Isolation and Characterisation of 1-Alkyl-3-Methylimidazolium Chloride Ionic Liquid-Tolerant and Biodegrading Marine Bacteria

PLoS ONE

Volumn 8, Issue 4, 2013, Pages

  Megaw, Julianne ^a   Busetti, Alessandro ^a   Gilmore, Brendan F ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 ALKYL 3 METHYLIMIDAZOLIUM CHLORIDE; HYDROCARBON; IONIC LIQUID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; BACTERIAL METABOLISM; BACTERIAL STRAIN; BACTERIUM ISOLATION; BIOREMEDIATION; BREVIBACTERIUM SANGUINIS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENVIRONMENTAL EXPOSURE; ENVIRONMENTAL IMPACT ASSESSMENT; ENVIRONMENTAL MANAGEMENT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MARINE BACTERIUM; MARINE ENVIRONMENT; NONHUMAN; RHODOCOCCUS ERYTHROPOLIS; SALINITY; STRAIN DIFFERENCE;

AQUATIC ORGANISMS; BIODEGRADATION, ENVIRONMENTAL; BREVIBACTERIUM; CHLORIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CULTURE MEDIA; IMIDAZOLES; IONIC LIQUIDS; MICROBIAL SENSITIVITY TESTS; RHODOCOCCUS;

BACTERIA (MICROORGANISMS); BREVIBACTERIUM SANGUINIS; RHODOCOCCUS ERYTHROPOLIS;

EID: 84875640579     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0060806     Document Type: Article

References (76)

