Fabrication, modeling and characterization of multi-crosslinked methacrylate copolymeric nanoparticles for oral drug delivery

International Journal of Molecular Sciences

Volumn 12, Issue 9, 2011, Pages 6194-6225

  Ngwuluka, Ndidi C ^a   Pillay, Viness ^a   Choonara, Yahya E ^a   Modi, Girish ^a   Naidoo, Dinesh ^a   du Toit, Lisa C ^a   Kumar, Pradeep ^a   Ndesendo, Valence M K ^a   Khan, Riaz A ^b  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

^b QASSIM UNIVERSITY   (Saudi Arabia)

Author keywords

Bioavailability; Chitosan; Crosslinking; Methacrylate copolymer; Molecular mechanics simulations; Nanocapsules; Nanoparticles; Nanotechnology; Oral drug delivery

Indexed keywords

CHITOSAN; EUDRAGIT; LEVODOPA; NANOCAPSULE; NANOPARTICLE; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; POLY(ACRYLATE METHACRYLATE); TRIPOLYPHOSPHATE; CROSS LINKING REAGENT; DOPAMINE RECEPTOR STIMULATING AGENT; METHACRYLIC ACID DERIVATIVE; POLYMER; POLYPHOSPHATE; TRIPHOSPHORIC ACID;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; CROSS LINKING; DRUG DELIVERY SYSTEM; DRUG FORMULATION; IN VITRO STUDY; INFRARED SPECTROSCOPY; MOLECULAR MODEL; NANOANALYSIS; NANOFABRICATION; NUCLEAR MAGNETIC RESONANCE IMAGING; PARTICLE SIZE; PH MEASUREMENT; PREDICTION; PROCESS DEVELOPMENT; SCANNING ELECTRON MICROSCOPY; STRUCTURE ANALYSIS; SURFACE CHARGE; SUSTAINED DRUG RELEASE; TABLET MATRIX; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL; ALGORITHM; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; HUMAN; NANOTECHNOLOGY; ORAL DRUG ADMINISTRATION; PH; PROCEDURES; ULTRASTRUCTURE;

ADMINISTRATION, ORAL; ALGORITHMS; CHITOSAN; COMPUTER SIMULATION; CROSS-LINKING REAGENTS; DOPAMINE AGENTS; DRUG DELIVERY SYSTEMS; HUMANS; HYDROGEN-ION CONCENTRATION; LECITHINS; LEVODOPA; MAGNETIC RESONANCE IMAGING; METHACRYLATES; MICROSCOPY, ELECTRON, SCANNING; MICROSCOPY, ELECTRON, TRANSMISSION; MODELS, MOLECULAR; NANOPARTICLES; NANOTECHNOLOGY; POLYMERS; POLYPHOSPHATES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 80053208423     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12096194     Document Type: Article

References (80)

