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Merck
CN

C8427

2′,7′-bis(2-Carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester Mixed isomers

Synonym(s):

BCECF-acetoxymethyl

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About This Item

UNSPSC Code:
12352200
PubChem Substance ID:
329775170
MDL number:
MFCD00036969

Key Documents

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InChI

1S/C42H40O21/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/h6,9,12-16H,7-8,10-11,17-21H2,1-5H3

SMILES string

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

InChI key

NTECHUXHORNEGZ-UHFFFAOYSA-N

form

solid

storage temp.

−20°C

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General description

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

Other Notes

Membrane-permeable fluorescent probe for cytoplasmic pH.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCC9719
MKBS0655V
MKBP7697V
SLBG6214V
SLBG3641V

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Sen Xu et al.
Analytical chemistry, 83(4), 1480-1483 (2011-01-20)
Detection of viable pathogenic bacteria has widespread application in food safety and human health. Antibody-based methods require a growth step which limits time-to-results performance. In this study, we use a mass-change sensitive cantilever biosensor and a probe, 2',7'-bis-(2-carboxyethyl)-5-(and-6)-carboxyfluorescein acetoxymethyl ester
Wen Liu et al.
American journal of physiology. Renal physiology, 302(1), F205-F215 (2011-10-01)
Epithelial Na(+) channel (ENaC)-mediated Na(+) absorption and BK channel-mediated K(+) secretion in the cortical collecting duct (CCD) are modulated by flow, the latter requiring an increase in intracellular Ca(2+) concentration ([Ca(2+)](i)), microtubule integrity, and exocytic insertion of preformed channels into
Christoph Elsing et al.
Anticancer research, 31(2), 459-465 (2011-03-08)
In cholangiocarcinogenesis, chronic inflammation and oxidative stress play a key role. The Na(+)/H(+) exchanger (NHE) forms a potential link between control of intra- and pericellular pH and tumor development. Therefore, the effects of oxidant stress were determined by the use
Corbin J Bachmeier et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(6), 998-1003 (2006-03-24)
The present study quantitatively compared the drug efflux transport kinetics of 2',7'-bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester (BCECF-AM) and its fluorescent metabolite 2',7'-bis(2-carboxyethyl)-5(6)-carboxyfluorescein (BCECF) in various blood-brain barrier (BBB) models. BCECF-AM was exposed to freshly isolated bovine brain microvessels (BBM), primary cultured bovine
Scott K Parks et al.
American journal of physiology. Cell physiology, 292(2), C935-C944 (2006-09-29)
Isolated mitochondria-rich (MR) cells from the rainbow trout gill epithelium were subjected to intracellular pH (pH(i)) imaging with the pH-sensitive dye BCECF-AM. MR cells were categorized into two distinct functional subtypes based on their ability to recover pH(i) from an
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