76-54-0

Usage

Uses

Used in Analytical Chemistry:
2',7'-DICHLOROFLUORESCEIN is used as a fluorescent probe for the determination of carbohydrates and hydrogen peroxide by fluorescence densitometry and chemiluminescence, respectively. This allows for sensitive and selective detection of these analytes in various samples.
Used in Biochemistry:
In biochemistry, 2',7'-DICHLOROFLUORESCEIN is used as an indicator for argentometry by the Fajans method, which is a technique for detecting and measuring the presence of silver ions in a solution.
Used in Cell Biology:
2',7'-DICHLOROFLUORESCEIN is used as a cellular antioxidant activity indicator, helping to assess the antioxidant capacity of cells and their ability to neutralize reactive oxygen species.
Used in Fluorescence and Laser Studies:
Due to its fluorescent properties, 2',7'-DICHLOROFLUORESCEIN is utilized as an additive in fluorescence and laser studies, contributing to the development of new fluorescent sensors and imaging techniques.
Used in Environmental and Biological Imaging:
A new fluorescent sensor for Cd2+ has been developed using 2',7'-DICHLOROFLUORESCEIN, which has potential applications in living cells imaging, as reported in Tetrahedron Lett. 2015, 56 (11), 1322-1327.
Used in Detection of Fluoride Ions:
2',7'-DICHLOROFLUORESCEIN has been employed in the colorimetric and fluorogenic signaling of fluoride ions, as described in Dyes Pigm. 2015, 112, 170-175, which can be useful in environmental monitoring and analysis.

Biological Activity

2',7'-dichlorofluorescein is an oxidation-sensitive fluorescent probe. 2′7′-dichlorofluorescein diacetate is oxidized to 2′7′-dichlorofluorescein in the presence of ROS (reactive oxygen species).

Biochem/physiol Actions

2′,7′-Dichlorofluorescein is an oxidation-sensitive fluorescent probe. 2′7′-dichlorofluorescein diacetate is oxidized to 2′7′-dichlorofluorescein in the presence of ROS (reactive oxygen species).

Upstream product

• 95-88-5 4-Chlororesorcinol 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 106070-31-9 2-(2,7-dichloro-3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid 
• 2044-85-1 2',7'-dichlorodihydrofluorescein diacetate 
• 108-46-3 recorcinol 
• 4091-99-0 2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid 
• 518-45-6 fluorescein free acid 
• 85-44-9 phthalic anhydride 

Downstream Products

• 2044-85-1 2',7'-dichlorodihydrofluorescein diacetate 
• 153753-60-7 2',7'-dichlorofluorescein ethoxycarbonylmethyl ester ethoxycarbonylmethyl ether 
• 1051906-87-6 2-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthene-9-yl)benzoic acid methyl ester 
• 1099599-99-1 O(Cl(OH)C₆HCH₂N(CH₃)CH₂C₆H₄B(OH)2)2CC₆H₄C(O)O 
• 719297-59-3 allyl 2-(6-(allyloxy)-2,7-dichloro-3-oxo-3H-xanthen-9-yl)benzoate 
• 2513-23-7 2'-Carboxy-5-chloro-2,4-dihydroxybenzophenone 
• 861669-90-1 2-[3,6-Bis-(2,2-dimethoxy-ethoxy)-2,7-dichloro-9H-xanthen-9-yl]-benzoic acid 
• 861669-89-8 2-[3,6-bis-(2,2-dimethoxyethoxy)-2,7-dichloro-9H-xanthen-9-yl]benzoic acid 2,2-dimethoxyethyl ester 

Relevant academic research and scientific papers

Regulative peroxidase activity of DNA-linked hemin by graphene oxide for fluorescence DNA sensing

The inhibition effect of graphene oxide toward the peroxidase activity of DNA-linked hemin was identified and conveniently utilized in the design of a homogenous fluorescence strategy for DNA sensing with high sensitivity. This journal is the Partner Organisations 2014.

Resveratrol-ZnO nanohybrid enhanced anti-cancerous effect in ovarian cancer cells through ROS

The use of nanotechnology in medicine and more specifically in drug delivery is expected to spread rapidly. Currently many substances are under investigation for drug delivery and more specifically for cancer therapy. Nano-conjugation of the drug is likely to provide protection against degradation, increasing bioavailability, and improvement in intracellular penetration, enhanced efficacy and control delivery of the drug. In this study, ZnO nanoparticles (NPs) conjugated with a well-known anti-proliferative and chemopreventive trans-resveratrol (RSV) has been designed, characterized and found to be a potential drug for ovarian cancer treatment. Nano-conjugate (RSV-ZnO) has been characterized by FTIR, Raman scattering and Transmission electron microscopy (TEM). Picosecond-resolved fluorescence studies of RSV-ZnO nano-conjugate reveal efficient electron migration from ZnO NPs to RSV, eventually enhancing the ROS activity compared to free RSV. Various in vivo and in vitro studies including MTT assay and apoptosis studies on ovarian cancer (PA1) cell lines reveals the RSV-ZnO nano-conjugate to be more effective in cancer cell death in comparison to free RSV. DCFH assay (in vitro) and DCFDA method (in vivo in PA1 cell lines) demonstrate the huge enhancement of antioxidant property (through ROS) in case of nano-conjugate. JC-1 staining method unravels the increase in depolarization of the mitochondrial membrane in the PA1 cell upon nano-conjugate, consistent with mitochondrial dysfunction. Finally we have performed a Western blot study by expression of some proteins like actin, Bax, Bcl-2 and Caspase-9 to confirm apoptosis.

