Abstract
Background: The pharmaceutical and cosmetic industries are constantly trying to develop new and more efficient delivery systems, as well as new functional ingredients, to overcome drawbacks, such as poor drug solubility, loading and release, as well as reduced stability. These challenges, namely, low drug solubility in water, usually lead to an insufficient systemic exposure and, consequently, low drug bioavailability.
Several applications of ionic liquids have been widely studied due to their valuable physicochemical properties. In consequence of this broad applicability, ionic liquids have recently been studied in the pharmaceutical field, particularly as functional excipients to improve the efficiency of drug delivery systems. Despite the potential utility of ionic liquids in drug delivery, concerns about their toxicity have been raised, since some of these salts are more toxic than certain organic solvents. Hence, studies concerning the safety of ionic liquids are fundamental.
Nanoparticles have also been studied to improve the efficiency of drug delivery. The main interest in nanosystems is due to the many advantages these systems may confer, particularly in terms of drug safety and efficiency.
In consequence of the valuable characteristics that both ionic liquids and nanoparticles hold, there has been an emergent interest in the synergetic effects arising from the combination of ionic liquids and nanoparticles. This approach may be key to develop more stable systems, with improved performance. However, for the preparation of these ionic liquid–nanoparticle systems, environmentally friendly procedures need to be developed, and the toxicity of the prepared systems needs to be carefully assessed.
Major advances: Herein, we reviewed the main characteristics and applicabilities of ionic liquids, as well as the impact of the synthesis and use of these salts on humans and the environment. Moreover, we also discuss recent developments in the use of ionic liquids in drug delivery. Finally, the prospective combination of ionic liquids and nanosystems towards drug delivery is also explored. In this matter, several studies are presented, showing that the combination of ionic liquids with nanoparticles to produce more efficient delivery systems has great potential. It is shown that ionic liquids improve the chemical and thermal stability of the particles and may change their size and morphology. Finally, some concerns about the combination of ionic liquids with nanoparticles, such as regulation gaps and the research needed for the widespread application of these combined systems in pharmaceuticals, are also addressed.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Álvarez MS, Esperança JMSS, Deive FJ et al (2015) A biocompatible stepping stone for the removal of emerging contaminants. Sep Purif Technol 153:91–98. https://doi.org/10.1016/j.seppur.2015.08.039
Amde M, Liu JF, Pang L (2015) Environmental application, fate, effects, and concerns of ionic liquids: a review. Environ Sci Technol 49:12611–12627. https://doi.org/10.1021/acs.est.5b03123
Astolfi P, Giorgini E, Gambini V et al (2017) Lyotropic liquid-crystalline Nanosystems as drug delivery agents for 5-fluorouracil: structure and cytotoxicity. Langmuir 33:12369–12378. https://doi.org/10.1021/acs.langmuir.7b03173
Balk A, Holzgrabe U, Meinel L (2015) Pro et contra’ ionic liquid drugs – challenges and opportunities for pharmaceutical translation. Eur J Pharm Biopharm 94:291–304. https://doi.org/10.1016/j.ejpb.2015.05.027
Bavandpour R, Karimi-Maleh H, Asif M et al (2015) Liquid phase determination of adrenaline uses a voltammetric sensor employing CuFe2O4 nanoparticles and room temperature ionic liquids. J Mol Liq. https://doi.org/10.1016/j.molliq.2015.07.054
