Fura-2-acetoxymethyl ester

Fura-2-acetoxymethyl ester, often abbreviated Fura-2AM, is a membrane-permeant derivative of the ratiometric calcium indicator Fura-2 used in biochemistry to measure cellular calcium concentrations by fluorescence.^[1] When added to cells, Fura-2AM crosses cell membranes and once inside the cell, the acetoxymethyl groups are removed by cellular esterases. Removal of the acetoxymethyl esters regenerates "Fura-2", the pentacarboxylate calcium indicator. Measurement of Ca²⁺-induced fluorescence at both 340 nm and 380 nm allows for calculation of calcium concentrations based 340/380 ratios. The use of the ratio automatically cancels out certain variables such as local differences in fura-2 concentration or cell thickness that would otherwise lead to artifacts when attempting to image calcium concentrations in cells.

Fura-2-acetoxymethyl ester

Names
Preferred IUPAC name (Acetyloxy)methyl 2-(5-{2-[5-methyl-2-(2,6,10,14-tetraoxo-3,5,11,13-tetraoxa-8-azapentadecan-8-yl)phenoxy]ethoxy}-6-(2,6,10,14-tetraoxo-3,5,11,13-tetraoxa-8-azapentadecan-8-yl)-1-benzofuran-2-yl)-1,3-oxazole-5-carboxylate
Other names Fura-2AM
Identifiers
CAS Number	108964-32-5 Y
3D model (JSmol)	Interactive image
ChemSpider	2610364 Y
PubChem CID	3364574
CompTox Dashboard (EPA)	DTXSID50148784
InChI InChI=1S/C44H47N3O24/c1-25-7-8-32(46(16-39(53)65-20-60-26(2)48)17-40(54)66-21-61-27(3)49)35(11-25)58-9-10-59-36-12-31-13-37(43-45-15-38(71-43)44(57)69-24-64-30(6)52)70-34(31)14-33(36)47(18-41(55)67-22-62-28(4)50)19-42(56)68-23-63-29(5)51/h7-8,11-15H,9-10,16-24H2,1-6H3 Y Key: VPSRLGDRGCKUTK-UHFFFAOYSA-N Y InChI=1/C44H47N3O24/c1-25-7-8-32(46(16-39(53)65-20-60-26(2)48)17-40(54)66-21-61-27(3)49)35(11-25)58-9-10-59-36-12-31-13-37(43-45-15-38(71-43)44(57)69-24-64-30(6)52)70-34(31)14-33(36)47(18-41(55)67-22-62-28(4)50)19-42(56)68-23-63-29(5)51/h7-8,11-15H,9-10,16-24H2,1-6H3 Key: VPSRLGDRGCKUTK-UHFFFAOYAI
SMILES O=C(OCOC(=O)CN(c4ccc(cc4OCCOc3cc1c(oc(c1)c2ncc(o2)C(=O)OCOC(=O)C)cc3N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)C)CC(=O)OCOC(=O)C)C
Properties
Chemical formula	C44H47N3O24
Molar mass	1001.85
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

References

1. Oakes, S. G; Martin Wj, 2nd; Lisek, C. A; Powis, G (1988). "Incomplete hydrolysis of the calcium indicator precursor fura-2 pentaacetoxymethyl ester (fura-2 AM) by cells". Analytical Biochemistry. 169 (1): 159–66. doi:10.1016/0003-2697(88)90267-9. PMID 3369679.{{cite journal}}: CS1 maint: numeric names: authors list (link)