Table of Contents Author Guidelines Submit a Manuscript
Journal of Nanomaterials
Volume 2016 (2016), Article ID 8384973, 11 pages
http://dx.doi.org/10.1155/2016/8384973
Research Article

Preparation and Loading with Rifampicin of Sub-50 nm Poly(ethyl cyanoacrylate) Nanoparticles by Semicontinuous Heterophase Polymerization

1Departamento de Procesos de Polimerización, Centro de Investigación en Química Aplicada, Boulevard Enrique Reyna No. 140, 25294 Saltillo, COAH, Mexico
2Síntesis de Polímeros, Centro de Investigación en Química Aplicada, Boulevard Enrique Reyna No. 140, 25294 Saltillo, COAH, Mexico
3Departamento de Química, Universidad de Guadalajara, Boulevard M. García-Barragán No. 1451, 44430 Guadalajara, JAL, Mexico
4Ingeniería Química, Universidad de Guadalajara, Boulevard M. García-Barragán No. 1451, 44430 Guadalajara, JAL, Mexico

Received 2 May 2016; Revised 23 June 2016; Accepted 28 June 2016

Academic Editor: Md Nurunnabi

Copyright © 2016 H. Saade 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. A. Graf, A. McDowell, and T. Rades, “Poly(alkycyanoacrylate) nanoparticles for enhanced delivery of therapeutics—is there real potential?” Expert Opinion on Drug Delivery, vol. 6, no. 4, pp. 371–387, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. G. Yordanov, “Poly (alkil cyanoacrylate) nanoparticles as drug carriers: 33 years later,” Bulgarian Journal of Chemistry, vol. 1, no. 2, pp. 61–72, 2012. View at Google Scholar
  3. C. Vauthier, D. Labarre, and G. Ponchel, “Design aspects of poly(alkylcyanoacrylate) nanoparticles for drug delivery,” Journal of Drug Targeting, vol. 15, no. 10, pp. 641–663, 2007. View at Publisher · View at Google Scholar · View at Scopus
  4. P. Couvreur, B. M. Kante, M. Roland, P. Guiot, P. Bauduin, and P. Speiser, “Polycyanoacrylate nanocapsules as potential lysosomotropic carriers: preparation, morphological and sorptive properties,” Journal of Pharmacy and Pharmacology, vol. 31, no. 1, pp. 331–332, 1979. View at Publisher · View at Google Scholar · View at Scopus
  5. S. J. Douglas, L. Illum, and S. S. Davis, “Particle size and size distribution of poly(butyl 2-cyanoacrylate) nanoparticles. II. Influence of stabilizers,” Journal of Colloid and Interface Science, vol. 103, no. 1, pp. 154–163, 1985. View at Publisher · View at Google Scholar · View at Scopus
  6. B. Seijo, E. Fattal, L. Roblot-Treupel, and P. Couvreur, “Design of nanoparticles of less than 50 nm diameter: preparation, characterization and drug loading,” International Journal of Pharmaceutics, vol. 62, no. 1, pp. 1–7, 1990. View at Publisher · View at Google Scholar · View at Scopus
  7. S. K. Das, I. G. Tucker, D. J. T. Hill, and N. Ganguly, “Evaluation of poly(isobutylcyanoacrylate) nanoparticles for mucoadhesive ocular drug delivery. I. Effect of formulation variables on physicochemical characteristics of nanoparticles,” Pharmaceutical Research, vol. 12, no. 4, pp. 534–540, 1995. View at Publisher · View at Google Scholar · View at Scopus
  8. S. C. Yang, H. X. Ge, Y. Hu, X. Q. Jiang, and C. Z. Yang, “Formation of positively charged poly(butyl cyanoacrylate) nanoparticles stabilized with chitosan,” Colloid and Polymer Science, vol. 278, no. 4, pp. 285–292, 2000. View at Publisher · View at Google Scholar · View at Scopus
  9. I. Bertholon-Rajot, D. Labarre, and C. Vauthier, “Influence of the initiator system, cerium–polysaccharide, on the surface properties of poly(isobutylcyanoacrylate) nanoparticles,” Polymer, vol. 46, no. 4, pp. 1407–1415, 2005. View at Publisher · View at Google Scholar · View at Scopus
  10. C. K. Weiss, U. Ziener, and K. A. Landfester, “A route to nonfunctionalized and functionalized poly(n-butylcyanoacrylate) nanoparticles: preparation in miniemulsion,” Macromolecules, vol. 40, no. 4, pp. 928–938, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. S. J. Douglas, L. Illum, S. S. Davis, and J. Krueter, “Particle size and size distribution of poly(butyl-2-cyanoacrylate) nanoparticles: I. Influence of physicochemical factors,” Journal of Colloid and Interface Science, vol. 101, no. 1, pp. 149–158, 1984. View at Publisher · View at Google Scholar · View at Scopus