1. Thomas, V.H.; Bhattachar, S.; Hitchingham, L.; Zocharski, P.; Naath, M.; Surendran, N.; Stoner, C.L.; El-Kattan, A. The road map to oral bioavailability: An industrial perspective. Expert Opin. Drug Metab. Toxicol. 2006, 2, 591-608.
2. Martinez, M.N.; Amidon, G.L. A mechanistic approach to understanding the factors affecting drug absorption: A review of fundamentals. J. Clin. Pharmacol. 2002, 42, 620-643.
3. Varma, M.V.S.; Kaushal, A.M.; Garg, A.; Garg, S. Factors affecting mechanism and kinetics of drug release from matrix-based oral controlled drug delivery systems. Am. J. Drug Deliv. 2004, 2, 43-57.
4. Hurst, S.; Loi, C.; Brodfuehrer, J.; El-Kattan, A. Impact of physiological, physicochemical and biopharmaceutical factors in absorption and metabolism mechanisms on the drug oral bioavailability of rats and humans. Expert Opin. Drug Metab. Toxicol. 2007, 3, 469-489.
5. Rasenack, N.; Müller, B.W. Micron-size drug particles: Common and novel micronization techniques. Pharm. Dev. Technol. 2004, 9, 1-13.
6. Thanos, C.G.; Liu, Z.; Reineke, J.; Edwards, E.; Mathiowitz, E. Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(Fumaric-Co-Sebacic) anhydride. Pharm. Res. 2003, 20, 1093-1100.
7. Chan, O.H.; Schmid, H.L.; Stilgenbauer, L.A.; Howson, W.; Horwell, D.C.; Stewart, B.H. Evaluation of a targeted prodrug strategy to enhance oral absorption of poorly water-soluble compounds. Pharm. Res. 1998, 15, 1012-1018.
8. Gomez-Orellana, I. Strategies to improve oral drug bioavailability. Expert Opin. Drug Deliv. 2005, 2, 419-433.
9. Baudy, R.B.; Butera, J.A.; Abou-Gharbia, M.; Chen, H.; Harrison, B.; Jain, U.; Magolda, R.; Sze, J.Y.; Brandt, M.R.; Cummons, T.A.; et al. Prodrugs of perzinfotel with improved oral bioavailability. J. Med. Chem. 2009, 52, 771-778.
10. Gwak, H.; Choi, J.; Choi, H. Enhanced bioavailability of piroxicam via salt formation with ethanolamines. Int. J. Pharm. 2005, 297, 156-161.
11. Thanou, M.; Verhoef, J.C.; Junginger, H.E. Oral drug absorption enhancement by chitosan and its derivatives. Adv. Drug Deliv. Rev. 2001, 52, 117-126.
12. Wong, S.M.; Kellaway, I.W.; Murdan, S. Enhancement of the dissolution rate and oral absorption of a poorly water soluble drug by formation of surfactant-containing microparticles. Int. J. Pharm. 2006, 317, 61-68.
13. Leuner, C.; Dressman, J. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 2000, 50, 47-60.
14. Vasconcelos, T.; Sarmento, B.; Costa, P. Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. Drug Discov. Today 2007, 12, 1068-1075.
15. Sant, V.P.; Smith, D.; Leroux, J. Enhancement of oral bioavailability of poorly water-soluble drugs by poly(ethylene glycol)-block-poly(alkyl acrylate-co-methacrylic acid) self-assemblies. J. Control. Release 2005, 104, 289-300.
16. Morishita, M.; Matsuzawa, A.; Takayama, K.; Isowa, K.; Nagai, T. Improving insulin enteral absorption using water-in-oil-in-water emulsion. Int. J. Pharm. 1998, 172, 189-198.
17. Dollo, G.; Le Corre, P.; Guérin, A.; Chevanne, F.; Burgot, J.L.; Leverge, R. Spray-dried redispersible oil-in-water emulsion to improve oral bioavailability of poorly soluble drugs. Eur. J. Pharm. Sci. 2003, 19, 273-280.
18. Araya, H.; Tomita, M.; Hayashi, M. The novel formulation design of o/w microemulsion for improving the gastrointestinal absorption of poorly water soluble compounds. Int. J. Pharm. 2005, 305, 61-74.
19. Constantinides, P.P. Lipid microemulsions for improving drug dissolution and oral absorption: physical and biopharmaceutical aspects. Pharm. Res. 1995, 12, 1561-1572.
20. Kuo, F.; Subramanian, B.; Kotyla, T.; Wilson, T.A.; Yoganathan, S.; Nicolosi, R.J. Nanoemulsions of an anti-oxidant synergy formulation containing gamma tocopherol have enhanced bioavailability and anti-inflammatory properties. Int. J. Pharm. 2008, 363, 206-213.
