Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2017, Article ID 8120367, 9 pages
https://doi.org/10.1155/2017/8120367
Research Article

Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin

1Department of Chemical Engineering, School of Engineering (ISEP), Polytechnic of Porto, 4200-072 Porto, Portugal
2CIQ/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal
3University Institute of Health Sciences (IUCS), 4585-116 Gandra, Portugal

Correspondence should be addressed to Jorge Garrido; tp.ppi.pesi@gjj

Received 12 January 2017; Revised 27 February 2017; Accepted 14 March 2017; Published 9 April 2017

Academic Editor: Artur M. S. Silva

Copyright © 2017 E. Manuela Garrido et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. M. F. F. Bernardes, M. Pazin, L. C. Pereira, and D. J. Dorta, “Impact of pesticides on environmental and human health,” in Toxicology Studies–Cells, Drugs and Environment, chapter 8, pp. 195–233, InTech, Rijeka, Croatia, 2015. View at Google Scholar
  2. W. Aktar, D. Sengupta, and A. Chowdhury, “Impact of pesticides use in agriculture: their benefits and hazards,” Interdisciplinary Toxicology, vol. 2, no. 1, pp. 1–12, 2009. View at Publisher · View at Google Scholar
  3. C. A. Damalas and I. G. Eleftherohorinos, “Pesticide exposure, safety issues, and risk assessment indicators,” International Journal of Environmental Research and Public Health, vol. 8, no. 5, pp. 1402–1419, 2011. View at Publisher · View at Google Scholar · View at Scopus
  4. C. Bolognesi, “Genotoxicity of pesticides: a review of human biomonitoring studies,” Mutation Research, vol. 543, no. 3, pp. 251–272, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. E. M. M. Del Valle, “Cyclodextrins and their uses: a review,” Process Biochemistry, vol. 39, no. 9, pp. 1033–1046, 2004. View at Publisher · View at Google Scholar · View at Scopus
  6. K. Uekama, F. Hirayama, and T. Irie, “Cyclodextrin drug carrier systems,” Chemical Reviews, vol. 98, no. 5, pp. 2045–2076, 1998. View at Publisher · View at Google Scholar · View at Scopus
  7. S. Gould and R. C. Scott, “2-Hydroxypropyl-β-cyclodextrin (HP-β-CD): a toxicology review,” Food and Chemical Toxicology, vol. 43, no. 10, pp. 1451–1459, 2005. View at Publisher · View at Google Scholar · View at Scopus
  8. European Food Safety Authority (EFSA), “Conclusion on the peer review of the pesticide risk assessment of the active substance terbuthylazine,” EFSA Journal, vol. 9, no. 1, p. 1969, 2011. View at Google Scholar
  9. P. Grenni, M. S. Rodríguez-Cruz, E. Herrero-Hernández, J. M. Marín-Benito, M. J. Sánchez-Martín, and A. B. Caracciolo, “Effects of wood amendments on the degradation of terbuthylazine and on soil microbial community activity in a clay loam soil,” Water, Air, and Soil Pollution, vol. 223, no. 8, pp. 5401–5412, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. E. Pannacci and A. Onofri, “Alternatives to terbuthylazine for chemical weed control in maize,” Communications in Biometry and Crop Science, vol. 11, no. 1, pp. 51–63, 2016. View at Google Scholar · View at Scopus
  11. E. Morillo, “Application of cyclodextrins in agrochemistry,” in Cyclodextrins and Their Complexes: Chemistry, Analytical Methods, Applications, H. Dodziuk, Ed., pp. 459–467, Wiley-VCH, Weinheim, Germany, 2006. View at Google Scholar
  12. D. L. Cruickshank, N. M. Rougier, V. J. Maurel et al., “Permethylated β-cyclodextrin/pesticide complexes: X-ray structures and thermogravimetric assessment of kinetic parameters for complex dissociation,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 75, no. 1-2, pp. 47–56, 2013. View at Publisher · View at Google Scholar · View at Scopus
  13. A. Gurarslan, J. Shen, Y. Caydamli, and A. E. Tonelli, “Pyriproxyfen cyclodextrin inclusion compounds,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 82, no. 3, pp. 489–496, 2015. View at Publisher · View at Google Scholar · View at Scopus
  14. J. Zhang, B. Li, H. Bi, and P. Zhang, “Clathration of chlorimuron-ethyl by β-cyclodextrin for improvement of water solubility,” Journal of Pesticide Science, vol. 40, no. 2, pp. 33–37, 2015. View at Publisher · View at Google Scholar · View at Scopus
  15. E. M. Garrido, M. Santos, P. Silva, F. Cagide, J. Garrido, and F. Borges, “Host-guest complexes of phenoxy alkyl acid herbicides and cyclodextrins. MCPA and β-cyclodextrin,” Journal of Environmental Science and Health. Part B Pesticides, Food Contaminants, and Agricultural Wastes, vol. 47, no. 9, pp. 869–875, 2012. View at Publisher · View at Google Scholar · View at Scopus
