Carboxyfluorescein diacetate

CA Index Name Spiro[isobenzofuran-l(3H),9 -[9H]xanthene]-5-carboxylic acid,3, 6 - (acetyloxy)-3-0X0- 

CAS Registry Number 79955-27-4 Merck Index Number Not listed Chemical Structure 

Chemical/Dye Class Huorescent, Xanthene Molecular Formula C25H16O9 Molecular Weight 460.39 pH Range 6.0-7.2 

Color Change at pH Weak green fluorescence (6.0) to strong green fluourescence (7.2) pKa 6.4 

Solubility Insoluble in water soluble in dimethyl sulfoxide UV-Visible (Xmax) 300 nm Melting Point 250°C 

Solubility Soluble in acetonitrile, chloroform, N,N-dimethylformamide, dimethyl sulfoxide, methanol 

Industrial Applications Not reported Safety/Toxicity Hepatotoxicity ploem mobility of xenobiotics retinal toxicity  

Sabnis, R. W. Handbook of Acid-base Indicators, CRC Press Boca Raton, 2008 pp 70-71. 

Mattingly, P. G. 5(6)-Methyl substituted fluorescein derivatives. PCT Int. Appl. WO 9320060,1993. 

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Breeuwer, P., Drocourt, J. L, Bunschoten, N., Zwietering, M. H., Rombouts, F. M. and Abee, T. Characterization of uptake and hydrolysis of fluorescein diacetate and carboxyfluorescein diacetate by intracellular esterases in Saccharomyces cerevisiae, which result in accumulation of fluores-... 

Permeabilization with carboxyfluorescein-diacetate. 6-carboxy-fluorescein-diacetate (CFDA) is a nonfluorescent, nonpolar reagent which enters the cell freely, where it becomes entrapped following enzymatic conversion to the hydrophilic fluorophore 6-carboxyfluorescein (CF, mw 370). Thus, labeled cells can then be replated onto unlabeled test cells to measure dye transfer via gap junction. This method has been successfully used to measure gap junction communication in early embryo cells (Goodall and Johnson, 1982 Kidder et al., 1987), and also to label tumor cells in culture (Price et al., 1995). We tried to extrapolate it for detection of gap junction formation among cultured cells. 

Goodall, H. and Johnson, M. H. (1982). Use of carboxyfluorescein diacetate to study formation of permeable channels between mouse blastomeres. Nature 295, 524-526. 

Esterase substrates have long been used as a measure of cell membrane integrity, with the fluorescent product being the marker retained. The one that has been used most often with fish cell lines is 5-carboxyfluorescein diacetate acetoxymethyl ester (CFDA-AM)174 CFDA-AM diffuses into cells rapidly and is converted by... 

Schirmer K, Herbrick JS, Greenberg BM, et al. 1997. An evaluation of the cytotoxicity and photocytotoxicity of intact and photomodified creosote through the use of a rainbow trout gill cell line, TRGILL-W1, and two flourescent indicator dyes, alamar blue and 5-carboxyfluorescein diacetate acetoxymethyleste. Can Tech Rep Fish Aquat Sci 2192 4. 

Symplasmic communication within explant cells during the initiation and development of somatic embryos was not intensively studied. Analysis of the distribution of CFDA (fluorescent tracer 5-(and-6) Carboxyfluorescein Diacetate) during the DSE in Arabidcrpsis explants showed the presence of the fluorochrome only in the protodermis and subprotodermis of the explants, indicating that the downregulation of plasmodesmata connection within an explant took place (Kurczyhska et al., 2007). 

Other Names Spiro[phthalan-l,9 -xaiithene]-6-carboxylic acid, 3, 6 -dihydroxy-3-oxo-, diacetate Terephthalic acid, (3,6,9-trihydroxyxantheii-9-yl)-, y-lactone, diacetate 6-Carboxyfluorescein diacetate... 

Other Names Spiro[isobenzofuran-l(3H),9 -[9H]xaiithene], 2,5-pyrrolidinedione derivative 5-(6)-Carboxyfluorescein diacetate succinimidyl ester CA Index Name 2,5-Pyrrolidinedione, l-[[[3, 6 -to(acetyloxy)-3-oxospiro-[isobenzofuran-l(3H), 9 -[9H]xanlhen]-5(or 6)-yl]carbonyl]oxy]-CAS Registry Number 150347-59-4 Merck Index Number Not listed Chemical Structure... 

De St Groth, B. F. Smith, A. L. Koh, W. Gitgis, L. Cook, M. C. Bertohno, R Carboxyfluorescein diacetate succinimidyl ester and the virgin lymphocyte a marriage made in heaven. Immunol. Cell Biol. 1999, 77, 530-538. 

Wang, X. Duan, X. Liu, L. Fang, Y. Tan, Y. Carboxyfluorescein diacetate succinimidyl ester fluorescent dye for cell labeling. Acta Biochim, Biophys. Sinica 2005,37, 379-385. 

Intracellular and cell surface Carboxyfluorescein diacetate Binds to both intracellular and cell surface proteins by reacting Fluorescence... 

The viability of cells is testable by using fluorescent esters, such as 6-carboxyfluorescein diacetate, which are non-fluorescent and which (being non-polar) can pass through the cell membrane. Inside the cell, the ester is hydrolysed to release the free fluorescent anion (6-carboxyfluorescein), which, if the membrane is intact, accumulates inside the cell. Fluorescence is also widely used to demonstrate the ramifications of nerve cells, by injection or takeup of fluorochromes into or by living cells. 

CA Index Name Spiro[isobenzofuran-l(3//),9 -[9//] xanthene]-5-carboxylic acid, 3, 6 -bis(acetyloxy)-3-oxo-Other Names 5-Carboxyfluorescein diacetate 5-CFDA Merck Index Number Not listed Chemical/Dye Class Xanthene Molecular Formula C25H16O9 Molecular Weight 460.39 Physical Form Colorless solid... 

Davenpeck, K. L. Chrest, F. J. Sterbinsky, S. A. Bickel, C. A. Bochner, B. S. Carboxyfluorescein diacetate labeling does not affect adhesion molecule expression or function in human neutrophils or eosinophils. J. Immunol. Methods 1995,188, 79-89. 

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