The inhibitory effects of nine ionic liquids (ILs) on the catalase activity were investigated using fluorescence, absorption ultraviolet-visible spectroscopy. The interactions of ILs and catalase on the molecular level were studied. The experimental results indicated that ILs could inhibit the catalase activity and their inhibitory abilities depended on their chemical structures. Fluorescence experiments showed that hydrogen bonding played an important role in the interaction process. The inhibitory abilities of ILs on catalase activity could be simply described by their hydrophobicity and hydrogen bonding abilities. Unexpected less inhibitory effects of trifluoromethanesulfonate (TfO−) might be ascribed to its larger size, which makes it difficult to go through the substrate channel of catalase to the active site.
ZhaoH.BakerG.A.“Ionic Liquids and Deep Eutectic Solvents for Biodiesel Synthesis: A Review”. J. Chem. Technol. Biotechnol2013; 88(1): 3–12.
2.
AlTuwaimM.S.AlkhaldiK.H.A.E.Al-JimazA.S.MohammadA.A.“Temperature Dependence of Physicochemical Properties of Imidazolium-, Pyroldinium-, and Phosphonium-Based Ionic Liquids”. J. Chem. Eng. Data2014; 59(6): 1955–1963.
3.
CostaS.P.F.PintoP.C.A.G.LapaR.A.S.SaraivaM.L.M.F.S.“Toxicity Assessment of Ionic Liquids with Vibrio Fischeri: An Alternative Fully Automated Methodology”. J. Hazard. Mater2015; 284: 136–142.
4.
VenturaS.P.M.GurbiszM.GhavreM.FerreiraF.M.M.GonçalvesF.BeadhamI.QuiltyB.CoutinhoJ.A.P.GathergoodN.“Imidazolium and Pyridinium Ionic Liquids from Mandelic Acid Derivatives: Synthesis and Bacteria and Algae Toxicity Evaluation”. ACS Sustain. Chem. Eng2013; 1(4): 393–402.
5.
DasR.N.RoyK.“Predictive Modeling Studies for the Ecotoxicity of Ionic Liquids Towards the Green Algae Scenedesmus Vacuolatus”. Chemosphere2014; 104: 170–176.
6.
MikkolaS.K.RobciucA.LokajováJ.HoldingA.J.LämmerhoferM.KilpeläinenI.HolopainenJ.M.KingA.W.WiedmerS.K.“Impact of Amphiphilic Biomass-Dissolving Ionic Liquids on Biological Cells and Liposomes”. Environ. Sci. Technol2015; 49(3): 1870–1878.
7.
BaileyM.M.TownsendM.B.JerniganP.L.SturdivantJ.Hough-TroutmanW.L.RascoJ.F.SwatloskiR.P.RogersR.D.HoodR.D.“Developmental Toxicity Assessment of the Ionic Liquid 1-Butyl-3-Methylimidazolium Chloride in CD-1 Mice”. Green Chem2008; 10(11): 1213–1217.
8.
LacrămăA.M.Popeţ L.OstafeV.“Use of Catalase from Spinach for Testing at Molecular Level the Toxicity of Some Ionic Liquids”. Ann. West Univ. Timisoara, Ser. Chem2007; 16(2): 191–200.
9.
StolteS.SchulzT.ChoC.W.ArningJ.StrassnerT.“Synthesis, Toxicity, and Biodegradation of Tunable Aryl Alkyl Ionic Liquids (TAAILs)”. ACS Sustain. Chem. Eng2013; 1(4): 410–418.
10.
YanF.XiaS.WangQ.MaP.“Predicting Toxicity of Ionic Liquids in Acetylcholinesterase Enzyme by the Quantitative Structure−Activity Relationship Method Using Topological Indexes”. J. Chem. Eng. Data2012; 57(8): 2252–2257.
11.