Metal-binding and redox properties of substituted linear and cyclic ATCUN motifs

The amino-terminal copper and nickel binding (ATCUN) motif is a short peptide sequence found in human serum albumin and other proteins. Synthetic ATCUN-metal complexes have been used to oxidatively cleave proteins and DNA, cross-link proteins, and damage cancer cells. The ATCUN motif consists of a tripeptide that coordinates Cu(II) and Ni(II) ions in a square planar geometry, anchored by chelation sites at the N-terminal amine, histidine imidazole and two backbone amides. Many studies have shown that the histidine is required for tight binding and square planar geometry. Previously, we showed that macrocyclization of the ATCUN motif can lead to high-affinity binding with altered metal ion selectivity and enhanced Cu(II)/Cu(III) redox cycling (Inorg. Chem. 2013, 52, 2729-2735). In this work, we synthesize and characterize several linear and cyclic ATCUN variants to explore how substitutions at the histidine alter the metal-binding and catalytic properties. UV-visible spectroscopy, EPR spectroscopy and mass spectrometry indicate that cyclization can promote the formation of ATCUN-like complexes even in the absence of imidazole. We also report several novel ATCUN-like complexes and quantify their redox properties. These findings further demonstrate the effects of conformational constraints on short, metal-binding peptides, and also provide novel redox-active metallopeptides suitable for testing as catalysts for stereoselective or regioselective oxidation reactions.

Ruthenium-porphyrin complexes induce apoptosis by inhibiting the generation of intracellular reactive oxygen species in the human hepatoma cell line (HepG2)

Two ruthenium(II)-porphyrin complexes, [(3-Py)Ru(phen)2(tmopp)] [1; phen = phenanthroline, tmopp = 5,10,15,20-tetrakis(4-methoxyphenyl) porphyrin] and [(4-Py)Ru(phen)2(tmopp)] (2), have been synthesized and characterized for the first time. It was found that the two ruthenium(II)-porphyrin complexes show significant antitumor activity in HepG2 cells. Flow cytometric analysis showed that complex 1 arrested the cell cycle in the G0/G1 phase and induced apoptosis in HepG2 cells. Fluorescence microscopy and flow cytometric analyses demonstrated that the generation of intracellular reactive oxygen species (ROS) was significantly inhibited in cells treated with either complex. The total antioxidant capacity of the complexes was detected by a 2,2′-azinobis(3-ethylbenzthiazoline-6- sulfonic acid) (ABTS) assay; this showed that both complexes are good free-radical scavengers. Ruthenium(II)-porphyrin complex 1 also was found to scavenge hydroxy radicals, as measured by the Fenton system. These data demonstrate that ruthenium(II)-porphyrin complexes exhibit antioxidant properties, probably through the involvement of a direct scavenging effect on a hydroxy radical. Taken together, the findings show that ruthenium(II)-porphyrin complexes induce apoptosis in HepG2 cells by inhibiting the generation of ROS and are potential anticancer therapeutic agents.

G-quadruplex DNAzyme as the turn on switch for fluorimetric detection of genetically modified organisms

A novel fluorescent sensor for detection of genetically modified organisms was developed, and in the sensor G-quadruplex DNAzyme (G-quadruplex-hemin complex) was used as the turn on switch.

Pyrocatalytic oxidation-strong size-dependent poling effect on catalytic activity of pyroelectric BaTiO3nano- And microparticles

Pyrocatalysis is an emerging advanced oxidation process for wastewater remediation with the potential for thermal energy harvesting and utilization. Although several studies explored the potential of new pyrocatalyst materials to degrade harmful organic water pollutants, the role of important material properties and electric poling procedures on the pyrocatalytic activity is still unclear. In this work, we investigate the interdependence between particle size, electric poling and pyrocatalytic activity of BaTiO3 powders with nominal particle sizes of 100, 200 and 500 nm by using the dichlorofluorescein redox assay. Depending on the particle size, the influence of surface area or phase composition on the pyrocatalytic activity predominates. Moreover, we demonstrate that poling of pyrocatalysts leads to a strong size-dependent increase of pyrocatalytic activity. This poling effect increases with particle size up to +247% and can be explained with size-dependent changes in phase composition and domain structure. Combining all results, the progression of the pyrocatalytic activity as a function of particle size was derived and a future strategy for maximizing the catalytic performance of pyrocatalysts was developed. This study greatly improves the understanding about the role of important material properties and electric poling on pyrocatalytic activity, thus enabling an effective catalyst design. With the help of highly active catalysts, the pyrocatalytic process can take the next step in its development into a new and energy-efficient advanced oxidation process for water remediation.

