Poly(ε-caprolactone) nanocapsules carrying the herbicide atrazine: Effect of chitosan-coating agent on physico-chemical stability and herbicide release profile

International Journal of Environmental Science and Technology

Volumn 11, Issue 6, 2014, Pages 1691-1700

  Grillo, R ^a,b   Rosa, A H ^a   Fraceto, L F ^a,b  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Atrazine; Chitosan; Coated polymeric nanoparticles; Environmental chemistry

Indexed keywords

CHITOSAN; COATINGS; ENCAPSULATION; NANOCAPSULES; NANOPARTICLES; POLYMERS; WEED CONTROL;

ECOLOGICAL AND ECONOMIC; ENCAPSULATION EFFICIENCY; ENVIRONMENTAL CHEMISTRY; GLOBAL APPLICATIONS; PHYSICO-CHEMICAL STABILITY; PHYSICOCHEMICAL PROPERTY; POLYMERIC NANOPARTICLES; PREPARATION PROCEDURES;

HERBICIDES;

ATRAZINE; BIOACTIVITY; CHITIN; COATING; CONCENTRATION (COMPOSITION); DIFFUSION; POLYMER;

EID: 84902950913     PISSN: 17351472     EISSN: 17352630     Source Type: Journal    
DOI: 10.1007/s13762-013-0358-1     Document Type: Article

References (45)

