- Endoplasmic Reticulum Targeting Reactive Oxygen Species Sensor Based on Dihydrofluorescein: Application of Endoplasmic Reticulum Stress
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Endoplasmic reticulum (ER) has a unique redox environment, which plays critical roles in the organelle's function and in its pathological responses such as ER stress. In this work, we introduce an ER-targeting fluorogenic reactive oxygen species (ROS) chemosensor (ER-Flu) from copper(I)-catalyzed alkyne-azide cycloaddition of 3-propargyl ester of 2′,7′-dichlorodihydrofluorescein diacetate and N3-glibenclamide, which were adopted as a fluorogenic ROS sensing module and an ER-targeting module, respectively. Thereby, a series of confocal microscopic experiments of ER-Flu demonstrated that the sensor localizes in ER of the live cells and that ROS are elevated in the cells by ER stress inducers such as thapsigargin, brefeldin A, and tunicamycin.
- Le, Hoa Thi,Jo, Hye-Ryeong,Oh, Se-Yun,Jung, Jinwook,Kim, Young Gi,Kang, Chulhun,Kim, Tae Woo
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supporting information
p. 279 - 285
(2020/12/21)
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- Chemistry of the carboxylic acid of dihydrofluorescein in oxidation and its application to fluorogenic ROS sensing
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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.
- Le, Hoa Thi,Nguyen, Dinh Phi Long,Shin, Hyo Seob,Jung, Woong,Kang, Chulhun,Kim, Tae Woo
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p. 461 - 468
(2021/07/19)
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- 5-hydroxymethylfurfural- and fluorescein-fused fluorescence probe of mast cells (RBL-2H3): Synthesis, photophysical properties, and bioimaging
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A fluorescent probe (Fluo-HMF) was developed via introduction of a furfural moiety into the fluorescein molecular skeleton, aiming at specially labeling cell membrane of mast cells. To illustrate its specificity, we designed and synthesized a series of fluorescent compounds based on fluorescein molecular skeleton. The fluorescent properties of Fluo-HMF were investigated, which were in accordance with theoretical calculations. Compared with other fluorescein derivatives, Fluo-HMF could specially label RBL-2H3 cells. The results suggested that Fluo-HMF could be used as a fluorescent probe for bioimaging on some related research of allergic mechanism.
- Huang, Limin,Wei, Di,Wu, Zibo,Hou, Yajing,Xie, Yitong,Liu, Zhenru,Wang, Cheng,Che, Delu,Lei, Yibo,He, Huaizhen
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p. 1963 - 1971
(2018/09/06)
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- Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging
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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.
- Chyan, Wen,Kilgore, Henry R.,Gold, Brian,Raines, Ronald T.
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p. 4297 - 4304
(2017/04/28)
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- A ratiometric fluorescent system for carboxylesterase detection with AIE dots as FRET donors
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A ratiometric fluorescent system for CaE detection with AIE dots as the FRET donors was designed. Upon enzymatic reaction, electrostatic interaction between the cationic TPE-N+ dots and the enzymatic reaction product - the negatively charged fluorescein molecules - allows the FRET process to proceed, thus affording the ratiometric fluorescence CaE assay.
- Wu, Yinglong,Huang, Shuailing,Zeng, Fang,Wang, Jun,Yu, Changmin,Huang, Jing,Xie, Huiting,Wu, Shuizhu
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supporting information
p. 12791 - 12794
(2015/08/18)
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- Synthesis of fluorescein aromatic esters in the presence of P 2O5/SiO2 as catalyst and their hydrolysis studies in the presence of lipase
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A series of fluorescein aryl esters were synthesized by the esterification of fluorescein with carboxylic acids in the presence of P2O 5/SiO2 and their hydrolytic properties were investigated. The rate of hydrolysis in the presence or absence of lipase, due to the increase of fluorescein concentration, was measured by monitoring of fluorescence of the solution and correlated with enzyme activity. In addition, the substitute effect on the aromatic ring of fluorescein esters was studied. In contrast to fluorescein diacetate or dibutyrate, fluorescein dibenzoate and fluorescein bis(4-methylbenzoate) were found to be better substrates for the fluorometric assay of lipase with the higher rate of hydrolysis and better Km value, respectively. As little as 9.3 ng mL-1 of lipase can be detected with fluorescein bis(4-methylbenzoate).
- Eshghi, Hossein,Mirzaie, Narges,Asoodeh, Ahmad
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experimental part
p. 120 - 126
(2012/01/13)
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- SUBSTANTIALLY PURE FLUORESCEIN
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The present invention is directed to an improved process for producing substantially pure fluorescein, as well as to substantially pure fluorescein compositions prepared by the process. The invention is particularly directed to the provision of pharmaceutical compositions for use in angiography. The substantially pure fluorescein produced by the process of the present invention is low in color, low in sodium chloride content, and substantially free of pyridine.
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Page/Page column 23
(2008/12/06)
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- Microwave-assisted functionalization of bromo-fluorescein and bromorhodamine derivatives
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The overall goal of this project was to develop methodologies that would allow organometallic couplings of fluorescein and rhodamine derivatives. Consequently, borylation, Suzuki, and Sonogashira reactions of fragments derived from compounds 1 and 2 were investigated. Conventional and microwave heating were compared throughout the study.
- Han, Jin Wook,Castro, Juan C.,Burgess, Kevin
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p. 9359 - 9362
(2007/10/03)
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