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분자활성 촉매반응 연구단
분자활성 촉매반응 연구단
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Overriding Phthalate Decomposition When Exploring Mycophenolic Acid Intermediates as Selenium-Based ROS Biological Probes

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Title
Overriding Phthalate Decomposition When Exploring Mycophenolic Acid Intermediates as Selenium-Based ROS Biological Probes
Author(s)
Mahesh B. Halle; Tesla Yudhistira; Kyung Jin Lee; Jae Hyuck Choi; Youngsam Kim; Hee-Sung Park; David G. Churchill
Publication Date
2018-10
Journal
ACS Omega, v.3, no.10, pp.13474 - 13483
Publisher
AMER CHEMICAL SOC
Abstract
Hypochlorous (OCl-) acid is the most well-known bacterial oxidant to be produced by neutrophils. Excess amounts of OCl- can cause various disorders in living systems. Herein, we have designed, synthesized, and characterized two novel organoselenium-based target molecules (Probe-1 and Probe-OCl) based on a synthetic intermediate of mycophenolic acid for the aqueous detection of OCl-. Probe 1 has been recently reported (Org. Lett. 2018, 20, 3557-3561); both probes show immediate turn-on fluorescence (<1 s) upon the addition of OCl-, display an increase in the fluorescence quantum yield (3.7-fold in Probe-1 and 11.6-fold in Probe-OCl), and are completely soluble in aqueous media without the help of any cosolvent. However, a decrease in the turn-on intensity with the oxidized version of Probe-1 in cell assays due to the anhydride/phthalate functionality suggests that probe degradation occurs based on hydrolytic action (a probe degradation half-life of ��1500 s at 15 ��M Probe-1 and 150 ��M OCl). Thus, the change of anhydride to methylamide begets Probe-OCl, which possesses more stability without sacrificing its water solubility properties and responses at short times. Further studies suggest that Probe-OCl is highly stable within physiological pH (pH = 7.4). Surprisingly, in live cell experiments involving U-2 OS cells and HeLa cells, Probe-OCl accumulated and aggregated in lipid droplets and gives a turn-on fluorescence response. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assays confirmed that Probe-OCl is not toxic. Cuvette aggregation studies were also performed (tetrahydrofuran/H2O) to demonstrate aggregation-induced fluorescence at longer times. Our current hypothesis is that the turn-on fluorescence effect is caused by the aggregation-induced emission mechanism available for Probe-OCl. In this case, in tandem, we reanalyzed the Mes-BOD-SePh derivative to compare and contrast cell localization as imaged by confocal microscopy; fluorescence emission occurs in the absence of, or prior to, Se oxidation. Copyright (c) 2018 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/5524
ISSN
2470-1343
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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