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Home > Mathematics and Science Textbooks > Chemistry > Studies on Fluorescent Probes for the Specific Detection of Reactive Oxygen Species and Reactive Nitrogen Species in Living Cells
Studies on Fluorescent Probes for the Specific Detection of Reactive Oxygen Species and Reactive Nitrogen Species in Living Cells

Studies on Fluorescent Probes for the Specific Detection of Reactive Oxygen Species and Reactive Nitrogen Species in Living Cells


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This dissertation, "Studies on Fluorescent Probes for the Specific Detection of Reactive Oxygen Species and Reactive Nitrogen Species in Living Cells" by Zhenning, Sun, 孫振宁, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. Abstract: Abstract of thesis entitled STUDIES ON FLUORESCENT PROBES FOR THE SPECIFIC DETECTION OF REACTIVE OXYGEN SPECIES AND REACTIVE NITROGEN SPECIES IN LIVING CELLS Submitted by SUN Zhen-Ning for the Degree of Doctor of Philosophy at The University of Hong Kong in September 2006 This project mainly focuses on the development of fluorescent probes for two biologically important oxidants - peroxynitrite and hypochlorite. On the basis of the similar chemical behavior between peroxynitrite - - (ONOO ) and peroxymonosulfate (HOOSO ), a reaction specific to peroxynitrite has been discovered (Scheme 1). On the basis of this specific reaction, several BODIPY-type fluorescent probes have been designed and synthesized according to the photoinduced electron transfer (PET) mechanism (Scheme 2). Among those probes, SZN-2 was found to be highly sensitive in specific detection of peroxynitrite 1 -- without interference from other competing oxidants, such as H O, O, NO, O, 2 2 2 2 and alkylperoxyl radical (ROO). Upon treatment with 7 equiv of peroxynitrite, probe SZN-2 showed up to 69-fold increase in fluorescence intensity. A linear correlation between emission intensity and concentration of peroxynitrite was observed. Moreover, the formation of peroxynitrite in living cells (J744.1 macrophages) can be visualized selectively by using probe SZN-2. This novel fluorescent probe should significantly facilitate studies of the biological roles of peroxynitrite in oxidative stress and many peroxynitrite-associated human diseases, such as rheumatoid arthritis, heart disease, atherosclerosis, and stroke. A fluorescent probe, SZN-3, has also been developed for the detection of hypochlorite on the basis of a specific reaction between methoxyphenol and hypochlorite (Scheme 3). This probe is highly sensitive and specific to hypochlorite. Upon treatment with 5 equiv of hypochlorite, probe SZN-3 showed up to 754-fold increase in fluorescence intensity. The reactivities of SZN-3 toward different reactive oxygen species (ROS) and reactive nitrogen species (RNS), including H O, 2 2 1 -- - - - - O, NO, O, OH, OCl, ONOO and alkylperoxyl radical (ROO ) were compared. 2 2 The results showed that fluorescence increased only upon reaction with OCl, demonstrating that probe SZN-3 has much higher selectivity towards hypochlorite than other ROS and RNS in an abiotic system. Moreover, using probe SZN-3, the formation of OCl has been successfully detected in an enzymatic system - (Myeloperoxidase/H O /Cl system) and in macrophages upon stimulation. This 2 2 new probe has provided an efficient tool for the evaluation of the roles of OCl in biological systems. Scheme 1 ONOO O OH CF CF RO 2.2 R = Me 2.1a R = H 3.23 Oxidant CF 3 No Reaction H O, OH, NO 2 2 RO 1 . O O 2, 2 R = Me 2.1a R = H 3.23 Scheme 2 O O CF CF 3 3 RO MeO NN NN B B Et NOC CONEt Et NOC CONEt F F F F 2 2 2 2 3.8 R = Me 2.14 (SZN-1) R = MOM 3.22 3.29 (SZN-2) R = H OH CF CF HO ONOO NN NN Et NOC CONEt Et NOC CONEt 2 2 F F 2 2 F F 3.29 (SZN-2) 2.15 non-fluorescent fluorescent Scheme 3 O O OMe OCl O O OH 4.1 4.2 OMe Oxidant No Reaction H O, OH, NO 2 2 1 . O O 2, 2 OH OMe


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Product Details
  • ISBN-13: 9781361427866
  • Publisher: Open Dissertation Press
  • Publisher Imprint: Open Dissertation Press
  • Height: 279 mm
  • No of Pages: 222
  • Weight: 526 gr
  • ISBN-10: 1361427868
  • Publisher Date: 27 Jan 2017
  • Binding: Paperback
  • Language: English
  • Spine Width: 12 mm
  • Width: 216 mm


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Studies on Fluorescent Probes for the Specific Detection of Reactive Oxygen Species and Reactive Nitrogen Species in Living Cells
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