Cayman Chemical | DAF-2 diacetate • 4,5-Diaminofluorescein diacetate (CAS 205391-02-2)

DAF-2 diacetate

Cayman Chemical Item Number 85165

4,5-Diaminofluorescein diacetate (CAS 205391-02-2)

DAF-2 diacetate (CAS 205391-02-2)

Synonyms

4,5-Diaminofluorescein diacetate

Formal Name

2-(3,6-diacetyloxy-4,5-diamino-9H-xanthen-9-yl)-benzoic acid

CAS Number

205391-02-2

Molecular Formula

C₂₄H₁₈N₂O₇

Formula Weight

446.4

Formulation

A solution in DMSO

Purity

>95%

Stability

1 year

Storage

-20°C

Shipping

WET ICE in continental US; may vary elsewhere

SMILES

CC(=O)Oc1ccc2c(Oc3c(N)c(ccc3C2c2ccccc2C(=O)O)OC(=O)C)c1N

Description

DAF-2 diacetate is a sensitive fluorescent indicator for the detection and bioimaging of nitric oxide (NO).^1,2 It is a cell-permeable derivative of DAF-2. Upon entry into the cell, DAF-2 diacetate is transformed into the less cell-permeable DAF-2 by cellular esterases thus preventing loss of signal due to diffusion of the molecule from the cell. In the presence of oxygen, DAF-2 reacts with NO to yield the highly fluorescent triazolofluorescein (DAF-2T). Fluorescence is monitored using excitation and emission wavelengths of 485 and 538 nm, respectively.² At neutral pH the detection limit for NO is 2-5 nM. DAF-2 diacetate can be utilized in cells which produce small amounts of NO, such as endothelial cells, as well as in cells which generate large amount of NO, such as macrophages.^1,2

1 Kojima, H., Sakurai, K., Kikuchi, K., et al. Development of a fluorescent indicator for nitric oxide based on the fluorescein chromophore. Chem Pharm Bull 46 373-375 (1998).

2 Nakatsubo, N., Kojima, H., Kikuchi, K., et al. Direct evidence of nitric oxide production from bovine aortic endothelial cells using new fluorescence indicators: Diaminofluoresceins. FEBS Lett 427 263-266 (1998).

Kojima, H., Sakurai, K., Kikuchi, K., et al. Development of a fluorescent indicator for nitric oxide based on the fluorescein chromophore. Chem Pharm Bull 46 373-375 (1998).

Nakatsubo, N., Kojima, H., Kikuchi, K., et al. Direct evidence of nitric oxide production from bovine aortic endothelial cells using new fluorescence indicators: Diaminofluoresceins. FEBS Lett 427 263-266 (1998).