195136-58-4

Basic information

• Product Name: 2',7'-DIFLUOROFLUORESCEIN
• Synonyms: OREGON GREEN(TM) 488;2',7'-DIFLUOROFLUORESCEIN;2',7'-Difluoro-3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one;2',7'-Difluoro-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
• CAS NO: 195136-58-4
• Molecular Formula: C₂₀H₁₀F₂O₅
• Molecular Weight: 368.29
• Mol File: 195136-58-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 591.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.70±0.1 g/cm3(Predicted)
• Solubility: Insoluble in water; soluble in N,Ndimethylformamide
• PKA: 4.8, (at 22℃);4.7, (at 22℃)
• CAS DataBase Reference: 2',7'-DIFLUOROFLUORESCEIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2',7'-DIFLUOROFLUORESCEIN(195136-58-4)
• EPA Substance Registry System: 2',7'-DIFLUOROFLUORESCEIN(195136-58-4)

Safety Data

• Hazardous Substances Data: 195136-58-4(Hazardous Substances Data)

Usage

Description

2',7'-Difluorofluorescein is a synthetic organic compound characterized by the presence of two fluorine atoms at the 2' and 7' positions of the fluorescein molecule. It exhibits unique fluorescent properties and is widely utilized in various scientific and industrial applications due to its chemical and optical characteristics.

Uses

Used in Biomedical Research:
2',7'-Difluorofluorescein is used as a reactant for the synthesis of biarsenical probes, which are essential tools in biomedical research. These probes play a crucial role in inhibiting protein tyrosine phosphatases, a class of enzymes that regulate various cellular processes, including signal transduction and cell growth. By employing 2',7'-difluorofluorescein in the development of these probes, researchers can study the functions and interactions of protein tyrosine phosphatases in detail, contributing to a better understanding of their roles in health and disease.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2',7'-difluorofluorescein serves as a valuable starting material for the creation of various fluorescent dyes and markers. Its unique chemical structure allows for the development of novel compounds with enhanced properties, such as increased brightness, improved photostability, and altered emission spectra. These synthesized dyes and markers find applications in a range of areas, including cell biology, molecular diagnostics, and environmental monitoring.
Used in Analytical Techniques:
2',7'-Difluorofluorescein is also employed in various analytical techniques, such as high-performance liquid chromatography (HPLC) and capillary electrophoresis (CE), as a fluorescence marker. Its distinct fluorescent properties enable the sensitive and selective detection of target molecules, making it an invaluable tool for the analysis of complex biological samples and the identification of specific compounds.

Upstream product

• 85-44-9 phthalic anhydride 
• 103068-41-3 4-fluororesorcinol 

Downstream Products

• 913689-08-4 2-(2,7-difluoro-3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid 
• 827020-43-9 bis(2,4-dinitrobenzenesulfonyl)-2',7'-difluorofluorescein 

Relevant articles and documents

Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif

Specialized cellular networks of oxidoreductases coordinate the dithiol/disulfide-exchange reactions that control metabolism, protein regulation, and redox homeostasis. For probes to be selective for redox enzymes and effector proteins (nM to μM concentrations), they must also be able to resist non-specific triggering by the ca. 50 mM background of non-catalytic cellular monothiols. However, no such selective reduction-sensing systems have yet been established. Here, we used rational structural design to independently vary thermodynamic and kinetic aspects of disulfide stability, creating a series of unusual disulfide reduction trigger units designed for stability to monothiols. We integrated the motifs into modular series of fluorogenic probes that release and activate an arbitrary chemical cargo upon reduction, and compared their performance to that of the literature-known disulfides. The probes were comprehensively screened for biological stability and selectivity against a range of redox effector proteins and enzymes. This design process delivered the first disulfide probes with excellent stability to monothiols yet high selectivity for the key redox-Active protein effector, thioredoxin. We anticipate that further applications of these novel disulfide triggers will deliver unique probes targeting cellular thioredoxins. We also anticipate that further tuning following this design paradigm will enable redox probes for other important dithiol-manifold redox proteins, that will be useful in revealing the hitherto hidden dynamics of endogenous cellular redox systems.

Fluorinated xanthene derivatives

The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.