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{{Short description|Fluorescent dye and complexometric indicator}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443494137 |
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| Watchedfields = changed |
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| Name = Calcein |
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| verifiedrevid = 443495228 |
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| ImageFile = Calcein.svg |
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| Name = Calcein |
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| ImageFile = Calcein.svg |
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<!-- | ImageSize = 301px --> |
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<!-- | ImageSize = 301px --> |
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| ImageName = |
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| ImageName = |
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| PIN = 2,2′,2′′,2′′′-benzofuran-1,9′-xanthene]-2′,7′-diyl)bis(methylenenitrilo)]tetraacetic acid |
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| IUPACName = |
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| OtherNames = Fluorexon |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 58589 |
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| ChemSpiderID = 58589 |
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| PubChem = 65079 |
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| PubChem = 65079 |
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| InChI = 1/C30H26N2O13/c33-21-7-23-19(5-15(21)9-31(11-25(35)36)12-26(37)38)30(18-4-2-1-3-17(18)29(43)45-30)20-6-16(22(34)8-24(20)44-23)10-32(13-27(39)40)14-28(41)42/h1-8,33-34H,9-14H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42) |
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| InChIKey = DEGAKNSWVGKMLS-UHFFFAOYAD |
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| SMILES1 = c1ccc2c(c1)C(=O)OC23c4cc(c(cc4Oc5c3cc(c(c5)O)CN(CC(=O)O)CC(=O)O)O)CN(CC(=O)O)CC(=O)O |
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| SMILES1 = c1ccc2c(c1)C(=O)OC23c4cc(c(cc4Oc5c3cc(c(c5)O)CN(CC(=O)O)CC(=O)O)O)CN(CC(=O)O)CC(=O)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DEGAKNSWVGKMLS-UHFFFAOYSA-N |
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| StdInChIKey = DEGAKNSWVGKMLS-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1461-15-0 |
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| CASNo = 1461-15-0 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = V0YM2B16TS |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 51903 |
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| ChEBI = 51903 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| SMILES = O=C(O5)c1ccccc1C (c3cc(CN(CC(O)=O) CC(O)=O)c(O)cc3O4) 5c2c4cc(O)c(CN(CC (O)=O)CC(O)=O)c2 |
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| ChEMBL = 1973733 |
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| SMILES = O=C(O5)c1ccccc1C(c3cc(CN(CC(O)=O)CC(O)=O)c(O)cc3O4)5c2c4cc(O)c(CN(CC(O)=O)CC(O)=O)c2 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>30</sub>H<sub>26</sub>N<sub>2</sub>O<sub>13</sub> |
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| Formula = C<sub>30</sub>H<sub>26</sub>N<sub>2</sub>O<sub>13</sub> |
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| MolarMass = 622.55 g/mol |
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| MolarMass = 622.53 g/mol |
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| Density = |
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| Density = |
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| MeltingPt = Decomposes |
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| MeltingPt = Decomposes |
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| BoilingPt = N/A |
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| BoilingPt = N/A |
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| Solubility = Slightly soluble |
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'''Calcein''', also known as '''fluorexon, ] complex''', is a ] ] with an ] and ] wavelengths of 495/515 nm, respectively. Calcein also self-] even at concentrations below 100mM<ref>Patel et al. Characterizing vesicle leakage by fluorescence lifetime measurements (doi: 10.1039/b908524f)</ref>. It is used as a ] for ] of ] ions with ], and for ] determination of calcium. It has the appearance of orange crystals. |