LuoY.R.WangS.H.YunM.X.LiX.Y.WangJ.J.SunZ.J.“The Toxic Effects of Ionic Liquids on the Activities of Acetylcholinesterase and Cellulase in Earthworms”. Chemosphere2009; 77(3): 313–318.
12.
ArningJ.StolteS.BoschenA.StockF.PitnerW.R.Welz-BiermannU.Jas-torffB.RankeJ.“Qualitative and Quantitative Structure Activity Relationships for the Inhibitory Effects of Cationic Head Groups, Functionalised Side Chains and Anions of Ionic Liquids on Acetylcholinesterase”. Green Chem2008; 10(1): 47–58.
13.
CunhaE.PintoP.C.A.G.CarvalhoJ.P.S.SaraivaM.L.M.F.S.“Automated Carboxylesterase Assay for the Evaluation of Ionic Liquids' Human Toxicity”. J. Hazard. Mater2013; 244–245: 563–569.
14.
CostaS.P.F.JustinaV.D.BicaK.VasiloiuM.PintoP.C.A.G.SaraivaM.L.M.F.S.“Automated Evaluation of Pharmaceutically Active Ionic Liquids’ (Eco)toxicity Through the Inhibition of Human Carboxylesterase and Vibrio Fischeri”. J. Hazard. Mater2014; 265: 133–141.
15.
PintoP.C.A.G.CostaA.D.F.LimaJ.L.F.C.SaraivaM.L.M.F.S.“Automated Evaluation of the Effect of Ionic Liquids on Catalase Activity”. Chemosphere2011; 82(11): 1620–1628.
16.
HouX.D.LiuQ.P.SmithT.J.LiN.ZongM.H.“Evaluation of Toxicity and Biodegradability of Cholinium Amino Acids Ionic Liquids”. PLoS One2013; 8(3): e59145.
17.
SkladanowskiA.C.StepnowskiP.KleszczynskiK.DmochowskaB.“AMP Deaminase in Vitro Inhibition by Xenobiotics: a Potential Molecular Method for Risk Assessment of Synthetic Nitro- and Polycyclic Musks, Imidazolium Ionic Liquids and N-Glucopyranosyl Ammonium Salts”. Environ. Toxicol. Pharmacol2005; 19(2): 291–296.
18.
TeeK.L.RoccatanoD.StolteS.ArningJ.JastorffB.SchwanebergU.“Ionic Liquid Effects on the Activity of Monooxygenase P450 BM-3”. Green Chem2008; 10(1): 117–123.
19.
FanY.ZhangS.WangQ.LiJ.FanH.ShanD.“Investigation of the Interaction of Pepsin with Ionic Liquids by Using Fluorescence Spectroscopy”. Appl. Spectrosc2013; 67(6): 648–655.
20.
DiCarloC.M.ComptonD.L.EvansK.O.LaszloJ.A.“Bioelectrocatalysis in Ionic Liquids. Examining Specific Cation and Anion Effects on Electrode-Immobilized Cytochrome c”. Bioelectrochemistry2006; 68(2): 134–143.
21.
BihariM.RussellT.P.HoaglandD.A.“Dissolution and Dissolved State of Cytochrome c in a Neat, Hydrophilic Ionic Liquid”. Biomacromolecules2010; 11(11): 2944–2948.
22.
WeiW.DanielsonN.D.“Fluorescence and Circular Dichroism Spectroscopy of Cytochrome c in Alkylammonium Formate Ionic Liquids”. Biomacromolecules2011; 12(2): 290–297.
23.
BakerS.N.ZhaoH.PandeyS.HellerW.T.BrightF.V.BakerG.A.“Fluorescence Energy Transfer Efficiency in Labeled Yeast Cytochrome c: A Rapid Screen for Ion Biocompatibility in Aqueous Ionic Liquids”. Phys. Chem. Chem. Phys2011; 13(9): 3642–3644.
24.
