Microencapsulation of cytarabine using poly(ethylene glycol)-poly(ε- caprolactone) diblock copolymers as surfactant agents

Drug Development and Industrial Pharmacy

Volumn 36, Issue 4, 2010, Pages 456-469

  Diab, Roudayna ^a   Hamoudeh, Misara ^a   Boyron, Olivier ^b   Elaissari, Abdelhamid ^a   Fessi, Hatem ^a  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

Amphiphilic diblock copolymers; Cytarabine; Double emulsion; Microparticles; Poly( caprolactone)

Indexed keywords

CYTARABINE; MACROGOL; POLYCAPROLACTONE; ANTINEOPLASTIC ANTIMETABOLITE; DELAYED RELEASE FORMULATION; DRUG CARRIER; EMULSION; MACROGOL DERIVATIVE; POLYESTER; POLYMER; SURFACTANT;

ARTICLE; CHEMICAL COMPOSITION; DRUG DELIVERY SYSTEM; EMULSION; EVAPORATION; GEL PERMEATION CHROMATOGRAPHY; HYDROPHILICITY; IN VITRO STUDY; INFRARED SPECTROSCOPY; LIGHT SCATTERING; MICROENCAPSULATION; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; PARTICLE SIZE; SYNTHESIS; ZETA POTENTIAL; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG FORMULATION; PROCEDURES;

ANTIMETABOLITES, ANTINEOPLASTIC; CYTARABINE; DELAYED-ACTION PREPARATIONS; DRUG CARRIERS; DRUG COMPOUNDING; EMULSIONS; MOLECULAR WEIGHT; PARTICLE SIZE; POLYESTERS; POLYETHYLENE GLYCOLS; POLYMERS; SURFACE-ACTIVE AGENTS;

EID: 77749295722     PISSN: 03639045     EISSN: 15205762     Source Type: Journal    
DOI: 10.3109/03639040903261989     Document Type: Article

References (62)

