Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization

Proceedings of the National Academy of Sciences of the United States of America

Volumn 111, Issue 37, 2014, Pages 13313-13318

  Zakrewsky, Michael ^a,b   Lovejoy, Katherine S ^c   Kern, Theresa L ^d   Miller, Tarryn E ^c   Le, Vivian ^b   Nagy, Amber ^d   Goumas, Andrew M ^d   Iyer, Rashi S ^d   DelSesto, Rico E ^e   Koppisch, Andrew T ^f   Fox, David T ^d   Mitragotri, Samir ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Santa Barbara   (United States)

^c Department of Materials Chemistry Materials Physics and Applications Division ^*  (United States)

^d LOS ALAMOS NATIONAL LABORATORY   (United States)

^e DIXIE STATE UNIVERSITY   (United States)

^f NORTHERN ARIZONA UNIVERSITY   (United States)

Author keywords

Antibacterial; Antibiotic resistance; Antimicrobial agents; Formulation; Ion pairing

Indexed keywords

IONIC LIQUID; IRRITANT AGENT;

ARTIFICIAL SKIN; BIOFILM; CELL DEATH; CYTOLOGY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; EPITHELIUM CELL; HUMAN; INFRARED SPECTROSCOPY; INTRADERMAL DRUG ADMINISTRATION; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; PHYSIOLOGY; PSEUDOMONAS AERUGINOSA; REPRODUCIBILITY; SALMONELLA ENTERICA; SKIN;

ADMINISTRATION, CUTANEOUS; BIOFILMS; CELL DEATH; DRUG DELIVERY SYSTEMS; EPITHELIAL CELLS; HUMANS; IONIC LIQUIDS; IRRITANTS; MICROBIAL SENSITIVITY TESTS; PSEUDOMONAS AERUGINOSA; REPRODUCIBILITY OF RESULTS; SALMONELLA ENTERICA; SKIN; SKIN, ARTIFICIAL; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84907192438     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1403995111     Document Type: Article

References (49)

