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6-Carboxyfluorescein

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6-Carboxyfluorescein
Names
Other names
6-FAM
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.164.295 Edit this at Wikidata
  • InChI=1S/C21H12O7/c22-11-2-5-14-17(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/h1-9,22-23H,(H,24,25) checkY
    Key: BZTDTCNHAFUJOG-UHFFFAOYSA-N checkY
  • InChI=1/C21H12O7/c22-11-2-5-14-17(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/h1-9,22-23H,(H,24,25)
    Key: BZTDTCNHAFUJOG-UHFFFAOYAC
  • c1cc2c(cc1C(=O)O)C3(c4ccc(cc4Oc5c3ccc(c5)O)O)OC2=O
Properties
C21H12O7
Molar mass 376.320 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

6-Carboxyfluorescein (6-FAM) is a fluorescent dye with an absorption wavelength of 495 nm and an emission wavelength of 517 nm. A carboxyfluorescein molecule is a fluorescein molecule with a carboxyl group added. They are commonly used as a tracer agents. It is used in the sequencing of nucleic acids and in the labelling nucleotides.

Commercially available FAM is a mixture of two isomers, 5-FAM and 6-FAM, and the correct name is 5(6)-carboxyfluorescein.

The dyes are membrane-impermeant and can be loaded into cells by microinjection or scrape loading.[1] It can be incorporated into liposomes, and allow for the tracking of liposomes as they pass through the body. In addition, carboxyfluorescein has been used to track division of cells.[2]

Popular derivatives for cell tracing purposes are Carboxyfluorescein diacetate succinimidyl ester (CFDA-SE) and Carboxyfluorescein succinimidyl ester (CFSE).

See also

References

  1. ^ Molecular Imaging Products Company (2005-08-26). "5-(and-6)-Carboxyfluorescein (5-(and-6)- FAM,mixed isomer) 100mg". Retrieved 2006-08-26.
  2. ^ Parish, Christopher (December 1999). "Fluorescent dyes for lymphocyte migration and proliferation studies". Immunology and Cell Biology. Blackwell Synergy. Retrieved 2006-08-26.