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'''Calcein''', also known as '''fluorexon, ] complex''', is a ] ] with ] and ] wavelengths of 495 and 515 nm, respectively, and has the appearance of orange crystals. Calcein self-] at concentrations above 70 mM and is commonly used as an indicator of lipid vesicle leakage.<ref>{{cite journal | last1 = Allen | first1 = T.M. | last2 = Cleland | first2 = L.G. | year = 1980| title = Serum-induced leakage of liposome contents | journal = Biochimica et Biophysica Acta (BBA) - Biomembranes | volume = 597 | issue = 2| pages = 418–426 | doi = 10.1016/0005-2736(80)90118-2 | pmid = 7370258 }}</ref><ref>Sendai virus induced leakage of liposomes containing gangliosides Yung Shyeng Tsao and Leaf Huang Biochemistry 1985 24 (5), 1092-1098</ref><ref>{{cite journal | last1 = Patel | first1 = H. | last2 = Tscheka | first2 = C. | last3 = Heerklotz | first3 = H. | year = 2009 | title = Characterizing vesicle leakage by fluorescence lifetime measurements | journal = Soft Matter | volume = 5 | issue = 15| pages = 2849–2851 | doi = 10.1039/B908524F | bibcode = 2009SMat....5.2849P }}</ref> It has also been traditionally used as a ] for ] of ] ions with ], and for ] determination of calcium. |
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==Applications== |
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==Applications== |
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The acetomethoxy derivate of calcein ('''calcein AM''') is used in biology as it can be transported through the cellular membrane into live cells, which makes it useful for testing of cell ] and for short-term labeling of cells. An acetomethoxy group obscures the part of the molecule that chelates Ca<sup>2+</sup>, Mg<sup>2+</sup>, Zn<sup>2+</sup> and other ions. After transport into the cells, intracellular esterases remove the acetomethoxy group, the molecule gets trapped inside and gives out strong green fluorescence. As dead cells lack active esterases, only live cells are labeled<ref>{{cite web |url=http://www.howstuffworks.com/light-microscope4.htm |title=How Light Microscopes Work |publisher=HowStuffWorks }}</ref> and counted by ]. |
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The non-fluorescent acetomethoxy derivate of calcein (calcein AM, AM = '''a'''cetoxy'''m'''ethyl) is used in biology as it can be transported through the cellular membrane into live cells, which makes it useful for testing of cell ] and for short-term labeling of cells. Alternatively, ], ], ] and ] may be used. An acetomethoxy group obscures the part of the molecule that chelates Ca<sup>2+</sup>, Mg<sup>2+</sup>, Zn<sup>2+</sup> and other ions. After transport into the cells, intracellular esterases remove the acetomethoxy group, the molecule gets trapped inside and gives out strong green fluorescence. As dead cells lack active esterases, only live cells are labeled<ref>{{cite web |url=http://www.howstuffworks.com/light-microscope4.htm |title=How Light Microscopes Work |date=25 May 2001 |publisher=HowStuffWorks }}</ref> and counted by ]. |
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Calcein is now rarely used as a Ca<sup>2+</sup> or Mg<sup>2+</sup> indicator because its fluorescence is directly sensitive to these ions only at strongly alkaline pH, and thus it is not particularly useful for measuring Ca<sup>2+</sup> or Mg<sup>2+</sup> in cells. Fluorescence of calcein is quenched strongly by Co<sup>2+</sup>, Ni<sup>2+</sup> and Cu<sup>2+</sup> and appreciably by Fe<sup>3+</sup> and Mn<sup>2+</sup> at physiological pH. This fluorescence quenching response can be exploited for detecting the opening of the mitochondrial permeability transition pore. Calcein is commonly used for cell tracing and in studies of endocytosis and gap junctions.<ref>{{cite book |author= |chapter=Fluorescent Indicators for Zn<sup>2+</sup> and Other Metal Ions—Section 19.7 |chapterurl=http://www.invitrogen.com/site/us/en/home/References/Molecular-Probes-The-Handbook/Indicators-for-Ca2-Mg2-Zn2-and-Other-Metal-Ions/Fluorescent-Indicators-for-Zn2-and-Other-Metal-Ions.html |title=Molecular Probes: The Handbook |publisher=invitrogen |url=http://www.invitrogen.com/site/us/en/home/References/Molecular-Probes-The-Handbook.html }}</ref> |
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Calcein is now rarely used as a Ca<sup>2+</sup> or Mg<sup>2+</sup> indicator because its fluorescence is directly sensitive to these ions only at strongly alkaline pH, and thus it is not particularly useful for measuring Ca<sup>2+</sup> or Mg<sup>2+</sup> in cells. Fluorescence of calcein is quenched strongly by Co<sup>2+</sup>, Ni<sup>2+</sup> and Cu<sup>2+</sup> and appreciably by Fe<sup>3+</sup> and Mn<sup>2+</sup> at physiological pH. This fluorescence quenching response can be exploited for detecting the opening of the ] (mPTP) and for measuring cell volume changes.