Bawa R (2010) Nanopharmaceuticals: Nanopharmaceuticals. Eur J Nanomed 3:122–127. https://doi.org/10.1515/EJNM.2010.3.1.34
Cao SW, Zhu YJ (2009) Iron oxide hollow spheres: microwave-hydrothermal ionic liquid preparation, formation mechanism, crystal phase and morphology control and properties. Acta Mater 57:2154–2165. https://doi.org/10.1016/j.actamat.2009.01.009
Cevasco G, Chiappe C (2014) Are ionic liquids a proper solution to current environmental challenges? Green Chem 16:2375. https://doi.org/10.1039/c3gc42096e
Chen FL, Sun IW, Paul Wang H, Huang CH (2009) Nanosize copper dispersed ionic liquids as an electrolyte of new dye-sensitized solar cells. J Nanomater 2009:1–4. https://doi.org/10.1155/2009/472950
Chen X, Liu J, Wang J (2010) Ionic liquids in the assay of proteins. Anal Methods 2:1222. https://doi.org/10.1039/c0ay00342e
Cheraghi S, Taher MA, Karimi-Maleh H (2016) A novel strategy for determination of paracetamol in the presence of morphine using a carbon paste electrode modified with CdO nanoparticles and ionic liquids. Electroanalysis 28:366–371. https://doi.org/10.1002/elan.201500357
Cheraghi S, Taher MA, Karimi-Maleh H, Moradi R (2017) Simultaneous detection of nalbuphine and diclofenac as important analgesic drugs in biological and pharmaceutical samples using a Pt: co nanostructure-based electrochemical sensor. J Electrochem Soc 164:B60–B65. https://doi.org/10.1149/2.0911702jes
Constatinescu D, Herrmann C, Weigärtner H (2010) Patterns of protein unfolding and protein aggregation in ionic liquids. Phys Chem Chem Phys 12:1756–1763. https://doi.org/10.1039/b921037g
Couling DJ, Bernot RJ, Docherty KM et al (2006) Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling. Green Chem 8:82–90. https://doi.org/10.1039/B511333D
Dake SA, Kulkarni RS, Kadam VN et al (2009) Phosphonium ionic liquid – a novel catalyst for benzyl halide oxidation. Synth Commun An Int J Rapid Commun Synth Org Chem 39:3898–3904. https://doi.org/10.1080/00397910902840835
Dobler D, Schmidts T, Klingenhoefer I, Runkel F (2012) Ionic liquids as ingredients in topical drug delivery systems. Int J Pharm 441:620–627. https://doi.org/10.1016/j.ijpharm.2012.10.035
Dobler D, Schmidts T, Zinecker C et al (2015) Hydrophilic ionic liquids as ingredients of gel-based dermal formulations. AAPS PharmSciTech 17:923–931. https://doi.org/10.1208/s12249-015-0421-y
dos Santos AD, Morais ARC, Melo C et al (2013) Solubility of pharmaceutical compounds in ionic liquids. Fluid Phase Equilib 356:18–29. https://doi.org/10.1016/j.fluid.2013.07.020
Ebrahimnezhad Z, Zarghami N, Keyhani M et al (2013) Inhibition of hTERT gene expression by silibinin-loaded PLGA-PEG-Fe3O4 in T47D breast cancer cell line. Bioimpacts 3:67–74. https://doi.org/10.5681/bi.2013.005
Egorova KS, Gordeev EG, Ananikov VP (2017) Biological activity of ionic liquids and their application in pharmaceutics and medicine. Chem Rev 1:A–BF. https://doi.org/10.1021/acs.chemrev.6b00562
Elkhodiry MA, Momah CC, Suwaidi SR et al (2016) Synergistic nanomedicine: passive, active, and ultrasound-triggered drug delivery in Cancer treatment. J Nanosci Nanotechnol 16:1–18. https://doi.org/10.1166/jnn.2016.11124
Esmaili M, Habibi-Yangjeh A (2011) Microwave-assisted preparation of CdS nanoparticles in a halide-free ionic liquid and their photocatalytic activities. Cuihua Xuebao/Chinese J Catal 32:933–938. https://doi.org/10.1016/S1872-2067(10)60217-3
Fan A, Chuah GK, Jaenicke S (2012) Phosphonium ionic liquids as highly thermal stable and efficient phase transfer catalysts for solid-liquid Halex reactions. Catal Today 198:300–304. https://doi.org/10.1016/j.cattod.2012.02.063
