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21877

Sigma-Aldrich

5(6)-Carboxyfluorescein

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

Synonyme(s) :

5(6)-FAM, 5,6-CF

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About This Item

Formule empirique (notation de Hill):
C21H12O7
Numéro CAS:
72088-94-9
Poids moléculaire :
376.32
Numéro CE :
276-331-1
Numéro MDL:
MFCD00151081
Code UNSPSC :
12171500
ID de substance PubChem :
329752213
Nomenclature NACRES :
NA.32

Gamme de produits

BioReagent

Niveau de qualité

200

Pureté

≥95% (HPLC)

Forme

powder

Pf

275 °C (dec.) (lit.)

Fluorescence

λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0

Adéquation

suitable for fluorescence

Chaîne SMILES 

OC(=O)c1ccc2c(c1)C(=O)OC23c4ccc(O)cc4Oc5cc(O)ccc35.OC(=O)c6ccc7C(=O)OC8(c9ccc(O)cc9Oc%10cc(O)ccc8%10)c7c6

InChI

1S/2C21H12O7/c22-11-2-5-15-17(8-11)27-18-9-12(23)3-6-16(18)21(15)14-4-1-10(19(24)25)7-13(14)20(26)28-21;22-11-2-5-14-17(8-11)27-18-9-12(23)3-6-15(18)21(14)16-7-10(19(24)25)1-4-13(16)20(26)28-21/h2*1-9,22-23H,(H,24,25)

Clé InChI

BPVHBBXCESDRKW-UHFFFAOYSA-N

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Catégories apparentées

Description générale

5(6)-Carboxyfluorescein, also known as 5(6)-FAM, is a fluorescent tracer and available as a mixture of 5-Carboxyfluorescein and 6-Carboxyfluorescein isomers. The fluorescence of 5(6)-Carboxyfluorescein is determined by the xanthene moiety. 5(6)-Carboxyfluorescein has two characteristic properties:
  • It has 2 wavelengths for maximum absorbance (465 and 490nm).
  • And its fluorescence emission, at 515nm(max.), increases as a function of pH in the physiological range of 6-7.4.

Application

5(6)-Carboxyfluorescein is used to characterize tumor cells and normal cells in vivo. It labels proteins derived through N-hydroxysuccinimide (NHS) ester-mediated derivatization. 5(6)-Carboxyfluorescein is suitable for detecting cell viability while developing an in vitro anthelmintic drug assay.

Autres remarques

A probe of intracellular pH

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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M L Graber et al.
Analytical biochemistry, 156(1), 202-212 (1986-07-01)
We evaluated four different fluoroprobes to determine their capabilities and limitations in measuring intracellular pH by the fluorescent indicator technique. In vitro, carboxyfluorescein, dimethylcarboxyfluorescein, biscarboxyethyl carboxyfluorescein, and 4-methylumbelliferone (4MU) all showed comparably intense fluorescence and excellent pH sensitivity near their
S Mordon et al.
Journal of photochemistry and photobiology. B, Biology, 13(3-4), 307-314 (1992-05-15)
The pH of the interstitial fluid of malignant tumours tends to be lower than that of normal tissue and is depressed by glucose administration. This study aimed to evaluate the effectiveness of dual-wavelength fluorometry using a pH-dependent indicator (5,6-carboxyfluorescein: 5,6-CF)
Charlemagne Gnoula et al.
Talanta, 71(5), 1886-1892 (2007-03-30)
A new in vitro assay for anthelmintic activity using Caenorhabditis elegans is based on the ability of 5(6)-carboxyfluorescein diacetate (CFDA) to indicate the worm's viability. It is shown for the first time that the treatment of a suspension of worms
Jorien Claes et al.
Blood, 124(10), 1669-1676 (2014-06-22)
Adhesion of Staphylococcus aureus to blood vessels under shear stress requires von Willebrand factor (VWF). Several bacterial factors have been proposed to interact with VWF, including VWF-binding protein (vWbp), a secreted coagulase that activates the host's prothrombin to generate fibrin.
D F Babcock
The Journal of biological chemistry, 258(10), 6380-6389 (1983-05-25)
Fluorescein and carboxyfluorescein have found recent application as probes of intracellular pH. The present study examines several parameters required for interpretation of the spectral information derived from fluorescein and carboxyfluorescein generated intracellularly from their permeant diacetate derivatives. Coefficients were determined
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