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{{chembox |
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{{chembox |
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| verifiedrevid = 443498996 |
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| verifiedrevid = 443499984 |
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| Name = Carboxyfluorescein |
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| Name = 6-Carboxyfluorescein |
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| ImageFile = 6-Carboxyfluorescein.svg |
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| ImageFile = 6-Carboxyfluorescein.svg |
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| ImageName = |
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| ImageName = |
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| IUPACName = |
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| OtherNames = 6-FAM |
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| OtherNames = 6-FAM |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 39073 |
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| ChEBI = 39073 |
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| ChEMBL = 1614944 |
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| PubChem = 76806 |
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| SMILES = c1cc2c(cc1C(=O)O)C3(c4ccc(cc4Oc5c3ccc(c5)O)O)OC2=O |
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| SMILES = c1cc2c(cc1C(=O)O)C3(c4ccc(cc4Oc5c3ccc(c5)O)O)OC2=O |
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| InChIKey = BZTDTCNHAFUJOG-UHFFFAOYAC |
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| InChIKey = BZTDTCNHAFUJOG-UHFFFAOYAC |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 3301-79-9 |
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| CASNo = 3301-79-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = JHJ853P6SM |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=21|H=12|O=7 |
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| C=21|H=12|O=7 |
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}} |
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| Section3 = {{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|305+351+338}} |
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'''Carboxyfluorescein''' refers to two fluorescent ]s with an excitation and emission of 492/517 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 |
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'''6-Carboxyfluorescein''' ('''6-FAM''') is a ] with an absorption wavelength of 495 nm and an emission wavelength of 517 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. |
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Commercially available FAM is a mixture of two isomers, 5-FAM and 6-FAM, and the correct name is 5(6)-carboxyfluorescein. |
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The dyes are membrane-impermeant and can be loaded into cells by ] or scrape loading.<ref name="carboxyfluorescein description">{{cite web |
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| last = Molecular Imaging Products Company |
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| last = Molecular Imaging Products Company |
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| first = |
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| authorlink = |
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| date = 2005-08-26 |
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| date = 2005-08-26 |
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| url = http://store.mipcompany.com/510.html |
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| url = http://store.mipcompany.com/510.html |
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| title = 5-(and-6)-Carboxyfluorescein (5-(and-6)- FAM,mixed isomer) 100mg |
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| title = 5-(and-6)-Carboxyfluorescein (5-(and-6)- FAM,mixed isomer) 100mg |
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| access-date = 2006-08-26 |
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| work = |
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}}</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 |
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| publisher = |
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| accessdate = 2006-08-26 |
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}}</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 |
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| last = Parish |
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| last = Parish |
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| first = Christopher |
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| first = Christopher |
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| authorlink = |
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| date = December 1999 |
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| date = December 1999 |
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| url = http://www.blackwell-synergy.com/doi/abs/10.1046/j.1440-1711.1999.00877.x |
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| url = http://www.nature.com/icb/journal/v77/n6/full/icb199966a.html |
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| title = Fluorescent dyes for lymphocyte migration and proliferation studies |
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| title = Fluorescent dyes for lymphocyte migration and proliferation studies |
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| work = Immunology and Cell Biology |
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| journal = Immunology and Cell Biology |
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| volume = 77 |
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| issue = 6 |
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| pages = 499–508 |
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| publisher = Blackwell Synergy |
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| publisher = Blackwell Synergy |
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| doi = 10.1046/j.1440-1711.1999.00877.x |
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| accessdate = 2006-08-26 |
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| pmid = 10571670 |
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}} {{Dead link|date=October 2010|bot=H3llBot}}</ref> |
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| s2cid = 2194612 |
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| access-date = 2006-08-26 |
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| url-access = subscription |
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}}</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. |
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Popular derivatives for cell tracing purposes are ] (CFDA-SE) and ] (CFSE). |
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==See also== |
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==See also== |
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{{Reflist}} |
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{{Reflist}} |
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{{DEFAULTSORT:Carboxyfluorescein6}} |
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