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Merck
CN

C3411

Sigma-Aldrich

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

≥90% (HPLC), Fluorescent indicator, powder

Synonym(s):

BCECF

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About This Item

Empirical Formula (Hill Notation):
C27H20O11
CAS Number:
85138-49-4
Molecular Weight:
520.44
Beilstein:
8375770
MDL number:
MFCD00036970
UNSPSC Code:
12352200
PubChem Substance ID:
24892612
NACRES:
NA.32

Key Documents

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Product Name

2′,7′-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein, ≥90% (HPLC)

Quality Level

100

Assay

≥90% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

OC(=O)CCc1cc2c(OC3=CC(=O)C(CCC(O)=O)=CC3=C2c4cc(ccc4C(O)=O)C(O)=O)cc1O

InChI

1S/C27H20O11/c28-19-10-21-17(7-12(19)2-5-23(30)31)25(16-9-14(26(34)35)1-4-15(16)27(36)37)18-8-13(3-6-24(32)33)20(29)11-22(18)38-21/h1,4,7-11,28H,2-3,5-6H2,(H,30,31)(H,32,33)(H,34,35)(H,36,37)

InChI key

DKROGDOAOXDINY-UHFFFAOYSA-N

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Application

2′,7′-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein has been used in a fluorescence-based screening assay, to determine the pH.

Biochem/physiol Actions

2′,7′-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein (BCECF) is useful to study multidrug resistance-associated protein (MRP) transporter action within the cell. BCECF is known to interfere with drug efflux interactions.
Fluorescent indicator for measurement of cytoplasmic pH in lymphocytes.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ5798
MKCZ5799
MKCW7045
MKCV6168
MKCV8221

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Adelaide S M Dennis et al.
Scientific reports, 8(1), 8795-8795 (2018-06-13)
Four hundred structurally diverse drug-like compounds comprising the Medicines for Malaria Venture's 'Pathogen Box' were screened for their effect on a range of physiological parameters in asexual blood-stage malaria (Plasmodium falciparum) parasites. Eleven of these compounds were found to perturb
Alexander A Tokmakov et al.
Biochemical and biophysical research communications, 517(1), 140-145 (2019-07-20)
Mitogen-activated protein kinases (MAPKs) are involved in the regulation of various cellular processes, including cell survival and apoptosis. Here, we report that Xenopus p42 MAPK becomes phosphorylated in apoptotic eggs, however this modification does not activate the enzyme. Using phosphorylation
High-throughput workflow for monitoring and mining bioprocess data: Application to infer E. coli physiological response to perturbations.
Heux S, et al.
Applied and Environmental Microbiology, AEM-05838 (2011)
Patrick Hofmann et al.
Cardiovascular research, 115(1), 230-242 (2018-08-15)
Long non-coding RNAs (lncRNAs) have been shown to regulate numerous processes in the human genome, but the function of these transcripts in vascular aging is largely unknown. We aim to characterize the expression of lncRNAs in endothelial aging and analyse
Corbin J Bachmeier et al.
Journal of pharmaceutical sciences, 93(4), 932-942 (2004-03-05)
2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein (BCECF) is a fluorescent probe used to examine multidrug resistance-associated protein (MRP) transporter activity in cells. BCECF is introduced into the cell as the nonfluorescent membrane permeable acetoxymethyl ester, BCECF-AM, where it is hydrolyzed to the membrane impermeable BCECF.
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