Nonlinear optical studies of the agricultural antibiotic morantel interacting with silica/water interfaces

Journal of the American Chemical Society

Volumn 127, Issue 45, 2005, Pages 15771-15777

  Konek, Christopher T ^a   Illg, Kimberly D ^a   Al Abadleh, Hind A ^a,b   Voges, Andrea B ^a   Yin, Grace ^a   Musorrafiti, Michael J ^a   Schmidt, Catherine M ^a   Geiger, Franz M ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b WILFRID LAURIER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; DISCHARGE (FLUID MECHANICS); HEALTH CARE; NONLINEAR OPTICS; SILICA; SOILS;

BIOTA; DRUG RESISTANCE; MORANTEL; SILICA-RICH SOIL;

ANTIBIOTICS;

AGRICULTURAL CHEMICAL; ANTIBIOTIC AGENT; GROUND WATER; MORANTEL; RUNOFF; SILICON DIOXIDE; WATER;

ADSORPTION; ARTICLE; CHEMICAL INTERACTION; CONCENTRATION (PARAMETERS); ENVIRONMENTAL RELEASE; MEASUREMENT; NONLINEAR SYSTEM; PH; SPECTROSCOPY; SURFACE PROPERTY; VIBRATION; WASTE COMPONENT REMOVAL;

ANTINEMATODAL AGENTS; ENVIRONMENT; LASERS; MORANTEL; OPTICS; SILICON DIOXIDE; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTRUM ANALYSIS; WATER;

EID: 27844603752     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054837b     Document Type: Article

References (85)

