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

被引:13
作者
Glanzmann, Nicolas [1 ]
Carmo, Arturene M. L. [2 ]
Antinarelli, Luciana M. R. [3 ]
Coimbra, Elaine S. [3 ]
Costa, Luiz Antonio S. [4 ]
da Silva, Adilson D. [1 ]
机构
[1] Univ Fed Juiz de Fora, Dept Quim, ICE, Campus Univ, BR-36036900 Juiz De Fora, MG, Brazil
[2] Inst Fed Sul Minas, Campus Muzambinho, BR-37890000 Muzambinho, MG, Brazil
[3] Univ Fed Juiz de Fora, Dept Parasitol Microbiol & Imunol, ICB, Campus Univ, BR-36036900 Juiz De Fora, MG, Brazil
[4] Univ Fed Juiz de Fora, Dept Quim, NEQC, ICE, Campus Univ, BR-36036900 Juiz De Fora, MG, Brazil
关键词
Ionic liquids; DFT calculations; NMR; Lypophilia; BASIS-SET; CHEMISTRY;
D O I
10.1007/s00894-018-3682-z
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
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 H-1, C-13 NMR 1D, and 2D spectroscopy. DFT calculations have also been performed in a way to help to provide an insightful structural analysis from C-13 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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页数:7
相关论文
共 48 条
[1]   ICM - A NEW METHOD FOR PROTEIN MODELING AND DESIGN - APPLICATIONS TO DOCKING AND STRUCTURE PREDICTION FROM THE DISTORTED NATIVE CONFORMATION [J].
ABAGYAN, R ;
TOTROV, M ;
KUZNETSOV, D .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1994, 15 (05) :488-506
[2]   Triazolium cations: from the "click" pool to multipurpose applications [J].
Aizpurua, Jesus M. ;
Fratila, Raluca M. ;
Monasterio, Zaira ;
Perez-Esnaola, Nerea ;
Andreieff, Elena ;
Irastorza, Aitziber ;
Sagartzazu-Aizpurua, Maialen .
NEW JOURNAL OF CHEMISTRY, 2014, 38 (02) :474-480
[3]  
Anastas P. T., 2000, GREEN CHEM THEORY PR, P132
[4]  
[Anonymous], 2015, Gaussian 09, Revision D.01
[5]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[6]   Gaussian basis set of double zeta quality for atoms Rb through Xe: application in non-relativistic and relativistic calculations of atomic and molecular properties [J].
Barros, C. L. ;
de Oliveira, P. J. P. ;
Jorge, F. E. ;
Canal Neto, A. ;
Campos, M. .
MOLECULAR PHYSICS, 2010, 108 (15) :1965-1972
[7]   A strategy for primary high throughput cytotoxicity screening in pharmaceutical toxicology [J].
Bugelski, PJ ;
Atif, U ;
Molton, S ;
Toeg, I ;
Lord, PG ;
Morgan, DG .
PHARMACEUTICAL RESEARCH, 2000, 17 (10) :1265-1272
[8]   Synthesis of 1,2,3-Triazolium-Based Ionic Liquid and Preliminary Pretreatment to Enhance Hydrolysis of Sugarcane Bagasse [J].
Carmo, Arturene M. L. ;
Stroppa, Pedro H. F. ;
Corrales, Roberta C. N. R. ;
Barroso, Anna B. N. ;
Ferreira-Leitao, Viridiana S. ;
Silva, Adilson D. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2014, 25 (11) :2088-2093
[9]   SELF-CONSISTENT PERTURBATION-THEORY OF DIAMAGNETISM .1. GAUGE-INVARIANT LCAO METHOD FOR NMR CHEMICAL-SHIFTS [J].
DITCHFIELD, R .
MOLECULAR PHYSICS, 1974, 27 (04) :789-807
[10]   On the solid, liquid and solution structural organization of imidazolium ionic liquids [J].
Dupont, J .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2004, 15 (03) :341-350