1. Galmarini CM, Mackey JR, Dumontet C. (2002). Nucleosides analogues and nucleobases in cancer treatment. Lancet Oncol, 3:415-24.
2. Lindner LH, Ostermann H, Hiddemann W, Kiani A, Würfel M, Illmer T, et al. (2008). AraU accumulation in patients with renal insufficiency as a potential mechanism for cytarabine neurotoxicity. Int J Hematol, 88:381-6.
3. Mangravite LM, Badagnani I, Giacomini KM. (2003). Nucleoside transporters in the disposition and targeting of nucleoside analogs in the kidney. Eur J Pharmacol, 479:269-81.
4. Braess J, Pförtner J, Kern W, Hiddemann W, Schleyer E. (1999). Cytidine deaminase - the methodological relevance of AraC deamination for ex vivo experiments using cultured cell lines, fresh leukemic blasts, and normal bone marrow cells. Ann Hematol, 78:514-20.
5. Milano G, Chamorey AL, Thyss A. (2002). Clinical pharmacology of nucleoside analogues. Bull Cancer, 89:71-5.
6. Diab R, Degobert G, Hamoudeh M, Dumontet C, Fessi H. (2007). Nucleoside analogue delivery systems in cancer therapy. Expert Opin Drug Deliv, 4:513-31.
7. Hamoudeh M, Diab R, Fessi H, Dumontet C, Cuchet D. (2008). Paclitaxel-loaded microparticles for intratumoral administration via the TMT technique: Preparation, characterization, and preliminary antitumoral evaluation. Drug Dev Ind Pharm, 34:698-707.
8. 2. Langmuir, 24:7432-41.
9. Mundargi RC, Babu VR, Rangaswamy V, Patel P, Aminabhavi TM. (2008). Nano/micro technologies for delivering macromolecular therapeutics using poly(D,L-lactide-co-glycolide) and its derivatives. J Control Release, 125:193-209.
10. Tsai M, Lu Z, Wang J, Yeh TK, Wientjes MG, Au JL. (2007). Effects of carrier on disposition and antitumor activity of intraperitoneal paclitaxel. Pharm Res, 24:1691-701.
11. Almond BA, Hadba AR, Freeman ST, Cuevas BJ, York AM, Detrisac CJ, et al. (2003). Efficacy of mitoxantrone-loaded albumin microspheres for intratumoral chemotherapy of breast cancer. J Control Release, 91:147-55.
12. Xie M, Zhou L, Hu T, Yao M. (2007). Intratumoral delivery of paclitaxel-loaded poly(lactic-co-glycolic acid) microspheres for Hep-2 laryngeal squamous cell carcinoma xenografts. Anticancer Drugs, 18:459-66.
13. Blanco MD, Gómez C, Olmo R, Muñíz E, Teijón JM. (2000). Chitosan microspheres in PLG films as devices for cytarabine release. Int J Pharm, 202:29-39.
14. Sastre RL, Olmo R, Teijón C, Muñíz E, Teijón JM, Blanco MD. (2007). 5-Fluorouracil plasma levels and biodegradation of subcutaneously injected drug-loaded microspheres prepared by spray-drying poly(D,L-lactide) and poly(D,L-lactide- coglycolide) polymers. Int J Pharm, 338:180-90.
15. Ustariz-Peyret C. (1999). Cephradin-plaga microspheres for sustained delivery to cattle. J Microencapsul, 16:181-94.
16. Govender T, Stolnik S, Garnett MC, Illum L, Davis SS. (1999). PLGA nanoparticles prepared by nanoprecipitation: Drug loading and release studies of a water soluble drug. J Control Release, 57:171-85.
17. Pistel KF, Kissel T. (2000). Effects of salt addition on the microencapsulation of proteins using W/O/W double emulsion technique. J Microencapsul, 17:467-83.
18. Mandal TK, Shekleton M, Onyebueke E, Washington L, Penson T. (1996). Effect of formulation and processing factors on the characteristics of biodegradable microcapsules of zidovudine. J Microencapsul, 13:545-57.
19. Leo E, Brina B, Forni F, Vandelli M. (2004). In vitro evaluation of PLA nanoparticles containing a lipophilic drug in water-soluble or insoluble form. Int J Pharm, 278:133-41.
20. Tewes F, Munnier E, Antoon B, Ngaboni Okassa L, Cohen-Jonathan S, Marchais H, et al. (2007). Comparative study of doxorubicin-loaded poly(lactide-co-glycolide) nanoparticles prepared by single and double emulsion methods. Eur J Pharm Biopharm, 66:488-92.
21. Quellec P, Gref R, Perrin L, Dellacherie E, Sommer F, Verbavatz JM, et al. (1998). Protein encapsulation within polyethylene glycol-coated nanospheres. I. Physicochemical characterization. J Biomed Mater Res, 42:45-54.
