The antimicrobial potential of ionic liquids: A source of chemical diversity for infection and biofilm control

International Journal of Antimicrobial Agents

Volumn 46, Issue 2, 2015, Pages 131-139

  Pendleton, Jack Norman ^a   Gilmore, Brendan F ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

Active pharmaceutical ingredient; Antibiotic resistance; Antimicrobial; Biocide; Disinfection; Ionic liquids

Indexed keywords

ANION; ANTIINFECTIVE AGENT; BIOCIDE; CETYLPYRIDINIUM CHLORIDE PLUS DOMIPHEN BROMIDE; COPPER; IMIDAZOLIUM SALT; IONIC LIQUID; MORPHOLINIUM; QUATERNARY AMMONIUM DERIVATIVE; SILVER; SOLVENT; SURFACTANT; TRIGEMINAL TRICATIONIC IONIC LIQUID; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; BACTERICIDAL ACTIVITY; BIODEGRADATION; BIOFILM; BIOREMEDIATION; CHIRALITY; DENATURATION; DRUG SCREENING; ECOTOXICITY; ENTEROCOCCUS FAECIUM; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; INFECTION CONTROL; KLEBSIELLA PNEUMONIAE; LD50; LIPOPHILICITY; MICROBIAL DIVERSITY; MINIMUM BACTERICIDAL CONCENTRATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; ROOM TEMPERATURE; STAPHYLOCOCCUS AUREUS; DRUG EFFECTS; HUMAN;

ANTI-INFECTIVE AGENTS; BIOFILMS; HUMANS; IONIC LIQUIDS;

EID: 84937632816     PISSN: 09248579     EISSN: 18727913     Source Type: Journal    
DOI: 10.1016/j.ijantimicag.2015.02.016     Document Type: Review

References (112)

1. M. Zignol, W. van Gemert, D. Falzon, C. Sismanidis, P. Glaziou, K. Floyd, and et al. Surveillance of anti-tuberculosis drug resistance in the world: an updated analysis, 2007-2010 Bull World Health Organ 90 2012 111-9D
2. A.T. Sheldon Antiseptic 'resistance': real or perceived threat? Clin Infect Dis 40 2005 1650 1656
3. J.Y. Maillard Bacterial resistance to biocides in the healthcare environment: should it be of genuine concern J Hosp Infect 65 2007 60 72
4. A.D. Russell Biocide use and antibiotic resistance: the relevance of laboratory findings to clinical and environmental situations Lancet Infect Dis 3 2003 794 803
5. A.H. Uttley, C.H. Collins, J. Naidoo, and R.C. George Vancomycin-resistant enterococci Lancet 1 1988 57 58
6. European Centre for Disease Prevention Control (ECDC) Annual epidemiological report on communicable diseases in Europe 2010 2010 ECDC Stockholm, Sweden
7. European Centre for Disease Prevention Control (ECDC) Annual epidemiological report 2011 - reporting on 2009 surveillance data and 2010 epidemic intelligence data 2011 ECDC Stockholm, Sweden
8. D. Davies Understanding biofilm resistance to antibacterial agents Nat Rev Drug Discovery 2 2003 114 122
9. H. Ceri, M.E. Olson, and R.J. Turner Needed, new paradigms in antibiotic development Expert Opin Pharmacother 11 2010 1233 1237
10. B.S. Tseng, W. Zhang, J.J. Harrison, T.P. Quach, J.L. Song, J. Penterman, and et al. The extracellular matrix protects Pseudomonas aeruginosa biofilms by limiting the penetration of tobramycin Environ Microbiol 15 2013 2865 2878
11. A.S. Messian, H. Nelis, and T. Coenye Investigating the role of matrix components in protection of Burkholderia cepacia complex biofilms against tobramycin J Cyst Fibros 13 2014 56 62
12. N. Doroshenko, B.S. Tseng, R.P. Howlin, J. Deacon, J.A. Wharton, P.J. Thurner, and et al. Extracellular DNA impedes the transport of vancomycin in Staphylococcus epidermidis biofilms preexposed to subinhibitory concentrations of vancomycin Antimicrob Agents Chemother 58 2014 7273 7282
13. NDM-1, and a novel erythromycin esterase gene carried on a unique genetic structure in Klebsiella pneumoniae sequence type 14 from India Antimicrob Agents Chemother 53 2009 5046 5054
