Mutagenicity of quaternary ammonium salts containing carbohydrate moieties

Journal of Hazardous Materials

Volumn 193, Issue , 2011, Pages 272-278

  Dmochowska, Barbara ^a   Piosik, Jacek ^a   Woziwodzka, Anna ^a   Sikora, Karol ^a   Wiśniewski, Andrzej ^a   Wegrzyn, Grzegorz ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Microbiological mutagenicity test; Mutagenicity; Quaternary ammonium salts

Indexed keywords

MUTAGENIC ACTIVITY; MUTAGENICITY; MUTAGENICITY ASSAY; QUATERNARY AMMONIUM SALT;

AMMONIUM COMPOUNDS; CARBOHYDRATES; HEALTH CARE; HEALTH HAZARDS; SAFETY TESTING;

SALTS;

GALACTOSE; GLUCOSE DERIVATIVE; MANNOSE; MUTAGENIC AGENT; N [2 (2',3',4',6' TETRA O ACETYL ALPHA DEXTRO MANNOPYRANOSYLOXY)ETHYL] N,N,N TRIMETHYLAMINIUM BROMIDE; N [2 (2',3',4',6' TETRA O ACETYL ALPHA DEXTRO MANNOPYRANOSYLOXY)ETHYL]PYRIDINIUM BROMIDE; N [2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYLOXY)ETHYL] N,N,N TRIMETHYLAMINIUM BROMIDE; N [2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYLOXY)ETHYL]PYRIDINIUM BROMIDE; N [2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYLOXY)ETHYL] N,N,N TRIMETHYLAMINIUM BROMIDE; N [2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYLOXY)ETHYL]PYRIDINIUM BROMIDE; N [2 (ALPHA DEXTRO MANNOPYRANOSYLOXY)ETHYL] N,N,N TRIMETHYLAMINIUM BROMIDE; N [2 (ALPHA DEXTRO MANNOPYRANOSYLOXY)ETHYL]PYRIDINIUM BROMIDE; N [2 (BETA DEXTRO GALACTOPYRANOSYLOXY)ETHYL] N,N,N TRIMETHYLAMINIUM BROMIDE; N [2 (BETA DEXTRO GALACTOPYRANOSYLOXY)ETHYL]PYRIDINIUM BROMIDE; N [2 (BETA DEXTRO GLUCOPYRANOSYLOXY)ETHYL] N,N,N TRIMETHYLAMINIUM BROMIDE; N [2 (BETA DEXTRO GLUCOPYRANOSYLOXY)ETHYL]PYRIDINIUM BROMIDE; QUATERNARY AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG;

AMMONIUM; BIOASSAY; BIOLUMINESCENCE; CARBOHYDRATE; HEALTH SERVICES; MICROBIAL ACTIVITY; MUTAGENICITY; SALT;

ARTICLE; BACTERIAL STRAIN; BIOLUMINESCENCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; MUTAGEN TESTING; MUTAGENICITY; NONHUMAN; VIBRIO HARVEYI;

CARBOHYDRATES; MAGNETIC RESONANCE SPECTROSCOPY; MUTAGENICITY TESTS; MUTAGENS; QUATERNARY AMMONIUM COMPOUNDS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; VIBRIO;

VIBRIO HARVEYI;

EID: 84860394034     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2011.07.064     Document Type: Article

References (52)