ZhaoH.BakerG.A.SongZ.OlubajoO.CrittleT.PetersD.“Designing Enzyme-Compatible Ionic Liquids That Can Dissolve Carbohydrates”. Green Chem2008; 10(6): 696–705.
25.
BakerS.N.McCleskeyT.M.PandeyS.BakerG.A.“Fluorescence Studies of Protein Thermostability in Ionic Liquids”. Chem. Commun2004(8, 940–941.
26.
HuangJ.L.NossM.E.SchmidtK.M.MurrayL.BunaganM.R.“The Effect of Neat Ionic Liquid on the Folding of Short Peptides”. Chem. Commun2011; 47(28): 8007–8009.
27.
McCartyT.A.PageP.M.BakerG.A.BrightF.V.“Behavior of Acrylodan-Labeled Human Serum Albumin Dissolved in Ionic Liquids”. Ind. Eng. Chem. Res2008; 47(3): 560–569.
28.
HellerW.T.O’NeillH.M.ZhangQ.BakerG.A.“Characterization of the Influence of the Ionic Liquid 1-Butyl-3-Methylimidazolium Chloride on the Structure and Thermal Stability of Green Fluorescent Protein”. J. Phys. Chem. B2010; 114(43): 13866–13871.
29.
LaiJ.Q.LiZ.LüY.H.YangZ.“Specific Ion Effects of Ionic Liquids on Enzyme Activity and Stability”. Green Chem2011; 13(7): 1860–1868.
30.
ConstantinescuD.WeingärtnerH.HerrmannC.“Protein Denaturation by Ionic Liquids and the Hofmeister Series: A Case Study of Aqueous Solutions of Ribonuclease A”. Angew. Chem. Int. Ed2007; 46(46): 8887–8889.
31.
ZhaoH.OlubajoO.SongZ.SimsA.L.PersonT.E.LawalR.A.HolleyL.A.“Effect of Kosmotropicity of Ionic Liquids on the Enzyme Stability in Aqueous Solutions”. Bioorg. Chem2006; 34(1): 15–25.
32.
ZhaoH.CampbellS.M.JacksonL.SongZ.OlubajoO.“Hofmeister Series of Ionic Liquids: Kosmotropic Effect of Ionic Liquids on the Enzymatic Hydrolysis of Enantiomeric Phenylalanine Methyl Ester”. Tetrahedron Asymmetr2006; 17(3): 377–383.
33.
YangZ.“Hofmeister Effects: an Explanation for the Impact of Ionic Liquids on Biocatalysis”. J. Biotechnol2009; 144(1): 12–22.
34.
ZhaoH.“Methods for Stabilizing and Activating Enzymes in Ionic Liquids – a Review”. J. Chem. Technol. Biotechnol2010; 85(7): 891–907.
35.
NaushadM.ALOthmanZ.A.KhanA.B.AliM.“Effect of Ionic Liquid on Activity, Stability, and Structure of Enzymes: A Review”. Inter. J. Biol. Macromol2012; 51(4): 555–560.
36.
FanY.LiY.CaiH.LiJ.MiaoJ.FuD.YangQ.“Fluorescence Spectrometry of the Interaction of Multi-Walled Carbon Nanotubes with Catalase”. J. Appl. Spectrosc2014; 81(5): 795–800.
37.
CanesiL.FabbriR.GalloG.VallottoD.MarcominiA.PojanaG.“Biomarkers in Mytilus Galloprovincialis Exposed to Suspensions of Selected Nanoparticles (Nano Carbon Black, C60 Fullerene, Nano-TiO2, Nano-SiO2)”. Aquat. Toxicol2010; 100(2): 168–177.
38.
FanY.LiY.DongX.HuG.HuaS.MiaoJ.ZhouD.“Extraction of Phenols from Water with Functionalized Ionic Liquids”. Ind. Eng. Chem. Res2014; 53(51): 20024–20031.
39.
