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

Name: 5(6)-Carboxy-2′,7′-dichlorofluorescein
Brand: SIGMA
Price: 213 USD
Availability: InStock

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

NACRES:

NA.32

PubChem Substance ID:

57647948

UNSPSC Code:

12352108

MDL number:

MFCD00037452

Key Documents

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Product Name

5(6)-Carboxy-2′,7′-dichlorofluorescein, BioReagent, suitable for fluorescence, ≥95% (TLC)

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)

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 key

WHFHRELKGQJJBQ-UHFFFAOYSA-N

product line

BioReagent

assay

≥95% (TLC)

form

solid

pKa

5.1

mp

≥250 °C (lit.)

solubility

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

fluorescence

λ_ex 504 nm; λ_em 529 nm in 0.1 M Tris pH 8.0

suitability

suitable for fluorescence

Quality Level

100

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Show Differences

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This Item	46935	70420	14562
Sigma-Aldrich 21882 5(6)-Carboxy-2′,7′-dichlorofluorescein	Sigma-Aldrich 46935 6-[Fluorescein-5(6)-carboxamido]hexanoic acid	Sigma-Aldrich 70420 Naphthofluorescein	Sigma-Aldrich 14562 2′,7′-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein tetrakis(acetoxymethyl) ester
suitability suitable for fluorescence	suitability suitable for fluorescence	suitability suitable for fluorescence	suitability -
fluorescence λ_ex 504 nm; λ_em 529 nm in 0.1 M Tris pH 8.0	fluorescence λ_ex 491 nm; λ_em 515 nm in 0.1 M Tris pH 9.0	fluorescence λ_ex 594 nm; λ_em 663 nm in 0.1 M Tris pH 9.0	fluorescence λ_ex 482 nm; λ_em 528 nm in 0.1 M Tris pH 8.0 (esterase)
form solid	form solid	form powder	form solid
solubility DMF: soluble, H₂O: soluble (pH ≥ 5), DMSO: soluble	solubility DMF: soluble, DMSO: soluble	solubility DMF: soluble, DMSO: soluble, H₂O: soluble (pH ≥ 8)	solubility DMF: soluble, DMSO: soluble, acetonitrile: soluble
Quality Level 100	Quality Level 200	Quality Level 100	Quality Level 100
assay ≥95% (TLC)	assay ≥90% (HPCE)	assay -	assay -

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[1]

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - 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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Development of a fluorescence-based assay for drug interactions with human Multidrug Resistance Related Protein (MRP2; ABCC2) in MDCKII-MRP2 membrane vesicles.

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

Effluxing ABC transporters in human corneal epithelium.

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)

Drug transporter expression in human macrophages.

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

Kinetic validation of the use of carboxydichlorofluorescein as a drug surrogate for MRP5-mediated transport.

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

Non-destructive micromethod for MRP1 functional assay in human lung tumor cells.

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

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