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CAY10455
Cayman Chemical Item Number 10005072
Description
The cellular trafficking of arachidonoyl ethanolamide (anandamide; AEA) by neurons is dominated by transport and/or hydrolysis by fatty acyl amide hydrolase (FAAH) within the neurons.1↗ CAY10455 is a labeled analog of AEA that is non-fluorescent when outside the cell. Upon transport into the cell interior, it is cleaved by esterases to give a bright fluorescence at 530 nm. CAY10455 uptake into C6 glioma cells is inhibited by AEA and its analogs, and conversely CAY10455 inhibits the uptake of tritiated AEA, indicating that they compete for the AEA transporter.2↗
1 Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. J Biol Chem 276(10) 6967-6973 (2001).
2 Muthian, S., Nithipatikom, K., Campbell, W.B., et al. Synthesis and characterization of a fluorescent substrate for the N-arachidonoylethanolamine (anandamide) transmembrane carrier. J Pharmacol Exp Ther 293 289-295 (2000).
Synonyms SKM 4-45-1
Formal Name [3',6'-bis(acetyloxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl]-2-[[1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl]amino]ethyl ester carbamic acid
CAS Number 290374-09-3
Molecular Formula C47H52N2O10
Formula Weight 804.9
Formulation A solution in methyl acetate
Purity >98%
λmax 226, 291 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCOC(=O)Nc1ccc2c(c1)C(=O)OC12c2ccc(OC(=O)C)cc2Oc2cc(ccc12)OC(=O)C
InCHI Code 1S/C45H48N2O10/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-42(50)46-26-27-53-44(52)47-33-20-23-37-36(28-33)43(51)57-45(37)38-24-21-34(54-31(2)48)29-40(38)56-41-30-35(55-32(3)49)22-25-39(41)45/h6-7,9-10,12-13,15-16,20-25,28-30H,4-5,8,11,14,17-1
InCHI Key LUTXTWGKKWURII-DOFZRALJSA-N |