21888

Sigma-Aldrich

5(6)-Carboxyfluorescein diacetate N-succinimidyl ester

BioReagent, suitable for fluorescence, ≥90% (HPLC)

Synonym(s):
CFSE
Empirical Formula (Hill Notation):
C29H19NO11
CAS Number:
Molecular Weight:
557.46
MDL number:
PubChem Substance ID:
NACRES:
NA.32
Pricing and availability is not currently available.

Quality Level

product line

BioReagent

assay

≥90% (HPLC)

mp

152-154 °C (lit.)

solubility

DMF: soluble
DMSO: soluble

fluorescence

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

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

CC(=O)Oc1ccc2c(Oc3cc(OC(C)=O)ccc3C24OC(=O)c5cc(ccc45)C(=O)ON6C(=O)CCC6=O)c1.CC(=O)Oc7ccc8c(Oc9cc(OC(C)=O)ccc9C8%10OC(=O)c%11ccc(cc%10%11)C(=O)ON%12C(=O)CCC%12=O)c7

InChI

1S/2C29H19NO11/c1-14(31)37-17-4-7-21-23(12-17)39-24-13-18(38-15(2)32)5-8-22(24)29(21)20-6-3-16(11-19(20)28(36)40-29)27(35)41-30-25(33)9-10-26(30)34;1-14(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/h2*3-8,11-13H,9-10H2,1-2H3

InChI key

LZFDYQHOQDFMOA-UHFFFAOYSA-N

General description

5-(and-6)-Carboxyfluorescein diacetate N-succinimidyl ester (CFSE) is a fluorescent dye, which is membrane permeable. It labels cells by covalently binding to intracellular molecules. CFSE is used to track lymphocyte migration and proliferation.

Application

5-Carboxyfluorescein diacetate N-succinimidyl ester has been used:
  • to label cells for flow cytometry
  • in lymphocyte proliferation assay
  • to determine the intracellular or intra-organellar pH in chloroplasts
  • to label Leishmania amazonensis and Leishmania major

5(6)-Carboxyfluorescein diacetate N-succinimidyl ester (CFSE) is an amine reactive fluorescent probe used to stain cells, especially immune cells, for analysis in applications such as flow cytometry. Forms green fluorescent conjugates on deacetylation.
Amine-reactive label for long term tracing of cells. Forms green fluorescent conjugates on deacetylation.

Biochem/physiol Actions

5(6)-Carboxyfluorescein diacetate N-succinimidyl ester is used as an indicator for esterase activity.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. At what concentration is Product 21888, 5(6)-Carboxyfluorescein diacetate N-succinimidyl ester, soluble in DMSO?

    We have found 5(6)-Carboxyfluorescein diacetate N-succinimidyl ester to be soluble in DMSO at a concentration of 1 mg/mL.

  4. What is the ratio between the (5) and (6) isomer of Product 21888, 5(6)-Carboxyfluorescein diacetate N-succinimidyl ester?

    Our Quality Control group does not routinely report the ratio; however, it is very likely that both isomers are present.

  5. Is Product 21888, 5(6)-Carboxyfluorescein diacetate N-succinimidyl ester, light sensitive?

    Yes. The powder and solutions (especially solutions) should be kept protected from ambient light whenever possible.

  6. Is Product 21888, 5(6)-Carboxyfluorescein diacetate N-succinimidyl ester, fluorescent? Are conjugates of this compound fluorescent?

    No. This compound and conjugates of this compound become fluorescent only when acted upon by an enzyme such as esterase. The enzyme removes the acetate groups.

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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Zhao D, et al.
BMC Gastroenterology, 15(1), 173-173 (2015)
A Reliable and Non-destructive Method for Monitoring the Stromal pH in Isolated Chloroplasts Using a Fluorescent pH Probe
Su PH and Lai YH
Frontiers in Plant Science, 8, 2079-2079 (2017)
Autophagic induction greatly enhances Leishmania major intracellular survival compared to Leishmania amazonensis in CBA/j-infected macrophages
Dias BRS, et al.
Frontiers in Microbiology, 9 (2018)
Lymphoproliferative responses to dendritic cell presentation of sensitizing allergens in atopic children with multiple allergies
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Annals of Allergy, Asthma & Immunology, 119(3), 274-283 (2017)
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