1. Binks B.P., Fletcher P.D., Salama I.E., Horsup D.I., Moore J.A. Quantitative prediction of the reduction of corrosion inhibitor effectiveness due to parasitic adsorption onto a competitor surface. Langmuir 2011, 27:469-473.
2. Singh S., Bhadani A., Kataria H., Kaur G., Kamboj R. Synthesis of glycerol-based pyridinium surfactants and appraisal of their properties. Ind. Eng. Chem. Res. 2009, 48:1673-1677.
3. Quaternary Ammonium Salts 2005, ITD Press, Poznań. R. Zielinski (Ed.).
4. Rabea E.I., Badawy M.E., Stevens C.V., Smagghe G., Steurbaut W. Chitosan as antimicrobial agent: applications and mode of action. Biomacromolecules 2003, 4:1457-1465.
5. Belalia R., Grelier S., Benaissa M., Coma V. New bioactive biomaterials based on quaternized chitosan. J. Agric. Food Chem. 2008, 56:1582-1588.
6. McDonnell G., Russell A.D. Antiseptics and disinfectants: activity, action, and resistance. Clin. Microbiol. Rev. 1999, 12:147-179.
7. Boethling R.S. Environmental fate and toxicity in wastewater-treatment of quaternary ammonium surfactants. Water Res. 1984, 18:1061-1076.
8. Levinson M.I. Rinse-added fabric softener technology at the close of the twentieth century. J. Surfactants Deterg. 1999, 2:223-235.
9. Cross J., Singer E.J. Cationic Surfactants 1994, Marcel Dekker Inc., New York.
10. Sarkar B., Xi Y., Megharaj M., Krishnamurti G.S., Naidu R. Synthesis and characterisation of novel organopalygorskites for removal of p-nitrophenol from aqueous solution: isothermal studies. J. Colloid Interface Sci. 2010, 350:295-304.
11. ® 2HT-75 organoclays. J. Hazard. Mater. 2010, 183:87-97.
12. Sarkar B., Xi Y., Megharaj M., Naidu R. Orange II adsorption on palygorskites modified with alkyl trimethylammonium and dialkyl dimethylammonium bromide-an isothermal and kinetic study. Appl. Clay Sci. 2011, 51:370-374.
13. Sarkar B., Megharaj M., Xi Y., Krishnamurti G.S., Naidu R. Sorption of quaternary ammonium compounds in soils: implications to the soil microbial activities. J. Hazard. Mater. 2010, 184:448-456.
14. García M.T., Campos E., Sanchez-Leal J., Ribosa I. Effect of the alkyl chain length on the anaerobic biodegradability and toxicity of quaternary ammonium based surfactants. Chemosphere 1999, 38:3473-3483.
15. García M.T., Ribosa I., Guindulain T., Sánchez-Leal J., Vives-Rego J. Fate and effect of monoalkyl quaternary ammonium surfactants in the aquatic environment. Environ. Pollut. 2001, 111:169-175.
16. Nałecz-Jawecki G., Grabińska-Sota E., Narkiewicz P. The toxicity of cationic surfactants in four bioassays. Ecotoxicol. Environ. Safe. 2003, 54:87-91.
17. Thorsteinsson T., Masson M., Kristinsson K.G., Hjalmarsdottir M.A., Hilmarsson H., Loftsson T. Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds. J. Med. Chem. 2003, 46:4173-4181.
18. Colomer A., Pinazo A., Manresa M.A., Vinardell M.P., Mitjans M., Infante M.R., Perez L. Cationic surfactants derived from lysine: effects of their structure and charge type on antimicrobial and hemolytic activities. J. Med. Chem. 2011, 54:989-1002.
19. Booij L.H., van der Broek L.A., Caulfield W., Dommerholt-Caris B.M., Clark J.K., van E.J., McGuire R., Muir A.W., Ottenheijm H.C., Rees D.C. Non-depolarizing neuromuscular blocking activity of bisquaternary amino di- and tripeptide derivatives. J. Med. Chem. 2000, 43:4822-4833.
20. El-Bayoumy K. Environmental carcinogens that may be involved in human breast cancer etiology. Chem. Res. Toxicol. 1992, 5:585-590.
21. Depledge M.H. The ecotoxicological significance of genotoxicity in marine invertebrates. Mutat. Res. 1998, 399:109-122.
22. Au W.W., Oberheitmann B., Heo M.Y., Hoffmann W., Oh H.Y. Biomarker monitoring for health risk based on sensitivity to environmental mutagens. Rev. Environ. Health 2001, 16:41-64.
23. Martin F.L. Genotoxins and the initiation of sporadic breast cancer. Mutagenesis 2001, 16:155-161.
24. Tornqvist M., Ehrenberg L. Estimation of cancer risk caused by environmental chemicals based on in vivo dose measurement. J. Environ. Pathol. Toxicol. Oncol. 2001, 20:263-271.
25. Barton H.A., Cogliano V.J., Flowers L., Valcovic L., Setzer R.W., Woodruff T.J. Assessing susceptibility from early-life exposure to carcinogens. Environ. Health Perspect. 2005, 113:1125-1133.
26. Shelby M.D., Bishop J.B., Mason J.M., Tindall K.R. Fertility, reproduction, and genetic disease: studies on the mutagenic effects of environmental agents on mammalian germ cells. Environ. Health Perspect. 1993, 100:283-291.
27. Podgorska B., Wegrzyn G. A modified Vibrio harveyi mutagenicity assay based on bioluminescence induction. Lett. Appl. Microbiol. 2006, 42:578-582.
28. Woziwodzka A., Gwizdek-Wisniewska A., Piosik J. Caffeine, pentoxifylline and theophylline form stacking complexes with IQ-type heterocyclic aromatic amines. Bioorg. Chem. 2011, 39:10-17.
29. Maron D.M., Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 1983, 113:173-215.
30. Mortelmans K., Zeiger E. The Ames Salmonella/microsome mutagenicity assay. Mutat. Res. 2000, 455:29-60.
