126605-73-0Relevant articles and documents
NbCl5-Promoted Synthesis of Fluorescein Dye Derivatives: Spectroscopic and Spectrometric Characterization and Their Application in Dye-Sensitized Solar Cells
da Silva, Bruno Henrique Sacoman Torquato,Bregadiolli, Bruna Andressa,Graeff, Carlos Frederico de Oliveira,da Silva-Filho, Luiz Carlos
, p. 261 - 269 (2017)
Fluorescein has several applications owing to its properties, such as high molar absorptivity, high fluorescence quantum yield, high photostability, and wavelengths of absorption and emission in the visible region. The syntheses of fluorescein derivatives between phenol and anhydride derivatives by using NbCl5 as a Lewis acid is described. The products have high yields and short reaction times are observed. The study of the UV/Vis and fluorescence spectra of these derivatives and their application in dye-sensitized solar cells is also described.
Molecular-level understanding of the photocatalytic activity difference between anatase and rutile nanoparticles
Kim, Wooyul,Tachikawa, Takashi,Moon, Gun-Hee,Majima, Tetsuro,Choi, Wonyong
, p. 14036 - 14041 (2014)
The generation of oxidants on illuminated photocatalysts and their participation in subsequent reactions are the main basis of the widely investigated photocatalytic processes for environmental remediation and selective oxidation. Here, the generation and the subsequent diffusion of ·OH from the illuminated TiO2 surface to the solution bulk were directly observed using a single-molecule detection method and this molecular phenomenon could explain the different macroscopic behavior of anatase and rutile in photocatalysis. The mobile ·OH is generated on anatase but not on rutile. Therefore, the photocatalytic oxidation on rutile is limited to adsorbed substrates whereas that on anatase is more facile and versatile owing to the presence of mobile ·OH. The ability of anatase to generate mobile COH is proposed as a previously unrecognized key factor that explains the common observations that anatase has higher activity than rutile for many photooxidative reactions.
The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides
Chen, Wei,Rosser, Ethan W.,Matsunaga, Tetsuro,Pacheco, Armando,Akaike, Takaaki,Xian, Ming
, p. 13961 - 13965 (2015)
Endogenous hydrogen polysulfides (H2Sn; n>1) have been recognized as important regulators in sulfur-related redox biology. H2Sn can activate tumor suppressors, ion channels, and transcription factors with higher potency than H2S. Although H2Sn are drawing increasing attention, their exact mechanisms of action are still poorly understood. A major hurdle in this field is the lack of reliable and convenient methods for H2Sn detection. Herein we report a H2Sn-mediated benzodithiolone formation under mild conditions. This method takes advantage of the unique dual reactivity of H2Sn as both a nucleophile and an electrophile. Based on this reaction, three fluorescent probes (PSP-1, PSP-2, and PSP-3) were synthesized and evaluated. Among the probes prepared, PSP-3 showed a desirable off/on fluorescence response to H2Sn and high specificity. The probe was successfully applied in visualizing intracellular H2Sn.
Extremely selective fluorescence detection of cysteine or superoxide with aliphatic ester hydrolysis
Murale, Dhiraj P.,Kim, Hwajin,Choi, Wan Sung,Kim, Youngsam,Churchill, David G.
, p. 46513 - 46516 (2014)
A novel fluorescence probe modality demonstrated with fluorescein affords a highly selective aqueous-based detection of cysteine over other biothiols, e.g. homocysteine, with a limit of detection of 11.3 μM.
Combinatorial Strategy to Identify Fluorescent Probes for Biothiol and Thiophenol Based on Diversified Pyrimidine Moieties and Their Biological Applications
Xie, Xilei,Li, Mengmeng,Tang, Fuyan,Li, Yong,Zhang, Leilei,Jiao, Xiaoyun,Wang, Xu,Tang, Bo
, p. 3015 - 3020 (2017)
We present a feasible paradigm of developing original fluorescent probes for target biomolecules via combinatorial chemistry. In this developmental program, pyrimidine moieties were investigated and optimized as unique recognition units for thiols for the first time through a parallel synthesis in combination with a rapid screening process. This time-efficient and cost-saving process effectively facilitated the developmental progress and provided detailed structure-reactivity relationships. As a result, Res-Biot and Flu-Pht were identified as optimal fluorescent probes for biothiol and thiophenol, respectively. Their favorable characteristics and superior applicability have been well demonstrated in both chemical and biological contexts. In particular, Res-Biot enables the direct visualization of biothiol fluctuations during oxidative stress and cell apoptosis, indicating its suitability in elucidation of a specific pathophysiological process in both living cells and living animals. Meanwhile, Flu-Pht is competent to visualize thiophenols without the interference from endogenous biothiols in living cells.
