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Merck

21877

5(6)-Carboxyfluorescein

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H12O7
CAS Number:
72088-94-9
Molecular Weight:
376.32
NACRES:
NA.32
PubChem Substance ID:
329752213
UNSPSC Code:
12171500
EC Number:
276-331-1
MDL number:
MFCD00151081

Product Name

5(6)-Carboxyfluorescein, BioReagent, suitable for fluorescence, ≥95% (HPLC)

InChI key

BPVHBBXCESDRKW-UHFFFAOYSA-N

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)

SMILES string

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

product line

BioReagent

assay

≥95% (HPLC)

form

powder

mp

275 °C (dec.) (lit.)

fluorescence

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

suitability

suitable for fluorescence

Quality Level

200

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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.

General description

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.

Other Notes

A probe of intracellular pH

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3136
BCCL9885
BCCL1131
BCCJ6813
BCCJ2293

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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
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)
Jagpreet S Nanda et al.
Methods in enzymology, 536, 87-94 (2014-01-16)
N-hydroxysuccinimde (NHS) ester-mediated derivitization involves the reaction of this amine-reactive group with the primary amines of a protein or a biomolecule. Using NHS chemistry allows one to conjugate various fluorescent probes, biotin, and cross-linkers to primary amines. For example, we
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.
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
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