14. K.K. Kumarasamy, M.A. Toleman, T.R. Walsh, J. Bagaria, F. Butt, R. Balakrishnan, and et al. Emergence of a new antibiotic resistance mechanism in India, Pakistan, and the UK: a molecular, biological, and epidemiological study Lancet Infect Dis 10 2010 597 602
15. P.C. Appelbaum Reduced glycopeptide susceptibility in methicillin-resistant Staphylococcus aureus (MRSA) Int J Antimicrob Agents 30 2007 398 408
16. J.W. Costerton, P.S. Stewart, and E.P. Greenberg Bacterial biofilms: a common cause of persistent infections Science 284 1999 1318 1322
17. M. Parsek, and P. Singh Bacterial biofilms: an emerging link to disease pathogenesis Annu Rev Microbiol 57 2003 677 701
18. J.B. Lyczak, C.L. Cannon, and G.B. Pier Lung infections associated with cystic fibrosis Clin Microbiol Rev 15 2002 194 222
19. D. Romero, and R. Kolter Will biofilm disassembly agents make it to market? Trends Microbiol 19 2011 304 306
20. L. Carson, P.K.W. Chau, M.J. Earle, M.A. Gilea, B.F. Gilmore, S.P. Gorman, and et al. Antibiofilm activities of 1-alkyl-3-methylimidazolium chloride ionic liquids Green Chem 11 2009 492 497
21. A. Busetti, D.E. Crawford, M.J. Earle, M.A. Gilea, B.F. Gilmore, S.P. Gorman, and et al. Antimicrobial and antibiofilm activities of 1-alkylquinolinium bromide ionic liquids Green Chem 12 2010 420 425
22. K.R. Seddon, A. Stark, and M.J. Torres Influence of chloride, water and organic solvents on the physical properties of ionic liquids Pure Appl Chem 72 2000 2275 2287
23. J.H. Davis Task-specific ionic liquids Chem Lett 33 2004 1072 1077
24. M. Freemantle Designer solvents - ionic liquids may boost clean technology development Chem Eng News 76 1998 32 37
25. M.J. Earle, and K.R. Seddon Ionic liquids: green solvents for the future M.A. Abraham, L. Moens, Clean solvents. Alternative media for chemical reactions and processing 2002 American Chemical Society Washington, DC 10 25
26. R.P. Swatloski, J.D. Holbrey, and R.D. Rogers Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate Green Chem 5 2003 361 363
27. S. Kucharski, and J. Pernak Efficacy of new quaternary ammonium salts against various bacteria and fungi I. Studies of compounds 1-11 Med Dosw Mikrobiol 30 1978 93 98 (in Polish)
28. B.F. Gilmore Antimicrobial ionic liquids P.A. Kokorin, Ionic liquids: applications and perspectives 2011 InTech Rijeka, Croatia 587 604
29. K.R. Seddon Ionic liquids for clean technology J Chem Technol Biotechnol 68 1997 351 356
30. M. Freemantle An introduction to ionic liquids 2009 The Royal Society of Chemistry Cambridge, UK
31. M. Petkovic, K.R. Seddon, L.P.N. Rebelo, and C. Silva Pereira Ionic liquids: a pathway to environmental acceptability Chem Soc Rev 40 2011 1383 1403
32. E.F. Borra, O. Seddiki, R. Angel, D. Eisenstein, P. Hickson, K.R. Seddon, and et al. Deposition of metal films on an ionic liquid as a basis for a lunar telescope Nature 447 2007 979 981
33. A. Modaressi, H. Sifaoui, M. Mielcarz, U. Domanska, and M. Rogalski Influence of the molecular structure on the aggregation of imidazolium ionic liquids in aqueous solutions Colloids Surf, A: Physicochem Eng Aspects 302 2007 181 185
34. J. Pernak, A. Czepukowicz, and R. Poźniak New ionic liquids and their antielectrostatic properties Ind Eng Chem Res 40 2001 2379 2383
35. J.D. Holbrey, and K.R. Seddon Ionic liquids Clean Technol Environ Policy 1 1999 223 236
36. J. Pernak, A. Syguda, I. Mirska, A. Pernak, J. Nawrot, A. Pradzyńska, and et al. Choline-derivative-based ionic liquids Chemistry 13 2007 6817 6827
37. J. Pernak, J. Rogoza, and I. Mirska Synthesis and antimicrobial activities of new pyridinium and benzimidazolium chlorides Eur J Med Chem 36 2001 313 320