22. Vangeytea P, Gautiera S, Jérôme R. (2004). About the methods of preparation of poly(ethylene oxide)-b-poly(ε-caprolactone) nanoparticles in water: Analysis by dynamic light scattering. Colloids Surf A, 242:203-11.
23. Tobio M, Gref R, Sanchez A, Langer R, Alonso MJ. (1998). Stealth PLA-PEG nanoparticles as protein carriers for nasal administration. Pharm Res, 15:270-5.
24. Ha JH, Kim SH, Han SY. (1997). Albumin release from bioerodible hydrogels based on semi-interpenetrating polymer networks composed of poly (epsilon-caprolactone) and poly(ethylene glycol) macromer. J Control Release, 49:253-62.
25. Hachicha W, Kodjikian L, Fessi H. (2006). Preparation of vancomycin microparticles: Importance of preparation parameters. Int J Pharm, 324:176-84.
26. Coccoli V, Luciani A, Orsi S, Guarino V, Causa F, Netti PA. (2008). Engineering of poly(epsilon-caprolactone) microcarriers to modulate protein encapsulation capability and release kinetic. J Manipulative Physiol Ther, 19:1703-11.
27. Rawat A, Majumder QH, Ahsan F. (2008). Inhalable large porous microspheres of low molecular weight heparin: In vitro and in vivo evaluation. J Control Release, 128:224-32.
28. Gómez C, Blanco MD, Bernardo MV, Olmo R, Muñiz E, Teijón JM. (2004). Cytarabine release from comatrices of albumin microspheres in a poly(lactide-co-glycolide) film: In vitro and in vivo studies. Eur J Pharm Biopharm, 57:225-33.
29. Bogner A, Thollet G, Basset D, Jouneau PH, Gauthier C. (2005). Wet STEM: A new development in environmental SEM for imaging nano-objects included in a liquid phase. Ultramicroscopy, 104:290-301.
30. Hamoudeh M, Fessi H, Mehier H, Faraj AA, Canet-Soulas E. (2008). Dirhenium decacarbonyl-loaded PLLA nanoparticles: Influence of neutron irradiation and preliminary in vivo administration by the TMT technique. Int J Pharm, 348:125-36.
31. Kricheldorf HR, Kreiser-Saunders I. (2000). Polylactones 49: Bu4Sn-initiated polymerizations of 1-caprolactone. Polymer, 41:3957-63.
32. Hua C, Dong CM. (2007). Synthesis, characterization, effect of architecture on crystallization of biodegradable poly(ε-caprolactone)-b- poly(ethylene oxide) copolymers with different arms and nanoparticles thereof. J Biomed Mater Res, 82:689-700.
33. Choi C, Chae SY, Kim TH, Kweon JK, Cho CS, Jang MK, et al. (2006). Synthesis and physicochemical characterization of amphiphilic block copolymer self-aggregates formed by poly(ethylene glycol)-block-poly(epsilon-caprolactone) . J Appl Polym Sci, 99:3520-7.
34. Du ZX, Xu JT, Yang Y, Fan ZQ. (2007). Synthesis and characterization of poly(e-caprolactone)-bpoly(ethylene glycol) block copolymers prepared by a salicylaldimine-aluminum complex. J Appl Polym Sci, 105:771-6.
35. Huang MH, Li S, Hutmacher DW, Schantz JT, Vacanti CA, Braud C, et al. (2004). Degradation and cell culture studies on block copolymers prepared by ring opening polymerization of epsilon-caprolactone in the presence of poly(ethylene glycol). Inc J Biomed Mater Res A, 69:417-27.
36. Dinarvand R, Moghadam SH, Sheikhi A, Atyabi F. (2005). Effect of surfactant HLB and different formulation variables on the properties of poly-D,L-lactide microspheres of naltrexone prepared by double emulsion technique. J Microencapsul, 22:139-51.
37. Vila A, Sanchez A, Evora C, Soriano I, Vila Jato JL, Alonso MJ. (2004). PEG-PLA nanoparticles as carriers for nasal vaccine delivery. J Aerosol Med, 17:174-85.
38. Stolnik S, Felumb NC, Heald CR, Garnett MC, IIlium L, Davis SS. (1997). Adsorption behaviour and conformation of selected poly(ethylene oxide) copolymers on the surface of a model colloidal drug carrier. Colloids Surf A Physicochem Eng Asp, 122:151-9.
39. Shen C, Guo S, Lu C. (2008). Degradation behaviors of monomethoxy poly(ethylene glycol)-b-poly(e-caprolactone) nanoparticles in aqueous solution. Polym Adv Technol, 19:66-72.
40. Shen C, Guo S, Lu C. (2007). Degradation behaviors of star-shaped poly(ethylene glycol)epoly (3-caprolactone) nanoparticles in aqueous solution. Polym Degrad Stab, 92:1891-8.
41. Li Y, Pei Y, Zhang X, Gu Z, Zhou Z, Yuan W, et al. (2001). PEGylated PLGA nanoparticles as protein carriers: Synthesis, preparation and biodistribution in rats. J Control Release, 71:203-11.
