14899-08-2Relevant articles and documents
Activation of fluorescence of lactone forms of rhodamine dyes by photodehydrogenation of aryl(hetaryl)pyrazolines
Traven,Dolotov,Ivanov
, p. 735 - 740 (2016)
Aryl(hetaryl)pyrazolines are effective photogenerators of acid providing an irreversible photochemical activation of fluorescence of rhodamine group dyes. The effect of solvent on two consecutive reactions, photodehydrogenation of pyrazoline and lactone ring opening of the dye was studied. An increase in solvent polarity leads to an increase in the rate of both reactions by different degrees. The systems under study are believed to be promising for the formation of recording media for multilayer optical file type disks of ultrahigh data storage capacity with fluorescent readout.
An unprecedented strategy for selective and sensitive fluorescence detection of nitric oxide based on its reaction with a selenide
Sun, Chengdong,Shi, Wen,Song, Yanchao,Chen, Wei,Ma, Huimin
, p. 8638 - 8640 (2011)
A new strategy that utilizes the interaction between NO and a selenide is reported for fluorescence detection of NO, in which rhodamine B selenolactone serves as a model selenide. The Royal Society of Chemistry 2011.
Erythromycin A as a Supramolecular Catalyst: Effect on Rhodamine B Lactonization
Barra, Monica,Cosa, Juan Jose,Rossi, Rita H. de
, p. 5850 - 5853 (1990)
The intramolecular lactonization reaction of rhodamine B base in chloroform solution is remarkably accelerated by the antibiotic erythromycin A.The rate increases by a factor of ca. 1010, a value significantly higher than typical enzymatic factors.This effect is ascribed to the formation of a host-guest complex between the dye and the antibiotic, a process that induces a conformational change conducive to the rehybridization of the central carbon atom of the dye.
Aspectroscopic/thermodynamic study of the rhodamine B lactone ->/<- zwitterion equilibrium
Hinckley, Daniel A.,Seybold, Paul G.
, p. 1053 - 1060 (1988)
Temperature dependences of the visible absorption spectra of rhodamine B (RB) in water and 18 alcohol solvents have been examined and utilized to estimate thermodynamic parameters (ΔG0, ΔH0, ΔS0) for the RB lactone->///3/mol*cm is estimated.The thermodynamic results suggest that the position of the RB L ->/- Z equilibrium is strongly influenced by self-association of the solvent.The position of the equilibrium in aliphatic alcohols can be predicted from the simple features of the solvent molecules.Consequences of the results regarding calculation of the natural radiative lifetime of the fluorescent state from absorption spectrum are discussed.
Imaging different interactions of mercury and silver with live cells by a designed fluorescence probe rhodamine b selenolactone
Shi, Wen,Sun, Shuna,Li, Xiaohua,Ma, Huimin
, p. 1206 - 1210 (2010)
Rhodamine B selenolactone has been designed, synthesized, and characterized as a new fluorescent probe for imaging both Hg2+ and Ag+ in live cells to better understand their distinct toxicities to organisms. The probe is designed based on the fact that selenium has a strong affinity for mercury and silver, and is constructed by incorporating a Se atom into the spirocyclic structure of rhodamine. It exhibits a rapid and specific spectroscopic off-on response to Hg2+ and Ag+ instead of other species, with detection limits of 23 nM Hg2+ and 52 nM Ag +. Moreover, the probe is membrane-permeable, and can react with Ag+ even in the presence of Cl- because of the higher affinity of Se than Cl- for Ag+, which makes it of potential use for imaging not only Hg2+ but also Ag+ in live cells. This applicability has been demonstrated by imaging Hg2+ and Ag+ in Hela cells. It is observed that the reaction of Ag + with the probe inside the cells occurs much slower than that of Hg2+, which is ascribed to the high concentration of cellular chloride ions inhibiting the formation of sufficient free Ag+. The present finding is helpful to get an insight into the different interaction mechanism of Hg2+ and Ag+ with cells, and more applications of the probe may be expected for studying the behaviors of Hg 2+ and Ag+ in various biosystems.
A selenolactone-based fluorescent chemodosimeter to monitor mecury/methylmercury species in vitro and in vivo
Chen, Xiaoqiang,Baek, Kyung-Hwa,Kim, Youngmee,Kim, Sung-Jin,Shin, Injae,Yoon, Juyoung
, p. 4016 - 4021 (2010)
A fluorescent probe based on selenolactone displays unique fluorescence enhancement and UV-vis spectral change for mercury/methylmercury species, which were attributed to deselenation reaction. The value of this system was successfully demonstrated by its use in detecting inorganic mercury/methylmercury species in cells and zebrafish.