1. Howdeshell, K. L.; Hotohkiss, A. K.; Thayer, K. A.; Vandernberg, J. G.; vom Saal, F. S. Nature 1999, 401, 763.
2. Anway, M. D.; Cupp, A. S.; Uzumcu, M.; Skinner, M. K. Science 2005, 308, 1466.
3. Hayes, T.; Haston, K.; Tsui, M.; Hoang, A.; Haeffele, C.; Conk, A. Nature 2002, 419, 895.
4. Aguzzi, A.; Montrasio, F.; Kaeser, P. S. Nat. Rev. Mol. Cell Biol. 2001, 2, 118.
5. Ferber, D. Science 2000, 288, 792.
6. Molbak, K.; Baggesen, D. L.; Aarestrup, F. M.; Ebbesen, J. M.; Engberg, J.; Frydendahl, K.; Gerner-Smidt, P.; Petersen, A. M.; Wegener, H. C. N. Engl. J. Med. 1999, 341, 1420.
7. Stackelberg, P. E.; Furlong, E. T.; Meyer, M. T.; Zaugg, S. D.; Henderson, A. K.; Reissman, D. B. Sci. Total Environ. 2004, 329, 99.
8. Jones, O. A.; Lester, J. N.; Vouvoulis, N. Trends Biotechnol. 2005, 23, 163.
9. Kolpin, D. W.; Furlong, E. T.; Meyer, M. T.; Thurman, E. M.; Zaugg, S. D.; Barber, L. B.; Buxton, H. T. Environ. Sci. Technol. 2002, 36, 1202.
10. Mellon, M.; Benbrook, C.; Benbrook, K. L. Hogging It: Estimates of Antimicrobial Abuse in Livestock; Union of Concerned Scientists: Cambridge, MA, 2001.
11. Hileman, B. Chem. Eng. News 2005, 83, 16.
12. Matson, P. A.; Parton, W. J.; Power, A. G.; Swift, M. J. Science 1997, 277, 504.
13. Vorosmarty, C. J.; Green, P.; Salisbury, J.; Lammers, R. B. Science 2000, 289, 284.
14. Evangelou, V. P. Environmental Soil and Water Chemistry; John Wiley & Sons: New York, 1998.
15. Stumm, W.; Morgan, J. J. Aquatic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1996.
16. Morel, F. M. M.; Hering, J. G. Principles and Applications of Aquatic Chemistry; Wiley-Interscience: New York, 1993.
17. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry, 2nd ed.; John Wiley and Sons: Hoboken, NJ, 2003.
18. Brown, G. E. Science 2001, 294, 67.
19. Brown, G. E.; Henrich, V. E.; Casey, W. H.; Clark, D. L.; Eggleston, C.; Felmy, A.; Goodman, D. W.; Graetzel, M.; Maciel, G.; McCarthy, M. I.; Nealson, K. H.; Sverjensky, D. A.; Toney, M. F.; Zachara, J. M. Chem. Rev. 1999, 99, 77.
20. Environmental Impact Statement. Pfizer Incorporated: New York, 1994.
21. Clarke's Analysis of Drugs and Poisons, 3rd ed.; Pharmaceutical Press: London, 2003.
22. Boxall, A. B. A.; Kolpin, D. W.; Halling-Sorensen, B.; Tolls, J. Environ. Sci. Technol. A-Pages 2003, 286.
23. Melancon, J. J. A Review of Morantel Citrate; Merial, 2001, 2005.
24. Lynch, M. J. M.; Burnett, D. M.; Newby, T. J. J. Agric. Food Chem. 1987, 35, 351.
25. 2000 FSIS National Residue Program - The "Blue Book": Food Safety and Inspection Service, USDA. 2000; http://www.fsis.usda.gov/OPHS/ blue2000/.
26. Morantel And Pyrantel Drug-Related Metabolites: US Department of Agriculture Food Saftey and Inspection Service: Athens, GA, 1991.
27. Schmitt, H.; van Beelen, P.; Tolls, J.; van Leeuwen, C. L. Environ. Sci. Technol. 2004, 38, 1148.
28. Tolls, J. Environ. Sci. Technol. 2001, 35, 3397.
29. d, Values: Introduction; United States Environmental Protection Agency, 2003; www.epa.gov/radiation/cleanup/partition.htm.
30. d, Values: Appendix E, Partition Coefficients for Chromium (VI); United States Environmental Protection Agency, 2003; www.epa.gov/radiation/cleanup/partition. htm.
31. Langmuir, D. Aqueous Environmental Geochemistry; Prentice-Hall: New Jersey, 1997.
32. Al-Abadleh, H. A.; Mifflin, A. L.; Bertin, P. A.; Nguyen, S. T.; Geiger, F. M. J. Phys. Chem. B. 2005, 109, 9691.
33. Sposito, G. The Surface Chemistry of Soils; Oxford University Press: New York, 1984.
34. Adamson, A. W. Physical Chemistry of Surfaces, 5th ed.; John Wiley & Sons: New York, 1990.
35. Masel, R. I. Principles of Adsorption and Reaction on Solid Surfaces; John Wiley & Sons: New York, 1996.
36. Bostick, B. C.; Fendorf, S.; Manning, B. A. Geochim. Cosmochim. Acta 2003, 67, 895.
37. Farquhar, M. L.; Charnock, J. M.; Livens, F. R.; Vaughan, D. J. Environ. Sci. Technol. 2002, 36, 1757.
38. Foster, A. L.; Brown, G. E.; Parks, G. A. Geochim. Cosmochim. Acta 2003, 67, 1937.
39. Paktunc, D.; Foster, A.; Laflamme, G. Environ. Sci. Technol. 2003, 37, 2067.
40. Smith, P. G.; Koch, I.; Gordon, R. A.; Mandoli, D. F.; Chapman, B. D.; Reimer, K. J. Environ. Sci. Technol. 2005, 39, 248.
