Thiolated chitosan nanoparticles for enhancing oral absorption of docetaxel: Preparation, in vitro and ex vivo evaluation

International Journal of Nanomedicine

Volumn 6, Issue 1, 2011, Pages 119-128

  Saremi, Shahrooz ^a,b   Atyabi, Fatemeh ^a   Akhlaghi, Seyedeh Parinaz ^a   Ostad, Seyed Nasser ^a   Dinarvand, Rassoul ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b R and D Department   (Iran)

Author keywords

Cytotoxicity; Mucoadhesive; Poly methyl methacrylate

Indexed keywords

CHITOSAN; DOCETAXEL; NANOPARTICLE; POLY(METHYL METHACRYLATE);

ANIMAL EXPERIMENT; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DELIVERY SYSTEM; EX VIVO STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; MALE; MOLECULAR WEIGHT; MORPHOLOGY; NANOMEDICINE; NONHUMAN; PHYSICAL CHEMISTRY; POLYMERIZATION; PURIFICATION; RAT; TRANSMISSION ELECTRON MICROSCOPY; VISCOMETRY; ZETA POTENTIAL;

ANIMALS; CACO-2 CELLS; CALORIMETRY, DIFFERENTIAL SCANNING; CELL SURVIVAL; CHITOSAN; DRUG DELIVERY SYSTEMS; HUMANS; JEJUNUM; MALE; MICROSCOPY, ELECTRON, SCANNING; MICROSCOPY, FLUORESCENCE; NANOPARTICLES; PARTICLE SIZE; POLYMERIZATION; POLYMETHYL METHACRYLATE; RATS; SULFHYDRYL COMPOUNDS; TAXOIDS;

RATTUS;

EID: 79251511860     PISSN: 11769114     EISSN: 11782013     Source Type: Journal    
DOI: 10.2147/IJN.S15500     Document Type: Article

References (46)

