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08951

Sigma-Aldrich

6-Carboxy-fluorescein diacetate N-succinimidyl ester

for fluorescence, ≥90.0% (HPLC)

Synonym(s):

6-Carboxy-di-O-acetylfluorescein N-succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C29H19NO11
CAS Number:
150206-15-8
Molecular Weight:
557.46
MDL number:
MFCD00269772
UNSPSC Code:
12352108
PubChem Substance ID:
329748646
NACRES:
NA.32

grade

for fluorescence

Assay

≥90.0% (HPLC)

solubility

DMF: soluble
DMSO: soluble

fluorescence

λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0 (after cleavage by esterase)

storage temp.

−20°C

SMILES string

CC(=O)Oc1ccc2c(Oc3cc(OC(C)=O)ccc3C24OC(=O)c5ccc(cc45)C(=O)ON6C(=O)CCC6=O)c1

InChI

1S/C29H19NO11/c1-14(31)37-17-4-7-20-23(12-17)39-24-13-18(38-15(2)32)5-8-21(24)29(20)22-11-16(3-6-19(22)28(36)40-29)27(35)41-30-25(33)9-10-26(30)34/h3-8,11-13H,9-10H2,1-2H3

InChI key

JGPOSNWWINVNFV-UHFFFAOYSA-N

Application

The succinimidyl ester group is capable of spontaneously and irreversibly binding to free amines. Utilized in flow cytometry experiments for tracking cell division in both mammalian cells and bacteria. Used in combination with several cell permeabilizers as an effective, nondestructive fluorescencent stain to quickly detect bacterial cells.

Other Notes

Reagent for continuously determining the intracellular pH in bacteria by fluorometry; labeling human intervertebral disk cells in vitro for fluorescence microscopy

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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P Breeuwer et al.
Applied and environmental microbiology, 62(1), 178-183 (1996-01-01)
A novel method based on the intracellular conjugation of the fluorescent probe 5 (and 6-)-carboxyfluorescein succinimidyl ester (cFSE) was developed to determine the intracellular pH of bacteria. cFSE can be taken up by bacteria in the form of its diacetate
H E Gruber et al.
Biotechnic & histochemistry : official publication of the Biological Stain Commission, 75(3), 118-123 (2000-08-19)
We have assessed the utility of an intracellular fluorochrome, 5-(and-6)-carboxyfluorescein diacetate succinimidyl ester (CFSE), as a tracking label for human intervertebral disc cells in vitro. Although 5 microM provides adequate intracellular labeling for whole cell fluorescent microscopic identification of labeled

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