Assessing the toxicity and biodegradability of deep eutectic solvents

Chemosphere

Volumn 132, Issue , 2015, Pages 63-69

  Wen, Qing ^a   Chen, Jing Xin ^a   Tang, Yu Lin ^a   Wang, Juan ^a   Yang, Zhen ^a  

^a SHENZHEN UNIVERSITY   (China)

Author keywords

Anti bacterial activity; Biodegradability; Deep eutectic solvents (DESs); Ionic liquids (ILs); Toxicity

Indexed keywords

BIODEGRADATION; BOTTLES; CHLORINE COMPOUNDS; ESCHERICHIA COLI; ETHYLENE; ETHYLENE GLYCOL; EUTECTICS; IONIC LIQUIDS; SALTS; SOLVENTS; TOXICITY; UREA;

ANTI-BACTERIAL ACTIVITY; ANTIBACTERIAL PROPERTIES; CELLULAR MEMBRANES; CHOLINE CHLORIDE; DEEP EUTECTIC SOLVENTS; ECOTOXICOLOGICAL; INHIBITORY EFFECT; IONIC LIQUID (ILS);

BIODEGRADABILITY;

ACETAMIDE; ACETYLCHOLINE; CHOLINE; DEEP EUTECTIC SOLVENT; ETHYLENE GLYCOL; GLYCEROL; SODIUM CHLORIDE; SOLVENT; UNCLASSIFIED DRUG; UREA; ANTIINFECTIVE AGENT;

ANTIMICROBIAL ACTIVITY; ASSESSMENT METHOD; BIODEGRADATION; COLIFORM BACTERIUM; CONCENTRATION (COMPOSITION); ECOTOXICOLOGY; HERB; INHIBITOR; MEMBRANE; ORGANIC COMPOUND; POLLUTION EFFECT; SALT; SOLVENT; TOXICITY;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL CELL WALL; BIODEGRADABILITY; BIODEGRADATION; CELL MEMBRANE; CONTROLLED STUDY; DRUG CYTOTOXICITY; ESCHERICHIA COLI; GARLIC; HYDRA; HYDROGEN BOND; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHYTOTOXICITY; STATIC ELECTRICITY; BACTERIUM; ECOTOXICOLOGY; METABOLISM; PROCEDURES;

ALLIUM SATIVUM; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; HYDRA; INVERTEBRATA;

ANTI-BACTERIAL AGENTS; BACTERIA; CHOLINE; ECOTOXICOLOGY; ETHYLENE GLYCOL; GLYCEROL; SOLVENTS; UREA;

EID: 84929145211     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2015.02.061     Document Type: Article

References (41)