1. Ajani JA, Takiuchi H. Recent developments in oral chemotherapy options for gastric carcinoma. Drugs. 1999;58 Suppl 3:85-90.
2. Feng SS, Dong Y. Poly (D,L-lactide-co-glycolide)/montmorillonite nanoparticles for oral delivery ofanticancer drugs. Biomaterials. 2005;26:6068-6076.
3. Arangoa MA, Ponchel G, Orecchioni AM, Renedo MJ, Duchene D, Irache JM. Bioadhesive potential of gliadin nanoparticulate systems. Eur J Pharm Sci. 2000;11:333-341.
4. Arechabala B, Coiffard C, Rivalland P, Coiffard LJM, de Roeck-Holtzhauer Y. Comparison of cytotoxicity of various surfactants tested on normal human fibroblast cultures using the neutral red test, MTT assay and LDH release. J Appl Toxicol. 1999;19:163-165.
5. Atyabi F, Aghaei Moghaddam F, Dinarvand R, Zohuriaan-Mehr MJ, Ponchel G. Thiolated chitosan coated poly hydroxyethyl methacrylate nanoparticles: synthesis and characterization. Carbohydr Polym. 2008;74:59-67.
6. Bernkop-Schnürch A, Kast CE. Chemically modified chitosans as enzyme inhibitors. Adv Drug Deliv Rev. 2001;52:127-137.
7. Mangatal L, Adeline MT, Guénard D, Guéritte-Voegelein F, Potier P. Application of the vicinal oxymination reaction with asymmetric induction to the hemisynthesis of taxol and analogues. Tetrahedron. 1989;45:4177-4190.
8. Kelland LR, Abel G. Comparative in vitro cytotoxicity of taxol and Taxotere against cisplatin-sensitive and -resistant human ovarian carcinoma cell lines. Cancer Chemother Pharmacol. 1992;30:444-450.
9. Eiermann W. Docetaxel - maximising outcomes towards cure in early breast cancer. Breast. 2006;15 Suppl 3:S13-S16.
10. Escobar PF, Rose PG. Docetaxel in ovarian cancer. Expert Opin Pharmacother. 2005;6(15):2719-2726.
11. Iwao-Koizumi K, Matoba R, Ueno N, et al. Prediction of docetaxel response in human breast cancer by gene expression profiling. J Clin Oncol. 2005;23(3):422-431.
12. Van Zuylen L, Verweij J, Sparreboom A. Role of formulation vehicles in taxane pharmacology. Invest New Drugs. 2001;19(2):125-141.
13. Shou M, Martinet M, Korzekwa KR, Krausz KW, Gonzalez FJ, Gelboin HV. Role of human cytochrome P450 3 A4 and 3 A5 in the metabolism of taxotere and its derivatives: enzyme specificity, interindividual distribution and metabolic contribution in human liver. Pharmacogenetics. 1998;8(5):391-401.
14. Malingre MM, Beijnen JH, Schellens JHM. Oral delivery of taxanes. Invest New Drugs. 2001;19(2):155-162.
15. Peracchia MT, Vauthier C, Passirani C, Couvreur P, Labarre D. Complement consumption by poly(ethylene glycol) in different conformations chemically coupled to poly(isobutyl 2-cyanoacrylate) nanoparticles. Life Sci. 1997;61(7):749-761.
16. Lemarchand C, Gref R, Couvreur P. Polysaccharide-decorated nanoparticles. Eur J Pharm Biopharm. 2004;58:327-341.
17. Bravo-Osuna I, Schmitz T, Bernkop-Schnürch A, Vauthier C, Ponchel G. Elaboration and characterization of thiolated chitosan-coated acrylic nanoparticles. Int J Pharm. 2006;316:170-175.
18. Chauvierre C, Labarre D, Couvreur P, Vauthier C. Novel polysaccharide- decorated poly(isobutyl cianoacrylate) nanoparticles. Pharm Res. 2003;20:1786-1793.
19. Chauvierre C, Labarre D, Couvreur P, Vauthier C. Radical polymerization of alkylcyanoacrylates initiated by the redox system dextrancerium (IV) under acidic aqueous conditions. Macromolecules. 2003;36:6018-6027.
20. Hassan EE, Gallo JM. A simple rheological method for the in vitro assessment of mucin-polymer bioadhesive bond strength. Pharm Res. 1990;7:491-495.
21. Roldo M, Hornof M, Caliceti P, Bernkop-Schnürch A. Mucoadhesive thiolated chitosans as platforms for oral controlled drug delivery: synthesis and in vitro evaluation. Eur J Pharm Biopharm. 2004;57(1):115-121.
22. Leitner VM, Guggi D, Krauland AH, Bernkop-Schnürch A. Nasal delivery of human growth hormone: in vitro and in vivo evaluation of a thiomer/glutathione microparticulate delivery system. J Control Release. 2004;100:87-95.
23. Bernkop-Schnürch A, Kast CE, Guggi D. Permeation enhancing polymers in oral delivery of hydrophilic macromolecules: thiomer/GSH systems. J Control Release. 2003;93:95-103.
