21882

Sigma-Aldrich

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

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

Empirical Formula (Hill Notation):
C21H10Cl2O7
CAS Number:
Molecular Weight:
445.21
MDL number:
PubChem Substance ID:

Quality Level

product line

BioReagent

assay

≥95% (TLC)

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

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Susan Pratt et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 27(5), 524-532 (2005-12-13)
Multidrug resistance protein-5 (MRP5, ABCC5) is a member of the ATP-binding cassette transporter superfamily that effluxes a broad range of natural and xenobiotic compounds such as cyclic GMP, antiviral compounds, and cancer chemotherapeutic agents including nucleoside-based drugs, antifolate agents and...
Ekkehard Stehfest et al.
Archives of toxicology, 80(3), 125-133 (2005-12-24)
Defense against toxic endo- and xenobiotics is a major concern of all living species and ABC transporters play a vital role in this defense system. Multidrug resistance associated proteins 1 (MRP1) is a cellular detoxifying factor supposed to transport a...
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...
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...
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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