Ferraz R, Branco LC, Prudêncio C et al (2011) Ionic liquids as active pharmaceutical ingredients. ChemMedChem 6:975–985. https://doi.org/10.1002/cmdc.201100082
Ferraz R, Costa-Rodrigues J, Fernandes MH et al (2015a) Antitumor activity of ionic liquids based on ampicillin. ChemMedChem 10:1480–1483. https://doi.org/10.1002/cmdc.201500142
Ferraz R, Prudêncio C, Vieira M et al (2015b) Ionic liquids synthesis – methodologies. Org Chem Curr Res 4:1–2. https://doi.org/10.4172/2161-0401.1000e139
Forte A, Melo CI, Bogel-Łukasik R, Bogel-Łukasik E (2012) A favourable solubility of isoniazid, an antitubercular antibiotic drug, in alternative solvents. Fluid Phase Equilib 318:89–95. https://doi.org/10.1016/j.fluid.2012.01.022
Frade RF, Afonso CA (2010) Impact of ionic liquids in environment and humans: an overview. Hum Exp Toxicol 29:1038–1054. https://doi.org/10.1177/0960327110371259
Fujita K, MacFarlane DR, Forsyth M (2005) Protein solubilising and stabilising ionic liquids. Chem Commun 70:4804. https://doi.org/10.1039/b508238b
Fumino K, Wulf A, Ludwig R (2009) Hydrogen bonding in Protic ionic liquids: reminiscent of water. Angew Chemie Int Ed 48:3184–3186. https://doi.org/10.1002/anie.200806224
Garcia MT, Gathergood N, Scammells PJ (2005) Biodegradable ionic liquids : part II. Effect of the anion and toxicology. Green Chem 7:9. https://doi.org/10.1039/b411922c
Ghandi K (2014) A review of ionic liquids, their limits and applications. Green Sustain Chem 4:44–53. https://doi.org/10.4236/gsc.2014.41008
Ghosh S, Parui S, Jana B, Bhattacharyya K (2015) Ionic liquid induced dehydration and domain closure in lysozyme: FCS and MD simulation. J Chem Phys. https://doi.org/10.1063/1.4931974
Goindi S, Arora P, Kumar N, Puri A (2014) Development of novel ionic liquid-based microemulsion formulation for dermal delivery of 5-fluorouracil. AAPS PharmSciTech. https://doi.org/10.1208/s12249-014-0103-1
Goindi S, Kaur R, Kaur R (2015) An ionic liquid-in-water microemulsion as a potential carrier for topical delivery of poorly water soluble drug: development, ex-vivo and in-vivo evaluation. Int J Pharm 495:913–923. https://doi.org/10.1016/j.ijpharm.2015.09.066
Gouveia W, Jorge TF, Martins S et al (2014) Toxicity of ionic liquids prepared from biomaterials. Chemosphere 104:51–56. https://doi.org/10.1016/j.chemosphere.2013.10.055
Handy ST (2011) Ionic liquids – classes and properties, 1st edn. InTech, Rijeka
Hare JI, Lammers T, Ashford MB et al (2017) Challenges and strategies in anti-cancer nanomedicine development: an industry perspective. Adv Drug Deliv Rev 108:25–38. https://doi.org/10.1016/j.addr.2016.04.025
Hassan SS, Carlson K, Mohanty SK et al (2017) Ultra-rapid catalytic degradation of 4-nitrophenol with ionic liquid recoverable and reusable ibuprofen derived silver nanoparticles. Environ Pollut:1–9. https://doi.org/10.1016/J.ENVPOL.2017.10.118
He Z, Alexandridis P (2016) Ionic liquid and nanoparticle hybrid systems: emerging applications. Adv Colloid Interf Sci. https://doi.org/10.1016/j.cis.2016.08.004
Ho TD, Canestraro AJ, Anderson JL (2011) Ionic liquids in solid-phase microextraction: a review. Anal Chim Acta 695:18–43. https://doi.org/10.1016/j.aca.2011.03.034
Holbrey JD, Reichert WM, Swatloski RP et al (2002) Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions. Green Chem 4:407–413. https://doi.org/10.1039/b204469b
Hough WL, Smiglak M, Rodríguez H et al (2007) The third evolution of ionic liquids: active pharmaceutical ingredients. New J Chem 31:1429. https://doi.org/10.1039/b706677p
Huang L, Chen Y-T, Li Y-X, Yu L-S (2016) Application of chiral ionic liquid-modified gold nanoparticles in the chiral recognition of amino acid enantiomers. Appl Spectrosc 70:1649–1654. https://doi.org/10.1177/0003702816645353
