6-Carboxyfluorescein

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 labeling of nucleotides.

6-Carboxyfluorescein
Names
Other names
6-FAM
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.295
UNII
  • 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 ?)
Infobox references

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 allows for the tracking of liposomes as they pass through the body. In addition, carboxyfluorescein has been used to track division of cells.[2] In vascular plants, 5(6)-carboxyfluorescein can be used as a symplastic tracer. It is able to move through the phloem due to its structural similarity to sucrose.[3] It is typically loaded into the leaves in order to gain access to the phloem.[4][5] This can be done by scraping, cutting, or weakening the leaf’s cuticle with an herbicide.

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. 77 (6): 499–508. doi:10.1046/j.1440-1711.1999.00877.x. PMID 10571670. S2CID 2194612. Retrieved 2006-08-26.
  3. Schulz, Alexander; Liesche, Johannes (2013). "Modeling the parameters for plasmodesmal sugar filtering in active symplasmic phloem loaders". Frontiers in Plant Science. 4: 207. doi:10.3389/fpls.2013.00207. ISSN 1664-462X. PMC 3685819. PMID 23802006.
  4. Martens, Helle Juel; Schulz, Alexander; Rademaker, Hanna; Andersen, Signe R.; Binczycki, Piotr; Gao, Chen; Liesche, Johannes (2019-04-01). "Direct Comparison of Leaf Plasmodesma Structure and Function in Relation to Phloem-Loading Type". Plant Physiology. 179 (4): 1768–1778. doi:10.1104/pp.18.01353. ISSN 0032-0889. PMC 6446768. PMID 30723179.
  5. Zambryski, P. C.; Hempel, F. D.; Barella, S.; Gisel, A. (1999-05-01). "Temporal and spatial regulation of symplastic trafficking during development in Arabidopsis thaliana apices". Development. 126 (9): 1879–1889. doi:10.1242/dev.126.9.1879. ISSN 0950-1991. PMID 10101122.
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