Fura-2-acetoxymethyl ester

Chembox new
ImageFile=Fura 2AM.pngImageSize=200px
IUPACName=Acetoxymethyl 2- [5- [bis [(acetoxymethoxy-oxo-methyl)methyl] amino] -4- [2- [2- [bis [(acetoxymethoxy-oxo-methyl)methyl] amino] -5-methyl-phenoxy] ethoxy] benzofuran-2-yl] oxazole-5-carboxylate
OtherNames=Fura-2AM
Section1= Chembox Identifiers
CASNo=108964-32-5
PubChem=3086531
SMILES=CC1=CC(=C(C=C1)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)OCCOC2=C(C=CC3=C2C=C(O3)C4=NC=C(O4)C(=O)OCOC(=O)C)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
Section2= Chembox Properties
Formula=C₄₄H₄₇N₃O₂₄
MolarMass=1001.85
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

Fura-2-acetoxymethyl ester, often abbreviated Fura-2AM, is a membrane-permeable derivative of the ratiometric calcium indicator Fura-2 used in biochemistry to measure cellular calcium concentrations by fluorescence. 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 Ca⁺²-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.

References