Plasmonic Enhanced Reactive Oxygen Species Activation on Low-Work-Function Tungsten Nitride for Direct Near-Infrared Driven Photocatalysis

Realizing near-infrared (NIR) driven photocatalytic reaction is one of the promising strategies to promote the solar energy utilization and photocatalytic efficiencies. However, effective reactive oxygen species (ROS) activation under NIR irradiation remains to be great challenge for nearly all previously reported photocatalysts. Herein, the cubic-phase tungsten nitride (WN) with strong plasmonic NIR absorption and low-work function (≈3.59?eV) is proved to be able to mediate direct ROS activation by both of experimental observation and theoretical simulation. The cubic WN nanocubes (NCs) are synthesized via the hydrothermal-ammonia nitridation process and its NIR-driven photocatalytic properties, including photocatalytic degradation, hydroxylation, and de-esterification, are reported for the first time in this work. The 3D finite element simulation results demonstrate the size dependent and wavelength tuned plasmonic NIR absorption of the WN NCs. The NIR-driven photocatalytic mechanism of WN NCs is proposed based on density functional theory (DFT) calculated electronic structure and facet dependent O2 (or H2O) molecular activation, radicals scavenging test, spin trapped electron paramagnetic resonance measurements, and ultraviolet photoelectronic spectrum (UPS). Overall, the results in this work pave a way for the application of low-work-function materials as highly reactive NIR photocatalyst.

Phthalocyanine–Virus Nanofibers as Heterogeneous Catalysts for Continuous-Flow Photo-Oxidation Processes

The generation of highly reactive oxygen species (ROS) at room temperature for application in organic synthesis and wastewater treatment represents a great challenge of the current chemical industry. In fact, the development of biodegradable scaffolds to support ROS-generating active sites is an important prerequisite for the production of environmentally benign catalysts. Herein, the electrostatic cocrystallization of a cationic phthalocyanine (Pc) and negatively charged tobacco mosaic virus (TMV) is described, together with the capacity of the resulting crystals to photogenerate ROS. To this end, a novel peripherally crowded zinc Pc (1) is synthesized. With 16 positive charges, this photosensitizer shows no aqueous aggregation, and is able to act as a molecular glue in the unidimensional assembly of TMV. A step-wise decrease of ionic strength in mixtures of both components results in exceptionally long fibers, constituted by hexagonally bundled viruses thoroughly characterized by electron and confocal microscopy. The fibers are able to produce ROS in a proof-of-concept microfluidic device, where they are immobilized and irradiated in several cycles, showing a resilient performance. The bottom-up approach also enables the light-triggered disassembly of fibers after use. This work represents an important example of a biohybrid material with projected application in light-mediated heterogeneous catalysis.

Ti(IV) doping: An effective strategy to boost Lewis acidic performance of ZnO catalyst in fluorescein dye synthesis

Zn1-xTixO NPs were efficiently synthesized using a simple solution free mechanochemical method. The synthesized ZnO and Ti(IV)-doped ZnO catalysts are exhibited polycrystallinity, a hexagonal crystal structure, and roughly spherical agglomerates. The surface areas of the Zn1-xTixO catalysts were positively correlated with the doping percentage of Ti(IV), which also enhanced the Lewis acidity of the NPs. The catalysts exhibited excellent activity during the synthesis of fluorescein dyes. This methodology was also extended to sulfone-fluorescein dye synthesis.

Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging

Fluorogenic probes are invaluable tools for spatiotemporal investigations within live cells. In common fluorogenic probes, the intrinsic fluorescence of a small-molecule fluorophore is masked by esterification until entry into a cell, where endogenous esterases catalyze the hydrolysis of the masking groups, generating fluorescence. The susceptibility of masking groups to spontaneous hydrolysis is a major limitation of these probes. Previous attempts to address this problem have incorporated auto-immolative linkers at the cost of atom economy and synthetic adversity. Here, we report on a linker-free strategy that employs adventitious electronic and steric interactions in easy-to-synthesize probes. We find that X···C = O n→π? interactions and acyl group size are optimized in 2′,7′-dichlorofluorescein diisobutyrate. This probe is relatively stable to spontaneous hydrolysis but is a highly reactive substrate for esterases both in vitro and in cellulo, yielding a bright, photostable fluorophore with utility in biomolecular imaging.