38. J. Pernak, J. Kalewska, H. Ksycinska, and J. Cybulski Synthesis and anti-microbial activities of some pyridinium salts with alkoxymethyl hydrophobic group Eur J Med Chem 36 2001 899 907
39. J. Pernak, K. Sobaszkiewicz, and I. Mirska Anti-microbial activities of ionic liquids Green Chem 5 2003 52 56
40. J. Pernak, and P. Chwala Synthesis and anti-microbial activities of choline-like quaternary ammonium chlorides Eur J Med Chem 38 2003 1035 1042
41. J. Pernak, I. Goc, and I. Mirska Anti-microbial activities of protic ionic liquids with lactate anion Green Chem 6 2004 323 329
42. A. Cieniecka-Roslonkiewicz, J. Pernak, J. Kubis-Feder, A. Ramani, A.J. Robertson, and K.R. Seddon Synthesis, anti-microbial activities and anti-electrostatic properties of phosphonium-based ionic liquids Green Chem 7 2005 855 862
43. H. Turkmen, N. Ceyhan, N. Ulku Karabay Yavasoglu, G. Ozdemir, and B. Cetinkaya Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents Eur J Med Chem 46 2011 2895 2900
44. B.F. Gilmore, G.P. Andrews, G. Borberly, M.J. Earle, M.A. Gilea, S.P. Gorman, and et al. Enhanced antimicrobial activities of 1-alkyl-3-methylimidazolium ionic liquids based on silver or copper containing anions New J Chem 37 2013 873 876
45. M. Blesic, M.H. Marques, N.V. Plechkova, K.R. Seddon, L.P.N. Rebelo, and A. Lopes Self-aggregation of ionic liquids: micelle formation in aqueous solution Green Chem 9 2007 481 490
46. J. Pernak, A. Skrzypezak, G. Lota, and E. Frackowiak Synthesis and properties of trigeminal tricationic ionic liquids Chemistry 13 2007 3106 3112
47. J. Luczak, J. Hupka, J. Thöming, and C. Jungnickel Self-organization of imidazolium ionic liquids in aqueous solution Colloids Surf, A: Physicochem Eng Aspects 329 2008 125 133
48. J. Luczak, C. Jungnickel, I. Lacka, S. Stolte, and J. Hupka Antimicrobial and surface activity of 1-alkyl-3-methylimidazolium derivatives Green Chem 12 2010 593 601
49. C. Jungnickel, J. Luczak, J. Ranke, J.F. Fernández, A. Müller, and J. Thöming Micelle formation of imidazolium ionic liquids in aqueous solution Colloids Surf, A: Physicochem Eng Aspects 316 2008 278 284
50. S.P. Denyer Mechanisms of action of antibacterial biocides Int Biodeterior Biodegrad 36 1995 227 245
51. F. Stock, J. Hoffmann, J. Ranke, R. Stormann, B. Ondruschka, and B. Jastorff Effects of ionic liquids on the acetylcholinesterase - a structure-activity relationship consideration Green Chem 6 2004 286 290
52. A.C. Skladanowski, P. Stepnowski, K. Kleszczyński, and B. Dmochowska 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 Pharmacol 19 2005 291 296
53. J. Ranke, S. Stolte, R. Störmann, J. Arning, and B. Jastorff Design of sustainable chemical products - the example of ionic liquids Chem Rev 107 2007 2183 2206
54. L. Furi, M.L. Ciusa, D. Knight, V. Di Lorenzo, N. Tocci, D. Cirasola, and et al. Evaluation of reduced susceptibility to quaternary ammonium compounds and bisbiguanides in clinical isolates and laboratory-generated mutants of Staphylococcus aureus Antimicrob Agents Chemother 57 2013 3488 3497
55. T.L. Reugg, E.M. Kim, B.A. Simmons, J.D. Keasling, S.W. Singer, T.S. Lee, and et al. An auto-inducible mechanism for ionic liquid resistance in microbial biofuel production Nat Commun 5 2014 3490
56. V.M. D'Costa, C.E. King, L. Kalan, M. Morar, W.W. Sung, C. Schwarz, and et al. Antibiotic resistance is ancient Nature 477 2011 457 461
57. UFT The UFT/Merck ionic liquids biological effects database 2011 Ionic Liquid Working Group (Centre for Environmental Research and Sustainable Technology), Merck KGaA
58. J. Pernak, K. Sobaszkiewicz, and J. Foksowicz-Flaczyk Ionic liquids with symmetrical dialkoxymethyl-substituted imidazolium cations Chemistry 10 2004 3479 3485
