oxime ether
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2022 ◽  
Vol 7 (2) ◽  
Bin Wang ◽  
Zongyu Cai ◽  
Siliang Chen ◽  
Ya Chen ◽  
Shixuan Jiao ◽  

2022 ◽  
Vol 20 (1) ◽  
Anna Czapka ◽  
Christian Grune ◽  
Patrick Schädel ◽  
Vivien Bachmann ◽  
Karl Scheuer ◽  

Abstract Background Insufficient solubility and stability of bioactive small molecules as well as poor biocompatibility may cause low bioavailability and are common obstacles in drug development. One example of such problematic molecules is 6-bromoindirubin-3'-glycerol-oxime ether (6BIGOE), a hydrophobic indirubin derivative. 6BIGOE potently modulates the release of inflammatory cytokines and lipid mediators from isolated human monocytes through inhibition of glycogen synthase kinase-3 in a favorable fashion. However, 6BIGOE suffers from poor solubility and short half-lives in biological aqueous environment and exerts cytotoxic effects in various mammalian cells. In order to overcome the poor water solubility, instability and cytotoxicity of 6BIGOE, we applied encapsulation into poly(d,l-lactide-co-glycolide) (PLGA)-based nanoparticles by employing formulation methods using the sustainable solvents Cyrene™ or 400 g/mol poly(ethylene glycol) as suitable technology for efficient drug delivery of 6BIGOE. Results For all preparation techniques the physicochemical characterization of 6BIGOE-loaded nanoparticles revealed comparable crystallinity, sizes of about 230 nm with low polydispersity, negative zeta potentials around − 15 to − 25 mV, and biphasic release profiles over up to 24 h. Nanoparticles with improved cellular uptake and the ability to mask cytotoxic effects of 6BIGOE were obtained as shown in human monocytes over 48 h as well as in a shell-less hen’s egg model. Intriguingly, encapsulation into these nanoparticles fully retains the anti-inflammatory properties of 6BIGOE, that is, favorable modulation of the release of inflammation-relevant cytokines and lipid mediators from human monocytes. Conclusions Our formulation method of PLGA-based nanoparticles by applying sustainable, non-toxic solvents is a feasible nanotechnology that circumvents the poor bioavailability and biocompatibility of the cargo 6BIGOE. This technology yields favorable drug delivery systems for efficient interference with inflammatory processes, with improved pharmacotherapeutic potential. Graphical Abstract

2022 ◽  
Sampath Kumar Kancharla ◽  
Saritha Birudaraju ◽  
Arani Pal ◽  
L. Krishnakanth Reddy ◽  

A series of fifteen novel isatin oxime ether-tethered aryl 1H-1,2,3-triazole hybrids 5a-o were designed and synthesized by employing Cu(I) catalyzed azide-alkyne [3+2] cycloaddition (CuAAC) between isatin oxime O-propargyl ether and...

2021 ◽  
Vol 11 (6) ◽  
pp. 47-50
Sachin V Patil

Some new oxime ether derivatives containing benzthiazole heterocyclic nuclei are synthesized. The reaction of 2-mercapto benzthiazole with α-halo ketones followed by reaction with hydroxylamine gave oxime derivatives which on reaction with alkyl halides viz. ethyl chloride, n-propyl chloride, and n-butyl chloride in absolute ethanol afforded the target compounds 4a-l. The structure of all the synthesized compounds was confirmed by spectroscopic methods like mass and NMR. All compounds after structural confirmation were tested for biological activities.

Processes ◽  
2021 ◽  
Vol 9 (11) ◽  
pp. 2019
Mehmet Abdullah Alagöz ◽  
Arzu Karakurt ◽  
Ceylan Hepokur ◽  
Emine Şalva ◽  
Tijen Önkol ◽  

In this study, 12 new 1-aryl-2-(3,5-dimethylpyrazol-1-yl)ethanone oxime ether derivatives were designed and synthesized to investigate their cytotoxic effects. The in vitro cytotoxic activities of the compounds were evaluated against cervix, colon, breast, glioma, neuroblastoma, and lung cancer cell lines, as well as a healthy cell line using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazo-lium bromide (MTT) assays with 5-fluorouracil (5-FU) as the reference compound. Compound 5f (IC50 = 5.13 µM) was found to be more effective than 5-FU (IC50 = 8.34 µM) in the C6 cancer cell line, and it had no cytotoxic effect on the L929 healthy cell line. Flow cytometry was used to investigate the mechanism of action of compound 5f on the cell cycle of the C6 cell line. The analysis showed that cell death was significantly due to apoptosis. These results indicate that compound 5f induces cell cycle arrest, and may be effective in treating glioma.

Synlett ◽  
2021 ◽  
Atsushi Kimishima ◽  
Masayoshi Arai ◽  
Hayato Saito ◽  
Violeta Petrova

AbstractAn asymmetric formal synthesis of trichodermamides B and C was achieved in 15 steps based on a tyrosine ester chiral-pool approach. Key features of this synthesis include stereoselective construction of a cis-1,2-oxazadecaline core by an acid-mediated tandem deprotection–intramolecular oxy-Michael reaction, oxime ether formation via an N-bromination–elimination sequence, and diene construction by a palladium-catalyzed demonomethylcarbonation.

Lu Yu ◽  
Lingling Xiao ◽  
Jiyan Chi ◽  
Zhangfei Tang ◽  
Jie Li ◽  

ChemMedChem ◽  
2021 ◽  
Rafael Filipe Arbuez Gomes ◽  
Vera M. S. Isca ◽  
Késsia Andrade ◽  
Patrícia Rijo ◽  
Carlos A. M. Afonso

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