1. European Chemicals Agency. Registration, evaluation, authorisation & restriction of chemicals (REACH).
2. Manahan SE (2006) Green chemistry and the ten commandments of sustainability. Columbia, Missouri U.S.A.: ChemChar Research, Inc.
3. Watson WJW, (2012) How do the fine chemical, pharmaceutical, and related industries approach green chemistry and sustainability? Green Chem 14: 251-259.
4. Visser A, Swatloski R, Rogers R, (2000) pH-dependent partitioning in room temperature ionic liquids provides a link to traditional solvent extraction behavior. Green Chem 2: 1-4.
5. Huddleston J, Willauer H, Swatloski R, Visser A, Rogers R (1998) Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction. Chem Commun: 1765-1766.
6. Welton T, (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99: 2071-2083.
7. Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun: 2399-2407.
8. de Souza R, Padilha J, Goncalves R, Dupont J, (2003) Room temperature dialkylimidazolium ionic liquid-based fuel cells. Electrochem Commun 5: 728-731.
9. Palomar J, Lemus J, Gilarranz MA, Rodriguez JJ, (2009) Adsorption of ionic liquids from aqueous effluents by activated carbon. Carbon 47: 1846-1856.
10. Bica K, Rijksen C, Nieuwenhuyzen M, Rogers RD, (2010) In search of pure liquid salt forms of aspirin: Ionic liquid approaches with acetylsalicylic acid and salicylic acid. Physical Chemistry Chemical Physics 12: 2011-2017.
11. Docherty K, Kulpa C, (2005) Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem 7: 185-189.
12. Samori C, Pasteris A, Galletti P, Tagliavini E, (2007) Acute toxicity of oxygenated and nonoxygenated imidazolium-based ionic liquids to Daphnia magna and Vibrio fischeri. Environmental Toxicology and Chemistry 26: 2379-2382.
13. Ranke J, Molter K, Stock F, Bottin-Weber U, Poczobutt J, et al. (2004) Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays. Ecotoxicol Environ Saf 58: 396-404.
14. Pretti C, Chiappe C, Pieraccini D, Gregori M, Abramo F, et al. (2006) Acute toxicity of ionic liquids to the zebrafish (Danio rerio). Green Chem 8: 238-240.
15. Wells AS, Coombe VT, (2006) On the freshwater ecotoxicity and biodegradation properties of some common ionic liquids. Organic Process Research & Development 10: 794-798.
16. Matzke M, Stolte S, Thiele K, Juffernholz T, Arning J, 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.
17. Swatloski RP, Holbrey JD, Memon SB, Caldwell GA, Caldwell KA, et al. (2004) Using caenorhabditis elegans to probe toxicity of 1-alkyl-3-methylimidazolium chloride based ionic liquids. Chemical Communications: 668-669.
18. Zhao H, (2005) Effect of ions and other compatible solutes on enzyme activity, and its implication for biocatalysis using ionic liquids. J Mol Catal B-Enzym 37: 16-25.
19. Bailey MM, Townsend MB, Jernigan PL, Sturdivant J, Hough-Troutman WL, et al. (2008) Developmental toxicity assessment of the ionic liquid 1-butyl-3-methylimidazolium chloride in CD-1 mice. Green Chem 10: 1213-1217.
20. Ranke J, Cox M, Müller A, Schmidt C, (2006) D (2006) Sorption, cellular distribution, and cytotoxicity of imidazolium ionic liquids in mammalian cells- influence of lipophilicity. Toxicological and Environmental Chemistry 88: 273-285.
21. Luczak J, Jungnickel C, Lacka I, Stolle S, Hupka J, (2010) Antimicrobial and surface activity of 1-alkyl-3-methylimidazolium derivatives. Green Chem 12: 593-601.
22. Radwan S, Mahmoud H, Khanafer M, Al-Habib A, Al-Hasan R, (2010) Identities of epilithic hydrocarbon-utilizing diazotrophic bacteria from the Arabian Gulf Coasts, and their potential for oil bioremediation without nitrogen supplementation. Microb Ecol 60: 354-363.
23. Csonka L, (1989) Physiological and genetic responses of bacteria to osmotic stress. Microbiol Rev 53: 121-147.
24. Gathergood N, Garcia M, Scammells P, (2004) Biodegradable ionic liquids: Part I. concept, preliminary targets and evaluation. Green Chem 6: 166-175.
25. Romero A, Santos A, Tojo J, Rodriguez A, (2008) Toxicity and biodegradability of imidazolium ionic liquids. J Hazard Mater 151: 268-273.
26. Gathergood N, Scammells P, (2002) Design and preparation of room-temperature ionic liquids containing biodegradable side chains. Aust J Chem 55: 557-560.
27. Atefi F, Teresa Garcia M, Singer RD, Scammells PJ, (2009) Phosphonium ionic liquids: Design, synthesis and evaluation of biodegradability. Green Chem 11: 1595-1604.
28. Ford L, Harjani JR, Atefi F, Teresa Garcia M, Singer RD, et al. (2010) Further studies on the biodegradation of ionic liquids. Green Chem 12: 1783-1789.
