- Reaction of Alcohols and Amines with Diacetyldihydrofluorescein (DADF): Conversion into Erythrosine-Derivatives on TLC-Plates by Ammonia and Iodine Vapors
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Reaction of deacetylcolchicine (2) and colchifoline (3) with diacetyldihydrofluorescein (1, DADF) afforded the corresponding amide and ester derivatives, converted on TLC-plates after exposure to ammonia and iodine vapors into red colored pigments.This re
- Sharma, Padam N.,Brossi, Arnold
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- 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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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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- CHIRAL PRODYES. ETHERS AND ESTERS OF DIHYDROFLUORESCEIN, PART 1: DIBENZYLDIHYDROFLUORESCEIN (DBDF) A NEW REAGENT
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Ethers and esters of dihydrofluorescein (4) were prepared by chemical modification of the benzyl ester (6), obtained by benzylation of fluorescein (1), and reduction of benzyl ester (3) with sodium borohydride.
- Tadic, Dragana,Brossi, Arnold
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p. 1975 - 1982
(2007/10/02)
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