Hwang JH, Park H, Choi DW et al (2017) Investigation of dermal toxicity of ionic liquids in monolayer-cultured skin cells and 3D reconstructed human skin models. Toxicol Vitr 46:194–202. https://doi.org/10.1016/j.tiv.2017.09.025
Imanishi A, Gonsui S, Tsuda T et al (2011) Size and shape of Au nanoparticles formed in ionic liquids by electron beam irradiation. Phys Chem Chem Phys 13:14823–14830. https://doi.org/10.1039/c1cp20643e
Itoh H, Naka K, Chujo Y (2004) Synthesis of gold nanoparticles modified with ionic liquid based on the imidazolium cation. J Am Chem Soc 126:3026–3027. https://doi.org/10.1021/ja039895g
Ji G, Shi Y, Pan L, Zheng Y (2011) Effect of ionic liquid amount (C8H15BrN2) on the morphology of Bi2Te3 nanoplates synthesized via a microwave-assisted heating approach. J Alloys Compd 509:6015–6020. https://doi.org/10.1016/j.jallcom.2011.02.142
Júlio A, Caparica R, Portugal Mota J et al (2017) Permeation of ionic liquids through the skin. Biomed Biopharm Res 14:233–241. https://doi.org/10.19277/bbr.14.2.165
Karimi-Maleh H, Shojaei AF, Tabatabaeian K et al (2016) Simultaneous determination of 6-mercaptopruine, 6-thioguanine and dasatinib as three important anticancer drugs using nanostructure voltammetric sensor employing Pt/MWCNTs and 1-butyl-3-methylimidazolium hexafluoro phosphate. Biosens Bioelectron 86:879–884. https://doi.org/10.1016/j.bios.2016.07.086
Khupse ND, Kumar A (2010) Ionic liquids: new materials with wide applications. Indian J Chem 49:635–648. http://hdl.handle.net/123456789/9662
Khupse ND, Kumar A (2011) The cosolvent-directed Diels-Alder reaction in ionic liquids. J Phys Chem A 115:10211–10217. https://doi.org/10.1021/jp205181e
Kim K-S, Choi S, Cha J-H et al (2006) Facile one-pot synthesis of gold nanoparticles using alcohol ionic liquids. J Mater Chem 16:1315. https://doi.org/10.1039/b601478j
Kim SY, Hwang JY, Shin US (2016) Preparation of nano/macroporous polycaprolactone microspheres for an injectable cell delivery system using room temperature ionic liquid and camphene. J Colloid Interface Sci 465:18–25. https://doi.org/10.1016/j.jcis.2015.11.055
Kowsari E, Ghezelbash MR (2012) Ionic liquid-assisted, facile synthesis of ZnO/SnO 2 nanocomposites, and investigation of their photocatalytic activity. Mater Lett 68:17–20. https://doi.org/10.1016/j.matlet.2011.10.028
Kubota K, Shibata A, Yamaguchi T (2016) The molecular assembly of the ionic liquid/aliphatic carboxylic acid/aliphatic amine as effective and safety transdermal permeation enhancers. Eur J Pharm Sci 86:75–83. https://doi.org/10.1016/j.ejps.2016.03.002
Kuzmina O, Hallett J (eds) (2016) Application, purification, and recovery of ionic liquids, first edit. Elsevier, Amsterdam
Lerma-García MJ, Simó-Alfonso EF, Zougagh M, Ríos Á (2013) Use of gold nanoparticle-coated sorbent materials for the selective preconcentration of sulfonylurea herbicides in water samples and determination by capillary liquid chromatography. Talanta 105:372–378. https://doi.org/10.1016/j.talanta.2012.10.056
Liu X, Liu R, Chen S, Liang B (2012) Hydrothermal synthesis of CdSe hierarchical dendrites using ionic liquid as template. Mater Lett 66:264–266. https://doi.org/10.1016/j.matlet.2011.08.007
Mahmoodi NO, Ghavidast A, Amirmahani N (2016) A comparative study on the nanoparticles for improved drug delivery systems. J Photochem Photobiol B Biol 162:681–693. https://doi.org/10.1016/j.jphotobiol.2016.07.037
Marrucho IM, Branco LC, Rebelo LPN (2014) Ionic liquids in pharmaceutical applications. Annu Rev Chem Biomol Eng 5:527–546. https://doi.org/10.1146/annurev-chembioeng-060713-040024
Matzke M, Stolte S, Thiele K et al (2007) The influence of anion species on the toxicity of 1-alkyl-3-methylimidazolium ionic liquids observed in an (eco)toxicological test battery. Green Chem 9:1198–1207. https://doi.org/10.1039/b705795d
