Specifications
- Purity
- ≥97% (NMR)
- Appearance
- White to light yellow powder
- Identity
- 1H-NMR
- Residual Solvent
- contains 10% acetic acid
Properties
- Solvents
- Soluble in DMSO or DMF.
- Density
- 1.54 g/cm3 (predicted)
Category: Fluorescent Detection, Fluorescent Detection
2′,7′-Difluorofluorescein, also called Oregon Green 488 (OG488) dye is a bright, green-fluorescent dye with excitation ideally suited to the 488 nm laser line and useful for fluorescent labeling. It has a high extinction coefficient and fluorescence quantum yield and while it is pH insensitive in the physiological range, with a pKa of 4.6 it can be used to as a fluorescent indicator for intracellular pH and monitor pH changes in acidic organelles or pathways. OG488 is a fluorinated analog of fluoresceins. The absorption and emission spectra of OG488 perfectly match those of fluorescein. Because of the near match of the absorption maxima on proteins (~498 nm and ~512 nm) to the strong 488 nm and 514 nm spectral lines of the argon-ion laser, the Oregon Green 488 fluorphore is an important dye for both confocal laser-scanning microscopy and flow cytometry applications. Conjugates of OG488 are more photostable than those of fluorescein, allowing increased acquisition of photons before photodestruction of the dye and making it particularly a useful substitute for fluoresceins for fluorescence imaging applications. OG488 has a lower pKa (pKa = 4.7 versus 6.4 for fluorescein), making the fluorescence essentially pH insensitive in the physiological pH range. However, the pH sensitivity in the weakly acidic range (pH 4 to 6) also makes the dye useful as pH indicators for acidic organelles of live cells. This cell-permeable non-fluorescent 2′,7′-Difluorofluorescein diacetate is cleaved by cellular esterases and oxidation, and converted to the highly fluorescent 2′,7′-Difluorofluorescein.
Synonyms | DFFDA, Oregon Green 488 DA, OG488 DA |
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Purity | ≥97% (NMR) |
Appearance | White to light yellow powder |
CAS-Number | 1027558-93-5 |
Molecular Formula | C24H14F2O7 |
Molecular Weight | 452.361 |
Identity | 1H-NMR |
Solvents | Soluble in DMSO or DMF. |
Density | 1.54 g/cm3 (predicted) |
Smiles | O=C(O1)C2=C(C=CC=C2)C31C4=C(C=C(OC(C)=O)C(F)=C4)OC5=CC(OC(C)=O)=C(F)C=C53 |
InChi Key | GVSQJSHJJCMOGU-UHFFFAOYSA-N |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | -20°C |
Handling Advice | Protect from light and moisture. |
Use / Stability | Stable for at least 2 years after receipt when stored at -20°C. |
Transportation | Not dangerous goods |
References | (1) A. Orte, et al., J. Phys. Chem. A 109, 734 (2005), (2) A. Orte, et al., J. Phys. Chem. A 109, 2840 (2005), (3) Y. Hama, et al., Bioconjug. Chem. 17, 1426 (2006), (4) J. Han & K. Burgess, Chem. Rev. 110, 2709 (2010), (5) R.W. Sabnis, Handbook of Fluorescent Dyes and Probes 297 (2015) |
InChi | InChI=1S/C24H14F2O7/c1-11(27)30-21-9-19-15(7-17(21)25)24(14-6-4-3-5-13(14)23(29)33-24)16-8-18(26)22(31-12(2)28)10-20(16)32-19/h3-10H,1-2H3 |
Quantity | 100 mg, Bulk |
cdx-Residual Solvent | contains 10% acetic acid |