21. Yin, Y.; Cui, F.; Mu, C.; Choi, M.; Kim, J.S.; Chung, S.; Shim, C.; Kim, D. Docetaxel microemulsion for enhanced oral bioavailability: Preparation and in vitro and in vivo evaluation. J. Control. Release 2009, 140, 86-94.
22. Gershanik, T.; Benita, S. Positively charged self-emulsifying oil formulation for improving oral bioavailability of progesterone. Pharm. Dev. Technol. 1996, 1, 147-157.
23. Kang, B.K.; Lee, J.S.; Chon, S.K.; Jeong, S.Y.; Yuk, S.H.; Khang, G.; Lee, H.B.; Cho, S.H. Development of self-microemulsifying drug delivery systems (smedds) for oral bioavailability enhancement of simvastatin in beagle dogs. Int. J. Pharm. 2004, 274, 65-73.
24. Carrier, R.L.; Miller, L.A.; Ahmed, I. The utility of cyclodextrins for enhancing oral bioavailability. J. Control. Release 2007, 123, 78-99.
25. Reddy, M.; Rehana, T.; Ramakrishna, S.; Chowdary, K.; Diwan, P. Cyclodextrin complexes of celecoxib: Molecular-modeling, characterization, and dissolution studies. AAPS J. 2004, 6, 68-76.
26. Song, Y.; Clizbe, L.; Bhakta, C.; Teng, W.; Li, W.; Wong, P.; Huang, B.; Sinha, U.; Park, G.; Reed, A.; et al. Substituted acrylamides as factor xa inhibitors: Improving bioavailability by p1 modification. Bioorg. Med. Chem. Lett. 2002, 12, 2043-2046.
27. Biron, E.; Chatterjee, J.; Ovadia, O.; Langenegger, D.; Brueggen, J.; Hoyer, D.; Schmid, H.; Jelinek, R.; Gilon, C.; Hoffman, A.; et al. Improving oral bioavailability of peptides by multiple n-methylation: somatostatin analogues13. Angew. Chem. Int. Ed. 2008, 47, 2595-2599.
28. Hu, L.; Tang, X.; Cui, F. Solid lipid nanoparticles (SLNs) to improve oral bioavailability of poorly soluble drugs. J. Pharm. Pharmacol. 2004, 56, 1527-1535.
29. Kesisoglou, F.; Panmai, S.; Wu, Y. Nanosizing-oral formulation development and biopharmaceutical evaluation. Adv. Drug Deliv. Rev. 2007, 59, 631-644.
30. Hans, M.L.; Lowman, A.M. Biodegradable nanoparticles for drug delivery and targeting. Curr. Opin. Solid State Mater. Sci. 2002, 6, 319-327.
31. Sahoo, S.K.; Labhasetwar, V. Nanotech approaches to drug delivery and imaging. Drug Discov. Today 2003, 8, 1112-1120.
32. Aliabadi, H.M.; Lavasanifar, A. Polymeric micelles for drug delivery. Expert Opin. Drug Deliv. 2006, 3, 139-162.
33. Almeida, A.J.; Souto, E. Solid lipid nanoparticles as a drug delivery system for peptides and proteins. Adv. Drug Deliv. Rev. 2007, 59, 478-490.
34. Bali, V.; Ali, M.; Ali, J. Study of surfactant combinations and development of a novel nanoemulsion for minimising variations in bioavailability of ezetimibe. Colloids Surf. B 2010, 76, 410-420.
35. Drulis-Kawa, Z.; Dorotkiewicz-Jach, A. Liposomes as delivery systems for antibiotics. Int. J. Pharm. 2010, 387, 187-198.
36. Gillies, E.R.; Fréchet, J.M.J. Dendrimers and dendritic polymers in drug delivery. Drug Discov. Today 2005, 10, 35-43.
37. Kumari, A.; Yadav, S.K.; Yadav, S.C. Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf. B 2010, 75, 1-18.
38. Jin, S.; Ye, K. Nanoparticle-mediated drug delivery and gene therapy. Biotechnol. Prog. 2007, 23, 32-41.
39. Mora-Huertas, C.E.; Fessi, H.; Elaissari, A. Polymer-based nanocapsules for drug delivery. Int. J. Pharm. 2010, 385, 113-142.
40. Shaikh, J.; Ankola, D.D.; Beniwal, V.; Singh, D.; Kumar, M.N.V.R. Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur. J. Pharm. Sci. 2009, 37, 223-230.
41. El-Shabouri, M.H. Positively charged nanoparticles for improving the oral bioavailability of Cyclosporin-A. Int. J. Pharm. 2002, 249, 101-108.
42. ®. Pharm. Res. 2009, 26, 1324-1331.
43. Pan, Y.; Li, Y.; Zhao, H.; Zheng, J.; Xu, H.; Wei, G.; Hao, J.; Cui, F. Bioadhesive polysaccharide in protein delivery system: chitosan nanoparticles improve the intestinal absorption of insulin in vivo. Int. J. Pharm. 2002, 249, 139-147.