1. Abbott A.P., Capper G., Davies D.L., Rasheed R.K., Tambyrajah V. Novel solvent properties of choline chloride/urea mixtures. Chem. Commun. 2003, 70-71. 10.1039/B210714G.
2. Beach M.J., Pascoe D. The role of Hydra vulgaris (Pallas) in assessing the toxicity of freshwater pollutants. Water Res. 1997, 32:101-106. 10.3724/SP.J.1035.2010.00754.
3. Broering J.M., Bommarius A.S. Evaluation of Hofmeister effects on the kinetic stability of proteins. J. Phys. Chem. B 2005, 109:20612-20619. 10.1021/jp053618+.
4. Clements R.G., Nabholz J.V., Zeeman M. Estimating toxicity of industrial chemicals to aquatic organisms using structure-activity relationships 1996, Environmental Effects Branch, Health and Environmental Review Division, Office of Pollution Prevention and Toxics, U.S. Environmental Protection Agency, Washington. second ed.
5. Coleman D., Gathergood N. Biodegradation studies of ionic liquids. Chem. Soc. Rev. 2010, 39:600-637. 10.1039/b817717c.
6. Collins K.D. Ions from the Hofmeister series and osmolytes: effects on proteins in solution and in the crystallization process. Methods 2004, 34:300-311. 10.1016/j.ymeth.2004.03.021.
7. Cornmell R.J., Winder C.L., Tiddy G.J.T., Goodacre R., Stephens G. Accumulation of ionic liquids in Escherichia coli cells. Green Chem. 2008, 10:836-841. 10.1039/B807214K.
8. Garcia-Celma J.J., Hatahet L., Kunz W., Fendler K. Specific anion and cation binding to lipid membranes investigated on a solid supported membrane. Langmuir 2007, 23:10074-10080. 10.1021/la701188f.
9. Hayyan M., Hashim M.A., Hayyan A., Al-Saadi M.A., AlNashef I.M., Mirghani M.E.S., Saheed O.K. Are deep eutectic solvents benign or toxic?. Chemosphere 2013, 90:2193-2195. 10.1016/j.chemosphere.2012.11.004.
10. Hayyan M., Hashim M.A., Al-Saadi M.A., Hayyan A., AlNashef I.M., Mirghani M.E.S. Assessment of cytotoxicity and toxicity for phosphonium-based deep eutectic solvents. Chemosphere 2013, 93:455-459. 10.1016/j.chemosphere.2013.05.013.
11. Hofmeister F. Zur lehre der wirkung der salze. Zweite mittheilung. Arch. Exp. Pathol. Pharmakol. 1888, 24:247-260.
12. Hou X.-D., Liu Q.-P., Smith T.J., Li N., Zong M.-H. Evaluation of toxicity and biodegradability of cholinium amino acids ionic liquids. PLoS ONE 2013, 8:e59145. 10.1371/journal.pone.0059145.
13. Huang Z.-L., Wu B.-P., Wen Q., Yang T.-X., Yang Z. Deep eutectic solvents can be viable enzyme activators and stabilizers. J. Chem. Technol. Biotechnol. 2014, 89:1975-1981. 10.1002/jctb.4285.
14. Jenkins H.D.W., Marcus Y. Viscosity B-coefficients of ions in solution. Chem. Rev. 1995, 95:2695-2724. 10.1021/cr00040a004.
15. Kommanee J., Preecharram S., Daduang S., Temsiripong Y., Dhiravisit A., Yamada Y., Thammasirirak S. Antibacterial activity of plasma from crocodile (Crocodylus siamensis) against pathogenic bacteria. Ann. Clin. Microbiol. Antimicrob 2012, 11:22. 10.1186/1476-0711-11-22.
16. Kunz W. Specific ion effects in colloidal and biological systems. Curr. Opin. Colloid Interface Sci. 2010, 15:34-39. 10.1016/j.cocis.2009.11.008.
17. Kunz W., Lo Nostro P., Ninham B.W. The present state of affairs with Hofffieister effects. Curr. Opin. Colloid Interface Sci. 2004, 9:1-18. 10.1016/j.cocis.2004.05.004.
18. Leontidis E. Hofmeister anion effects on surfactant self-assembly and the formation of mesoporous solids. Curr. Opin. Colloid Interface Sci. 2002, 7:81-91. 10.1016/S1359-0294(02)00010-9.
19. Modica-Napolitano J.S., Aprille J.R. Delocalized lipophilic cations selectively target the mitochondria of carcinoma cells. Adv. Drug Delivery Rev. 2001, 49:63-70. 10.1016/S0169-409X(01)00125-9.
20. Nockemann P., Thijs B., Driesen K., Janssen C.R., Van Hecke K., Van Meervelt L., Kossmann S., Kirchner B., Binnemans K. Choline saccharinate and choline acesulfamate: ionic liquids with low toxicities. J. Phys. Chem. B 2007, 111:5254-5263. 10.1021/jp068446a.
21. OECD guideline for testing of chemicals, adopted by the council on 17th July 1992 - Ready biodegradability.
