Synthesis, characterization, and NMR studies of 1,2,3-triazolium ionic liquids: a good perspective regarding cytotoxicity

被引:0
作者
Nicolas Glanzmann
Arturene M. L. Carmo
Luciana M. R. Antinarelli
Elaine S. Coimbra
Luiz Antônio S. Costa
Adilson D. da Silva
机构
[1] Universidade Federal de Juiz de Fora,Departamento de Química, I.C.E
[2] Instituto Federal do Sul de Minas,Departamento de Parasitologia, Microbiologia e Imunologia, I.C.B
[3] Universidade Federal de Juiz de Fora,NEQC – Núcleo de Estudos em Química Computacional, Departamento de Química, I.C.E.
[4] Universidade Federal de Juiz de Fora,undefined
来源
Journal of Molecular Modeling | 2018年 / 24卷
关键词
Ionic liquids; DFT calculations; NMR; Lypophilia;
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摘要
Ionic liquids (ILs) have been extensively studied and are considered green solvents capable of replacing traditional organic solvents. In this study, seven 1,2,3-triazolium derivative ILs have been synthesized. In order to study the effect of the cation nature on the ILs cytotoxicity, their structures were first identified by 1H, 13C NMR 1D, and 2D spectroscopy. DFT calculations have also been performed in a way to help to provide an insightful structural analysis from 13C NMR spectroscopy. The comparison made with the NMR experimental shifts was quite important to show that the 1,2,3-triazolium derivatives have the expected structure shown here. The in vitro cytotoxicity of ILs toward macrophages showed that among the compounds tested, five did not exhibit expressive cytotoxicity on mammalian cells. Besides the well-established relationship between the carbonic chain size of the cation and the cytotoxicity, the log P of the compounds predicts that the toxicity increases with the size of the carbon chain, demonstrating that the most cytotoxic compound is also the most lipophilic one. The low cytotoxicity effect of ILs on mammalian cells points to their potential application in large-scale by industry.
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[1]  
Neto BAD(2012)The impressive chemistry, applications and features of ionic liquids: properties, catalysis & catalysts and trends J Braz Chem Soc 23 987-1007
[2]  
Spencer J(2011)Probing the structure-property relationship of regioisomeric ionic liquids with click chemistry Green Chem 13 3345-3349
[3]  
Nulwala HB(2011)Fractionation of bagasse into cellulose, hemicelluloses, and lignin with ionic liquid treatment followed by alkaline extraction J Agric Food Chem 59 8691-8701
[4]  
Tang CN(2009)Versatile synthesis of 1, 2, 3-triazolium-based ionic liquids ARKIVOC 12 193-208
[5]  
Kail BW(2014)Triazolium cations: from the "click" pool to multipurpose applications New J Chem 38 474-480
[6]  
Lan W(2008)Applications of ionic liquids in the chemical industry Chem Soc Rev 37 123-150
[7]  
Liu C-F(2002)Ionic liquid (molten salt) phase organometallic catalysis Chem Rev 102 3667-3692
[8]  
Sun R-C(2004)On the solid, liquid and solution structural organization of imidazolium ionic liquids J Braz Chem Soc 15 341-350
[9]  
Khan SS(2011)Room-temperature ionic liquids: solvents for synthesis and catalysis. 2 Chem Rev 111 3508-3576
[10]  
Hanelt S(2010)Ionic liquids and catalysis: recent progress from knowledge to applications Appl Catal A-Gen 373 1-56