5809-23-4Relevant academic research and scientific papers
A rhodol-based fluorescent chemosensor for hydrazine and its application in live cell bioimaging
Tiensomjitr, Khomsan,Noorat, Rattha,Wechakorn, Kanokorn,Prabpai, Samran,Suksen, Kanoknetr,Kanjanasirirat, Phongthon,Pewkliang, Yongyut,Borwornpinyo, Suparerk,Kongsaeree, Palangpon
, p. 228 - 233 (2017)
A rhodol cinnamate fluorescent chemosensor (RC) has been developed for selective detection of hydrazine (N2H4). In aqueous medium, the rhodol-based probe exhibited high selectivity for hydrazine among other molecules. The addition of hydrazine triggered a fluorescence emission with 48-fold enhancement based on hydrazinolysis and a subsequent ring-opening process. The chemical probe also displayed a selective colorimetric response toward N2H4 from colorless solution to pink, readily observed by the naked eye. The detection limit of RC for hydrazine was calculated to be 300?nM (9.6?ppb). RC is membrane permeable and was successfully demonstrated to detect hydrazine in live HepG2 cells by confocal fluorescence microscopy.
Rhodol-based fluorescent probes for the detection of fluoride ion and its application in water, tea and live animal imaging
Jin, Xilang,Gao, Jingkai,Wang, Ting,Feng, Wan,Li, Rong,Xie, Pu,Si, Lele,Zhou, Hongwei,Zhang, Xianghan
, (2020)
Herein, we presented two novel turn-on colorimetric and fluorescent probes based on a F? triggered Si[sbnd]O bond cleavage reaction, which displayed several desired properties for the quantitative detection for F?, such as high specificity, rapid response time (within 3 min) and naked-eye visualization. The fluorescence intensity at 574 nm (absorbance at 544 nm) of the solution was found to increase linearly with the concentration of F? (0.00–30.0 μM) with the detection limit was estimated to be 0.47 μM/0.48 μM. Based on these excellent optical properties, the probes were employed to monitor F? in real water samples and tea samples with satisfactory. Furthermore, it was successfully applied for fluorescent imaging of F? in living nude mice, suggesting that it could be used as a powerful tool to predict and explore the biological functions of F? in physiological and pathological processes.
A Molecular Chameleon with Fluorescein and Rhodamine Spectroscopic Behaviors
Li, Ling,Wang, Chunyan,Wu, Jianjian,Tse, Yu Chung,Cai, Yue-Peng,Wong, Keith Man-Chung
, p. 205 - 213 (2016)
A new class of fluorescein/rhodamine hybrids with two spirolactone rings was reported to exhibit dual-output fluorescent behaviors independently. Isolation and characterization for two diastereomers, trans-RhOH and cis-RhOH, have been made and their X-ray crystal structures determined. In a basic environment, the spirolactone ring on the hydroxyl side will be opened to give a fluorescein-like optical output with the lowest absorptions at 485 and 530 nm emission. On the other hand, a rhodamine-like optical output, i.e., 528 nm absorption and 575 nm emission, will be switched on by a H+ or a Hg2+ ion, attributed to the spirolactone ring opening on the amino side. In a methanol-buffer system with different pH values, the corresponding pKa values for the hydroxyl and amino groups were determined as 5.7 and 2.3, respectively. Selective Hg2+-sensing properties have also been discussed, and log Ks values of about 3.60 and 3.73 were determined. Confocal microscopic images of Caenorhabditis elegans incubated with RhOH were found to show enhanced fluorescent intensity with a Hg2+ ion, demonstrating the potential application of RhOH for in vivo biological imaging.
Dual-site lysosome-targeted fluorescent probe for separate detection of endogenous biothiols and SO2 in living cells
Wu, Ming-Yu,Wang, Yue,Liu, Yan-Hong,Yu, Xiao-Qi
, p. 4232 - 4238 (2018)
Biothiols and SO2 play crucial roles in many physiological and pathological processes. To unravel their complicated interrelationship and cellular cross-talk, it would be highly desirable to develop single-molecule fluorescent probes that can selectively detect biothiols and SO2via different emission channels. Here, a novel chromenylium derivative, BPO-Py-diNO2, based on the rational design of dual recognition sites for biothiols and SO2 selectively and sensitively responded to biothiols with near-infrared fluorescence, and to SO2 with green fluorescence. The emission shift for the two channels was 170 nm. BPO-Py-diNO2 was selectively enriched in lysosomes. It could also be used to evaluate dual-channel imaging of endogenous biothiols and SO2 in living HeLa cells, and it could be used for monitoring the mutual interconversion of biothiols and SO2.
Selective Hg2+ sensing behaviors of rhodamine derivatives with extended conjugation based on two successive ring-opening processes
Wang, Chunyan,Wong, Keith Man-Chung
, p. 13432 - 13441 (2013)
A novel class of rhodamine derivatives with two spirolactam moieties have been synthesized, and their two stereoisomers of cis- and trans-forms have been successfully separated and isolated, as well as structurally characterized by X-ray crystallography. Attributed to the successive ring-openings of two spirolactam moieties, different solution color, electronic absorption and emission responses were exhibited upon addition of various concentrations of mercury(II) ion. Arising from two successive ring-opening processes in the presence of various concentration of Hg(II) ion, two reporting states with different spectroscopic properties were suggested, that is, the first state showing pink color (absorption maximum at 496 nm) but no emission, while the second state giving purple color (absorption maximum at 593 nm) and red emission (emission maximum at 620 nm). The mechanism of such different spectroscopic responses was also proposed and has also been supported by computational studies. An extension of the present work to the study of the corresponding chemodosimeters from the compounds with two spirolactam groups has been made, in which a stoichiometric and irreversible Hg(II)-promoted reaction of thiosemicarbazides was utilized to form 1,3,4-oxadiazoles.