29. Neumann J, Grundmann O, Thoeming J, Schulte M, Stolte S, (2010) Anaerobic biodegradability of ionic liquid cations under denitrifying conditions. Green Chem 12: 620-627.
30. Stolte S, Abdulkarim S, Arning J, Blomeyer-Nienstedt A, Bottin-Weber U, et al. (2008) Primary biodegradation of ionic liquid cations, identification of degradation products of 1-methyl-3-octylimidazolium chloride and electrochemical wastewater treatment of poorly biodegradable compounds. Green Chem 10: 214-224.
31. Stepnowski P, Zaleska A, (2005) Comparison of different advanced oxidation processes for the degradation of room temperature ionic liquids. Journal of Photochemistry and Photobiology A-Chemistry 170: 45-50.
32. Siedlecka EM, Czerwicka M, Neumann J, Stepnowski P, Fernández JF, et al. (2011) Ionic liquids: Methods of degradation and recovery, ionic liquids: Theory, properties, new approaches. In: Alexander Kokorin, editor. IONIC LIQUIDS:THEORY, PROPERTIES,NEW APPROACHES. pp. 701-722.
33. Hopkins G, Munakata J, Semprini L, McCarty P, (1993) Trichloroethylene concentration effects on pilot field-scale in-situ groundwater bioremediation by phenol-oxidizing microorganisms. Environ Sci Technol 27: 2542-2547.
34. Gallego J, Loredo J, Llamas J, Vazquez F, Sanchez J, (2001) Bioremediation of diesel-contaminated soils: Evaluation of potential in situ techniques by study of bacterial degradation. Biodegradation 12: 325-335.
35. Anderson R, Vrionis H, Ortiz-Bernad I, Resch C, Long P, et al. (2003) Stimulating the in situ activity of geobacter species to remove uranium from the groundwater of a uranium-contaminated aquifer. Appl Environ Microbiol 69: 5884-5891.
36. Farhadian M, Vachelard C, Duchez D, Larroche C, (2008) In situ bioremediation of monoaromatic pollutants in groundwater: A review. Bioresour Technol 99: 5296-5308.
37. Janssen D, Dinkla I, Poelarends G, Terpstra P, (2005) Bacterial degradation of xenobiotic compounds: Evolution and distribution of novel enzyme activities. Environ Microbiol 7: 1868-1882.
38. Boethling RS, Sommer E, DiFiore D, (2007) Designing small molecules for biodegradability. Chem Rev 107: 2207-2227.
39. Coleman D, Gathergood N, (2010) Biodegradation studies of ionic liquids. Chem Soc Rev 39: 600-637.
40. Whyte L, Bourbonniere L, Greer C, (1997) Biodegradation of petroleum hydrocarbons by psychrotrophic Pseudomonas strains possessing both alkane (alk) and naphthalene (nah) catabolic pathways. Appl Environ Microbiol 63: 3719-3723.
41. Rahman K, Rahman T, Kourkoutas Y, Petsas I, Marchant R, et al. (2003) Enhanced bioremediation of n-alkane in petroleum sludge using bacterial consortium amended with rhamnolipid and micronutrients. Bioresour Technol 90: 159-168.
42. Abrusci C, Palomar J, Pablos JL, Rodriguez F, Catalina F, (2011) Efficient biodegradation of common ionic liquids by Sphingomonas paucimobilis bacterium. Green Chem 13: 709-717.
43. Coleman D, Spulak M, Teresa Garcia M, Gathergood N, (2012) Antimicrobial toxicity studies of ionic liquids leading to a 'hit' MRSA selective antibacterial imidazolium salt. Green Chem 14: 1350-1356.
44. Modelli A, Sali A, Galletti P, Samori C, (2008) Biodegradation of oxygenated and non-oxygenated imidazolium-based ionic liquids in soil. Chemosphere 73: 1322-1327.
45. Mihelcic J, Luthy R, (1988) Microbial-degradation of acenaphthene and naphthalene under denitrification conditions in soil-water systems. Appl Environ Microbiol 54: 1188-1198.
46. Moscoso F, Teijiz I, Sanroman MA, Deive FJ, (2012) On the suitability of a bacterial consortium to implement a continuous PAHs biodegradation process in a stirred tank bioreactor. Industrial and Engineering Chemistry Research 51: 15895-15900.
47. Deive FJ, Rodriguez A, Varela A, Rodrigues C, Leitao MC, et al. (2011) Impact of ionic liquids on extreme microbial biotypes from soil. Green Chem 13: 687-696.
48. Gonzalez J, Kiene R, Moran M, (1999) Transformation of sulfur compounds by an abundant lineage of marine bacteria in the alpha-subclass of the class proteobacteria. Appl Environ Microbiol 65: 3810-3819.
49. Hedlund B, Geiselbrecht A, Bair T, Staley J, (1999) Polycyclic aromatic hydrocarbon degradation by a new marine bacterium, Neptunomonas naphthovorans gen. nov., sp. nov. Appl Environ Microbiol 65: 251-259.
50. Galushko A, Minz D, Schink B, Widdel F, (1999) Anaerobic degradation of naphthalene by a pure culture of a novel type of marine sulphate-reducing bacterium. Environ Microbiol 1: 415-420.