31. Klein G., Walczak R., Krasnowska E., Błaszczak A., Lipińska B. Characterization of heat-shock response of the marine bacterium Vibrio harveyi. Mol. Microbiol. 1995, 16:801-811.
32. Dmochowska B., Pellowska-Januszek L., Skorupa E., Nowacki A., Stock F., Stepnowski P., Wisniewski A. Synthesis of new quaternary ammonium salts-derivatives of phenyl glucopyranosides. Pol. J. Chem. 2006, 80:1513-1521.
33. Skorupa E., Dmochowska B., Pellowska-Januszek L., Wojnowski W., Chojnacki J., Wisiewski A. Synthesis and structure of selected quaternary N-(1,4-anhydro-5-deoxy-2, 3-O-isopropylidene-d,l-ribitol-5-yl)ammonium salts. Carbohydr. Res. 2004, 339:2355-2362.
34. Podgorska B., Pazdro K., Pempkowiak J., Wegrzyn G. The use of a novel Vibrio harveyi luminescence mutagenicity assay in testing marine water for the presence of mutagenic pollution. Mar. Pollut. Bull. 2007, 54:808-814.
35. Podgorska B., Pazdro K., Wegrzyn G. The use of the Vibrio harveyi luminescence mutagenicity assay as a rapid test for preliminary assessment of mutagenic pollution of marine sediments. J. Appl. Genet. 2007, 48:409-412.
36. Podgorska B., Krolicka A., Lojkowska E., Wegrzyn G. Rapid detection of mutagens accumulated in plant tissues using a novel Vibrio harveyi mutagenicity assay. Ecotoxicol. Environ. Safe. 2008, 70:231-235.
37. Chec E., Podgorska B., Wegrzyn G. Comparison of the use of mussels and semipermeable membrane devices for monitoring and assessment of accumulation of mutagenic pollutants in marine environment in combination with a novel microbiological mutagenicity assay. Environ. Monit. Assess. 2008, 140:83-90.
38. Angerer J., Ewers U., Wilhelm M. Human biomonitoring: state of the art. Int. J. Hyg. Environ. Health 2007, 210:201-228.
39. Podgorska B., Wegrzyn G. The use of marine bacteria in mutagenicity assays. Pol. J. Microbiol. 2007, 56:227-231.
40. Pateiro-Moure M., Pérez-Novo C., Arias-Estévez M., López-Periago E., Martínez-Carballo E., Simal-Gandara J. Influence of copper on the adsorption and desorption of paraquat, diquat, and difenzoquat in vineyard acid soils. J. Agric. Food Chem. 2007, 55:6219-6226.
41. Cruz-Guzman M., Celis R., Hermosin M.C., Koskinen W.C., Cornejo J. Adsorption of pesticides from water by functionalized organobentonites. J. Agric. Food Chem. 2005, 53:7502-7511.
42. Pateiro-Moure M., Arias-Estévez M., López-Periago E., Martínez-Carballo E., Simal-Gándara J. Occurrence and downslope mobilization of quaternary herbicide residues in vineyard-devoted soils. Bull. Environ. Contam. Toxicol. 2008, 80:407-411.
43. Pateiro-Moure M., Martínez-Carballo E., Arias-Estévez M., Simal-Gándara J. Determination of quaternary ammonium herbicides in soils. Comparison of digestion, shaking and microwave-assisted extractions. J. Chromatogr. A 2008, 1196-1197:110-116.
44. Pateiro-Moure M., Nóvoa-Muñoz J.C., Arias-Estévez M., López-Periago E., Martínez-Carballo E., Simal-Gándara J. Quaternary herbicides retention by the amendment of acid soils with a bentonite-based waste from wineries. J. Hazard. Mater. 2009, 164:769-775.
45. Pateiro-Moure M., Pérez-Novo C., Arias-Estévez M., Rial-Otero R., Simal-Gándara J. Effect of organic matter and iron oxides on quaternary herbicide sorption-desorption in vineyard-devoted soils. J. Colloid Interface Sci. 2009, 333:431-438.
46. Pateiro-Moure M., Bermúdez-Couso A., Fernández-Calviño D., Arias-Estévez M., Rial-Otero R., Simal-Gándara J. Paraquat and diquat sorption on iron oxide coated quartz particles and the effect of phosphates. J. Chem. Eng. Data 2010, 55:2668-2672.
47. Pateiro-Moure M., Arias-Estévez M., Simal-Gándara J. Competitive and non-competitive adsorption/desorption of paraquat, diquat and difenzoquat in vineyard-devoted soils. J. Hazard. Mater. 2010, 178:194-201.
48. Bermúdez-Couso A., Arias-Estévez M., Nóvoa-Muñoz J.C., López-Periago E., Soto-González B., Simal-Gándara J. Seasonal distributions of fungicides in soils and sediments of a small river basin partially devoted to vineyards. Water Res. 2007, 41:4515-4525.
49. Arias-Estévez M., López-Periago E., Martínez-Carballo E., Simal-Gándara J., Mejuto J.C., García-Río L. The mobility and degradation of pesticides in soils and the pollution of groundwater resources. Agric. Ecosyst. Environ. 2008, 123:247-260.
50. Rial-Otero R., Cancho-Grande B., Perez-Lamela C., Simal-Gándara J., Arias-Estévez M. Simultaneous determination of the herbicides diquat and paraquat in water. J. Chromatogr. Sci. 2006, 44:539-542.
51. González-Rodríguez R.M., Rial-Otero R., Cancho-Grande B., Simal-Gándara J. Occurrence of fungicide and insecticide residues in trade samples of leafy vegetables. Food Chem. 2008, 107:1342-1347.
52. González-Rodríguez R.M., Rial-Otero R., Cancho-Grande B., Gonzalez-Barreiro C., Simal-Gándara J.J. A review on the fate of pesticides during the processes within the food-production chain. Crit. Rev. Food Sci. Nutr. 2011, 51:99-114.