22. Paiva A., Craveiro R., Aroso I., Martins M., Reis R.L., Duarte A.R.C. Natural deep eutectic solvents - Solvents for the 21st century. ACS Sust. Chem. Eng. 2014, 2:1063-1071. 10.1021/sc500096j.
23. Pernak P., Chwala P. Synthesis and anti-microbial activities of choline-like quaternary ammonium chlorides. Eur. J. Med. Chem. 2003, 38:1035-1042. 10.1016/j.ejmech.2003.09.004.
24. Petkovic M., Ferguson J., Bohn A., Trindade J., Martins I., Carvalho M.B., Leitão M.C., Rodrigues C., Garcia H., Ferreira R., Seddon K.R., Rebelo L.P.N., Pereira C.S. Exploring fungal activity in the presence of ionic liquids. Green Chem. 2009, 11:889-894. 10.1039/b823225c.
25. Petkovic M., Ferguson J.L., Gunaratne H.Q.N., Ferreira R., Leitão M.C., Seddon K.R., Rebeloa L.P.N., Pereira C.S. Novel biocompatible cholinium-based ionic liquids - toxicity and biodegradability. Green Chem. 2010, 12:643-649. 10.1039/B922247B.
26. Petkovic M., Seddon K.R., Rebelo L.P.N., Pereira C.S. Ionic liquids: a pathway to environmental acceptability. Chem. Soc. Rev. 2011, 40:1383-1403. 10.1002/chin.201127270.
27. Petkovic M., Hartmann D.O., Adamová G., Seddon K.R., Rebelo L.P.N., Pereira C.S. Unravelling the mechanism of toxicity of alkyltributylphosphonium chlorides in Aspergillus nidulans conidia. New J. Chem. 2012, 36:56-63. 10.1039/C1NJ20470J.
28. Pham T.P.T., Cho C.-W., Yun Y.-S. Environmental fate and toxicity of ionic liquids: A review. Water Res. 2010, 44:352-372. 10.1016/j.watres.2009.09.030.
29. Radošević K., Bubalo M.C., Srček V.G., Grgas D., Dragičević T.L., Redovnikovic I.R. Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol. Environ. Saf. 2015, 112:46-53. 10.1016/j.ecoenv.2014.09.034.
30. Russell A. Similarities and differences in the responses of microorganisms to biocides. J. Antimicrob. Chemother. 2003, 52(2003):750-763. 10.1093/jac/dkg422.
31. Samoriỳ C. Ionic liquids and their biological effects towards microorganisms. Curr. Org. Chem. 2011, 15:1888-1904. 10.2174/138527211795703658.
32. Stolte S., Steudte S., Areitioaurtena O., Pagano F., Thöming J., Stepnowski P., Igartua A. Ionic liquids as lubricants or lubrication additives: an ecotoxicity and biodegradability assessment. Chemosphere 2012, 89:1135-1141. 10.1016/j.chemosphere.2012.05.102.
33. Tetko I.V., Gasteiger J., Todeschini R., Mauri A., Livingstone D., Ertl P., Palyulin V.A., Radchenko E.V., Zefirov N.S., Makarenko A.S., Tanchuk V.Y., Prokopenko V.V. Virtual computational chemistry laboratory - design and description. J. Comput. -Aided. Mol. Des. 2005, 19:453-463. 10.1007/s10822-005-8694-y.
34. USDA National Nutrient Database for Standard Reference: http://ndb.nal.usda.gov.
35. VCCLAB, Virtual Computational Chemistry Laboratory, http://www.vcclab.org,%202005.
36. Ventura S.P.M., e Silva F.A., Gonçalves A.M.M., Pereira J.L., Gonçalves F., Coutinho J.A.P. Ecotoxicity analysis of cholinium-based ionic liquids to Vibrio fischeri marine bacteria. Environ. Saf. 2014, 102:48-54. 10.1016/j.ecoenv.2014.01.003.
37. Vlachy N., Jagoda-Cwiklik B., Vácha R., Touraud D., Jungwirth P., Kunz W. Hofmeister series and specific interactions of charged headgroups with aqueous ions. Adv. Colloid Interface Sci. 2009, 146:42-47. 10.1016/j.cis.2008.09.010.
38. Wilby, O.K., The Hydra regeneration assay. In: Proceedings of Workshop Organized by Association Française de Teratologie, Royaumont, France, June 3, 1988, pp. 108-124.
39. Wu B.-P., Wen Q., Xu H., Yang Z. Insights into the impact of deep eutectic solvents on horseradish peroxidase: activity, stability and structure. J. Mol. Catal. B: Enzym. 2014, 101:101-107. 10.1016/j.molcatb.2014.01.001.
40. Zeisel S.H., da Costa K.A. Choline: an essential nutrient for public health. Nutr. Rev. 2009, 67:615-623. 10.1111/j.1753-4887.2009.00246.x.
41. Zhang Q.H., Vigier K.D.O., Royer S., JérÔme F. Deep eutectic solvents: syntheses, properties and applications. Chem. Soc. Rev. 2012, 41:7108-7146. 10.1039/C2CS35178A.