran]-6'-carboxylic acid acetoxymethyl ester 2',7'-Biscarboxyethyl-6-carboxyfluorescein acetoxymethyl ester

Chemical Properties

Boiling point	692.41°C (rough estimate)
density	1.2837 (rough estimate)
refractive index	1.6500 (estimate)
Fp	85 °C
storage temp.	-20°C
solubility	acetonitrile: 25mg/mL DMF: soluble DMSO: soluble
form	White to off-white solid
color	Orange to red
Appearance	white powder
Major Application	diagnostic assay manufacturing hematology histology
InChIKey	NTECHUXHORNEGZ-UHFFFAOYSA-N
SMILES	CC(=O)OCOC(=O)CCc1cc2c(Oc3cc(OCOC(C)=O)c(CCC(=O)OCOC(C)=O)cc3C24OC(=O)c5cc(ccc45)C(=O)OCOC(C)=O)cc1OCOC(C)=O
CAS DataBase Reference	117464-70-7(CAS DataBase Reference)

Safety Data

Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S22:Do not breathe dust . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . less more
WGK Germany	3
Storage Class	10 - Combustible liquids

Hazard Information

Description

BCECF AM ester is a widely-used fluorescent indicator for estimating intracellular pH. 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. 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. This approach is amenable to either spectrofluorometry or flow cytometry. BCECF AM can also be used to investigate intracellular changes in other ions, including potassium.

Chemical Properties

pale yellow to yellow powder

Uses

Cell-permeable ester of BCECF that, on hydrolysis by cytosolic esterases, yields the intracellularly trapped pH-indicator BCECF. Allows simultaneous recording of cell volume changes and intracellular pH in single osteosarcoma cells.

General Description

Material is an isomeric mixture of lactones, acetates, and AM esters

Biological Activity

Non-charged, non-fluorescent pH indicator. Readily and rapidly diffuses through cell membranes.

References

[1] T J RINK T P R Y Tsien. Cytoplasmic pH and free Mg2+ in lymphocytes.[J]. Journal of Cell Biology, 1982, 95 1: 189-196. DOI: 10.1083/jcb.95.1.189
[2] PINAR OZKAN Raj M. A rapid method for measuring intracellular pH using BCECF-AM[J]. Biochimica et biophysica acta. General subjects, 2002, 1572 1: Pages 143-148. DOI: 10.1016/s0304-4165(02)00303-3
[3] CAROLINE DIVE. Polar fluorescein derivatives as improved substrate probes for flow cytoenzymological assay of cellular esterases[J]. Molecular and Cellular Probes, 1988, 2 2: Pages 131-145. DOI: 10.1016/0890-8508(88)90035-7
[4] NATHAN O’CONNOR Randi B S. Ratio imaging: practical considerations for measuring intracellular Ca2+ and pH in living cells.[J]. Methods in cell biology, 2013, 114: 387-406. DOI: 10.1016/b978-0-12-407761-4.00016-6
[5] SUE CHOW Ian T David Hedley. Flow cytometric calibration of intracellular pH measurements in viable cells using mixtures of weak acids and bases[J]. Cytometry Part B: Clinical Cytometry, 1996, 24 4: 360-367. DOI: 10.1002/(sici)1097-0320(19960801)24:4<360::aid-cyto7>3.0.co;2-j
[6] LáSZLó BALKAY. Flow cytometric determination of intracellular free potassium concentration[J]. Cytometry Part B: Clinical Cytometry, 1998, 28 1: 42-49. DOI: 10.1002/(sici)1097-0320(19970501)28:1<42::aid-cyto5>3.0.co;2-j

Abs/Em Maxima

440; 490/530 nm

Excitation / Emission Maximum

440-490 nm/535 nm

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