44. Sarmento, B.; Ribeiro, A.; Veiga, F.; Ferreira, D.; Neufeld, R. Oral bioavailability of insulin contained in polysaccharide nanoparticles. Biomacromolecules 2007, 8, 3054-3060.
45. Leroux, J.; Cozens, R.M.; Roesel, J.L.; Galli, B.; Doelker, E.; Gurny, R. PH-sensitive nanoparticles: An effective means to improve the oral delivery of hiv-1 protease inhibitors in dogs. Pharm. Res. 1996, 13, 485-487.
46. Kawashima, Y.; Yamamoto, H.; Takeuchi, H.; Kuno, Y. Mucoadhesive dl-lactide/glycolide copolymer nanospheres coated with chitosan to improve oral delivery of elcatonin. Pharm. Dev. Technol. 2000, 5, 77-85.
47. ®): PLGA nanoparticles containing vitamin E TPGS. J. Control. Release 2003, 86, 33-48.
48. Mittal, G.; Sahana, D.K.; Bhardwaj, V.; Ravi Kumar, M.N.V. Estradiol loaded PLGA nanoparticles for oral administration: effect of polymer molecular weight and copolymer composition on release behavior in vitro and in vivo. J. Control. Release 2007, 119, 77-85.
49. Garcia-Fuentes, M.; Torres, D.; Alonso, M.J. New surface-modified lipid nanoparticles as delivery vehicles for salmon calcitonin. Int. J. Pharm. 2005, 296, 122-132.
50. Yang, S.; Zhu, J.; Lu, Y.; Liang, B.; Yang, C. Body distribution of camptothecin solid lipid nanoparticles after oral administration. Pharm. Res. 1999, 16, 751-757.
51. He, W.; Horn, S.W.; Hussain, M.D. Improved bioavailability of orally administered mifepristone from PLGA nanoparticles. Int. J. Pharm. 2007, 334, 173-178.
52. Zhang, Q.; Shen, Z.; Nagai, T. Prolonged hypoglycemic effect of insulin-loaded polybutylcyanoacrylate nanoparticles after pulmonary administration to normal rats. Int. J. Pharm. 2001, 218, 75-80.
53. De, T.K.; Hoffman, A.S. A reverse microemulsion polymerization method for preparation of bioadhesive polyacrylic acid nanoparticles for mucosal drug delivery: Loading and release of timolol maleate. Artif. Cells, Blood Substit., Biotechnol. 2001, 29, 31-46.
54. Desgouilles, S.; Vauthier, C.; Bazile, D.; Vacus, J.; Grossiord, J.; Veillard, M.; Couvreur, P. The design of nanoparticles obtained by solvent evaporation: A comprehensive study. Langmuir 2003, 19, 9504-9510.
55. Budhian, A.; Siegel, S.J.; Winey, K.I. Haloperidol-loaded PLGA nanoparticles: Systematic study of particle size and drug content. Int. J. Pharm. 2007, 336, 367-375.
56. Galindo-Rodríguez, S.A.; Puel, F.; Briançon, S.; Allémann, E.; Doelker, E.; Fessi, H. Comparative scale-up of three methods for producing ibuprofen-loaded nanoparticles. Eur. J. Pharm. Sci. 2005, 25, 357-367.
57. Zweers, M.L.T.; Grijpma, D.W.; Engbers, G.H.M.; Feijen, J. The preparation of monodisperse biodegradable polyester nanoparticles with a controlled size. J. Biomed. Mater. Res. Part B 2003, 66B, 559-566.
58. Byrappa, K.; Ohara, S.; Adschiri, T. Nanoparticles synthesis using supercritical fluid technology - towards biomedical applications. Adv. Drug Deliv. Rev. 2008, 60, 299-327.
59. Varshosaz, J.; Hassanzadeh, F.; Mahmoudzadeh, M.; Sadeghi, A. Preparation of cefuroxime axetil nanoparticles by rapid expansion of supercritical fluid technology. Powder Technol. 2009, 189, 97-102.
60. Wang, G.; Uludag, H. Recent developments in nanoparticle-based drug delivery and targeting systems with emphasis on protein-based nanoparticles. Expert Opin. Drug Deliv. 2008, 5, 499-515.
61. Krauland, A.H.; Alonso, M.J. Chitosan/cyclodextrin nanoparticles as macromolecular drug delivery system. Int. J. Pharm. 2007, 340, 134-142.
62. Gan, Q.; Wang, T. Chitosan nanoparticle as protein delivery carrier-systematic examination of fabrication conditions for efficient loading and release. Colloids Surf. B 2007, 59, 24-34.
63. Grant, J.; Blicker, M.; Piquette-Miller, M.; Allen, C. Hybrid films from blends of chitosan and egg phosphatidylcholine for localized delivery of paclitaxel. J. Pharm. Sci. 2005, 94, 1512-1527.
