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{{chembox {{chembox
| verifiedrevid = 388071359 | verifiedrevid = 443499984
| Name = Carboxyfluorescein | Name = 6-Carboxyfluorescein
| ImageFile = 6-Carboxyfluorescein.svg | ImageFile = 6-Carboxyfluorescein.svg
| ImageName = | ImageName =
| IUPACName =
| OtherNames = 6-FAM | OtherNames = 6-FAM
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 69262 | ChemSpiderID = 69262
| 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) | 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)
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 39073 | ChEBI = 39073
| ChEMBL = 1614944
| PubChem = 76806
| SMILES = c1cc2c(cc1C(=O)O)C3(c4ccc(cc4Oc5c3ccc(c5)O)O)OC2=O | SMILES = c1cc2c(cc1C(=O)O)C3(c4ccc(cc4Oc5c3ccc(c5)O)O)OC2=O
| InChIKey = BZTDTCNHAFUJOG-UHFFFAOYAC | InChIKey = BZTDTCNHAFUJOG-UHFFFAOYAC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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) | StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BZTDTCNHAFUJOG-UHFFFAOYSA-N | StdInChIKey = BZTDTCNHAFUJOG-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 3301-79-9 | CASNo = 3301-79-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = JHJ853P6SM
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=21|H=12|O=7 | C=21|H=12|O=7
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|305+351+338}}
}} }}
}} }}


'''Carboxyfluorescein''' refers to two fluorescent ]s with an excitation and emission of 492/517&nbsp;nm, respectively. They are commonly used as a tracer agents. The dyes are membrane-impermeant and can be loaded into cells by ] or scrape loading.<ref name="carboxyfluorescein description">{{cite web '''6-Carboxyfluorescein''' ('''6-FAM''') is a ] with an absorption wavelength of 495&nbsp;nm and an emission wavelength of 517&nbsp;nm. A carboxyfluorescein molecule is a ] molecule with a ] 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.

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 ] or scrape loading.<ref name="carboxyfluorescein description">{{cite web
| last = Molecular Imaging Products Company | last = Molecular Imaging Products Company
| first =
| authorlink =
| date = 2005-08-26 | date = 2005-08-26
| url = http://store.mipcompany.com/510.html | url = http://store.mipcompany.com/510.html
| title = 5-(and-6)-Carboxyfluorescein (5-(and-6)- FAM,mixed isomer) 100mg | title = 5-(and-6)-Carboxyfluorescein (5-(and-6)- FAM,mixed isomer) 100mg
⚫ | access-date = 2006-08-26
| work =
⚫ }}</ref> It can be incorporated into ], and allows for the tracking of liposomes as they pass through the body. In addition, carboxyfluorescein has been used to track division of cells.<ref name="Use of Carboxyfluoresceine in Cell Studies">{{cite journal
| publisher =
⚫ | accessdate = 2006-08-26
⚫ }}</ref> It can be incorporated into ], and allow for the tracking of liposomes as they pass through the body. In addition, carboxyfluorescein has been used to track division of cells.<ref name="Use of Carboxyfluoresceine in Cell Studies">{{cite web
| last = Parish | last = Parish
| first = Christopher | first = Christopher
| authorlink =
| date = December 1999 | date = December 1999
| url = http://www.blackwell-synergy.com/doi/abs/10.1046/j.1440-1711.1999.00877.x | url = http://www.nature.com/icb/journal/v77/n6/full/icb199966a.html
| title = Fluorescent dyes for lymphocyte migration and proliferation studies | title = Fluorescent dyes for lymphocyte migration and proliferation studies
| work = Immunology and Cell Biology | journal = Immunology and Cell Biology
| volume = 77
| issue = 6
| pages = 499–508
| publisher = Blackwell Synergy | publisher = Blackwell Synergy
| doi = 10.1046/j.1440-1711.1999.00877.x
⚫ | accessdate = 2006-08-26
| pmid = 10571670
}} {{Dead link|date=October 2010|bot=H3llBot}}</ref>
| s2cid = 2194612
⚫ | access-date = 2006-08-26
| url-access = subscription
}}</ref> In vascular plants, 5(6)-carboxyfluorescein can be used as a symplastic tracer. It is able to move through the ] due to its structural similarity to sucrose.<ref>{{Cite journal|last1=Schulz|first1=Alexander|last2=Liesche|first2=Johannes|date=2013|title=Modeling the parameters for plasmodesmal sugar filtering in active symplasmic phloem loaders|journal=Frontiers in Plant Science|language=en|volume=4|pages=207|doi=10.3389/fpls.2013.00207|pmid=23802006|issn=1664-462X|pmc=3685819|doi-access=free}}</ref> It is typically loaded into the leaves in order to gain access to the phloem.<ref>{{Cite journal|last1=Martens|first1=Helle Juel|last2=Schulz|first2=Alexander|last3=Rademaker|first3=Hanna|last4=Andersen|first4=Signe R.|last5=Binczycki|first5=Piotr|last6=Gao|first6=Chen|last7=Liesche|first7=Johannes|date=2019-04-01|title=Direct Comparison of Leaf Plasmodesma Structure and Function in Relation to Phloem-Loading Type|journal=Plant Physiology|language=en|volume=179|issue=4|pages=1768–1778|doi=10.1104/pp.18.01353|issn=0032-0889|pmid=30723179|pmc=6446768}}</ref><ref>{{Cite journal|last1=Zambryski|first1=P. C.|last2=Hempel|first2=F. D.|last3=Barella|first3=S.|last4=Gisel|first4=A.|date=1999-05-01|title=Temporal and spatial regulation of symplastic trafficking during development in Arabidopsis thaliana apices|url=https://dev.biologists.org/content/126/9/1879|journal=Development|language=en|volume=126|issue=9|pages=1879–1889|doi=10.1242/dev.126.9.1879|issn=0950-1991|pmid=10101122|url-access=subscription}}</ref> This can be done by scraping, cutting, or weakening the leaf’s cuticle with an herbicide.

Popular derivatives for cell tracing purposes are ] (CFDA-SE) and ] (CFSE).


==See also== ==See also==
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{{Reflist}} {{Reflist}}


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