Interaction of the macrolide antimicrobial clarithromycin with dissolved humic acid

Environmental Science and Technology

Volumn 42, Issue 2, 2008, Pages 422-428

  Sibley, Samuel D ^a   Pedersen, Joel A ^a,b  

^a University of Wisconsin Madison   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; COMPLEXATION; DISSOLUTION; PH EFFECTS;

ELLIOT SOIL HUMIC ACID (ESHA); SORPTION DATA;

ORGANIC ACIDS;

CLARITHROMYCIN; FUNCTIONAL GROUP; HUMIC ACID; ORGANIC COMPOUND; POTASSIUM ION; SODIUM ION; ANTIINFECTIVE AGENT; ERYTHROMYCIN; OCTANOL; WATER;

BINDING ENERGY; COMPLEXATION; DISSOLUTION; ORGANIC ACIDS; PH EFFECTS;

ANTIBIOTICS; CATION EXCHANGE CAPACITY; HUMIC ACID; HYDROPHOBICITY; SORPTION;

ACIDITY; ANALYTICAL PARAMETERS; ARTICLE; CATION EXCHANGE; CHEMICAL BINDING; CHEMICAL MODEL; CHEMICAL REACTION; COMPARATIVE STUDY; COMPLEX FORMATION; DESORPTION; DETOXIFICATION; ENERGY; ENVIRONMENTAL FACTOR; EXPERIMENTAL STUDY; HYDROPHOBICITY; HYSTERESIS; IONIC STRENGTH; LINEAR SYSTEM; PH; PKA; PROTON TRANSPORT; ADSORPTION; CHEMISTRY; HUMIC SUBSTANCE; OSMOLARITY;

1-OCTANOL; ADSORPTION; ANTI-BACTERIAL AGENTS; CLARITHROMYCIN; ERYTHROMYCIN; HUMIC SUBSTANCES; HYDROGEN-ION CONCENTRATION; OSMOLAR CONCENTRATION; WATER;

EID: 40949098705     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es071467d     Document Type: Article

References (59)