Effect of solvent-water mixtures on the prototropic equilibria of fluorescein and on the spectral properties of the monoanion
Klonis, Nectarios,Sawyer, William H.
, p. 179 - 185 (2000)
A spectral resolution procedure was used to resolve the absorption, excitation and emission spectra of the fluorescein monoanion in a number of solvent-water mixtures. This permitted an analysis of the effect of the solvent environment on the spectral properties of the monoanion and on the lactone/monoanion/dianion transitions of fluorescein. The monoanion excitation and emission spectra show relatively small changes with changing environment, a behavior that is related to the hydrogen-bonding environment of the solvent-water mixtures. There is also a general increase in the quantum yield of the monoanion from 0.36 in water to values up to 0.49 in the solvent-water mixtures. The presence of solvent also results in a general increase in the lactone content and in the monoanion:dianion and lactone:monoanion ratios. General polarity effects alone cannot account for the observed effects on the prototropic transitions indicating that specific solute-solvent effects involving hydrogen bonding perturb the prototropic equilibria of fluorescein.
Tetrazine-Responsive Self-immolative Linkers
Neumann, Kevin,Jain, Sarthak,Gambardella, Alessia,Walker, Sarah E.,Valero, Elsa,Lilienkampf, Annamaria,Bradley, Mark
, p. 91 - 95 (2017)
Molecules that undergo activation or modulation following the addition of benign external small-molecule chemical stimuli have numerous applications. Here, we report the highly efficient “decaging” of a variety of moieties by activation of a “self-immolative” linker, by application of water-soluble and stable tetrazine, including the controlled delivery of doxorubicin in a cellular context.
Chemistry of the carboxylic acid of dihydrofluorescein in oxidation and its application to fluorogenic ROS sensing
Le, Hoa Thi,Nguyen, Dinh Phi Long,Shin, Hyo Seob,Jung, Woong,Kang, Chulhun,Kim, Tae Woo
, p. 461 - 468 (2021)
The conjugation site of dihydrofluorescein (H2F) is important for the rational design of H2F-based reactive oxygen species (ROS) sensors. Despite the prevalence of H2F analogs detecting cellular ROS, the role of the carboxylic acid of H2F in oxidation is still unclear. To get insight into the conjugation site of H2F, we synthesized H2F diacetate (2) and its amide derivative (3). The absorption and emission spectra of deacetylated 2 and 3 in the presence of H2O2/hematin showed that the carboxylic acid of H2F plays a crucial role in the oxidation of H2F. NMR and HPLC analysis of the oxidation product of deacetylated 3 showed a quantitative and fast generation of non-fluorescent spirolactam (F-Lactam). As regards these observations, we untouched the carboxylic acid at the 3rd position and designed an H2F-based ROS sensor (7) that conjugated the lipophilic chain at the 5th position instead. A series of confocal microscopic experiments of 7 demonstrated that 7 prefers the ER location and that ROS are elevated in the cells by ER stress inducers.
H2S donors with optical responses
Pluth, Michael D.,Zhao, Yu,Cerda, Matthew M.
, p. 149 - 164 (2020)
Reactive sulfur species, including hydrogen sulfide (H2S), are important biological mediators and play key roles in different pathophysiological conditions. Small molecules that release H2S on demand, often referred to as “H2S donors,” constitute a key investigative tool for H2S-related research. A significant challenge, however, is correlating the rate of H2S release from such donors in complex systems with biological outcomes, because release rates are commonly perturbed by different biological environments. In this chapter, we outline an approach to use H2S donors that provide a fluorescent response upon H2S release to address this problem. These compounds leverage the intermediate release of carbonyl sulfide (COS), which is quickly converted to H2S by the endogenous enzyme carbonic anhydrase (CA), to provide activatable donors with an optical response. The described donors are activated by biological thiols and provide a fluorescence response that correlates directly with H2S delivery, which allows for delivered H2S levels to be measured in real time by fluorescence techniques.
