Calcein acetoxymethyl ester

CA Index Name Glycine, A,A -[[3, 6 -bis(acetyloxy)-3-oxospiro[isobenzofuran-l(3//),9 -[9//]xanthene]-2, 7 -diyl]bis(methylene)]bis[N-[2-[(acetyloxy)methoxy]-2-oxoethyl]-, l,l -bis[(acetyloxy)methyl] ester Other Names Calcein 0,0 -diacetate tetrakis(acetoxy-methyl)ester Glycine, N,A -[[3, 6 -bis(acetyloxy)-3-ox-ospiro[isobenzofuran-l(3//) 9 -[9//]xanthene]-2, 7 -diyl] bis(methylene)]bis[N-[2-[(acetyloxy)methoxy]-2-oxoe-thyl]-, bis[(acetyloxy)methyl] ester Spiro[isoben-zofuran-l(3/7),9 -[9/7]xanthene], glycine derivative Calcein AM Calcein acetoxymethyl ester NSC 689290... 

Jonsson, B. Liminga, G. Csoka, K. Fridborg, H. Dhar, S. Nygren, P. Larsson, R. Cytotoxic activity of calcein acetoxymethyl ester (calcein/AM) on primary cultures of human hematological and solid tumors. Eur. J. Cancer 1996, 32A, 883-887. 

Liminga, G. Nygren, R Dhar, S. Nilsson, K. Larsson, R. Cytotoxic effect of calcein acetoxymethyl ester on human tumor cell lines drug delivery by intracellular trapping. Anti-Cancer Drugs 1995, 6, 578-585. 

Fluorescent dyes such as calcein-AM and rhodamine derivatives have been demonstrated to be P-gp substrates (400-407). These compounds can be used in any competition assay in which the test compound is added with these dyes. Any reduction in the dye efflux would be indicative of the inhibitory properties of the test compounds toward P-gp. Both rhodamine 123 and calcein-AM have been used in high-throughput assays, including the NCI assay, to screen large numbers of compounds as inhibitors of P-gp in several cell types. Calcein-AM itself is a weakly fluorescent molecule. When the acetoxymethyl ester group is cleaved by... 

The acetoxymethyl ester form of the calcein dye (calcein-AM) has been widely used as an assay to measure viable cells for microscopy, flow cytometry, and some plate-based methods. Calcein-AM is a cell-permeable non-fluorescent compound added to cells as a solution in DMSO. Non-specific esterase activity present in viable cells removes the lipophilic AM group, resulting in conversion of the non-fluorescent calcein-AM into a green fluorescent calcein molecule that is generally retained inside viable cells. 

The acetoxymethyl ester of calcein (Calcein-AM) is a highly lipid soluble and nonfluorescent compound that can rapidly penetrate cell plasma membranes. Once Calcein-AM is taken up into the cells, the ester bond can be quickly and irreversibly converted to hydrophilic, nonpermeable and intensively fluorescent free acid form, Calcein. When traversing the cell plasma membrane, Calcein-AM can be pumped out of the cells by P-gp. Inhibition of P-gp causes an increase in the cellular level of Calcein-AM and subsequently the appearance of fluorescent Calcein. Calcein AM uptake studies in P-gp expressing cells have been extensively used as a screening tool for P-gp inhibitors (Polli et ah, 2001). 

Other Names Calcein Blue AM, Calcein Blue acetoxymethyl ester CellTrace Calcein Blue AM Merck Index Number Not listed Chemical/Dye Class Coumarin... 

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