42. Morikawa MA, Yoshihara M, Endo T, Kimizuka N. (2005). Alpha-helical polypeptide microcapsules formed by emulsiontemplated self-assembly. Chem Eur J, 11:1574-8.
43. Lecaroz C, Gamazo C, Renedo MJ, Blanco-Prieto MJ. (2006). Biodegradable micro- and nanoparticles as long-term delivery vehicles for gentamicin. J Microencapsul, 23:782-92.
44. Mao S, Xu J, Cai C, Germershaus O, Schaper A, Kissel T. (2007). Effect of WOW process parameters on morphology and burst release of FITC-dextran loaded PLGA microspheres. Int J Pharm, 334:137-48.
45. Bitz C, Doelker E. (1996). Influence of the preparation method on residual solvents biodegradable microspheres. Int J Pharm, 131:171-81.
46. O'Donnell PB, McGinity JW. (1997). Preparation of microspheres by the solvent evaporation technique. Adv Drug Deliv Rev, 28:25-42.
47. Sipos P, Csoka I, Srcic S, Pintye-Hodi K, Eros I. (2005). Influence of preparation conditions on the properties of Eudragit microspheres produced by a double emulsion method. Drug Dev Res, 64:41-54.
48. Xie J, Wang CH. (2007). Encapsulation of proteins in biodegradable polymeric microparticles using electrospray in the Taylor Cone-Jet mode. Biotechnol Bioeng, 97:1278-90.
49. Shah PP, Mashru RC, Rane YM, Thakkar A. (2008). Design and optimization of mefloquine hydrochloride microparticles for bitter taste masking. AAPS PharmSciTech, 9:377-89.
50. Chawla JS, Amiji MM. (2002). Biodegradable poly(ocaprolactone) nanoparticles for tumor targeted delivery of tamoxifen. Int J Pharm, 249:127-38.
51. Jeong JC, Lee J, Cho K. (2003). Effects of crystalline microstructure on drug release behavior of poly(epsilon-caprolactone) microspheres. J Control Release, 92:249-58.
52. Della Porta G, Reverchon E. (2008). Nanostructured microspheres produced by supercritical fluid extraction of emulsions. Biotechnol Bioeng, 100:1020-33.
53. Park HY, Oh KS, Koo HM, Cho SH, Chung SJ, Lim YT, et al. (2008). Heparin-immobilized pluronic/PVA composite microparticles for the sustained delivery of ionic drug. J Microencapsul, 25:106-10.
54. Hombreiro Pérez M, Zinutti C, Lamprecht A, Ubrich N, Astier A, Hoffman M, et al. (2000). The preparation and evaluation of poly(epsilon- caprolactone) microparticles containing both a lipophilic and a hydrophilic drug. J Control Release, 65:429-38.
55. Poletto FS, Jäger E, Ré MI, Guterres SS, Pohlmann AR. (2007). Rate-modulating PHBHV/PCL microparticles containing weak acid model drugs. Int J Pharm, 345:70-80.
56. Wechter WJ, Johnson MA, Hall CM, Warner DT, Berger AE, Wenzel AH, et al. (1975). Ara-cytidine acylates. Use of drug design predictors in structure-activity relationship correlation. J Med Chem, 18:339-44.
57. Sun X, Duan YR, He Q, Lu J, Zhang ZR. (2005). PELGE nanoparticles as new carriers for the delivery of plasmid DNA. Chem Pharm Bull, 53:599-603.
58. Dorati R, Genta I, Tomasi C, Modena T, Colonna C, Pavanetto F, et al. (2008). Polyethylenglycol-co-poly-D,L-lactide copolymer based microspheres: Preparation, characterization and delivery of a model protein. J Microencapsul, 25:330-8.
59. Fernández-Carballido A, Pastoriza P, Barcia E, Montejo C, Negro S. (2008). PLGA/PEG-derivative polymeric matrix for drug delivery system applications: Characterization and cell viability studies. Int J Pharm, 352:50-7.
60. Patel ZS, Ueda H, Yamamoto M, Tabata Y, Mikos AG. (2008). In vitro and in vivo release of vascular endothelial growth factor from gelatin microparticles and biodegradable composite scaffolds. Pharm Res, 25:2370-8.
61. Klose D, Siepmann F, Elkharraz K, Krenzlin S, Siepmann J. (2006). How porosity and size affect the drug release mechanisms from PLGA-based microparticles. Int J Pharm, 314:198-206.
62. Hombreiro-Pérez M, Siepmann J, Zinutti C, Lamprecht A, Ubrich N, Hoffman M, et al. (2003). Non-degradable microparticles containing a hydrophilic and/or a lipophilic drug: preparation, characterization and drug release modeling. J Control Release, 88:413-28.