1. Mellon, M.; Benbrook, C.; Benbrook, K. L. Hogging It: Estimates of Antimicrobial Abuse in Livestock. UCS Publications: Cambridge, MA, 2001.
2. McAllister, T. A.; Yanke, L. J.; Inglis, G. D.; Olsen, M. E. Is antibiotic use in dairy cattle causing antibiotic resistance? Adv. Dairy Technol. 2001, 13, 229-247.
3. McEwen, S. A.; Fedorka-Cray, P. J. Antimicrobial use and resistance in animals. Clin. Infect. Dis. 2002, 34, S93-S106.
4. McFarland, J. W.; Berger, C. M.; Froshauer, S. A.; Hayashi, S. F.; Hecker, S. J.; Jaynes, B. H.; Jefson, M. R.; Kamicker, B. J.; Lipinski, C. A.; Lundy, K. M.; Reese, C. P.; Vu, C. B. Quantitative structure-activity relationships among macrolide antibacterial agents: In vitro and in vivo potency against. Pasteurella multocida J. Med. Chem. 1997, 40, 1340-1346.
5. a) for human and veterinary antibiotics. Water Res. 2004, 38, 2874-2890.
6. Gaynor, M.; Mankin, A. S. Macrolide antibiotics: Binding site, mechanism of action, resistance. Front. Med. Chem. 2005, 2, 21-35.
7. Rodvold, K. A. Clinical pharmacokinetics of clarithromycin. Clin. Pharmacokinet. 1999, 37, 385-398.
8. Gobel, A.; McArdell, C. S.; Suter, M. J.; Giger, W. Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry. Anal. Chem. 2004, 76, 4756-4764.
9. Karthikeyan, K. G.; Meyer, M. T. Occurrence of antibiotics in wastewater treatment facilities in WI, USA. Sci. Total Environ. 2006, 361, 196-207.
10. Kolpin, D.W.; Furlong, E.T.; Meyer, M.T.; Thurman, E.M.; Zaugg, S.D.; Barber, L.B.; Buxton, H. T. Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999-2000: A national reconnaissance. Environ. Sci. Technol. 2002, 36, 1202-1211.
11. Sacher, F.; Lange, F. T.; Brauch, H. J.; Blankenhorn, I. Pharmaceuticals in groundwaters: Analytical methods and results of a monitoring program in Baden-Württemberg, Germany. J. Chromatogr. A. 2001, 938, 199-210.
12. Kinney, C. A.; Furlong, E. T.; Zaugg, S. D.; Burkhardt, M. R.; Werner, S. L.; Cahill, J. D.; Jorgensen, G. R. Survey of organic wastewater contaminants in biosolids destined for land application. Environ. Sci. Technol. 2006, 40, 7207-7215.
13. Kumar, K.; Thompson, A.; Singh, A. K.; Chander, Y.; Gupta, S. C. Enzyme-linked immunosorbent assay for ultratrace determination of antibiotics in aqueous samples. J. Environ. Qual. 2004, 33, 250-256.
14. Kinney, C. A.; Furlong, E. T.; Werner, S. L.; Cahill, J. D. Presence and distribution of wastewater-derived pharmaceuticals in soil irrigated with reclaimed water. Environ. Toxicol. Chem. 2006, 25, 317-326.
15. Gustafsson, O.; Gschwend, P. M. Aquatic colloids: Concepts, definitions, and current challenges. Limnol. Oceanogr. 1997, 42, 519-528.
16. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry, 2nd ed; Wiley-Interscience: Hoboken, NJ, 2003.
17. Ong, H. L.; Bisque, R. E. Coagulation of humic colloids by metal ions. Soil Science. 1968, 106, 220-224.
18. Conte, P.; Piccolo, A. Conformational arrangement of dissolved humic substances. Influence of solution composition on association of humic molecules. Environ. Sci. Technol. 1999, 33, 1682-1690.
19. Sutton, R.; Sposito, G. Molecular structure in soil humic substances: The new view. Environ. Sci. Technol. 2005, 39, 9009-9015.
20. Burkhard, J. Estimating dissolved organic carbon partition coefficients for nonionic organic chemicals. Environ. Sci. Technol. 2000, 34, 4663-4668.
21. doc values. Adv. Environ. Res. 2002, 6, 577-593.
22. Sithole, B. B.; Guy, R. D. Models for tetracycline in aquatic environments. Water, Air, Soil Pollut. 1987, 32, 303-314.
23. Holten-Lützhoft, H. C.; Vaes, W. H. J.; Freidig, A. P.; Halling-Sørensen, B.; Hermens, J. L. M. Influence of pH and other modifying factors on the distribution behavior of 4-quinolones to solid phases and humic acids studied by "negligible-depletion" SPME-HPLC. Environ. Sci. Technol. 2000, 34, 4989-4994.
24. MacKay, A. A.; Canterbury, B. Oxytetracycline sorption to organic matter by metal-bridging. J. Environ. Qual. 2005, 34, 1964-1971.
25. Gu, C.; Karthikeyan, K. G.; Sibley, S. D.; Pedersen, J. A. Complexation of the antibiotic tetracycline with humic acid. Chemosphere. 2007, 66, 1494-1501.
26. Schlautman, M. A.; Morgan, J. J. Effects of aqueous chemistry on the binding of polycyclic aromatic hydrocarbons by dissolved humic materials. Environ. Sci. Technol. 1993, 27, 961-969.
27. Schimpf, M. E.; Wahlund, K. G. Asymmetrical flow field-flow fractionation as a method to study the behavior of humic acids in solution. J. Microcolumn Sep. 1997, 9, 535-543.
28. Nakagawa, Y.; Itai, S.; Yoshid, T.; Nagai, T. Physicochemical properties and stability in the acid solution of a new macrolide antibiotic, clarithromycin, in comparison with erythromycin. Chem. Pharm. Bull. 1992, 40, 725-728.
29. Schwarzenbach, R. P.; Strierli, R.; Folsom, B. R.; Zeyer, J. Compound properties relevant for assessing the environmental partitioning of nitrophenols. Environ. Sci. Technol. 1988, 22, 83-92.
30. Carter, W. C.; Suffet, I. W. Binding of DDT to dissolved humic materials. Environ. Sci. Technol. 1982, 16, 735-740.