Melo CI, Bogel-Łukasik R, Nunes da Ponte M, Bogel-Łukasik E (2013) Ammonium ionic liquids as green solvents for drugs. Fluid Phase Equilib 338:209–216. https://doi.org/10.1016/j.fluid.2012.11.029
Meng H, Chen X-W, Wang J-H (2010) Ionic liquid templated porous nano-TiO2 particles for the selective isolation of cytochrome c. Nanotechnology 21:385704. https://doi.org/10.1088/0957-4484/21/38/385704
Menne S, Anouti M, Balducci A (2013) Aprotic and protic ionic liquids in lithium ion batteries: a comparative study. In: 224th ECS Meet. p 4033
Micaêlo NM, Soares CM (2008) Protein structure and dynamics in ionic liquids. Insights from molecular dynamics simulation studies. J Phys Chem B 112:2566–2572. https://doi.org/10.1021/jp0766050
Miran MS, Kinoshita H, Yasuda T et al (2011) Hydrogen bonds in protic ionic liquids and their correlation with physicochemical properties. Chem Commun 47:12676–12678. https://doi.org/10.1039/c1cc14817f
Mitkare SS, Lakhane KG, Kokulwar PU (2013) Ionic liquids: novel applications in drug delivery. Res J Pharm Technol 6:1367–1381
Mizuuchi H, Jaitely V, Murdan S, Florence AT (2008) Room temperature ionic liquids and their mixtures: potential pharmaceutical solvents. Eur J Pharm Sci 33:326–331. https://doi.org/10.1016/j.ejps.2008.01.002
Moniruzzaman M, Kamiya N, Goto M (2010a) Ionic liquid based microemulsion with pharmaceutically accepted components: formulation and potential applications. J Colloid Interface Sci 352:136–142. https://doi.org/10.1016/j.jcis.2010.08.035
Moniruzzaman M, Tamura M, Tahara Y et al (2010b) Ionic liquid-in-oil microemulsion as a potential carrier of sparingly soluble drug: characterization and cytotoxicity evaluation. Int J Pharm 400:243–250. https://doi.org/10.1016/j.ijpharm.2010.08.034
Nandi S, Parui S, Halder R et al (2017) Interaction of proteins with ionic liquid, alcohol and DMSO and in situ generation of gold nano-clusters in a cell. Biophys Rev. https://doi.org/10.1007/s12551-017-0331-1
Noda A, Susan H, Bin MA, Kudo K et al (2003) Brønsted acid-base ionic liquids as proton-conducting nonaqueous electrolytes. J Phys Chem B 107:4024–4033. https://doi.org/10.1021/jp022347p
Oommen E, Hummel A, Allmannsberger L et al (2017) IgA antibodies to myeloperoxidase in patients with eosinophilic granulomatosis with polyangiitis (Churg-Strauss). Clin Exp Rheumatol 35:98–101. https://doi.org/10.1007/128
Otvagina KV, Mochalova AE, Sazanova TS et al (2016) Preparation and characterization of facilitated transport membranes composed of chitosan-styrene and chitosan-acrylonitrile copolymers modified by methylimidazolium based ionic liquids for CO2 separation from CH4 and N2. Membranes (Basel) 6:1–19. https://doi.org/10.3390/membranes6020031
Ozokwelu D, Zhang S, Okafor O et al (2017) Novel catalytic and separation processes based on ionic liquids, 1st edn. Elsevier, Amsterdam
Padmanabhan P, Kumar A, Kumar S et al (2016) Nanoparticles in practice for molecular-imaging applications: an overview. Acta Biomater 41:1–16. https://doi.org/10.1016/j.actbio.2016.06.003
Pajuste K, Plotniece A, Kore K et al (2011) Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative. Open Chem 9:143–148. https://doi.org/10.2478/s11532-010-0132-x
Pernak J, Smiglak M, Griffin ST et al (2006) Long alkyl chain quaternary ammonium-based ionic liquids and potential applications. Green Chem 8:798. https://doi.org/10.1039/b604353d
Petkovic M, Seddon KR, Rebelo LPN, Silva Pereira C (2011) Ionic liquids: a pathway to environmental acceptability. Chem Soc Rev 40:1383–1403. https://doi.org/10.1039/C004968A
