142231-06-9Relevant academic research and scientific papers
Design of fluorescent probes with optimized responsiveness and selectivity to GSH
Chen, Ji-An,Zhang, Zhen-Yu,Gao, Jie,Tan, Jia-Hui,Gu, Xian-Feng
, p. 1226 - 1230 (2019)
We designed and synthesized a series of BODIPY based probes with fast and distinct ratiometric responsiveness for discriminative detection of GSH from Cys and Hcy. The discriminative detection is based on the different products obtained by the SNAr between probes and thiol-containing amino acids. The amino group of the obtained thioether from the reaction with Cys or Hcy but not GSH would trigger an intramolecular nucleophilic substitution through five- or six-membered cyclic transition state, finally yielding an amino substituted derivative. To achieve highly discriminative detection and fast response, a series of structure modifications and improvements have been made by elongating the π-conjugation and introducing electron withdrawing groups, finally affording probe BOD-DBNPF with optimized responsiveness and selectivity. Importantly, BOD-DBNPF was successfully used for the selective detection of GSH from Cys with distinct fluorescent ratiometric responses in living HeLa cells.
Rational design of fluorescent probes for targeted: In vivo nitroreductase visualization
Chen, Ji-An,Gao, Jie,Gu, Xianfeng,Li, Mimi,Tan, Jiahui,Yin, Xiaofan,Zhao, Zhen
, p. 4744 - 4747 (2020/07/13)
Nitroreductase (NTR) has been recognized as a biomarker for identifying the hypoxic status of cancers. Therefore, it is of high scientific interest to design effective fluorescent probes for tracking NTR activity. However, studies on elucidation of the structure-performance relationship of fluorescent probes and those providing valuable insight into optimized probe design have rarely been reported. Three BODIPY based fluorescent probes were made by conjugation of para-, ortho-, and meta-nitrobenzene to the BODIPY core via a thiolether bond, respectively. Our study revealed that the linkage and nitro substituent position significantly influence the capability of nitroreductase detection.
Novel fluorescent dye can be multi-functional and its preparation method and application
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Paragraph 0096; 0097, (2017/03/28)
The invention belongs to the field of chemicobiology, and provides a novel fluorescent dye capable of multifunctionalization, and a preparation method and application thereof. The novel fluorescent dye capable of multifunctionalization is based on a BODIPY parent, and is prepared by carrying out Knoevenagel reaction on a raw material pyrrole aldehyde for synthesizing BODIPY and propyl dicyan. The modification of the Knoevenagel reaction is utilized to achieve the goal of regulating the spectrum property of the fluorescent dye. Cl-BODIPY-2CN active chlorine can quickly perform nucleophilic substitution reaction with multiple mercapto or amino compounds, and the optical properties of the fluorescent dye obviously change in the substitution process. The Cl-BODIPY-2CN is used for detecting ONOO-. The fluorescent dye provided by the invention has the advantages of high light stability and high reaction sensitivity, and can be subjected to functionalized application in many aspects. The preparation method has the advantages of simple and accessible raw materials, low cost, higher yield and high light stability.
2- and 3-monohalogenated BODIPY dyes and their functionalized analogues: Synthesis and spectroscopy
Leen, Volker,Leemans, Tom,Boens, Noel,Dehaen, Wim
experimental part, p. 4386 - 4396 (2011/10/04)
Starting from appropriately halogenated acylpyrroles, a wide range of reactive 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives can be obtained. The fluorescent dyes display excellent reactivity in nucleophilic aromatic substitution, transi
Oxidative Halogenation of Substituted Pyrroles with Cu(II). Part III. Bromination and Chlorination of 2-Benzoylpyrrole
Petruso, S.,Caronna, S.
, p. 355 - 357 (2007/10/02)
The bromination of 2-benzoylpyrrole with copper (II) bromide in the homogenous and heterogenous phase is described, giving 4- and 5-monobromo derivatives whose ratio decreases as the temperature is increased.The same reaction with copper(II) chloride in acetonitrile at 60 deg C produces 5-chloro-2-benzoylpyrrole as the major product. 4,5-Dihalopyrroles in good yields are obtained with an excess of halogenating agent.
Process for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-A]pyrrole-1,1-dicarboxylates
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, (2008/06/13)
5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylates of the formula STR1 are prepared from 2-halopyrroles. Hydrolysis and β-decarboxylation of these compounds affords ketorolac and related compounds.
