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Sigma-Aldrich

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:
Molecular Weight:
445.21
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Quality Level

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

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

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L Payen et al.
Biochemical pharmacology, 60(12), 1967-1975 (2000-12-08)
Organic anion secretion by human hepatocytes was characterized using primary liver parenchymal cell cultures and the anionic fluorescent dye carboxy-2',7'-dichlorofluorescein (CF). Probenecid, a well-known common blocker of the membrane transport process for anions, was shown to increase CF accumulation in
Sanna Siissalo et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 71(2), 332-338 (2008-09-09)
The aim of this work was to develop a screening method for MRP2 efflux substrates using the well-characterized, human-based intestinal Caco-2 cell model as a platform. MRP2 has a significant role in drug absorption and disposition and is known to
B Laupèze et al.
Life sciences, 68(11), 1323-1331 (2001-03-10)
Multidrug resistance proteins (MRPs) such as MRP1, MRP2 and MRP3 are membrane efflux pumps involved in multidrug resistance and handling organic anions. In the present study, MRP activity was investigated in normal mature leucocytes and CD34-positive hematopoietic cells from peripheral
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
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)

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