Prabhu Charan KT, Pothanagandhi N, Vijayakrishna K et al (2014) Poly(ionic liquids) as “smart” stabilizers for metal nanoparticles. Eur Polym J 60:114–122. https://doi.org/10.1016/j.eurpolymj.2014.09.004
Pretti C, Chiappe C, Baldetti I et al (2009) Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio. Ecotoxicol Environ Saf 72:1170–1176. https://doi.org/10.1016/j.ecoenv.2008.09.010
Rabieh S, Bagheri M (2014) Effect of ionic liquid [C4mim][Cl] on morphology of nanosized-zinc oxide. Mater Lett 122:190–192. https://doi.org/10.1016/j.matlet.2014.02.037
Rajiv Gandhi R, Gowri S, Suresh J, Sundrarajan M (2013) Ionic liquids assisted synthesis of ZnO nanostructures: controlled size, morphology and antibacterial properties. J Mater Sci Technol 29:533–538. https://doi.org/10.1016/j.jmst.2013.03.007
Rancoule C, Magné N, Vallard A et al (2016) Nanoparticles in radiation oncology: from bench-side to bedside. Cancer Lett 375:256–262. https://doi.org/10.1016/j.canlet.2016.03.011
Ranke J, Müller A, Bottin-Weber U et al (2007) Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. Ecotoxicol Environ Saf 67:430–438. https://doi.org/10.1016/j.ecoenv.2006.08.008
Reis CP, Neufeld RJ, Ribeiro AJ, Veiga F (2006a) Nanoencapsulation II. Biomedical applications and current status of peptide and protein nanoparticulate delivery systems. Nanomed Nanotechnol Biol Med 2:53–65. https://doi.org/10.1016/j.nano.2006.04.009
Reis CP, Neufeld RJ, Ribeiro AJ, Veiga F (2006b) Nanoencapsulation I. Methods for preparation of drug-loaded polymeric nanoparticles. Nanomed Nanotechnol Biol Med 2:8–21. https://doi.org/10.1016/j.nano.2005.12.003
Reis CP, Veiga FJ, Ribeiro AJ et al (2008) Nanoparticulate biopolymers deliver insulin orally eliciting pharmacological response. J Pharm Sci 97:5290–5305. https://doi.org/10.1002/jps.21347
Ren S, Hou Y, Wu W, Liu W (2010) Purification of ionic liquids: sweeping solvents by nitrogen. J Chem Eng Data 55:5074–5077. https://doi.org/10.1021/je100641a
Romero A, Santos A, Tojo J, Rodríguez A (2008) Toxicity and biodegradability of imidazolium ionic liquids. J Hazard Mater 151:268–273. https://doi.org/10.1016/j.jhazmat.2007.10.079
Safari J, Zarnegar Z (2014) Advanced drug delivery systems: nanotechnology of health design a review. J Saudi Chem Soc 18:85–99. https://doi.org/10.1016/j.jscs.2012.12.009
Sahbaz Y, Nguyen TH, Ford L et al (2017) Ionic liquid forms of weakly acidic drugs in oral lipid formulations: preparation, characterization, in vitro digestion, and in vivo absorption studies. Mol Pharm 14:3669–3683. https://doi.org/10.1021/acs.molpharmaceut.7b00442
Saji VS, Choe HC, Yeung KWK (2010) Nanotechnology in biomedical applications : a review Han Cheol Choe. Int J Nano Biomater 3:119–139. https://doi.org/10.1504/IJNBM.2010.037801
Santos de Almeida T, Júlio A, Caparica R et al (2015) Ionic liquids as solubility/permeation enhancers for topical formulations: skin permeation and cytotoxicity characterization. Toxicol Lett:S293. https://doi.org/10.1016/j.toxlet.2015.08.841
Santos de Almeida T, Júlio A, Portugal Mota J et al (2017a) An emerging integration between ionic liquids and nanotechnology: general uses and future prospects in drug delivery. Ther Deliv 6:461–473. https://doi.org/10.4155/tde-2017-0002
Santos de Almeida T, Júlio A, Saraiva N et al (2017b) Choline- versus imidazole-based ionic liquids as functional ingredients in topical delivery systems: cytotoxicity, solubility, and skin permeation studies. Drug Dev Ind Pharm 6:1858–1865. https://doi.org/10.1080/03639045.2017.1349788
Selvam T, MacHoke A, Schwieger W (2012) Supported ionic liquids on non-porous and porous inorganic materials – a topical review. Appl Catal A Gen 445–446:92–101. https://doi.org/10.1016/j.apcata.2012.08.007
Shamshina JL, Barber PS, Rogers RD (2013) Ionic liquids in drug delivery. Exper Opin Drug Deliv 10:1–15. https://doi.org/10.1517/17425247.2013.808185