31. 4 concentration. Environ. Sci. Technol. 1995, 29, 951-959.
32. Herbelin, A.; Westall, J. C. FITEQL 4.0: A computer program for determination of chemical equilibrium constants from experimental data. Department of Chemistry, Oregon State University: Corvallis, Oregon, 1999.
33. Wang, P. H.; Lien, E. J. Effects of different buffer species on partition coefficients of drugs used in quantitative structure-activity relationships. J. Pharm. Sci. 1980, 69, 662-668.
34. Johnson, C. A.; Westall, J. C. Distribution of hydrophobic ionogenic organic compounds between octanol and water: Organic bases. Environ. Sci. Technol. 1990, 24, 1869-1875.
35. Slater, B.; McCormack, A.; Avdeef, A.; Comer, J. E. A. pH-metric log P. 4. Comparison of partition coefficients determined by HPLC and Potentiometrie methods to literature values. J. Pharm. Sci. 1994, 83, 1280-1283.
36. Alvarez-Puebla, R. A.; Garrido, J. J. Effect of pH on the aggregation of a gray humic acid in colloidal and solid states. Chemosphere 2005, 59, 659-667.
37. Piccolo, A.; Cellano, G. Hydrogen bonding interactions between the herbicide glyphosate and water soluble humic substances. Environ. Toxicol. Chem. 1994, 13, 1737-1741.
38. Nielsen, T.; Siigur, K.; Helweg, C.; Jørgensen, O.; Hansen, P. E.; Kirso, U. Sorption of polycyclic aromatic compounds to humic acid as studied by high-performance liquid chromotography. Environ. Sci. Technol. 1997, 31, 1102-1108.
39. Martin-Neto, L.; Traghetta, D. G.; Vaz, C. M. P.; Crestana, S.; Sposito, G. On the interaction mechanisms of atrazine and hydroxyatrazine with humic substances. J. Environ. Qual. 2001, 30, 520-525.
40. Arnold, C. G.; Ciani, A.; Muller, S. R.; Amirbahman, A.; Schwarzenbach, R. P. Association of triorganotin compounds with dissolved humic acids. Environ. Sci. Technol. 1998, 32, 2976-2983.
41. Karthikeyan, K. G.; Chorover, J. Humic acid complexation of basic and neutral polycyclic aromatic compounds. Chemosphere. 2002, 48, 955-964.
42. Polyakova, I. V.; Pisarev, O. A. Influence of polyfunctional interactions between organic zwitter-ion eremomycin and carboxylic cation exchangers on forming concentration front. J. Chromatogr. A. 2005, 1092, 135-141.
43. Weber, W. J.; McGinley, P. M.; Katz, L. E. A distributed reactivity model for sorption by soils and sediments. 1. Conceptual basis and equilibrium assessments. Environ. Sci. Technol. 1992, 26, 1955-1962.
44. Xing, B.; Pignatello, J. J.; Gigliotti, B. Competitive sorption between atrazine and other organic compounds in soils and model sorbents. Environ. Sci. Technol. 1996, 30, 2432-2440.
45. Bonn, B. A.; Fish, W. Measurement of electrostatic and site-specific associations of alkali metal cations with humic acid. J. Soil Sci. 1993, 44, 335-345.
46. Sander, M.; Lu, Y.; Pignatello, J. J. A thermodynamically based method to quantify true sorption hysteresis. J. Environ. Qual. 2005, 34, 1063-1072.
47. Huang, W.; Yu, H.; Weber, W. J. Hysteresis in the sorption and desorption of hydrophobic organic contaminants by soils and sediments. 1. A comparative analysis of experimental protocols. J. Contam. Hydrol. 1998, 31, 129-148.
48. Essington, M. E. Soil and Water Chemistry: An Integrative Approach. CRC Press: Boca Raton, FL, 2003.
49. Tolls, J. Sorption of veterinary pharmaceuticals - a review. Environ. Sci. Technol. 2001, 35, 3397-3406.
50. Kim, Y.; Heinze, T. M.; Kim, S.; Cerniglia, C. E. Adsorption and clay-catalyzed degradation of erythromycin A on homoionic clays. J. Environ. Qual. 2004, 33, 257-264.
51. Akkanen, J.; Kukkonen, J. V. K. The bioavailability of two hydrophobic organic compounds in the presence of dissolved organic matter. Environ. Toxicol. Chem. 2002, 22, 518-524.
52. Halling-Sørensen, B.; Sengeløv, G.; Ingerslev, F.; Jensen, L. B. Reduced antimicrobial potencies of Oxytetracycline, tylosin, sulfadiazin, streptomycin, ciprofloxacin, and olaquindox due to environmental processes. Arch. Environ. Contam. Toxicol. 2003, 44, 7-16.
53. Chiou, C. T.; Malcolm, R. L.; Brinton, T. I.; Kile, D. E. Water solubility enhancement of some organic pollutants and pesticides by dissolved humic and fulvic acids. Environ. Sci. Technol. 1986, 20, 502-508.
54. McCarthy, J. F.; Zachara, J. M. Subsurface transport of contaminants. Environ. Sci. Technol. 1989, 23, 496-502.
55. Aiken, G.; Cotsaris, E. Soil and hydrology: Their effect on NOM. JAWWA. 1995, 87, 36-45.
56. Seol, Y.; Lee, L. S. Effect of dissolved organic matter in treated effluents on sorption of atrazine and prometryn by soils. Soil Sci. Soc. Am. J. 2000, 64, 1976-1983.
57. Seol, Y.; Lee, L. S. Coupled effects of treated effluent irrigation and wetting-drying cycles on transport of triazines through unsaturated soil columns. J. Environ. Qual. 2001, 30, 1644-1652.
58. Speight, J. Lange's Handbook of Chemistry, 15th ed.; McGraw-Hill: New York, NY, 1999.
59. O'Neil, M. J.; Heckelman, P. E.; Koch, C. B.; Roman, K. J. The Merck Index, 14th ed.; Merck & Co., Inc.: Whitehouse Station, NJ, 2006.