59. S. Stolte, J. Arning, U. Bottin-Weber, M. Matzke, F. Stock, K. Thiele, and et al. Anion effects on the cytotoxicity of ionic liquids Green Chem 8 2006 621 629
60. S. Stolte, M. Matzke, J. Arning, A. Boschen, W. Pitner, U. Welz-Biermann, and et al. Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids Green Chem 9 2007 1170 1179
61. J. Ranke, A. Othman, P. Fan, and A. Müller Explaining ionic liquid water solubility in terms of cation and anion hydrophobicity Int J Mol Sci 10 2009 1271 1289
62. A. Cornellas, L. Perez, F. Comelles, I. Ribosa, A. Manresa, and M.T. Garcia Self-aggregation and antimicrobial activity of imidazolium and pyridinium based ionic liquids in aqueous solution J Colloid Interface Sci 355 2011 164 171
63. G. Laverty, M. McLaughlin, C. Shaw, S.P. Gorman, and B.F. Gilmore Antimicrobial activity of short, synthetic cationic lipopeptides Chem Biol Drug Des 75 2010 563 569
64. W.L. Hough, M. Smiglak, H. Rodriguez, R.P. Swatloski, S.K. Spear, D.T. Daly, and et al. The third evolution of ionic liquids: active pharmaceutical ingredients New J Chem 31 2007 1429 1436
65. W.L. Hough, and R.D. Rogers Ionic liquids then and now: from solvents to materials to active pharmaceutical ingredients Bull Chem Soc Jpn 80 2007 2262 2269
66. M. McLaughlin, M.J. Earle, M.A. Gilea, B.F. Gilmore, S.P. Gorman, and K.R. Seddon Cytotoxicity of 1-alkylquinolinium bromide ionic liquids in murine fibroblast NIH 3T3 cells Green Chem 13 2011 2794 2800
67. J. Pernak, N. Borucka, F. Walkiewicz, B. Markiewicz, P. Fochtman, S. Stolte, and et al. Synthesis, toxicity, biodegradability and physicochemical properties of 4-benzyl-4-methylmorpholinium-based ionic liquids Green Chem 13 2011 2901 2910
68. M. Petkovic, J.L. Ferguson, H.Q.N. Gunaratne, R. Ferreira, M.C. Leitao, K.R. Seddon, and et al. Novel biocompatible cholinium-based ionic liquids - toxicity and biodegradability Green Chem 12 2010 643 649
69. F. Walkiewicz, K. Materna, A. Kropacz, A. Michalczyk, R. Gwiazdowski, T. Praczyk, and et al. Multifunctional long-alkyl-chain quaternary ammonium azolate based ionic liquids New J Chem 34 2010 2281 2289
70. J. Cybulski, A. Wïniewska, A. Kulig-Adamiak, Z. Dąbrowski, T. Praczyk, A. Michalczyk, and et al. Mandelate and prolinate ionic liquids: synthesis, characterization, catalytic and biological activity Tetrahedron Lett 52 2011 1325 1328
71. S.M. Saadeh, Z. Yasseen, F.A. Sharif, and H.M. Abu Shawish New room temperature ionic liquids with interesting ecotoxicological and antimicrobial properties Ecotoxicol Environ Safety 9 2009 1805 1809
72. M. Rebros, H. Gunaratne, J. Ferguson, K. Seddon, and G. Stephens A high throughput screen to test the biocompatibility of water-miscible ionic liquids Green Chem 11 2009 402 408
73. J. Pernak, and J. Feder-Kubis Synthesis and properties of chiral ammonium-based ionic liquids Chemistry 11 2005 4441 4449
74. E.E. Alberto, L.L. Rossato, S.H. Alves, D. Alves, and A.L. Braga Imidazolium ionic liquids containing selenium: synthesis and antimicrobial activity Org Biomol Chem 9 2011 1001 1003
75. 50) of ionic liquids Ecotoxicol Environ Safety 67 2007 423 429
76. D.J. Couling, R.J. Bernot, K.M. Docherty, J.K. Dixon, and E.J. Maginn Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling Green Chem 8 2006 82 90
77. C. Pretti, C. Chiappe, I. Baldetti, S. Brunini, G. Monni, and L. Intorre Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio Ecotoxicol Environ Safety 72 2009 1170 1176
78. J. Pernak, and M. Branicka Synthesis and aqueous ozonation of some pyridinium salts with alkoxymethyl and alkylthiomethyl hydrophobic groups Ind Eng Chem Res 43 2004 1966 1974