Shamsuri AA, Abdullah DK (2010) Ionic liquids: preparations and limitations. Makara 14:101–106. https://doi.org/10.7454/mss.v14i2.677
Sheikhshoaie M, Sheikhshoaie I, Ranjbar M (2017) Analysis of kojic acid in food samples uses an amplified electrochemical sensor employing V2O5 nanoparticle and room temperature ionic liquid. J Mol Liq 229:489–494. https://doi.org/10.1016/j.molliq.2017.02.039
Snelders DJM, Dyson PJ (2011) Efficient synthesis of β-chlorovinylketones from acetylene in chloroaluminate ionic liquids. Org Lett 13:4048–4051. https://doi.org/10.1021/ol201182t
Sprenger KG, Plaks JG, Kaar JL, Pfaendtner J (2017) Elucidating sequence and solvent specific design targets to protect and stabilize enzymes for biocatalysis in ionic liquids. Phys Chem Chem Phys 19:17426–17433. https://doi.org/10.1039/C7CP03013D
Stoimenovski J, MacFarlane DR, Bica K, Rogers RD (2010) Crystalline vs. ionic liquid salt forms of active pharmaceutical ingredients: a position paper. Pharm Res 27:521–526. https://doi.org/10.1007/s11095-009-0030-0
Stoppa A, Hunger J, Buchner R (2009) Conductivities of binary mixtures of ionic liquids with polar solvents conductivities of binary mixtures of ionic liquids with polar solvents. J Chem Eng Data 54:472–479. https://doi.org/10.1021/je800468h
Takahashi C, Ogawa N, Kawashima Y, Yamamoto H (2015) Observation of antibacterial effect of biodegradable polymeric nanoparticles on Staphylococcus epidermidis biofilm using FE-SEM with an ionic liquid. Microscopy 64:169–180. https://doi.org/10.1093/jmicro/dfv010
Tang B, Bi W, Tian M, Row KH (2012) Application of ionic liquid for extraction and separation of bioactive compounds from plants. J Chromatogr B 904:1–21. https://doi.org/10.1016/j.jchromb.2012.07.020
Tharun J, Kathalikkattil AC, Roshan R et al (2014) Microwave-assisted, rapid cycloaddition of allyl glycidyl ether and CO 2 by employing pyridinium-based ionic liquid catalysts. Catal Commun 54:31–34. https://doi.org/10.1016/j.catcom.2014.05.016
Thuy Pham TP, Cho CW, Yun YS (2010) Environmental fate and toxicity of ionic liquids: a review. Water Res 44:352–372. https://doi.org/10.1016/j.watres.2009.09.030
Tiwari G, Tiwari R, Bannerjee S et al (2012) Drug delivery systems: an updated review. Int J Pharm Investig 2:2. https://doi.org/10.4103/2230-973X.96920
Tong L, Liu Y, Rong H, Gong L (2013) Microwave-assisted synthesis of hierarchical ZnO nanostructures. Mater Lett 112:5–7. https://doi.org/10.1016/j.matlet.2013.08.119
Torimoto T, Tsuda T, Okazaki KI, Kuwabata S (2010) New frontiers in materials science opened by ionic liquids. Adv Mater 22:1196–1221. https://doi.org/10.1002/adma.200902184
Ueno K, Watanabe M (2011) From colloidal stability in ionic liquids to advanced soft materials using unique media. Langmuir 27:9105–9115. https://doi.org/10.1021/la103942f
Van Rantwijk F, Sheldon RA (2007) Biocatalysis in ionic liquids biocatalysis in ionic liquids. Chem Rev 107:2757–2785. https://doi.org/10.1021/cr050946x
Ventura SPM, Marques CS, Rosatella AA et al (2012) Toxicity assessment of various ionic liquid families towards Vibrio fischeri marine bacteria. Ecotoxicol Environ Saf 76:162–168. https://doi.org/10.1016/j.ecoenv.2011.10.006
Wang S, Zhang Y, Ma HL et al (2013) Ionic-liquid-assisted facile synthesis of silver nanoparticle-reduced graphene oxide hybrids by gamma irradiation. Carbon NY 55:245–252. https://doi.org/10.1016/j.carbon.2012.12.033
Wang C, Zhu J, Zhang D et al (2018) Ionic liquid – microemulsions assisting in the transdermal delivery of Dencichine: preparation, in-vitro and in-vivo evaluations, and investigation of the permeation mechanism. Int J Pharm 535:120–131. https://doi.org/10.1016/j.ijpharm.2017.10.024