1. Baker EA (1982) Chemistry and morphology of plant epicuticular waxes. In: Cutler DJ, Alvin KL, Price AL (eds) The plant cuticle. Academic Press, London, pp 139-165.
2. Bilensoy E, Sarisozen C, Esendagli G, Dogan AL, Aktas Y, Sen M, Mungan NA (2009) Intravesical cationic nanoparticles of chitosan and polycaprolactone for the delivery of Mitomycin C to bladder tumors. Int J Pharm 371(1-2): 170-176. doi: 10. 1016/j. ijpharm. 2008. 12. 015.
3. Breckenridge CB, Eldridge JC, Stevens JT, Simpkins JW (2010) Symmetrical triazine herbicides: a review of regulatory toxicity endpoints. In: Krieger RI, Hayes WJ (eds) Handbook of pesticide toxicology, vol 2. 3rd edn. Elsevier/Academic Press, Boston, pp 1711-1723.
4. Calvo P, VilaJato JL, Alonso MJ (1997) Evaluation of cationic polymer-coated nanocapsules as ocular drug carriers. Int J Pharm 153(1): 41-50. doi: 10. 1016/S0378-5173(97)00083-5.
5. Chakravarthi SS, Robinson DH (2011) Enhanced cellular association of paclitaxel delivered in chitosan-PLGA particles. Int J Pharm 409(1-2): 111-120. doi: 10. 1016/j. ijpharm. 2011. 02. 034.
6. Clemente-Napimoga JT, Moreira JA, Grillo R, de Melo NFS, Fraceto LF, Napimoga MH (2012) 15d-PGJ2-loaded in nanocapsules enhance the antinociceptive properties into rat temporomandibular hypernociception. Life Sci 90(23-24): 944-949. doi: 10. 1016/j. lfs. 2012. 04. 035.
7. Costa P, Manuel J, Lobo S (2001) Modeling and comparison of dissolution profiles. Eur J Pharm Sci 13(2): 123-133. doi: 10. 1016/S0928-0987(01)00095-1.
8. Dash TK, Konkimalla VB (2012) Poly-epsilon-caprolactone based formulations for drug delivery and tissue engineering: a review. J Control Release 158(1): 15-33. doi: 10. 1016/j. jconrel. 2011. 09. 064.
9. de Melo NFS, Grillo R, Guilherme VA, de Araujo DR, de Paula E, Rosa AH, Fraceto LF (2011) Poly(lactide-co-glycolide) nanocapsules containing benzocaine: influence of the composition of the oily nucleus on physico-chemical properties and anesthetic activity. Pharm Res 28(8): 1984-1994. doi: 10. 1007/s11095-011-0425-6.
10. Fessi H, Puisieux F, Devissaguet JP, Ammoury N, Benita S (1989) Nanocapsule formation by interfacial polymer deposition following solvent displacement. Int J Pharm 55(1): R1-R4. doi: 10. 1016/0378-5173(89)90281-0.
11. Garcia-Fuentes M, Alonso MJ (2012) Chitosan-based drug nanocarriers: where do we stand? J Control Release 161(2): 496-504. doi: 10. 1016/j. jconrel. 2012. 03. 017.
12. Govender T, Riley T, Ehtezazi T, Garnett MC, Stolnik S, Illum L, Davis SS (2000) Defining the drug incorporation properties of PLA-PEG nanoparticles. Int J Pharm 199(1): 95-110. doi: 10. 1016/S0378-5173(00)00375-6.
13. Grangeot M, Chauvel B, Gauvrit C (2006) Spray retention, foliar uptake and translocation of glufosinate and glyphosate in Ambrosia artemisiifolia. Weed Res 46(2): 152-162. doi: 10. 1111/j. 1365-3180. 2006. 00495. x.
14. Gref R, Quellec P, Sanchez A, Calvo P, Dellacherie E, Alonso MJ (2001) Development and characterization of CyA-loaded poly(lactic acid)poly(ethylene glycol)PEG micro- and nanoparticles. Comparison with conventional PLA particulate carriers. European Journal of Pharmaceutics and Biopharmaceutics 51(2): 111-118. doi: 10. 1016/S0939-6411(00)00143-0.
15. Grillo R, de Melo NFS, de Araujo DR, de Paula E, Rosa AH, Fraceto LF (2010a) Polymeric alginate nanoparticles containing the local anesthetic bupivacaine. J Drug Target 18(9): 688-699. doi: 10. 3109/10611861003649738.
16. Grillo R, de Melo NFS, de Lima R, Lourenco RW, Rosa AH, Fraceto LF (2010b) Characterization of atrazine-loaded biodegradable poly(hydroxybutyrate-co-hydroxyvalerate) microspheres. J Polym Environ 18(1): 26-32. doi: 10. 1007/s10924-009-0153-8.
17. Grillo R, Pereira Ado E, de Melo NF, Porto RM, Feitosa LO, Tonello PS, Dias Filho NL, Rosa AH, Lima R, Fraceto LF (2011) Controlled release system for ametryn using polymer microspheres: preparation, characterization and release kinetics in water. J Hazard Mater 186(2-3): 1645-1651. doi: 10. 1016/j. jhazmat. 2010. 12. 044.
18. Grillo R, dos Santos NZP, Maruyama CR, Rosa AH, de Lima R, Fraceto LF (2012) Poly(epsilon-caprolactone)nanocapsules as carrier systems for herbicides: physico-chemical characterization and genotoxicity evaluation. J Hazard Mater 231: 1-9. doi: 10. 1016/j. jhazmat. 2012. 06. 019.
19. Gupta NK, Tomar P, Sharma V, Dixit VK (2011) Development and characterization of chitosan coated poly-(varepsilon-caprolactone) nanoparticulate system for effective immunization against influenza. Vaccine 29(48): 9026-9037. doi: 10. 1016/j. vaccine. 2011. 09. 033.
20. Guterres SS, Poletto FS, Colomé LM, Raffin RP, Pohlmann AR (2010) Polymeric nanocapsules for drug delivery an overview. In: Fanun M (ed) Colloids in drug delivery, vol 1. 3rd edn. CRC Press, pp 71-98.
