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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

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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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Carmen Vale-González et al.
Journal of neuroscience research, 85(1), 90-98 (2006-11-01)
Palytoxin (PTX) is a potent marine phycotoxin that binds to the Na,K-ATPase, converting this pump into an open channel. We have recently shown (Vale et al., 2006) that PTX causes an irreversible increase in the cytosolic calcium concentration ([Ca(2+)](c)) in
Arno Hueber et al.
Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie, 243(9), 942-946 (2005-04-19)
This study was performed to evaluate the safety and efficacy of photodynamic therapy with the carboxyfluorescein ester BCECF-AM as an adjunctive treatment procedure for pterygium surgery to reduce the rate of recurrence. In this nonrandomized prospective clinical trial, 19 eyes
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
Clark Undem et al.
PloS one, 7(9), e46303-e46303 (2012-10-03)
Excessive production of endothelin-1 (ET-1), a potent vasoconstrictor, occurs with several forms of pulmonary hypertension. In addition to modulating vasomotor tone, ET-1 can potentiate pulmonary arterial smooth muscle cell (PASMC) growth and migration, both of which contribute to the vascular
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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