  16. S. Benfeito, T. Rodrigues, J. Garrido, F. Borges, and E. M. Garrido, “Host-guest interaction between herbicide oxadiargyl and hydroxypropyl-β-cyclodextrin,” The Scientific World Journal, vol. 2013, Article ID 825206, 6 pages, 2013. View at Publisher · View at Google Scholar · View at Scopus
  17. J. Garrido, F. Cagide, M. Melle-Franco, F. Borges, and E. M. Garrido, “Microencapsulation of herbicide MCPA with native β-cyclodextrin and its methyl and hydroxypropyl derivatives: an experimental and theoretical investigation,” Journal of Molecular Structure, vol. 1061, no. 1, pp. 76–81, 2014. View at Publisher · View at Google Scholar · View at Scopus
  18. C. Fernandes, I. Encarnação, A. Fonseca, J. Garrido, F. Borges, and E. M. Garrido, “Cyclodextrins: a valuable resource to attain environmental sustainability,” in Cyclodextrins: Synthesis, Chemical Applications and Role in Drug Delivery, F. G. Ramirez, Ed., Nova Science Publishers, Hauppauge, NY, USA, 2015. View at Google Scholar
  19. T. Higuchi and K. A. Connors, “Phase solubility techniques,” Advances in Analytical Chemistry and Instrumentation, vol. 4, pp. 117–212, 1965. View at Google Scholar
  20. S. S. Jambhekar and P. Breen, “Cyclodextrins in pharmaceutical formulations I: structure and physicochemical properties, formation of complexes, and types of complex,” Drug Discovery Today, vol. 21, no. 2, pp. 356–362, 2016. View at Publisher · View at Google Scholar · View at Scopus
  21. P. Mura, “Analytical techniques for characterization of cyclodextrin complexes in aqueous solution: a review,” Journal of Pharmaceutical and Biomedical Analysis, vol. 101, pp. 238–250, 2014. View at Publisher · View at Google Scholar · View at Scopus
  22. F. Rodante, G. Catalani, and M. Guidotti, “Thermal analysis and kinetic study of decomposition processes of some commercial pesticides. I. Triazine derivatives,” Journal of Thermal Analysis and Calorimetry, vol. 53, no. 3, pp. 937–956, 1998. View at Publisher · View at Google Scholar · View at Scopus
  23. D. A. Skoog, F. J. Holler, and T. A. Nieman, Principles of Instrumental Analysis, Saunders College Pub, 1998.
  24. K. Uekama, F. Hirayama, and S. Nasu, “Determination of the stability constants for inclusion complexes of cyclodextrins with various drug molecules by high performance liquid chromatography,” Chemical and Pharmaceutical Bulletin, vol. 26, no. 11, pp. 3477–3484, 1978. View at Publisher · View at Google Scholar · View at Scopus
  25. M. V. G. de Araújo, E. K. B. Vieira, G. S. Lázaro et al., “Inclusion complexes of pyrimethamine in 2-hydroxypropyl-β-cyclodextrin: characterization, phase solubility and molecular modelling,” Bioorganic and Medicinal Chemistry, vol. 15, no. 17, pp. 5752–5759, 2007. View at Publisher · View at Google Scholar · View at Scopus
  26. T. Loftsson, D. Hreinsdóttir, and M. Másson, “Evaluation of cyclodextrin solubilization of drugs,” International Journal of Pharmaceutics, vol. 302, no. 1-2, pp. 18–28, 2005. View at Publisher · View at Google Scholar · View at Scopus
  27. V. M. Rao and V. J. Stella, “When can cyclodextrins be considered for solubilization purposes?” Journal of Pharmaceutical Sciences, vol. 92, no. 5, pp. 927–932, 2003. View at Publisher · View at Google Scholar · View at Scopus
  28. V. R. Sinha, R. Anitha, S. Ghosh, A. Nanda, and R. Kumria, “Complexation of celecoxib with β-cyclodextrin: characterization of the interaction in solution and in solid state,” Journal of Pharmaceutical Sciences, vol. 94, no. 3, pp. 676–687, 2005. View at Publisher · View at Google Scholar · View at Scopus
  29. B. Yang, J. Lin, Y. Chen, and Y. Liu, “Artemether/hydroxypropyl-β-cyclodextrin host–guest system: characterization, phase-solubility and inclusion mode,” Bioorganic and Medicinal Chemistry, vol. 17, no. 17, pp. 6311–6317, 2009. View at Publisher · View at Google Scholar · View at Scopus
  30. C. Jullian, J. Morales-Montecinos, G. Zapata-Torres et al., “Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins,” Bioorganic and Medicinal Chemistry, vol. 16, no. 9, pp. 5078–5084, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. C. Franco, L. Schwingel, I. Lula, R. D. Sinisterra, L. S. Koester, and V. L. Bassani, “Studies on coumestrol/β-cyclodextrin association: inclusion complex characterization,” International Journal of Pharmaceutics, vol. 369, no. 1-2, pp. 5–11, 2009. View at Publisher · View at Google Scholar · View at Scopus
  32. K. Uekama, T. Fujinaga, F. Hirayama et al., “Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation,” Journal of Pharmaceutical Sciences, vol. 72, no. 11, pp. 1338–1341, 1983. View at Publisher · View at Google Scholar · View at Scopus