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Merck
CN

21882

5(6)-Carboxy-2′,7′-dichlorofluorescein

BioReagent, suitable for fluorescence, ≥95% (TLC)

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About This Item

Empirical Formula (Hill Notation):
C21H10Cl2O7
CAS Number:
111843-78-8
Molecular Weight:
445.21
MDL number:
MFCD00037452
UNSPSC Code:
12352108
PubChem Substance ID:
57647948
NACRES:
NA.32

Key Documents

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product line

BioReagent

Quality Level

100

Assay

≥95% (TLC)

form

solid

pKa 

5.1

mp

≥250 °C (lit.)

solubility

DMF: soluble
DMSO: soluble
H2O: soluble (pH ≥ 5)

fluorescence

λex 504 nm; λem 529 nm in 0.1 M Tris pH 8.0

suitability

suitable for fluorescence

SMILES string

OC(=O)c1ccc(c(c1)C(O)=O)C2=C3C=C(Cl)C(=O)C=C3Oc4cc(O)c(Cl)cc24.OC(=O)c5ccc(C(O)=O)c(c5)C6=C7C=C(Cl)C(=O)C=C7Oc8cc(O)c(Cl)cc68

InChI

1S/2C21H10Cl2O7/c22-13-4-11-17(6-15(13)24)30-18-7-16(25)14(23)5-12(18)19(11)10-3-8(20(26)27)1-2-9(10)21(28)29;22-13-4-11-17(6-15(13)24)30-18-7-16(25)14(23)5-12(18)19(11)9-2-1-8(20(26)27)3-10(9)21(28)29/h2*1-7,24H,(H,26,27)(H,28,29)

InChI key

WHFHRELKGQJJBQ-UHFFFAOYSA-N

Application

5(6)-Carboxy-2′,7′-dichlorofluorescein may be used as a specific substrate/probe to study the identity, activity and specificity of multidrug resistance protein 2 (MRP2) molecules.
suitable as pH-indicator

Other Notes

Fluorescent intracellular pH indicator in the pH 4-5 range

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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
BCCM0665
BCCD8352
BCCB9166
BCBV0154
BCBQ2931V

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Kati-Sisko Vellonen et al.
Journal of pharmaceutical sciences, 99(2), 1087-1098 (2009-07-23)
ATP-binding cassette (ABC) transporters are able to efflux their substrate drugs from the cells. We compared expression of efflux proteins in normal human corneal epithelial tissue, primary human corneal epithelial cells (HCEpiC), and corneal epithelial cell culture model (HCE model)
Christian Lechner et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 75(2), 284-290 (2010-03-24)
To establish a fluorescence-based assay for drug interactions with the ABC-export-protein MRP2 (ABCC2). Apical membrane vesicles were isolated by differential centrifugation from polarized MDCKII cells and MDCKII cells transfected with human MRP2. Vesicle fractions were characterized by electron microscopy, determination
Amélie Moreau et al.
Fundamental & clinical pharmacology, 25(6), 743-752 (2011-01-08)
Macrophages represent major cellular targets of various drugs, especially antibiotics and anti-viral drugs. Factors that may govern intracellular accumulation of drugs in these cells, especially those related to activity of drug transporters, are consequently likely important to consider. The present
Phyllanthin and hypophyllanthin inhibit function of P-gp but not MRP2 in Caco-2 cells.
Sukhaphirom N, Vardhanabhuti N, et al.
J. Pharm. Pharm. Sci., 65, 292-299 (2013)
M Nedergaard et al.
Analytical biochemistry, 187(1), 109-114 (1990-05-15)
Derivatives of fluorescein sensitive to pH are extensively utilized for the determination of intracellular pH (pHi). Available dyes have pKa values of approximately 7.0, and are not well suited for measuring acidic pHi. We examined the fluorescein derivative, 5 (and
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