LeeS.H.LeeS.B.“Octanol/Water Partition Coefficients of Ionic Liquids”. J. Chem. Technol. Biotechnol2009; 84(2): 202–207.
40.
HauruL.K.J.HummelM.KingA.KilpeläinenI.SixtaH.“Role of Solvent Parameters in the Regeneration of Cellulose from Ionic Liquid Solutions”. Biomacromolecules2012; 13(9): 2896–2905.
41.
PhamT.P.T.ChoC.W.YunY.S.“Environmental Fate and Toxicity of Ionic Liquids: A Review”. Water Res2010; 44(2): 352–372.
42.
AzimiO.EmamiZ.SalariH.ChamaniJ.“Probing the Interaction of Human Serum Albumin with Norfloxacin in the Presence of High-Frequency Electromagnetic Fields: Fluorescence Spectroscopy and Circular Dichroism Investigations”. Molecules2011; 16(12): 9792–9818.
43.
LiuZ.GuoX.FengZ.JiaL.“Spectroscopic Investigation of the Interaction of Pyridinium Surfactant with Bovine Serum Albumin”. J. Solution Chem2015; 44(2): 293–306.
44.
RossP.D.SubramanianS.“Thermodynamics of Protein Association Reactions: Forces Contributing to Stability”. Biochemistry1981; 20(11): 3096–3102.
45.
JakopitschC.DroghettiE.SchmuckenschlagerF.FurtmüllerP.G.SmulevichG.ObingerC.“Role of the Main Access Channel of Catalase-Peroxidase in Catalysis”. J. Biol. Chem2005; 280(51): 42411–42422.
46.
VlasitsJ.JakopitschC.SchwanningerM.HolubarP.ObingerC.“Hydrogen Peroxide Oxidation by Catalase-Peroxidase Follows a Non-Scrambling Mechanism”. FEBS Lett2007; 581(2): 320–324.
47.
LungwitzR.StrehmelV.SpangeS.“The Dipolarity/Polarisability of 1-Alkyl-3-Methylimidazolium Ionic Liquids as Function of Anion Structure and the Alkyl Chain Length”. New J. Chem2010; 34(6): 1135–1140.
Ab RaniM.A.BrantA.CrowhurstL.DolanA.LuiM.HassanN.H.HallettJ.P.HuntP.A.NiedermeyerH.Perez-ArlandisJ.M.SchremsM.WeltonT.WildingR.“Understanding the Polarity of Ionic Liquids”. Phys. Chem. Chem. Phys2011; 13(37): 16831–16840.
50.
DomínguezL.Sosa-PeinadoA.HansbergW.“How Catalase Recognizes H2O2 in a Sea of Water”. Proteins2014; 82(1): 45–56.
PergerT.M.Bešter-RogačM.“Thermodynamics of Micelle Formation of Alkyltrimethylammonium Chlorides from High Performance Electric Conductivity Measurements”. J. Colloid Interface Sci2007; 313(1): 288–295.
53.
ChenW.T.HsuW.Y.LinM.Y.TaiC.C.WangS.P.SunI.W.“Isolated BMI+ Cations are More Than Isolated PF6− Anions in the Room Temperature 1-Butyl-3-Methylimidazolium Hexafluorophosphate (BMI–PF6) Ionic Liquid”. J. Chin. Chem. Soc2010; 57(6): 1293–1298.
54.
BharmoriaP.TrivediT.J.PabbathiA.SamantaA.KumarA.“Ionic Liquid-Induced All-α to α + β Conformational Transition in Cytochrome c with Improved Peroxidase Activity in Aqueous Medium”. Phys. Chem. Chem. Phys2015; 17(15): 10189–10199.
55.
BravoJ.VerdaguerN.TormoJ.BetzelC.SwitalaJ.LoewenP.C.FitaI.“Crystal Structure of Catalase HPII from Escherichia Coli”. Structure1995; 3(5): 491–502.
