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Sigma-Aldrich

2′,7′-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein tetrakis(acetoxymethyl) ester

BioReagent, for fluorescence

Synonym(s):

BCECF-AM

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About This Item

Empirical Formula (Hill Notation):
C39H36O19
Molecular Weight:
808.69
MDL number:
MFCD01862636
UNSPSC Code:
12352108
NACRES:
NA.32

grade

for fluorescence

Quality Level

100

product line

BioReagent

form

solid

solubility

DMF: soluble
DMSO: soluble
acetonitrile: soluble

fluorescence

λex 482 nm; λem 528 nm in 0.1 M Tris pH 8.0 (esterase)

storage temp.

2-8°C

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Application

An uncharged, nonfluorescent molecule that is useful for noninvasive bulk loading of cell suspension because it is capable of permeating the cell membrane. Cellular nonspecific esterases cleave its lipophilic blocking groups, resulting in a charged, fluorescent form of the molecule. Compared to the parent compound, this charged derivative leaks out of the cell at a much slower rate. Utilized for pH measurements in perfused tissues, intercellular spaces, mammalian cells, plant cells, bacteria, and yeast. Also, employed to investigate in assays for cellular functional properties such as adhesion, multi-drug resistance, viability and cytotoxicity, apoptosis and chemotaxis.
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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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R S Haworth et al.
Biochimica et biophysica acta, 1098(1), 79-89 (1991-12-13)
We have tested the efficacy of fluorescent probes for the measurement of intracellular pH in Saccharomyces cerevisiae. Of the compounds tested (fluorescein, carboxyseminaphthorhodafluor-1 (C.SNARF-1) and 2',7'bis(carboxyethyl)-5(6')-carboxyfluorescein), C.SNARF-1 was found to be the most useful indicator of internal pH. Fluorescence microscopy
M T Alonso et al.
The Biochemical journal, 272(2), 435-443 (1990-12-01)
The effects of arachidonic acid and thrombin on calcium movements have been studied in fura-2-loaded platelets by a procedure which allows simultaneous monitoring of the uptake of manganese, a calcium surrogate for Ca2+ channels, and the release of Ca2+ from
P J Harris et al.
The American journal of physiology, 266(1 Pt 1), C73-C80 (1994-01-01)
The lateral intercellular spaces (LIS) of reabsorptive epithelia are the site of the proposed local osmotic gradient responsible for transepithelial transport. We developed techniques for loading the LIS of living cultured renal cells (MDCK and LLC-PK1) with the fluorescent dye
H W van Veen et al.
The Journal of biological chemistry, 269(47), 29509-29514 (1994-11-25)
The strictly aerobic, polyphosphate-accumulating Acinetobacter johnsonii strain 210A degrades its polyphosphate when oxidative phosphorylation is impaired. The endproducts of this degradation, divalent metal ions and inorganic phosphate, are excreted as a neutral metal-phosphate (MeHPO4) chelate via the electrogenic MeHPO4/H+ symport
I D Weiner et al.
The American journal of physiology, 256(5 Pt 2), F957-F964 (1989-05-01)
The compound 2'-7'-bis(carboxyethyl)-5(6)-carboxyfluorescein (BCECF) is being extensively used to measure intracellular pH (pHi) in a variety of tissue preparations. Use of this dye in the isolated perfused rabbit cortical collecting tubule (CCT) revealed two previously unreported findings. Apical incubation via
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