  12. N. Behan, C. Birkinshaw, and N. Clarke, “Poly n-butyl cyanoacrylate nanoparticles: a mechanistic study of polymerisation and particle formation,” Biomaterials, vol. 22, no. 11, pp. 1335–1344, 2001. View at Publisher · View at Google Scholar · View at Scopus
  13. C. Chauvierre, D. Labarre, and P. Couvreur, “Radical emulsion polymerization of alkylcyanoacrylates initiated by the redox system dextran-cerium (IV) under acidic aqueous conditions,” Macromolecules, vol. 36, no. 16, pp. 6018–6027, 2003. View at Publisher · View at Google Scholar
  14. A. Bootz, T. Russ, F. Gores, M. Karas, and J. Kreuter, “Molecular weights of poly(butyl cyanoacrylate) nanoparticles determined by mass spectrometry and size exclusion chromatography,” European Journal of Pharmaceutics and Biopharmaceutics, vol. 60, no. 3, pp. 391–399, 2005. View at Publisher · View at Google Scholar · View at Scopus
  15. J. Wu and J.-H. Duan, “Study of co-encapsulated doxorubicin and curcumin poly(butyl cyanoacrylate) nanoparticles and reversion of multidrug resistance in MCF-7/ADR cell line,” Journal of Chemical and Pharmaceutical Research, vol. 5, no. 10, pp. 415–423, 2013. View at Google Scholar · View at Scopus
  16. S. Snipstad, S. Westrøm, Y. Mørch, M. Afadzi, A. Åslund, and C. de Lange Davies, “Contact-mediated intracellular delivery of hydrophobic drugs from polymeric nanoparticles,” Cancer Nanotechnology, vol. 5, no. 1, article 8, 2014. View at Publisher · View at Google Scholar · View at Scopus
  17. H. E. Shahmabadi, F. Movahedi, M. K. M. Esfahani et al., “Efficacy of Cisplatin-loaded polybutyl cyanoacrylate nanoparticles on the glioblastoma,” Tumor Biology, vol. 35, no. 5, pp. 4799–4806, 2014. View at Publisher · View at Google Scholar · View at Scopus
  18. S. K. B. Doun, S. E. Alavi, S. K. B. Esfahani, H. E. Shahmabadi, F. Alavi, and S. Hamzei, “Efficacy of Cisplatin-loaded poly butyl cyanoacrylate nanoparticles on the ovarian cancer: an in vitro study,” Tumor Biology, vol. 35, no. 8, pp. 7491–7497, 2014. View at Publisher · View at Google Scholar · View at Scopus
  19. X. Zhao, W. Li, Q. Luo, and X. Zhang, “Enhanced bioavailability of orally administered flurbiprofen by combined use of hydroxypropyl-cyclodextrin and poly(alkyl-cyanoacrylate) nanoparticles,” European Journal of Drug Metabolism and Pharmacokinetics, vol. 39, no. 1, pp. 61–67, 2014. View at Publisher · View at Google Scholar · View at Scopus
  20. H. Saade, S. Torres, C. Barrera, J. Sánchez, Y. Garza, and R. G. López, “Effect of pH and monomer dosing rate in the anionic polymerization of ethyl cyanoacrylate in semicontinuous operation,” International Journal of Polymer Science, vol. 2015, Article ID 827059, 9 pages, 2015. View at Publisher · View at Google Scholar · View at Scopus
  21. A. Des Rieux, V. Fievez, M. Garinot, Y.-J. Schneider, and V. Préat, “Nanoparticles as potential oral delivery systems of proteins and vaccines: a mechanistic approach,” Journal of Controlled Release, vol. 116, no. 1, pp. 1–27, 2006. View at Publisher · View at Google Scholar · View at Scopus
  22. M. Elsabahy and K. L. Wooley, “Design of polymeric nanoparticles for biomedical delivery applications,” Chemical Society Reviews, vol. 41, no. 7, pp. 2545–2561, 2012. View at Publisher · View at Google Scholar · View at Scopus
  23. D. Thassu, M. Deleers, and Y. Pathak, Nanoparticulate Drug Delivery System, Informa Healthcare, New York, NY, USA, 2007.
  24. L. L. I. J. Booysen, L. Kalombo, E. Brooks et al., “In vivo/in vitro pharmacokinetic and pharmacodynamic study of spray-dried poly-(dl-lactic-co-glycolic) acid nanoparticles encapsulating rifampicin and isoniazid,” International Journal of Pharmaceutics, vol. 444, no. 1-2, pp. 10–17, 2013. View at Publisher · View at Google Scholar · View at Scopus