51. Wang W, Shao Z, (2012) Diversity of flavin-binding monooxygenase genes (almA) in marine bacteria capable of degradation long-chain alkanes. FEMS Microbiol Ecol 80: 523-533.
52. Rockne K, Strand S, (1998) Biodegradation of bicyclic and polycyclic aromatic hydrocarbons in anaerobic enrichments. Environ Sci Technol 32: 3962-3967.
53. Geiselbrecht A, Hedlund B, Tichi M, Staley J, (1998) Isolation of marine polycyclic aromatic hydrocarbon (PAH)-degrading cycloclasticus strains from the gulf of mexico and comparison of their PAH degradation ability with that of puget sound cycloclasticus strains. Appl Environ Microbiol 64: 4703-4710.
54. Innovotech Incorporated. Manufacturer's instructions: The MBEC Physiology & Genetics (P & G) assay.
55. Al-Saleh E, Drobiova H, Obuekwe C, (2009) Predominant culturable crude oil-degrading bacteria in the coast of kuwait. Int Biodeterior Biodegrad 63: 400-406.
56. Garcia M, Gathergood N, Scammells P, (2005) Biodegradable ionic liquids- part II. effect of the anion and toxicology. Green Chem 7: 9-14.
57. Stepnowski P, Storoniak P, (2005) Lipophilicity and metabolic route prediction of imidazolium ionic liquids. Environmental Science and Pollution Research 12: 199-204.
58. Carson L, Chau PKW, Earle MJ, Gilea MA, Gilmore BF, et al. (2009) Antibiofilm activities of 1-alkyl-3-methylimidazolium chloride ionic liquids. Green Chem 11: 492-497.
59. Tang S, Wang Y, Schumann P, Stackebrandt E, Lou K, et al. (2008) Brevibacterium album sp nov., a novel actinobacterium isolated from a saline soil in china. Int J Syst Evol Microbiol 58: 574-577.
60. Blasco R, Martinez-Luque M, Madrid M, Castillo F, Moreno-Vivian C, (2001) Rhodococcus sp RB1 grows in the presence of high nitrate and nitrite concentrations and assimilates nitrate in moderately saline environments. Arch Microbiol 175: 435-440.
61. Wauters G, Haase G, Avesani V, Charlier J, Janssens M, et al. (2004) Identification of a novel Brevibacterium species isolated from humans and description of Brevibacterium sanguinis sp nov. J Clin Microbiol 42: 2829-2832.
62. Trenz S, Engesser K, Fischer P, Knackmuss H, (1994) Degradation of fluorene by Brevibacterium sp strain dpo-1361- a novel C-C bond-cleavage mechanism via 1,10-dihydro-1,10-dihydroxyfluoren-9-one. J Bacteriol 176: 789-795.
63. Samanta S, Chakraborti A, Jain R, (1999) Degradation of phenanthrene by different bacteria: Evidence for novel transformation sequences involving the formation of 1-naphthol. Appl Microbiol Biotechnol 53: 98-107.
64. Pirniki M, Atlas R, Bartha R, (1974) Hydrocarbon metabolism by Brevibacterium erythrogenes- normal and branched alkanes. J Bacteriol 119: 868-878.
65. Chaillan F, Le Fleche A, Bury E, Phantavong Y, Grimont P, et al. (2004) Identification and biodegradation potential of tropical aerobic hydrocarbon-degrading microorganisms. Res Microbiol 155: 587-595.
66. Larkin M, Kulakov L, Allen C, (2005) Biodegradation and Rhodococcus- masters of catabolic versatility. Curr Opin Biotechnol 16: 282-290.
67. de Carvalho CCCR, da Fonseca MMR, (2005) The remarkable Rhodococcus erythropolis. Appl Microbiol Biotechnol 67: 715-726.
68. Liu CW, Chang WN, Liu HS, (2009) Bioremediation of n-alkanes and the formation of biofloccules by Rhodococcus erythropolis NTU-1 under various saline conditions and sea water. Biochem Eng J 45: 69-75.
69. Mariano AP, Kataoka, Ana Paula de Arruda Geraldes, de Angelis DF, Bonotto DM, (2007) Laboratory study on the bioremediation of diesel oil contaminated soil from a petrol station. Brazilian J Microbiol 38: 346-353.
70. Harjani JR, Farrell J, Garcia MT, Singer RD, Scammells PJ, (2009) Further investigation of the biodegradability of imidazolium ionic liquids. Green Chem 11: 821-829.
71. Loh K, Wang S, (1997) Enhancement of biodegradation of phenol and a nongrowth substrate 4-chlorophenol by medium augmentation with conventional carbon sources. Biodegradation 8: 329-338.
72. Boopathy R, (2000) Factors limiting bioremediation technologies. Bioresour Technol 74: 63-67.
73. Costerton J, Stewart P, Greenberg E, (1999) Bacterial biofilms: A common cause of persistent infections. Science 284: 1318-1322.
74. Stewart P, Costerton J, (2001) Antibiotic resistance of bacteria in biofilms. Lancet 358: 135-138.
75. Mah T, O'Toole G, (2001) Mechanisms of biofilm resistance to antimicrobial agents. Trends Microbiol 9: 34-39.
76. Singh R, Paul D, Jain RK, (2006) Biofilms: Implications in bioremediation. Trends Microbiol 14: 389-397.