79. W.A. Jacobs, and M. Heidelberger On a new group of bactericidal substances obtained from hexamethylenetetramine Proc Natl Acad Sci USA 1 1915 226 228
80. G. Domagk Chemotherapy of bacterial infections Angew Chem 48 1935 657 667 (in German)
81. W. Hough-Troutman, M. Smiglak, S. Griffin, W.M. Reichert, I. Mirska, J. Jodynis-Liebert, and et al. Ionic liquids with dual biological function: sweet and anti-microbial, hydrophobic quaternary ammonium-based salts New J Chem 33 2009 26 33
82. S.P. Denyer, and G.S.A.B. Stewart Mechanisms of action of disinfectants Int Biodeterior Biodegrad 41 1998 261 268
83. C.J. Ioannou, G.W. Hanlon, and S.P. Denyer Action of disinfectant quaternary ammonium compounds against Staphylococcus aureus Antimicrob Agents Chemother 51 2007 296 306
84. T. Maeda, Y. Manabe, M. Yamamoto, M. Yoshida, K. Okazaki, H. Nagamune, and et al. Synthesis and antimicrobial characteristics of novel biocides, 4,4′-(1,6-hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium iodide)s Chem Pharm Bull (Tokyo) 47 1999 1020 1023
85. A. Patrzykat, C.L. Friedrich, L. Zhang, V. Mendoza, and R.E. Hancock Sublethal concentrations of pleurocidin-derived antimicrobial peptides inhibit macromolecular synthesis in Escherichia coli Antimicrob Agents Chemother 46 2002 605 614
86. R.S. Dias, J. Innerlohinger, O. Glatter, M.G. Miguel, and B. Lindman Coil-globule transition of DNA molecules induced by cationic surfactants: a dynamic light scattering study J Phys Chem B 109 2005 10458 10463
87. O.V. Vieira, D.O. Hartmann, C.M. Cardoso, D. Oberdoerfer, M. Baptista, M.A. Santos, and et al. Surfactants as microbicides and contraceptive agents: a systematic in vitro study PLoS ONE 3 2008 e2913
88. M.R. Yeaman, and N.Y. Yount Mechanisms of antimicrobial peptide action and resistance Pharmacol Rev 55 2003 27 55
89. J. Haldar, P. Kondaiah, and S. Bhattacharya Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles Incorporation of multiple head groups leads to impressive antibacterial activity J Med Chem 48 2005 3823 3831
90. J. Feder-Kubis, and K. Tomczuk The effect of the cationic structures of chiral ionic liquids on their antimicrobial activities Tetrahedron 69 2013 4190 4198
91. J. Feder-Kubis, M. Kubicki, and J. Pernak 3-Alkoxymethyl-1-(1R,2S,5R)-(-)-menthoxymethylimidazolium salts-based chiral ionic liquids Tetrahedron: Asymmetry 21 2010 2709 2718
92. N. Bodor, J.J. Kaminski, and S. Selk Soft drugs 1. Labile quaternary ammonium salts as soft antimicrobials J Med Chem 23 1980 469 474
93. S.T. Giolando, R.A. Rapaport, R.J. Larson, T.W. Federle, M. Stalmans, and P. Masscheleyn Environmental fate and effects of DEEDMAC: a new rapidly biodegradable cationic surfactant for use in fabric softeners Chemosphere 30 1995 1067 1083
94. T. Thorsteinsson, M. Masson, K. Kristinsson, M. Hjalmarsdottir, H. Hilmarsson, and T. Loftsson Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds J Med Chem 46 2003 4173 4181
95. N. Gathergood, M.T. Garcia, and P.J. Scammells Biodegradable ionic liquids: Part I. Concept, preliminary targets and evaluation Green Chem 6 2004 166 175
96. K.M. Docherty, M.V. Joyce, K.J. Kulacki, and C.F. Kulpa Microbial biodegradation and metabolite toxicity of three pyridinium-based cation ionic liquids Green Chem 12 2010 701 712
97. The 12 principles of green chemistry∗(green chemistry: Theory and practice, Oxford University Press: New York, 1998, p.30.) [Internet].: ACS / Oxford University Press; 2012. http://www.acs.org/content/acs/en/greenchemistry/what-is-green-chemistry/principles/12-principles-of-green-chemistry.html.
