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5(6)-Carboxyfluorescein

Name: 5(6)-Carboxyfluorescein
Brand: SIGMA

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

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Properties

product line

BioReagent

Quality Level

200

assay

≥95% (HPLC)

form

powder

mp

275 °C (dec.) (lit.)

fluorescence

λ_ex 492 nm; λ_em 517 nm in 0.1 M Tris pH 8.0

suitability

suitable for fluorescence

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

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)

InChI key

BPVHBBXCESDRKW-UHFFFAOYSA-N

Description

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. [1] 5(6)-Carboxyfluorescein has two characteristic properties:

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

Application

5(6)-Carboxyfluorescein is used to characterize tumor cells and normal cells in vivo.[2] It labels proteins derived through N-hydroxysuccinimide (NHS) ester-mediated derivatization. [3] 5(6)-Carboxyfluorescein is suitable for detecting cell viability while developing an in vitro anthelmintic drug assay.[4]

Other Notes

A probe of intracellular pH[5][6]

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1 of 1

This Item	447293	8.51082	86826
Sigma-Aldrich 21877 5(6)-Carboxyfluorescein	Sigma-Aldrich 447293 5(6)-Carboxyfluorescein	Sigma-Aldrich 8.51082 5(6)-Carboxyfluorescein	Sigma-Aldrich 86826 5-Carboxyfluorescein
suitability suitable for fluorescence	suitability -	suitability -	suitability suitable for fluorescence
fluorescence λ_ex 492 nm; λ_em 517 nm in 0.1 M Tris pH 8.0	fluorescence -	fluorescence -	fluorescence λ_ex 492 nm; λ_em 517 nm in 0.1 M Tris pH 8.0
form powder	form powder	form powder	form powder
Quality Level 200	Quality Level 100	Quality Level 200	Quality Level 100
assay ≥95% (HPLC)	assay ≥89.5% (HPLC)	assay -	assay ≥95% (HPLC)
product line BioReagent	product line -	product line Novabiochem^®	product line BioReagent

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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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5(6)-Carboxyfluorescein diacetate as an indicator of Caenorhabditis elegans viability for the development of an in vitro anthelmintic drug assay.

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

Characterization of tumorous and normal tissue using a pH-sensitive fluorescence indicator (5,6-carboxyfluorescein) in vivo.

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)

Labeling a protein with fluorophores using NHS ester derivitization.

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

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Global Trade Item Number

SKU	GTIN
21877-1G-F	04061838775603
21877-5G-F	04061838775610

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