24. Bravo-Osuna I, Teutonico D, Arpicco S, Vauthier C, Ponchel G. Characterization of chitosan thiolation and application to thiol quantification onto nanoparticle surface. Int J Pharm. 2007;340(1-2): 173-181.
25. Cui F, Qian F, Yin C. Preparation and characterization of mucoadhesive polymer-coated nanoparticles. Int J Pharm. 2006;316:154-161.
26. Huang M, Khor E, Lim LY. Uptake and cytotoxicity of chitosan molecules and nanoparticles: effects of molecular weight and degree of deacetylation. Pharm Res. 2004;21(2):344-356.
27. Kafedjiiski K, Föger F, Werle M, Bernkop-Schnürchrch A. Synthesis and in vitro evaluation of a novel chitosan-glutathione conjugate. Pharm Res. 2005;22(9):1480-1488.
28. Guggi D, Bernkop-Schnürch A. Improved paracellular uptake by the combination of different types of permeation enhancers. Int J Pharm. 2005;288:141-150.
29. Bernkop-Schnürch A, Schwarz V, Steininger S. Polymers with thiol groups: a new generation of mucoadhesive polymers. Pharm Res. 1999;16:876-881.
30. Kast CE, Bernkop-Schnürch A. Thiolated polymersthiomers: development and in vitro evaluation of chitosan-thioglycolic acid conjugates. Biomaterials. 2001;22:2345-2352.
31. Cheon Lee S, Kim C, Chan Kwon I, Chung H, Young Jeong S. Polymeric micelles of poly(2-ethyl-2-oxazoline)-block-poly([var epsilon]-caprolactone) copolymer as a carrier for paclitaxel. J Control Rel. 2003;89(3):437-446.
32. Barr WH, Riegelman S. Intestinal drug absorption and metabolism. I. Comparison of methods and models to study physiological factors of in vitro and in vivo intestinal absorption. J Pharm Sci. 1970;59(2): 154-163.
33. Bravo-Osuna I, Ponchel G, Vauthier C. Tuning of shell and core characteristics of chitosan-decorated acrylic nanoparticles. Eur J Pharm Sci. 2007;30(2):143-154.
34. Chen M-C, Wong H-S, Lin K-J, et al. The characteristics, biodistribution and bioavailability of a chitosan-based nanoparticulate system for the oral delivery of heparin. Biomaterials. 2009;30(34):6629-6637.
35. Vila A, Sanchez A, Janes K, et al. Low molecular weight chitosan nanoparticles as new carriers for nasal vaccine delivery in mice. Eur J Pharm Biopharm. 2004;57(1):123-131.
36. Lin YH, Chen CT, Liang HF, et al. Novel nanoparticles for oral insulin delivery via the paracellular pathway. Nanotechnology. 2007; 18(10):1-11.
37. Janes KA, Alonso MJ. Depolymerized chitosan nanoparticles for protein delivery: preparation and characterization. J Appli Polym Sci. 2003;88(12):2769-2776.
38. Mao S, Shuai X, Unger F, Simon M, Bi D, Kissel T. The depolymerization of chitosan: effects on physicochemical and biological properties. Int J Pharm. 2004;281(1-2):45-54.
39. Bravo-Osuna I, Ponchel G, Vauthier C. Tuning of shell and core characteristics of chitosan-decorated acrylic nanoparticles. Eur J Pharm Sci. 2007;30:143-154.
40. Passirani C, Barratt G, Devissaguet J-P, Labarre D. Interactions of nanoparticles bearing heparin or dextran covalently bound to poly(methyl methacrylate) with the complement system. Life Sci. 1998;62(8):775-785.
41. Feng SS, Wina KY. Effects of particle size and surface coating on cellular uptake of polymeric nanoparticles for oral delivery of anticancer drugs. Biomaterials. 2005;26:2713-2722.
42. Florence AT. Nanoparticle uptake by the oral route: fulfilling its potential? Drug Discov Today Technol. 2005;2(1):75-81.
43. Norris DA, Sinko PJ. Effect of size, surface charge, and hydrophobicity on the translocation of polystyrene microspheres through gastrointestinal mucin. J Appl Polym Sci. 1997;63:1481-1492.
44. Akhlaghi SP, Saremi S, Ostad SN, Dinarvand R, Atyabi F. Discriminated effects of thiolated chitosan-coated pMMA paclitaxel-loaded nanoparticles on different normal and cancer cell lines. Nanomedicine. 2010;6(5):689-697.
45. Esmaeili F, Dinarvand R, Ghahremani MH, Ostad SN, Esmaily H, Atyabi F. Cellular cytotoxicity and in-vivo biodistribution of docetaxel poly(lactide-co-glycolide) nanoparticles. Anticancer Drugs. 2010;21: 43-52.
46. Zhao J, Kim JE, Reed E, Li QQ. Molecular mechanism of antitumor activity of taxanes in lung cancer. Int J Oncol. 2005;27(247-256).