21. Hack B, Egger H, Uhlemann J, Henriet M, Wirth W, Vermeer AWP, Duff DG (2012) Advanced agrochemical formulations through encapsulation strategies? Chem Ing Tech 84(3): 223-234. doi: 10. 1002/cite. 201100212.
22. ICH (1996) Guidance for Industry-Q2B. Validation of analytical procedures. In: International conference on harmonization.
23. Jiang JK, Oberdorster G, Biswas P (2009) Characterization of size, surface charge, and agglomeration state of nanoparticle dispersions for toxicological studies. J Nanopart Res 11(1): 77-89. doi: 10. 1007/s11051-008-9446-4.
24. Khan KA (1975) The concept of dissolution efficiency. J Pharm Pharmacol 27(1): 48-49.
25. Korsmeyer RW, Gurny R, Doelker E, Buri P, Peppas NA (1983) Mechanisms of solute release from porous hydrophilic polymers. Int J Pharm 15: 25-35.
26. Kumar P, Kumar P, Rajoria G, Narang RK (2012) Techniques for preparation of pharmaceutical coated nanoparticles: a comprehensive review. Am J Pharm Tech Res 3: 121-135.
27. Maynard AD (2011) Don't define nanomaterials. Nature 475: 31.
28. Mazzarino L, Travelet C, Ortega-Murillo S, Otsuka I, Pignot-Paintrand I, Lemos-Senna E, Borsali R (2012) Elaboration of chitosan-coated nanoparticles loaded with curcumin for mucoadhesive applications. J Colloid Interface Sci 370(1): 58-66. doi: 10. 1016/j. jcis. 2011. 12. 063.
29. Moraes CM, de Matos AP, Grillo R, de Melo NF, de Paula E, Dias Filho NL, Rosa AH, Fraceto LF (2011) Screening of formulation variables for the preparation of poly(epsilon-caprolactone) nanocapsules containing the local anesthetic benzocaine. J Nanosci Nanotechnol 11(3): 2450-2457.
30. Mora-Huertas CE, Fessi H, Elaissari A (2010) Polymer-based nanocapsules for drug delivery. Int J Pharm 385(1-2): 113-142. doi: 10. 1016/j. ijpharm. 2009. 10. 018.
31. Nagarwal RC, Kumar R, Pandit JK (2012) Chitosan coated sodium alginate-chitosan nanoparticles loaded with 5-FU for ocular delivery: in vitro characterization and in vivo study in rabbit eye. Eur J Pharm Sci 47(4): 678-685. doi: 10. 1016/j. ejps. 2012. 08. 008.
32. Paavola A, Yliruusi J, Kajimoto Y, Kalso E, Wahlstrom T, Rosenberg P (1995) Controlled release of lidocaine from injectable gels and efficacy in rat sciatic nerve block. Pharm Res 12(12): 1997-2002. doi: 10. 1023/A: 1016264527738.
33. Pathan AK, Kimberley MO, Forster WA, Steele KD, Gaskin RE (2007) Effects of retention and uptake on biological performance of glyphosate. In: Gaskyn RE (ed) Proceedings of the 8th International Symposium on Adjuvants for Agrochemicals. International Society for Agrochemical Adjuvants, USA.
34. Prego C, Garcia M, Torres D, Alonso MJ (2005) Transmucosal macromolecular drug delivery. J Control Release 101(1-3): 151-162. doi: 10. 1016/j. jconrel. 2004. 07. 030.
35. Radad K, Al-Shraim M, Moldzio R, Rausch WD (2012) Recent advances in benefits and hazards of engineered nanoparticles. Environ Toxicol Pharmacol 34(3): 661-672. doi: 10. 1016/j. etap. 2012. 07. 011.
36. Sabir MI, Xu XX, Li L (2009) A review on biodegradable polymeric materials for bone tissue engineering applications. J Mater Sci 44(21): 5713-5724. doi: 10. 1007/s10853-009-3770-7.
37. Schaffazick SR, Guterres SSU, Freitas LD, Pohlmann AR (2003) Physicochemical characterization and stability of the polymeric nanoparticle systems for drug administration. Quim Nova 26(5): 726-737.
38. Siepmann J, Peppas NA (2001) Mathematical modeling of controlled drug delivery. Adv Drug Deliv Rev 48(2-3): 137-138.
39. Siepmann J, Siepmann F (2008) Mathematical modeling of drug delivery. Int J Pharm 364(2): 328-343. doi: 10. 1016/j. ijpharm. 2008. 09. 004.
40. Silva MD, Cocenza DS, de Melo NFS, Grillo R, Rosa AH, Fraceto LF (2010) Alginate nanoparticles as a controlled release system for clomazone herbicide. Quim Nova 33(9): 1868-1873. doi: 10. 1590/S0100-40422010000900009.
41. Silva MD, Cocenza DS, Grillo R, de Melo NFS, Tonello PS, de Oliveira LC, Cassimiro DL, Rosa AH, Fraceto LF (2011) Paraquat-loaded alginate/chitosan nanoparticles: preparation, characterization and soil sorption studies. J Hazard Mater 190(1-3): 366-374. doi: 10. 1016/j. jhazmat. 2011. 03. 057.
42. Silva MD, Cocenza DS, Rosa AH, Fraceto LF (2012) Effect of the association of clomazone in alginate/chitosan nanoparticles under soil sorption. Quim Nova 35(1): 102-107.
43. Taylor P (2011) The wetting of leaf surfaces. Curr Opin Colloid In 16(4): 326-334. doi: 10. 1016/j. cocis. 2010. 12. 003.
44. Tobio M, Sanchez A, Vila A, Soriano I, Evora C, Vila-Jato JL, Alonso MJ (2000) The role of PEG on the stability in digestive fluids and in vivo fate of PEG-PLA nanoparticles following oral administration. Colloid Surf B 18(3-4): 315-323. doi: 10. 1016/S0927-7765(99)00157-5.
45. Wu L, Zhang J, Watanabe W (2011) Physical and chemical stability of drug nanoparticles. Adv Drug Deliv Rev 63(6): 456-469. doi: 10. 1016/j. addr. 2011. 02. 001.