1. Davies D (2003) Understanding biofilm resistance to antibacterial agents. Nat Rev Drug Discov 2(2):114-122.
2. Flemming HC, Wingender J. (2010) The biofilm matrix. Nat Rev Microbiol 8(9):623-633.
3. Hall-Stoodley L, Costerton JW, Stoodley P. (2004) Bacterial biofilms: From the natural environment to infectious diseases. Nat Rev Microbiol 2(2):95-108.
4. Lindsay D, von Holy A (2006) Bacterial biofilms within the clinical setting: What healthcare professionals should know. J Hosp Infect 64(4):313-325.
5. Goossens H (2003) Susceptibility of multi-drug-resistant Pseudomonas aeruginosa in intensive care units: Results from the European MYSTIC study group. Clin Microbiol Infect 9(9):980-983.
6. Trøstrup H, et al. (2013) Pseudomonas aeruginosa biofilm aggravates skin inflammatory response in BALB/c mice in a novel chronic wound model. Wound Repair Regen 21(2):292-299.
7. Baker BS (2006) The role of microorganisms in atopic dermatitis. Clin Exp Immunol 144(1):1-9.
8. James GA, et al. (2008) Biofilms in chronic wounds. Wound Repair Regen 16(1):37-44.
9. Rice LB (2006) Unmet medical needs in antibacterial therapy. Biochem Pharmacol 71(7):991-995.
10. Prausnitz MR, Langer R. (2008) Transdermal drug delivery. Nat Biotechnol 26(11): 1261-1268.
11. Hahn BL, Sohnle P.G. (2013) Direct translocation of staphylococci from the skin surface to deep organs. Microb Pathog 63(0):24-29.
12. Koga T, Matsuda T, Matsumoto T., Furue M. (2003) Therapeutic approaches to subcutaneous mycoses. Am J Clin Dermatol 4(8):537-543.
13. Musk DJ, Jr, Hergenrother PJ (2006) Chemical countermeasures for the control of bacterial biofilms: Effective compounds and promising targets. Curr Med Chem 13(18):2163-2177.
14. Kasimanickam RK, Ranjan A, Asokan G.V., Kasimanickam VR, Kastelic J.P. (2013) Prevention and treatment of biofilms by hybrid- and nanotechnologies. Int J Nano-medicine 8:2809-2819.
15. Williams AC, Barry B.W. (2004) Penetration enhancers. Adv Drug Deliv Rev 56(5): 603-618.
16. Nguyen KT, et al. (2013) Deficient cytokine expression and neutrophil oxidative burst contribute to impaired cutaneous wound healing in diabetic, biofilm-containing chronic wounds. Wound Repair Regen 21(6):833-841.
17. Barker JNWN, Mitra RS, Griffiths CEM, Dixit VM, Nickoloff B.J. (1991) Keratinocytes as initiators of inflammation. Lancet 337(8735):211-214.
18. Welton T (1999) Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem Rev 99(8):2071-2084.
19. Pernak J, Goc I, Mirska I. (2004) Anti-microbial activities of protic ionic liquids with lactate anion. Green Chem 6(7):323-329.
20. Pernak J, Sobaszkiewicz K, Mirska I. (2003) Anti-microbial activities of ionic liquids. Green Chem 5(1):52-56.
21. Petkovic M, et al. (2010) Novel biocompatible cholinium-based ionic liquids-toxicity and biodegradability. Green Chem 12(4):643-649.
22. Abbott AP, Boothby D, Capper G., Davies DL, Rasheed R.K. (2004) Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids. J Am Chem Soc 126(29):9142-9147.
23. Hough WL, et al. (2007) The third evolution of ionic liquids: Active pharmaceutical ingredients. New J Chem 31(8):1429-1436.
24. Moniruzzaman M, Tamura M, Tahara Y., Kamiya N, Goto M. (2010) Ionic liquid-in-oil microemulsion as a potential carrier of sparingly soluble drug: Characterization and cytotoxicity evaluation. Int J Pharm 400(1-2):243-250.
25. Dobler D, Schmidts T, Klingenhöfer I, Runkel F. (2013) Ionic liquids as ingredients in topical drug delivery systems. Int J Pharm 441(1-2):620-627.
26. Gilmore BF (2011) Antimicrobial ionic liquids. Ionic Liquids: Applications and Perspectives, ed Kokorin A (InTech, Rijeka, Croatia), pp 587-604.
27. Karande P, Jain A, Ergun K., Kispersky V, Mitragotri S. (2005) Design principles of chemical penetration enhancers for transdermal drug delivery. Proc Natl Acad Sci USA 102(13):4688-4693.
28. Mah TF, et al. (2003) A genetic basis for Pseudomonas aeruginosa biofilm antibiotic resistance. Nature 426(6964):306-310.
29. Mireles JR, 2nd, Toguchi A, Harshey RM (2001) Salmonella enterica serovar typhi-murium swarming mutants with altered biofilm-forming abilities: Surfactin inhibits biofilm formation. J Bacteriol 183(20):5848-5854.
30. Perkins MA, Osborne R, Rana F.R., Ghassemi A., Robinson M.K. (1999) Comparison of in vitro and in vivo human skin responses to consumer products and ingredients with a range of irritancy potential. Toxicol Sci 48(2):218-229.
31. Kahlmeter G (2014) European Committee on Antimicrobial Susceptibility Testing (EUCAST) Database. Available at www.eucast.org. Accessed August 10, 2014.
32. Seddon KR (1999) Ionic liquids: Designer solvents? Proceedings of the International George Papatheodorou Symposium, eds Boghosian S, Dracapoulos V, Kontoyannis CG, Voyiatzis GA (Institute of Chemical Engineering and High Temperature Processes, Patras, Greece), pp 131-135.
33. Smith KB, Bridson RH, Leeke G.A. (2010) Crystallisation of APIs from Ionic Liquids. J Pharm Pharmacol 62(10):1412-1413.
34. Tsai J-C, Lo Y-L, Lin C-Y, Sheu H-M, Lin J-C (2004) Feasibility of rapid quantitation of stratum corneum lipid content by Fourier transform infrared spectrometry. J Spectrosc 18(3):423-431.
35. Tetko IV, Bruneau P. (2004) Application of ALOGPS to predict 1-octanol/water distribution coefficients, logP, and logD, of AstraZeneca in-house database. J Pharm Sci 93(12):3103-3110.
36. Bickers DR, et al.; American Academy of Dermatology Association; Society for Investigative Dermatology (2006) The burden of skin diseases-2004: A joint project of the American Academy of Dermatology Association and the Society for Investigative Dermatology. J Am Acad Dermatol 55(3):490-500.
37. DiNubile MJ, Lipsky B.A. (2004) Complicated infections of skin and skin structures: When the infection is more than skin deep. J Antimicrob Chemother 53(Suppl 2): ii37-ii50.
38. Klevens RM, et al.; Active Bacterial Core surveillance (ABCs) MRSA Investigators (2007) Invasive methicillin-resistant Staphylococcus aureus infections in the United States. JAMA 298(15):1763-1771.
39. Wolcott RD, et al. (2010) Chronic wounds and the medical biofilm paradigm. J Wound Care 19(2):45-46, 48-50, 52-53.
40. de Lissovoy G, et al. (2009) Surgical site infection: Incidence and impact on hospital utilization and treatment costs. Am J Infect Control 37(5):387-397.
41. Pizzo PA, et al. (1986) A randomized trial comparing ceftazidime alone with combination antibiotic therapy in cancer patients with fever and neutropenia. N Engl J Med 315(9):552-558.
42. Bjarnsholt T, et al. (2008) Why chronic wounds will not heal: A novel hypothesis. Wound Repair Regen 16(1):2-10.
43. Fazli M, et al. (2009) Nonrandom distribution of Pseudomonas aeruginosa and Staphylococcus aureus in chronic wounds. J Clin Microbiol 47(12):4084-4089.
44. Stolte S, et al. (2007) Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids. Green Chem 9(11):1170-1179.
45. Ketonis C, et al. (2011) Vancomycin bonded to bone grafts prevents bacterial colonization. Antimicrob Agents Chemother 55(2):487-494.
46. Lovejoy KS, et al. (2012) Utilization of metal halide species ambiguity to develop amorphous, stabilized pharmaceutical agents as ionic liquids. Cryst Growth Des 12(11):5357-5364.
47. Lovejoy KS, et al. (2013) Evaluation of ionic liquids on phototrophic microbes and their use in biofuel extraction and isolation. J Appl Phycol 25(4):973-981.
48. Karande P, Jain A, Mitragotri S. (2004) Discovery of transdermal penetration enhancers by high-throughput screening. Nat Biotechnol 22(2):192-197.
49. Ceri H, et al. (1999) The Calgary Biofilm Device: New technology for rapid determination of antibiotic susceptibilities of bacterial biofilms. J Clin Microbiol 37(6): 1771-1776.