Thermogravimetric and differential thermal analyses of fluorescein dye in inert and static air atmosphere
Arshad, Muhammad,Masud, Khalid,Saeed, Aamer,Qureshi, Ammad Hussain,Shabir, Ghulam
, p. 1385 - 1390 (2018)
Fluorescein dye was prepared and characterized on the basis of microanalytical methods, FTIR, NMR and UV–visible spectroscopy in order to ensure its purity. Thermoanalytical study by TG, DTA and DTG was conducted in air as well as in inert atmosphere to determine the mode of decomposition and stability. The dye follows two-step and three-step decomposition pattern in air and nitrogen, respectively. The first stage of decomposition in both environments yields carbon monoxide and oxygen, whereas carbon monoxide and acetylene are the common products of second-stage decomposition except anthracene which is released only in air. The third step evolves ketene and acetylene under inert condition and the residue (observed at 1133?K) is a highly conjugated cyclic system. Char is the only residue which is identified at the end of decomposition under air after 893?K. The intermediates formed during the decomposition processes were also investigated. A possible mechanism of the thermal decomposition is proposed depending on pyrolysis, MS and IR spectral data.
Fluorescein as a Visible-Light-Induced Oxidase Mimic for Signal-Amplified Colorimetric Assay of Carboxylesterase by an Enzymatic Cascade Reaction
Liu, Li,Sun, Chaoqun,Yang, Juan,Shi, Ying,Long, Yijuan,Zheng, Huzhi
, p. 6148 - 6154 (2018)
We have found that fluorescein possesses high visible-light-induced oxidase mimetic activity and could transform colorless 3,3′,5,5′-tetramethylbenzidine (TMB) into blue oxidized TMB (oxTMB) without unstable and destructive H2O2 under visible-light illumination. Instead, fluorescein uses oxygen as a mild and green electron acceptor, and its activity can be easily controlled by the switching “on/off” of visible light. In addition, the visible-light-induced catalytic mechanism was elucidated in detail and, as the main reactive species h+ and O2.? accounted for TMB oxidation. Based on the fact that fluorescein diacetate (FDA) possessed no activity and generated active fluorescein in situ in the presence of carboxylesterase (CaE), a signal-amplified sensing platform through a cascade reaction for CaE detection was constructed. Our proposed sensing system displayed excellent analytical performance for the detection of CaE in a wide linear range from 0.040 to 20 U L?1 with a low detection limit of 0.013 U L?1. This work not only changes the conventional concept that fluorescein is generally considered to be photocatalytically inert, but also provides a novel sensing strategy by tailoring the enzyme mimetic activity of fluorescein derivatives with analyte.
Synthesis and evaluation of intrinsic bioactivity of fluorescein and phenolphthalein derivatives
Bharathkumar, Kuruba,Durairaj, Arulappan,Mohanapriya, Raman,Obadiah, Asir,Ramanathan, Subramanian,Santhoshkumar, Palanichamy,Vasanthkumar, Samuel
, (2021/09/28)
Fluorescein and phenolphthalein derivatives have been synthesized and screened for their bioactivity via molecular docking, cytotoxicity and antioxidant studies. In molecular docking studies, the compounds 3d have exhibited better glide score and hydrogen bonding ability when docked with t-RNA Dimethylallyltransferase. Antioxidant capabilities were evaluated via DPPH and ABTS radical scavenging activity. In this screening, compound 3d exhibited better inhibition efficiency in the DPPH and ABTS methods. Cytotoxicity of the compounds was assessed by the cell sustainability assay against human cervical cancer cell line (HeLa). All the synthesized compounds exhibited cytotoxic effects against HeLa cells and compounds 3d displayed better activity (IC50) than the standard drug (doxorubicin).
