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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

Key Documents

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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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1 of 4

This Item
4472938.5108286826
5(6)-Carboxyfluorescein BioReagent, suitable for fluorescence, ≥95% (HPLC)

Sigma-Aldrich

21877

5(6)-Carboxyfluorescein

5(6)-Carboxyfluorescein Dye content 90 %

Sigma-Aldrich

447293

5(6)-Carboxyfluorescein

5(6)-Carboxyfluorescein Novabiochem®

Sigma-Aldrich

8.51082

5(6)-Carboxyfluorescein

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

Sigma-Aldrich

86826

5-Carboxyfluorescein

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

suitable for fluorescence

fluorescence

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

fluorescence

-

fluorescence

-

fluorescence

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

form

powder

form

powder

form

powder

form

powder

assay

≥95% (HPLC)

assay

≥89.5% (HPLC)

assay

-

assay

≥95% (HPLC)

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

100

product line

BioReagent

product line

-

product line

Novabiochem®

product line

BioReagent

Application

5(6)-Carboxyfluorescein is used to characterize tumor cells and normal cells in vivo.[1] It labels proteins derived through N-hydroxysuccinimide (NHS) ester-mediated derivatization. [2] 5(6)-Carboxyfluorescein is suitable for detecting cell viability while developing an in vitro anthelmintic drug assay.[3]

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. [4] 5(6)-Carboxyfluorescein has two characteristic properties:
  • It has 2 wavelengths for maximum absorbance (465 and 490nm).[1]
  • And its fluorescence emission, at 515nm(max.), increases as a function of pH in the physiological range of 6-7.4.[1]

Other Notes

A probe of intracellular pH[5][6]

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)
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
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
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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