64. Hafner, A.; Lovrić, J.; Voinovich, D.; Filipović-Grčić, J. Melatonin-loaded lecithin/chitosan nanoparticles: Physicochemical characterisation and permeability through caco-2 cell monolayers. Int. J. Pharm. 2009, 381, 205-213.
65. Ho, E.A.; Vassileva, V.; Allen, C.; Piquette-Miller, M. In vitro and in vivo characterization of a novel biocompatible polymer-lipid implant system for the sustained delivery of paclitaxel. J. Control. Release 2005, 104, 181-191.
66. Lim Soo, P.; Cho, J.; Grant, J.; Ho, E.; Piquette-Miller, M.; Allen, C. Drug release mechanism of paclitaxel from a chitosan-lipid implant system: Effect of swelling, degradation and morphology. Eur. J. Pharm. Biopharm. 2008, 69, 149-157.
67. Sonvico, F.; Cagnani, A.; Rossi, A.; Motta, S.; Di Bari, M.T.; Cavatorta, F.; Alonso, M.J.; Deriu, A.; Colombo, P. Formation of self-organized nanoparticles by lecithin/chitosan ionic interaction. Int. J. Pharm. 2006, 324, 67-73.
68. Zahedi, P.; De Souza, R.; Piquette-Miller, M.; Allen, C. Chitosan-phospholipid blend for sustained and localized delivery of docetaxel to the peritoneal cavity. Int. J. Pharm. 2009, 377, 76-84.
69. Beun, S.; Glorieux, T.; Devaux, J.; Vreven, J.; Leloup, G. Characterization of nanofilled compared to universal and microfilled composites. Dental Mater. 2007, 23, 51-59.
70. Gojny, F.H.; Wichmann, M.H.G.; Fiedler, B.; Schulte, K. Influence of different carbon nanotubes on the mechanical properties of epoxy matrix composites - a comparative study. Compos. Sci. Technol. 2005, 65, 2300-2313.
71. Gomoll, A.H.; Fitz, W.; Scott, R.D.; Thornhill, T.S.; Bellare, A. Nanoparticulate fillers improve the mechanical strength of bone cement. Acta Orthop. 2008, 79, 421-427.
72. Park, J.H.; Jana, S.C. The relationship between nano-and micro-structures and mechanical properties in pmma-epoxy-nanoclay composites. Polymer 2003, 44, 2091-2100.
73. Rapoport, L.; Nepomnyashchy, O.; Verdyan, A.; Popovitz-Biro, R.; Volovik, Y.; Ittah, B.; Tenne, R. Polymer nanocomposites with fullerene-like solid lubricant. Adv. Eng. Mater. 2004, 6, 44-48.
74. Saha, M.C.; Kabir, M.E.; Jeelani, S. Enhancement in thermal and mechanical properties of polyurethane foam infused with nanoparticles. Mater. Sci. Eng. A 2008, 479, 213-222.
75. Zhang, M.Q.; Rong, M.Z.; Zhang, H.B.; Friedrich, K. Mechanical properties of low nano-silica filled high density polyethylene composites. Polym. Eng. Sci. 2003, 43, 490-500.
76. Tajiri, T.; Morita, S.; Sakamoto, R.; Suzuki, M.; Yamanashi, S.; Ozaki, Y.; Kitamura, S. Release mechanisms of acetaminophen from polyethylene oxide/polyethylene glycol matrix tablets utilizing magnetic resonance imaging. Int. J. Pharm. 2010, 395, 147-153.
77. Warhurst, D.; Craig, J.; Adagu, I.; Meyer, D.; Lee, S. The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids. Malar. J. 2003, 2, 26.
78. Pearlman, D.A.; Case, D.A.; Caldwell, J.W.; Ross, W.S.; Cheatham, T.E.; DeBolt, S.; Ferguson, D.; Seibel, G.; Kollman, P. AMBER, a package of computer programs for applying molecular mechanics, normal mode analysis, molecular dynamics and free energy calculations to simulate the structural and energetic properties of molecules. Comput. Phys. Commun. 1995, 91, 1-41.
79. Golovnya, R.V.; Zhuravleva, I.L.; Zenin, S.V.; Polyakov, V.A.; Sergeev, G.B. Determination of thermodynamic characteristics of complexing of amines with alkyl and aryl phosphates by the NMR method. Russ. Chem. Bull. 1973, 22, 2528-2530.
80. Kumar, P.; Pillay, V.; Choonara, Y.E.; Modi, G.; Naidoo, D.; du Toit, L.C. In silico theoretical molecular modeling for alzheimer's disease: The nicotine-curcumin paradigm in neuroprotection and neurotherapy. Int. J. Mol. Sci. 2011, 12, 694-724.