1000182-40-0Relevant academic research and scientific papers
Development of Lysosome-Targeted Fluorescent Probes for Cys by Regulating the Boron-dipyrromethene (BODIPY) Molecular Structure
Gao, Jinhua,Tao, Yuanfang,Zhang, Jian,Wang, Nannan,Ji, Xin,He, Jinling,Si, Yubing,Zhao, Weili
, p. 11246 - 11256 (2019)
Our previous discovery suggested that substituents on the 1,7 positions delicately modulate the sensing ability of the meso-arylmercapto boron-dipyrromethene (BODIPY) to biothiols. In this work, the impact of delicate modulations on the sensing ability is investigated. Therefore, 1,7-dimethyl, 3,5-diaryl substituted BODIPY is designed and developed and its conformationally restricted species with a meso-arylmercapto moiety (DM-BDP-SAr and DM-BDP-R-SAr) as selective fluorescent probes for Cys. Moreover, the lysosome-target probes (Lyso-S and Lyso-D) based on DM-BDP-SAr carrying one or two morpholinoethoxy moieties were developed. They were able to detect Cys selectively in vitro with low detection limits. Both Lyso-S and Lyso-D localized nicely in lysosomes in living HeLa cells and exhibited red fluorescence for Cys. Moreover, a novel fluorescence quenching mechanism was proposed from the calculations by density functional theory (DFT). The probes may go through intersystem crossing (from singlet excited state to triplet excited state) to result in fluorescence quenching.
Endogenous peroxynitrite activated fluorescent probe for revealing anti‐tuberculosis drug induced hepatotoxicity
Wang, Nannan,Wang, Han,Zhang, Jian,Ji, Xin,Su, Huihui,Liu, Jinying,Wang, Jiamin,Zhao, Weili
supporting information, p. 1584 - 1588 (2021/10/12)
Pyrazinamide (PZA), isoniazid (INH) and rifampicin (RFP) are all commonly used anti-tuberculosis drugs in clinical practice, and long-term medication may cause severe liver damage and toxicity. The level of peroxynitrite (ONOO–) generated in liver has long been regarded as a biomarker for the prediction and measurement of drug-induced liver injury (DILI). In this article, we constructed a BODIPY-based fluorescent probe (BDP-Py+) that enabled quickly and sensitively detect and image ONOO– in vivo. Utilizing this probe, we demonstrated the change of ONOO– content in cells and mice model of DILI induced by acetaminophen (APAP), and for the first time revealed the mechanism of liver injury induced by antituberculosis drug PZA. Moreover, BDP-Py+ could be applied to screen out and evaluate the hepatotoxicity of different anti-tuberculosis drugs. Comparing with the existing serum enzymes detection and H&E staining, the probe could achieve early diagnosis of DILI before solid lesions in liver via monitoring the up-regulation of ONOO– levels. Collectively, this work will promote the understanding of the pathogenesis of anti-tuberculosis drug induced liver injury (ATB-DILI), and provide a powerful tool for the early diagnosis and treatment of DILI.
2,3-disubstituted pyrrole or 2,3,4-trisubstituted pyrrole prepared by one-pot method and preparation method thereof
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Paragraph 0145-0150, (2019/10/08)
The invention provides 2,3-disubstituted pyrrole or 2,3,4-trisubstituted pyrrole prepared by a one-pot method and a preparation method thereof. Ketoxime and p-toluenesulfonyl chloride generate ketoxime sulfonate under alkaline conditions, the ketoxime sulfonate is not separated, Neber rearrangement is carried out under the conditions to obtain a nitrogen heterocyclic propylene intermediate, and the nitrogen heterocyclic propylene intermediate and proton-containing ketone at an alpha position are subjected to ring opening and cyclization to obtain the 2,3-disubstituted pyrrole or 2,3,4-trisubstituted pyrrole. The invention firstly provides the method for preparing the 2,3-disubstituted pyrrole or 2,3,4-trisubstituted pyrrole through the steps that the ketoxime and p-toluenesulfonyl chloride generate the ketoxime sulfonate under the alkaline conditions, the ketoxime sulfonate is not separated, and the intermediate obtained by the Neber rearrangement under the conditions and the ketone are subjected to the ring opening and cyclization, the synthesis step is simplified, the yield is improved, and the range of application of the reaction is expanded.
Pd(II)/Bu4NBr/DMSO catalytic system for practical synthesis of indoles and pyrroles from imines through aerobic dehydrogenative cyclization
Tan, Wei Wen,Hou, Xiaoya,Yoshikai, Naohiko
, p. 2727 - 2733 (2015/05/05)
N-Aryl- and N-allylimines derived typically from substituted acetophenones undergo palladium(II)-catalyzed dehydrogenative cyclization reactions in the presence of tetrabutylammonium bromide and molecular oxygen in DMSO to afford indole and pyrrole deriva
Aerobic synthesis of pyrroles and dihydropyrroles from imines: Palladium(II)-catalyzed intramolecular C-H dehydrogenative cyclization
Shi, Zhuangzhi,Suri, Mamta,Glorius, Frank
, p. 4892 - 4896 (2013/06/04)
sp3ectacularly mild! An efficient PdII-catalyzed intramolecular dehydrogenative cyclization of imines affords (dihydro)pyrrole products using molecular oxygen as the sole oxidant. This mild formal sp 3-C-H functionalization allows rapid and atom-economical assembly of (dihydro)pyrrole rings from inexpensive and readily available allylamines and ketones. A broad range of functional groups are tolerated. Copyright
α-Palladation of imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-allylimines to pyrroles
Chen, Zhiyuan,Lu, Beili,Ding, Zhenhua,Gao, Ke,Yoshikai, Naohiko
supporting information, p. 1966 - 1969 (2013/06/04)
We report here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization.
Palladium-catalysed aerobic oxidative Heck-type alkenylation of Csp 3-H for pyrrole synthesis
Meng, Lingkui,Wu, Kun,Liu, Chao,Lei, Aiwen
supporting information, p. 5853 - 5855 (2013/07/19)
The first palladium-catalysed aerobic oxidative intramolecular alkenylation of Csp3-H bonds was described. The reaction conditions were mild and molecular oxygen was used as the terminal oxidant. Kinetic studies showed that the Csp3-H metallation step was a slow step.
Homoallylic ketones and pyrroles by way of copper-catalyzed cascade additions of alkylsubstituted vinyl Grignard reagents to esters
Doerr, Aurelie A.,Lubell, William D.
, p. 1006 - 1017 (2008/03/28)
Exploring the scope of the copper-catalyzed cascade addition of vinyl Grignard reagents to carboxylic esters, a set of substituted homoallylic ketones (γ.δ-unsaturated ketones) have been synthesized in 11%-94% yields from treatment of methyl 4-methoxybenz
