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Calcein

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Revision as of 11:46, 7 August 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Calcein
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.507 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/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)Key: DEGAKNSWVGKMLS-UHFFFAOYSA-N
  • 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)Key: DEGAKNSWVGKMLS-UHFFFAOYAD
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
  • 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
Properties
Chemical formula C30H26N2O13
Molar mass 622.55 g/mol
Melting point Decomposes
Boiling point N/A
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Calcein, also known as fluorexon, fluorescein complex, is a fluorescent dye with an excitation and emission wavelengths of 495/515 nm, respectively. Calcein also self-quenches even at concentrations below 100mM. It is used as a complexometric indicator for titration of calcium ions with EDTA, and for fluorometric determination of calcium. It has the appearance of orange crystals.

Applications

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 viability and for short-term labeling of cells. An acetomethoxy group obscures the part of the molecule that chelates Ca, Mg, Zn 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 and counted by flow cytometry.

Calcein is now rarely used as a Ca or Mg 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 or Mg in cells. Fluorescence of calcein is quenched strongly by Co, Ni and Cu and appreciably by Fe and Mn 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.

The acetoxymethyl ester of calcein is also used to detect drug interactions with multidrug resistance proteins (ABC transporters ATP-binding cassette transporter genes) in intact cells as it is an excellent substrate of the multidrug resistance transporter 1 (MDR1) P-glycoprotein and the de:Multidrug Resistance-Related Protein (MRP1). 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.

Calcein is also used for marking freshly hatched fish and for labeling of bones in live animals.

References

  1. Patel et al. Characterizing vesicle leakage by fluorescence lifetime measurements (doi: 10.1039/b908524f)
  2. "How Light Microscopes Work". HowStuffWorks.
  3. "Fluorescent Indicators for Zn and Other Metal Ions—Section 19.7". Molecular Probes: The Handbook. invitrogen. {{cite book}}: External link in |chapterurl= (help); Unknown parameter |chapterurl= ignored (|chapter-url= suggested) (help)
  4. Glavinas H, Krajcsi P, Cserepes J, Sarkadi B (2004). "The role of ABC transporters in drug resistance, metabolism and toxicity". Curr Drug Deliv. 1 (1): 27–42. doi:10.2174/1567201043480036. PMID 16305368. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. more detailed description of the assay/ http://www.solvo.com/pdfs/SOLVO%20Calcein%20Assay.pdf
  6. a detailed description of the method http://www.solvo.com/pdfs/MDQ%20flyer.pdf
  7. Karászi E, Jakab K, Homolya L; et al. (2001). "Calcein assay for multidrug resistance reliably predicts therapy response and survival rate in acute myeloid leukaemia". Br. J. Haematol. 112 (2): 308–14. doi:10.1046/j.1365-2141.2001.02554.x. PMID 11167823. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  8. "Marking fry using calcein". Game & Wildlife Conservation Trust.
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