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Cu(II) immobilized on Fe3O4@APTMS-DFX nanoparticles: an efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles with cytotoxic activity
RSC Medicinal Chemistry ( IF 4.1 ) Pub Date : 2017-09-15 00:00:00 , DOI: 10.1039/c7md00302a
Faezeh Taghavi 1 , Mostafa Gholizadeh 1 , Amir Sh Saljooghi 1 , Mohammad Ramezani 2
Affiliation  

Cu(II) immobilized on deferasirox loaded amine functionalized magnetic nanoparticles (Cu(II)/Fe3O4@APTMS-DFX) as a novel magnetically recyclable heterogeneous catalyst is able to catalyze the [3 + 2] cycloaddition reactions of various organic nitriles with sodium azide. Using this method, a series of 5-substituted-1H-tetrazoles under mild conditions in DMSO were prepared. The reaction involves mild reaction conditions with efficient transformation capability. The developed catalyst could be easily separated by applying an external magnetic field. Furthermore, it could be recycled for 5 runs with negligible leaching of copper from the surface of the catalyst. The catalyst was characterized by various techniques such as FT-IR, TGA, VSM, SEM-EDX, and ICP-OES. Several derivatives of 1H-tetrazoles were prepared using this catalyst, and their structures were confirmed using different techniques. Then, the synthesized anthraquinones were evaluated for their cytotoxicity against several cell lines including MCF-7, MAD-MD-231, HT-29, HeLa, neuro-2a and L-929. The results obtained from the MTT assay revealed that the 6 derivatives exhibited a high level of cytotoxicity. In order to determine the cytotoxicity mechanism, 2 derivatives with the highest cytotoxic activity were selected, and an apoptosis assay was carried out by flow cytometry, which supported that apoptosis is the major mechanism.

中文翻译:

固定在 Fe3O4@APTMS-DFX 纳米颗粒上的 Cu(II):一种用于合成具有细胞毒活性的 5-取代 1H-四唑的有效催化剂

Cu( II ) 固定在载有地拉罗司的胺官能化磁性纳米粒子 (Cu( II )/Fe 3 O 4 @APTMS-DFX) 上作为一种新型可磁回收的多相催化剂,能够催化各种有机腈的 [3 + 2] 环加成反应与叠氮化钠。使用这种方法,一系列 5-取代-1 H在温和条件下在DMSO中制备-四唑。该反应涉及温和的反应条件,具有高效的转化能力。通过施加外部磁场可以很容易地分离开发的催化剂。此外,它可以循环使用 5 次,而铜从催化剂表面的浸出可忽略不计。该催化剂通过多种技术进行表征,例如 FT-IR、TGA、VSM、SEM-EDX 和 ICP-OES。1 H的几个导数使用这种催化剂制备了-四唑,并使用不同的技术确认了它们的结构。然后,评估合成的蒽醌对包括 MCF-7、MAD-MD-231、HT-29、HeLa、neuro-2a 和 L-929 在内的几种细胞系的细胞毒性。从 MTT 测定中获得的结果表明,这 6 种衍生物表现出高水平的细胞毒性。为了确定细胞毒性机制,选择了2个具有最高细胞毒活性的衍生物,并通过流式细胞仪进行了细胞凋亡测定,支持细胞凋亡是主要机制。
更新日期:2017-09-15
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