41. Takahashi, Y.; Ohtaku, N.; Mitsunobu, S.; Yuita, K.; Nomura, M. Anal. Sci. 2003, 19, 891.
42. Weckhuysen, B. M.; Wachs, I. E.; Schoonheydt, R. A. Chem. Rev. 1996, 96, 3327.
43. Stack, A. G.; Higgins, S. R.; Eggleston, C. M. Geochim. Cosmochim. Acta 2001, 65, 3055.
44. Fitts, J. P.; Shang, X.; Flynn, G. W.; Heinz, T. F.; Eisenthal, K. B. J. Phys. Chem. B 2005, 109, 7981.
45. Liu, D. F.; Ma, G.; Allen, H. C. Environ. Sci. Technol. 2005, 39, 2025.
46. Van, E. C. Y.; Eisenthal, K. B. J. Phys. Chem. B 1999, 103, 6056.
47. Liu, Y.; Dadap, J. I.; Zimdars, D.; Eisenthal, K. B. J. Phys. Chem. B 1999, 103, 2480.
48. Baldelli, S.; Schnitzer, C.; Campbell, D. J.; Shultz, M. J. J. Phys. Chem. B 1999, 103, 2789.
49. Allen, H. C.; Gragson, D. E.; Richmond, G. L. J. Phys. Chem. B 1999, 103, 660.
50. Wei, X.; Miranda, P. B.; Shen, Y. R. Phys. Rev. Lett. 2001, 86, 1554.
51. Steel, W. H.; Damkaci, F.; Nolan, R.; Walker, R. A. J. Am. Chem. Soc. 2002, 124, 4824.
52. Walker, R. A.; Gruetzmacher, J. A.; Richmond, G. L. J. Am. Chem. Soc. 1998, 120, 6991.
53. Eisenthal, K. B. Chem. Rev. 1996, 96, 1343.
54. Zhang, X.; Esenturk, O.; Walker, R. A. J. Am. Chem. Soc. 2001, 123, 10768.
55. Konek, C. T.; Musorrafiti, M. J.; Al-Abadleh, H. A.; Bertin, P. A.; Nguyen, S. T.; Geiger, F. M. J. Am. Chem. Soc. 2004, 126, 11754.
56. Voges, A. B.; Al-Abadleh, H. A.; Geiger, F. M. Development of Nonlinear Optical Spectroscopies for Studying Heterogeneous Environmental Catalytic Processes. In Environmental Catalysis; Grassian, V. H., Ed.; CRC Press: Boca Raton, FL, 2005.
57. Mifflin, A. L.; Gerth, K. A.; Weiss, B. M.; Geiger, F. M. J. Phys. Chem. A 2003, 107, 6212.
58. Mifflin, A. L.; Gerth, K. A.; Geiger, F. M. J. Phys. Chem. A 2003, 107, 9620.
59. Al-Abadleh, H. A.; Voges, A. B.; Bertin, P. A.; Nguyen, S. T.; Geiger, F. M. J. Am. Chem. Soc. 2004, 126, 11126.
60. Uray, G.; Verdino, P.; Belaj, F.; Kappe, C. O.; Fabian, W. M. F. J. Org. Chem. 2001, 66, 6685.
61. Jug, K.; Hahn, G. J. Comput. Chem. 1983, 4, 410.
62. Shen, Y. R. The Principles of Nonlinear Optics: John Wiley & Sons: New York, 1984.
63. Shen, Y. R. Nature 1989, 337, 519.
64. Shen, Y. R. Surf. Sci. 1994, 299-300, 551.
65. Eisenthal, K. B. Equilibrium and Dynamic Processes at Inlerfaces by Second Harmonic and Sum Frequency Generation. In Annual Review of Physical Chemistry; Strauss, H. L., Babcock, G. T., Leone, S. R., Eds.; Annual Reviews Inc: Palo Alto, CA, 1992; Vol. 43, p 627.
66. Heinz, T. F. Nonlinear Surface Electromagnetic Phenomena; Elsevier Publishers: Dordrecht, The Netherlands, 1991.
67. Al-Abadleh, H. A.; Mifflin, A. L.; Musorrafiti, M. J.; Geiser, F. M. J. Phys. Chem. B. 2005, 109, 16852.
68. Simpson, G. J.; Rowlen, K. L. Anal. Chem. 2000, 72, 3399.
69. Simpson, G. J.; Rowlen, K. L. Anal. Chem. 2000, 72, 3407.
70. Simpson, G. J.; Westerbuhr, S. G.; Rowlen, K. L. Anal. Chem. 2000, 72, 887.
71. Boyd, R. W. Nonlinear Optics; Academic Press: New York, 1992.
72. Miranda, P. B.; Shen, Y. R. J. Phys. Chem. B 1999, 103, 3292.
73. Richmond, G. L. Chem. Rev. 2002, 102, 2693.
74. Buck, M.; Himmelhaus, M. J. Vac. Sci. Technol. A-Vac. Surf. Films 2001, 19, 2717.
75. Wei, X.; Hong, S. C.; Lvovsky, A. I.; Held, H.; Shen, Y. R. J. Phys. Chem. B 2000, 104, 3349.
76. Richter, L. J.; Petralli-Mallow, T. P.; Stephenson, J. C. Opt. Lett. 1998, 23, 1594.
77. vanderHam, E. W. M.; Vrehen, Q. H. F.; Eliel, E. R. Surf. Sci. 1996, 368, 96.
78. Hommel, E. L.; Ma, G.; Allen, H. C. Anal. Sci. 2001, 17, 1325.
79. Watry, M. R.; Brown, M. G.; Richmond, G. L. Appl. Spectrosc. 2001, 55, 321A.
80. Esenturk, O.; Walker, R. A. J. Phys. Chem. B 2004, 108, 10631.
81. Vuges, A. B.; Al-Abadleh, H. A.; Musorrafiti, M. J.; Bertin, P. A.; Nguyen, S. T.; Geiger, F. M. J. Phys. Chem. B 2004, 108, 18675.
82. Chen, C. Y.; Even, M. A.; Wang, J.; Chen, Z. Macromolecules 2002, 35, 9130.
83. Opdahl, A.; Phillips, R. A.; Somorjai, G. A. J. Phys. Chem. B 2002, 106, 5212.
84. Hesse, M.; Meier, H.; Zeeh, B. Spektroskopische Methoden in der Organischen Chemie, 4th ed.; G. Thieme: Stuttgart, New York, 1991.
85. Hicks, J. M.; Kemnitz, K.; Eisenthal, K. B.; Heinz, T. F. J. Phys. Chem. 1986, 90, 560.