Wasserscheid P, Welton T (2008) Ionic liquids in synthesis, 2nd edn. Wiley, Weinheim
Weissig V, Pettinger TK, Murdock N (2014) Nanopharmaceuticals (part 1): products on the market. Int J Nanomedicine 9:4357–4373. https://doi.org/10.2147/IJN.S46900
Wells AS, Coombe VT (2006) On the freshwater ecotoxicity and biodegradation properties of some common ionic liquids. Org Process Res Dev 10:794–798. https://doi.org/10.1021/op060048i
Wolfram J, Zhu M, Yang Y et al (2015) Safety of nanoparticles in medicine. Curr Drug Targets 16:1671–1681. https://doi.org/10.1002/jmri.23741.Proton
Xia J, Li H, Luo Z et al (2009) Microwave-assisted synthesis of flower-like and leaf-like CuO nanostructures via room-temperature ionic liquids. J Phys Chem Solids 70:1461–1464. https://doi.org/10.1016/j.jpcs.2009.08.006
Xu X, Zhang M, Feng J, Zhang M (2008) Shape-controlled synthesis of single-crystalline cupric oxide by microwave heating using an ionic liquid. Mater Lett 62:2787–2790. https://doi.org/10.1016/j.matlet.2008.01.046
Yuan J, Mecerreyes D, Antonietti M (2013) Poly(ionic liquid)s: an update. Prog Polym Sci 38:1009–1036. https://doi.org/10.1016/j.progpolymsci.2013.04.002
Zahmakıran M, Ozkar S (2011) Metal nanoparticles in liquid phase catalysis; from recent advances to future goals. Nanoscale 3:3462–3481. https://doi.org/10.1039/c1nr10201j
Zakrewsky M, Lovejoy KS, Kern TL et al (2014) Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization. Proc Natl Acad Sci 111:13313–13318. https://doi.org/10.1073/pnas.1403995111
Zappi D, Caminiti R, Ingo GM et al (2017) Biologically friendly room temperature ionic liquids and nanomaterials for the development of innovative enzymatic biosensors. Talanta 175:566–572. https://doi.org/10.1016/j.talanta.2017.07.081
Zazo H, Colino CI, Lanao JM (2016) Current applications of nanoparticles in infectious diseases. J Control Release 224:86–102. https://doi.org/10.1016/j.jconrel.2016.01.008
Zhang D, Wang H, Cui X et al (2016a) Evaluations of imidazolium ionic liquids as novel skin permeation enhancers for drug transdermal delivery. Pharm Dev Technol 7450:1–10. https://doi.org/10.3109/10837450.2015.1131718
Zhang W, Kochovski Z, Lu Y et al (2016b) Internal morphology-controllable self-assembly in poly(ionic liquid) nanoparticles. ACS Nano 10:7731–7737. https://doi.org/10.1021/acsnano.6b03135
Zhou Y, Antonietti M (2003) A novel tailored bimodal porous silica with well-defined inverse opal microstructure and super-microporous lamellar nanostructure. Chem Commun (Camb):2564–2565. https://doi.org/10.1039/b307444g
Zhu A, Wang J, Han L, Fan M (2009) Measurements and correlation of viscosities and conductivities for the mixtures of imidazolium ionic liquids with molecular solutes. Chem Eng J 147:27–35. https://doi.org/10.1016/j.cej.2008.11.013
Acknowledgments
Ana Júlio would like to thank the Foundation for Science and Technology, I.P., who financed her work under the project UDI/DTP/04567/2016.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2021 The Editor(s) (if applicable) and The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
de Almeida, T.S., Caparica, R., Júlio, A., Reis, C.P. (2021). An Overview on Ionic Liquids: A New Frontier for Nanopharmaceuticals. In: Yata, V., Ranjan, S., Dasgupta, N., Lichtfouse, E. (eds) Nanopharmaceuticals: Principles and Applications Vol. 1. Environmental Chemistry for a Sustainable World, vol 46. Springer, Cham. https://doi.org/10.1007/978-3-030-44925-4_5
Download citation
DOI: https://doi.org/10.1007/978-3-030-44925-4_5
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-44924-7
Online ISBN: 978-3-030-44925-4
eBook Packages: Earth and Environmental ScienceEarth and Environmental Science (R0)