Dual signaling of thallium(III) ions via oxidative cleavage of a sulfonhydrazide linkage
Ahn, Sangdoo,Chang, Suk-Kyu,Choi, Myung Gil,Lee, Yu Jeong,Park, Tae Jung,Yoo, Jae Hoon
, (2020)
The thallium is widely used in various research and industrial applications but is very toxic. In this work, we developed a novel reaction-based dual signaling probe for the selective and sensitive determination of Tl3+ via the oxidative cleavage of a rhodamine–dansylhydrazide conjugate. The designed probe showed pronounced colorimetric and fluorescence signaling behavior toward Tl3+ with a detection limit of 1.3 × 10–7 M (0.027 ppm), as well as selectivity over other common metal ions, anions, and oxidants. The Tl3+ signaling process required less than 2 min and was not influenced by the solution pH within the range of 4.0–5.5; however, the signal diminished significantly above pH 6.0. To demonstrate the practical applicability of the designed probe, a simple and convenient colorimetric assay for the determination of Tl3+ in commercial reagents was established using an office scanner as a readily available signal capturing device.
Ratiometric Signaling of Hypochlorite by the Oxidative Cleavage of Sulfonhydrazide-Based Rhodamine-Dansyl Dyad
Lee, Hyo Jin,Cho, Min Jeoung,Chang, Suk-Kyu
, p. 8644 - 8649 (2015)
(Figure Presented). A reaction-based probe 1 for hypochlorite signaling was designed by the conjugation of two fluorophores, rhodamine and dansyl moieties, by the reaction of rhodamine B base with dansylhydrazine. Probe 1 exhibited pronounced hypochlorite-selective chromogenic and fluorescent signaling behavior over other oxidants used in practical applications, such as hydrogen peroxide, peracetic acid, and ammonium persulfate, as well as commonly encountered metal ions and anions. Signaling was attributed to the hypochlorite-induced oxidative cleavage of the sulfonhydrazide linkage of the probe. In particular, favorable ratiometric fluorescence signaling was possible by utilizing the emissions of the two fluorophores. A detection limit of 1.13 × 10-6 M (0.058 ppm) was estimated for the determination of hypochlorite. A paper-based test strip was prepared and was used as a semiquantitative indicator for the presence of hypochlorite in aqueous solutions. The probe was also successfully applied for the determination of hypochlorite in practical tap water samples.
Pressure Effects on Equilibrium between Lactone and Zwitterion Forms of Rhodamine B in Primary Alcohols
Sueishi, Yoshimi,Sugiyama, Yukie,Yamamoto, Shunzo,Nishimura, Norio
, p. 572 - 574 (1994)
The equilibrium between lactone and zwitterion forms of Rhodamine B was studied in primary alcohols and at high pressures.The effects of solvent polarity and pressure on the equilibrium constant were examined by using a Kirkwood-type equation.
A Fluorogenic ONOO--Triggered Carbon Monoxide Donor for Mitigating Brain Ischemic Damage
Chen, Xiaohua,Guo, Xinjian,Li, Jin,Lu, Xicun,Luo, Xiao,Qi, Suhua,Qian, Xuhong,Sun, Haitao,Sun, Zhenrong,Wang, Bin,Xing, Linfeng,Yang, Youjun
, (2022/02/10)
Ischemia-reperfusion (I/R) injuries are from the secondary radicals of ONOO-. Direct radical scavenging is difficult because of their high reactivity. ONOO- is longer-lived than the radicals in the biological milieu. Scavenging ONOO- suppresses radical generation preventively. CO is neuroprotective during ischemia. With the scaffold of carbon-caged xanthene, we designed an OONO-triggered CO donor (PCOD585). Notably, PCOD585 exhibited a concomitant fluorescence turn-on upon ONOO-detection, facilitating microscopic monitoring. PCOD585 was cytoprotective in oxygen-glucose deprivation (OGD)-insulted PC-12 cells. It was permeable to the blood-brain barrier and further exhibited neuroprotective effects to MCAO rats by reducing infarction volume, cell apoptosis, and brain edema.