<ref>{{cite journal | last1 = Hamann | first1 = J.F. | last2 = Kiilgard | last3 = Litman | first3 = T. | last4 = Alvarez-Leefmans | first4 = J. | last5 = Zeuthen | first5 = T. | year = 2002 | title = Measurement of cell volume changes by fluorescence self-quenching | journal = J. Fluorescence | volume = 12 | issue = 2| pages = 139–145 | doi = 10.1023/a:1016832027325 | s2cid = 20539474 }}</ref> Calcein is commonly used for cell tracing and in studies of endocytosis, cell migration, and gap junctions.<ref>{{cite book |chapter=Fluorescent Indicators for Zn<sup>2+</sup> and Other Metal Ions—Section 19.7 |chapter-url=http://www.invitrogen.com/site/us/en/home/References/Molecular-Probes-The-Handbook/Indicators-for-Ca2-Mg2-Zn2-and-Other-Metal-Ions/Fluorescent-Indicators-for-Zn2-and-Other-Metal-Ions.html |title=Molecular Probes: The Handbook |publisher=invitrogen |url=http://www.invitrogen.com/site/us/en/home/References/Molecular-Probes-The-Handbook.html }}</ref> |
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The acetoxymethyl ester of calcein is also used to detect drug interactions with '''multidrug resistance proteins''' (ABC transporters ]) in intact cells as it is an excellent substrate of the multidrug resistance transporter 1 (MDR1) ] and the ] (MRP1).<ref>{{cite journal |author=Glavinas H, Krajcsi P, Cserepes J, Sarkadi B |title=The role of ABC transporters in drug resistance, metabolism and toxicity |journal=Curr Drug Deliv |volume=1 |issue=1 |pages=27–42 |year=2004 |month=January |pmid=16305368 |doi= 10.2174/1567201043480036|url=http://www.bentham-direct.org/pages/content.php?CDD/2004/00000001/00000001/005AU.SGM}}</ref> The calcein AM assay can be used as a model for drug-drug interactions, for screening transporter substrates and/or inhibitors;<ref>more detailed description of the assay/ http://www.solvo.com/pdfs/SOLVO%20Calcein%20Assay.pdf</ref> and also to determine in vitro drug resistance of cells, including samples from patients.<ref>a detailed description of the method http://www.solvo.com/pdfs/MDQ%20flyer.pdf</ref><ref>{{cite journal |doi=10.1046/j.1365-2141.2001.02554.x |author=Karászi E, Jakab K, Homolya L, ''et al.'' |title=Calcein assay for multidrug resistance reliably predicts therapy response and survival rate in acute myeloid leukaemia |journal=Br. J. Haematol. |volume=112 |issue=2 |pages=308–14 |year=2001 |month=February |pmid=11167823 |url=http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0007-1048&date=2001&volume=112&issue=2&spage=308}}</ref> |
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The acetoxymethyl ester of calcein is also used to detect drug interactions with '''multidrug resistance proteins''' (ABC transporters ]) in intact cells as it is an excellent substrate of the multidrug resistance transporter 1 (MDR1) ] and the ] (MRP1).<ref>{{cite journal |vauthors=Glavinas H, Krajcsi P, Cserepes J, Sarkadi B |title=The role of ABC transporters in drug resistance, metabolism and toxicity |journal=Curr Drug Deliv |volume=1 |issue=1 |pages=27–42 |date=January 2004 |pmid=16305368 |doi= 10.2174/1567201043480036|url=http://www.bentham-direct.org/pages/content.php?CDD/2004/00000001/00000001/005AU.SGM|archive-url=https://archive.today/20120719164339/http://www.bentham-direct.org/pages/content.php?CDD/2004/00000001/00000001/005AU.SGM|url-status=usurped|archive-date=2012-07-19}}</ref> The calcein AM assay can be used as a model for drug-drug interactions, for screening transporter substrates and/or inhibitors; and also to determine in vitro drug resistance of cells, including samples from patients.<ref>{{cite journal |doi=10.1046/j.1365-2141.2001.02554.x |vauthors=Karászi E, Jakab K, Homolya L |title=Calcein assay for multidrug resistance reliably predicts therapy response and survival rate in acute myeloid leukaemia |journal=Br. J. Haematol. |volume=112 |issue=2 |pages=308–14 |date=February 2001 |pmid=11167823 |display-authors=etal|doi-access=free }}</ref> |
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Calcein is also used for marking freshly hatched ]<ref>{{cite web |url=http://www.gct.org.uk/text03.asp?PageId=331 |title=Marking fry using calcein |publisher=Game & Wildlife Conservation Trust}}</ref> and for labeling of ]s in live animals. |
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Calcein is also used for marking freshly hatched fish<ref>{{cite web|url=http://www.gct.org.uk/text03.asp?PageId=331 |title=Marking fry using calcein |publisher=Game & Wildlife Conservation Trust |url-status=dead |archive-url=https://web.archive.org/web/20060925083308/http://www.gct.org.uk/text03.asp?PageId=331 |archive-date=September 25, 2006 }}</ref> and for labeling of ]s in live animals. |
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==References== |
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==References== |
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