  25. https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/1/r3501pis.pdf.
  26. L. Balaita, V. Maier, L. Verestiuc, and M. Popa, “Polymer nanoparticles for release of rifampicin,” Advanced Science, Engineering and Medicine, vol. 5, no. 2, pp. 96–104, 2013. View at Publisher · View at Google Scholar
  27. M. Rajan and V. Raj, “Formation and characterization of chitosan-polylacticacid-polyethylene glycol-gelatin nanoparticles: a novel biosystem for controlled drug delivery,” Carbohydrate Polymers, vol. 98, no. 1, pp. 951–958, 2013. View at Publisher · View at Google Scholar · View at Scopus
  28. D. Pooja, L. Tunki, H. Kulhari, B. B. Reddy, and R. Sistla, “Characterization, biorecognitive activity and stability of WGA grafted lipid nanostructures for the controlled delivery of Rifampicin,” Chemistry and Physics of Lipids, vol. 193, pp. 11–17, 2015. View at Publisher · View at Google Scholar · View at Scopus
  29. R. Ledezma, M. E. Treviño, L. E. Elizalde et al., “Semicontinuous heterophase polymerization under monomer starved conditions to prepare nanoparticles with narrow size distribution,” Journal of Polymer Science, Part A: Polymer Chemistry, vol. 45, no. 8, pp. 1463–1473, 2007. View at Publisher · View at Google Scholar · View at Scopus
  30. M. G. Pérez-Garca, M. Rabelero, S. M. Nuño-Donlucas et al., “Semicontinuous heterophase polymerization of n-butyl methacrylate: effect of monomer feeding rate,” Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, vol. 49, no. 7, pp. 539–546, 2012. View at Publisher · View at Google Scholar · View at Scopus
  31. M. G. Pérez-García, A. G. Alvarado, M. Rabelero et al., “Semicontinuous heterophase polymerization of methyl and hexyl methacrylates to produce latexes with high nanoparticles content,” Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, vol. 51, no. 2, pp. 144–155, 2014. View at Publisher · View at Google Scholar · View at Scopus
  32. J. J. Krackeler and H. Naidus, “Particle size and molecular weight distributions of various polystyrene emulsions,” Journal of Polymer Science Part C, vol. 27, no. 1, pp. 207–235, 1969. View at Google Scholar · View at Scopus
  33. M. A. El-Egakey, V. Bentele, and J. Kreuter, “Molecular weights of polycyanoacrylate nanoparticles,” International Journal of Pharmaceutics, vol. 13, no. 3, pp. 349–352, 1983. View at Publisher · View at Google Scholar · View at Scopus
  34. M. G. Han, S. Kim, and S. X. Liu, “Synthesis and degradation behavior of poly(ethyl cyanoacrylate),” Polymer Degradation and Stability, vol. 93, no. 7, pp. 1243–1251, 2008. View at Publisher · View at Google Scholar · View at Scopus
  35. G. Yordanov and Z. Bedzhova, “Poly(ethyl cyanoacrylate) colloidal particles tagged with Rhodamine 6G: preparation and physicochemical characterization,” Central European Journal of Chemistry, vol. 9, no. 6, pp. 1062–1070, 2011. View at Publisher · View at Google Scholar · View at Scopus
  36. D. P. Otto and M. M. de Villiers, “Why is the nanoscale special (or not)? Fundamental properties and how it relates to the design of nano-enabled drug delivery systems,” Nanotechnology Reviews, vol. 2, no. 2, pp. 171–199, 2013. View at Publisher · View at Google Scholar · View at Scopus
  37. M. H. Shoaib, J. Tazeen, H. A. Merchant, and R. I. Yousuf, “Evaluation of drug release kinetics from ibuprofen matrix tablets using HPMC,” Pakistan Journal of Pharmaceutical Sciences, vol. 19, no. 2, pp. 119–124, 2006. View at Google Scholar · View at Scopus
  38. C. Vauthier, C. Dubernet, E. Fattal, H. Pinto-Alphandary, and P. Couvreur, “Poly(alkylcyanoacrylates) as biodegradable materials for biomedical applications,” Advanced Drug Delivery Reviews, vol. 55, no. 4, pp. 519–548, 2003. View at Publisher · View at Google Scholar · View at Scopus
  39. P. Couvreur and C. Vauthier, “Polyalkylcyanoacrylate nanoparticles as drug carrier: present state and perspectives,” Journal of Controlled Release, vol. 17, no. 2, pp. 187–198, 1991. View at Publisher · View at Google Scholar · View at Scopus