817638-71-4Relevant academic research and scientific papers
Visualization of nitroxyl in living cells by a chelated copper(II) coumarin complex
Zhou, Yi,Liu, Ke,Li, Ju-Ying,Fang, Yuan,Zhao, Tian-Chu,Yao, Cheng
, p. 1290 - 1293 (2011)
The coumarin-based probe Cu(II)-COT1 was successfully developed for the detection of HNO on the basis of the reduction reaction. In addition, highly selective "turn on" type fluorogenic behavior upon the addition of Angeli's salt (Na2N2O3) was also applied to bioimaging in A375 cells.
In Cellulo Generation of Fluorescent Probes for Live-Cell Imaging of Cylooxygenase-2
Kaur, Jatinder,Bhardwaj, Atul,Wuest, Frank
supporting information, p. 3326 - 3337 (2020/12/09)
Live-cell imaging with fluorescent probes is an essential tool in chemical biology to visualize the dynamics of biological processes in real-time. Intracellular disease biomarker imaging remains a formidable challenge due to the intrinsic limitations of conventional fluorescent probes and the complex nature of cells. This work reports the in cellulo assembly of a fluorescent probe to image cyclooxygenase-2 (COX-2). We developed celecoxib-azide derivative 14, possessing favorable biophysical properties and excellent COX-2 selectivity profile. In cellulo strain-promoted fluorogenic click chemistry of COX-2-engaged compound 14 with non/weakly-fluorescent compounds 11 and 17 formed fluorescent probes 15 and 18 for the detection of COX-2 in living cells. Competitive binding studies, biophysical, and comprehensive computational analyses were used to describe protein-ligand interactions. The reported new chemical toolbox enables precise visualization and tracking of COX-2 in live cells with superior sensitivity in the visible range.
Unusual absence of FRET in triazole bridged coumarin-hydroxyquinoline, an active sensor forHg2+detection
Chatterjee, Soumit,Dey, Swapan,Hira, Sumit K.,Mondal, Surajit,Nayek, Hari Pada,Patra, Niladri
, p. 1211 - 1221 (2020/10/02)
A triazole-bridged coumarin conjugated quinoline sensor has been ‘click’-synthesized by Cu(i) catalyzed Huisgen cycloaddition, and it exhibited high selectivity for toxicHg2+. Surprisingly, no evidence of energy transfer from the quinoline moiety to coumarin has been found, substantiated by time-resolved fluorescence study. The possible binding mode of this sensor toHg2+has been establishedviaNMR study, steady-state and time-resolved fluorescence spectroscopy, which is further supported by TDDFT calculations. The sensor has been found to be cell membrane permeable and non-toxic, and hence is suitable for intracellularHg2+detection.
Cellular target identification of Withangulatin A using fluorescent analogues and subsequent chemical proteomics
Zhu, Tianyu,Chen, Chen,Wang, Sisi,Zhang, Yi,Zhu, Dongrong,Li, Lingnan,Luo, Jianguang,Kong, Lingyi
, p. 8231 - 8234 (2019/07/16)
Withangulatin A (WA) has been reported to exhibit potent antitumor activity. However, its possible mechanism and direct proteomic targets remain unknown. Herein we report the subcellular localization of WA by designing and synthesizing its fluorescent analogues with coumarin moieties. Furthermore, sarco/endoplasmic reticulum calcium-ATPase (SERCA)2 was identified as the potential target of WA for its antitumor activity by chemical proteomics.
Discovery of quinazoline-based fluorescent probes to α1-adrenergic receptors
Zhang, Wei,Ma, Zhao,Li, Wenhua,Li, Geng,Chen, Laizhong,Liu, Zhenzhen,Du, Lupei,Li, Minyong
supporting information, p. 502 - 506 (2015/05/27)
α1-Adrenergic receptors (α1-ARs), as the essential members of G protein-coupled receptors (GPCRs), can mediate numerous physiological responses in the sympathetic nervous system. In the current research, a series of quinazoline-based small-molecule fluorescent probes to α1-ARs (1a-1e), including two parts, a pharmacophore for α1-AR recognition and a fluorophore for visualization, were well designed and synthesized. The biological evaluation results displayed that these probes held reasonable fluorescent properties, high affinity, accepted cell toxicity, and excellent subcellular localization imaging potential for α1-ARs.
Generation of profluorescent isoindoline nitroxides using click chemistry
Morris, Jason C.,McMurtrie, John C.,Bottle, Steven E.,Fairfull-Smith, Kathryn E.
scheme or table, p. 4964 - 4972 (2011/08/05)
Novel profluorescent nitroxides bearing a triazole linker between the coumarin fluorophore and an isoindoline nitroxide were prepared in good yields using the copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (CuAAC). Nitroxides containing 7-hydroxy and 7-diethylamino substitution on their coumarin rings displayed significant fluorescence suppression, and upon reaction with methyl radicals, normal fluorescence emission was returned. The fluorescence emission for the 7-hydroxycoumarin nitroxide and its diamagnetic analogue was found to be strongly influenced by pH with maximal fluorescence emission achieved in basic solution. Solvent polarity was also shown to affect fluorescence emission. The significant difference in fluorescence output between the nitroxides and their corresponding diamagnetic analogues makes these compounds ideal tools for monitoring processes involving free-radical species.
A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes
Sivakumar, Krishnamoorthy,Xie, Fang,Cash, Brandon M.,Long, Su,Barnhill, Hannah N.,Wang, Qian
, p. 4603 - 4606 (2007/10/03)
(Chemical equation presented) Copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of nonfluorescent 3-azidocoumarins and terminal alkynes afforded intense fluorescent 1,2,3-triazole products. The mild condition of this reaction allowed us to construct a large library of pure fluorescent coumarin dyes. Since both azide and alkyne are quite inert to biological systems, this reaction has potential in bioconjugation and bioimaging applications.