A highly sensitive and rapidly responding fluorescent probe based on a rhodol fluorophore for imaging endogenous hypochlorite in living mice
Zhang, Yanhui,Ma, Lin,Tang, Chunchao,Pan, Shengnan,Shi, Donglei,Wang, Shaojing,Li, Minyong,Guo, Yuan
, p. 725 - 731 (2018)
Hypochlorous (HOCl) acid is generated as a defense tool in the immune system and plays a vital role in killing a wide range of pathogens. There is therefore great interest in developing fluorescent probes that can endogenously respond to the change in concentration of HOCl in vivo. To address this challenge, we here present a rapidly responding fluorescent probe RO610 to image endogenous HOCl in living mice. The development of RO610 was based on a novel water-soluble and pH-independent fluorescent xanthene dye, 2′-formylrhodol ROA, which exhibits highly selective and sensitive responses to HOCl/ClO- over other reactive species. Moreover, adding a little more than 5 equiv. of ClO- to the solution of RO610 resulted in a clearly observable fluorescence enhancement (48-fold) within 30 s. Based on these properties, RO610 was used to detect ClO- in A549 cells without interference by other oxidants. It was applied for the imaging of endogenous HOCl in living nude mice with satisfactory results.
Novel Rhodafluors: Synthesis, Photophysical, pH and TD-DFT Studies
Patil, Supriya S.,Thorat, Kishor G.,Mallah, Ramnath,Sekar, Nagaiyan
, p. 2187 - 2197 (2016)
An efficient protocol for the synthesis of new rhodol derivatives has been developed. The synthesis involves condensation of 2-hydroxy benzophenone derivatives with 1, 3-dihydroxy benzene derivatives in solvents such as ionic liquid (N-methyl-2-pyrrolidonium hydrogen sulfate) and methane sulphonic acid. Both ionic liquid and methane sulphonic acid were found to be promising self-catalyzed solvents to bring out the conversion to form desired rhodols in excellent yields. In N-methyl-2-pyrrolidonium hydrogen sulfate reaction proceeds faster compared to methane sulphonic acid. The new fluorophores are investigated for their photophysical properties in various microenvironments and systematically characterized by means of density functional theory and time dependent density functional theory. Photophysical properties of the new rhodafluors found sensitive towards change in the pH of media and thus can be used as efficient pH sensors.
A novel colorimetric fluorescent probe for SO2 and its application in living cells imaging
Wu, Ming-Yu,Wu, Jing,Wang, Yue,Liu, Yan-Hong,Yu, Xiao-Qi
, (2018)
A novel chromenylium-based fluorescent probe was exploited for sulphur dioxide (SO2) detecting. The probe displayed a remarkable fluorescence turn-on response towards SO2 based on the nucleophilic addition reaction to the carbon-carbon double bond with 105 nm Stock shift. The probe was successfully applied for the quantification of SO2.The linear detection range was from 0–160 μM with the detection limit as low as 99.27 nM. It also exhibited high selectivity for SO2 than other reactive species and amino acids. Furthermore, cell staining experiments indicated that the probe was cell membrane permeable and could be used for high-performance imaging of SO2 in living cells. The superior properties of the probe made it highly promising for use in chemical and biological applications.
A novel dual-mode turn-on optional chemodosimeter for the visualization of Pd0 with a low detection limit
Liu, Mengmeng,Leng, Taohua,Wang, Kai,Shen, Yongjia,Wang, Chengyun
, p. 25 - 32 (2017)
Rhodol is an ideal platform for fluorescent probes owing to its spirolactone framework and excellent photochemical properties. Herein, a novel rhodol-based colorimetric and fluorescent turn-on probe, DER-1, for the detection of Pd0, was rationally developed with an allyl carbamate group as the response unit. Base on the Pd0-triggered cleavage reaction and rhodol spiroring-opening mechanism, the proposed probe exhibited a high selectivity and sensitivity towards Pd0. Upon addition of Pd(PPh3)4, a significant fluorescence enhancement at 547?nm was observed with an obvious color change from colorless to pink, which can be easily identified by naked-eye. In addition, the fluorescence intensity at 547?nm was linearly proportional to the concentration of Pd0 in the range of 0–1.5?μM, and the detection limit was calculated to be 1.14?nM. That is, probe DER-1 can be quite a sensitive fluorescent turn-on probe for the quantitative detection of Pd0 in pretty low dose.
Ring-restricted N-nitrosated rhodamine as a green-light triggered, orange-emission calibrated and fast-releasing nitric oxide donor
He, Haihong,He, Tingting,Zhang, Ziqian,Xu, Xiu,Yang, Huibin,Qian, Xuhong,Yang, Youjun
, p. 1497 - 1499 (2018)
Nitric oxide (NO) donors are versatile tools for nitric oxide biology. The biological response of NO is dependent on the transient concentration and the sustained duration. N-Nitrosated rhodamines are photo-triggered and photo-calibrated NO donors. We recently discovered that suppression of the dihedral angle between the N-nitroso fragment with the rhodamine scaffold facilitates NO release. Inspired by this discovery, we developed a fast-releasing NO donor (NOD575) suitable for biological applications, e.g., the pulmonary arterial smooth muscle cells (PASMCs).