98. D. Coleman, M. Spulak, M.T. Garcia, and N. Gathergood Antimicrobial toxicity studies of ionic liquids leading to a 'hit' MRSA selective antibacterial imidazolium salt Green Chem 14 2012 1350 1356
99. J. Megaw, A. Busetti, and B.F. Gilmore Isolation and characterisation of 1-alkyl-3-methylimidazolium chloride ionic liquid-tolerant and biodegrading marine bacteria PLoS ONE 8 2013 e60806
100. J. Cybulski, A. Wisniewska, A. Kulig-Adamiak, L. Lewicka, A. Cieniecka-Roslonkiewicz, K. Kita, and et al. Long-alkyl-chain quaternary ammonium lactate based ionic liquids Chemistry 14 2008 9305 9311
101. M.T. Garcia, I. Ribosa, L. Perez, A. Manresa, and F. Comelles Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium- and pyridinium-based ionic liquids in aqueous solution Langmuir 29 2013 2536 2545
102. M.H. Fatemi, and P. Izadiyan Cytotoxicity estimation of ionic liquids based on their effective structural features Chemosphere 84 2011 553 563
103. K. Fukumoto, M. Yoshizawa, and H. Ohno Room temperature ionic liquids from 20 natural amino acids J Am Chem Soc 127 2005 2398 2399
104. I. Kolodkin-Gal, D. Romero, S. Cao, J. Clardy, R. Kolter, and R. Losick d-Amino acids trigger biofilm disassembly Science 328 2010 627 629
105. M.R. Cole, M. Li, B. El-Zahab, M.E. Janes, D. Hayes, and I.M. Warner Design, synthesis, and biological evaluation of β-lactam antibiotic-based imidazolium- and pyridinium-type ionic liquids Chem Biol Drug Des 78 2011 33 41
106. R. Ferraz, L.C. Branco, I.M. Marrucho, J.M.M. Araujo, L.P.N. Rebelo, M. Nunes da Ponte, and et al. Development of novel ionic liquids based on ampicillin Med Chem Commun 3 2013 494 497
107. B.F. Gilmore, and M.J. Earle Development of ionic liquid biocides against microbial biofilms: designer microbicides for infection control Chim Oggi 29 2011 32 35
108. J. Pernak, J. Feder-Kubis, A. Cieniecka-Roslonkiewicz, C. Fischmeister, S.T. Griffin, and R.D. Rogers Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(-)-menthoxymethyl substituent New J Chem 31 2007 879 892
109. E.B. Anderson, and T.E. Long Imidazole- and imidazolium-containing polymers for biology and material science applications Polymer 51 2010 2447 2454
110. M.B. Yagci, S. Bolca, J.P.A. Heuts, W. Ming, and G. de With Antimicrobial polyurethane coatings based on ionic liquid quaternary ammonium compounds Prog Org Coat 72 2011 343 347
111. S.Y. Choi, H. Rodriguez, A. Mirjafari, D.F. Gilpin, S. McGrath, K.R. Malcolm, and et al. Dual functional ionic liquids as plasticisers and antimicrobial agents for medical polymers Green Chem 13 2011 1527 1535
112. S.Y. Choi, H. Rodriguez, H.Q.N. Gunaratne, A.V. Puga, D. Gilpin, S. McGrath, and et al. Dual functional ionic liquids as antimicrobials and plasticisers for medical grade PVCs RSC Adv 4 2014 8567 8581