Preparation, optimization and in vitro characterization of stearoyl-gemcitabine polymeric micelles: A comparison with its self-assembled nanoparticles

International Journal of Pharmaceutics

Volumn 468, Issue 1-2, 2014, Pages 142-151

  Daman, Zahra ^a   Ostad, Seyednaser ^a   Amini, Mohsen ^a   Gilani, Kambiz ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Pancreatic cancer; Poly(ethylene glycol) poly(dl lactide); Polymeric micelles; Self assembly; Stearoyl gemcitabine

Indexed keywords

GEMCITABINE; MACROGOL; NANOPARTICLE; POLYLACTIDE; PRODRUG; STEAROYL GEMCITABINE; UNCLASSIFIED DRUG; 4-(N)-STEAROYLGEMCITABINE; ANTINEOPLASTIC ANTIMETABOLITE; DEOXYCYTIDINE; DRUG CARRIER; MACROGOL DERIVATIVE; MICELLE; POLYESTER; POLYMER; SOLVENT;

ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG EFFICACY; DRUG FORMULATION; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; MICELLE; NANOENCAPSULATION; PARTICLE SIZE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SUSTAINED DRUG RELEASE; ZETA POTENTIAL; ANALOGS AND DERIVATIVES; CELL SURVIVAL; CHEMISTRY; COMPARATIVE STUDY; DOSE RESPONSE; DRUG EFFECTS; KINETICS; MEDICINAL CHEMISTRY; NANOTECHNOLOGY; PANCREAS TUMOR; PATHOLOGY; PHARMACEUTICS; PROCEDURES; SOLUBILITY; SYNTHESIS; TUMOR CELL LINE;

ANTIMETABOLITES, ANTINEOPLASTIC; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; DEOXYCYTIDINE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG CARRIERS; DRUG STABILITY; HUMANS; KINETICS; MICELLES; NANOPARTICLES; NANOTECHNOLOGY; PANCREATIC NEOPLASMS; PARTICLE SIZE; POLYESTERS; POLYETHYLENE GLYCOLS; POLYMERS; PRODRUGS; SOLUBILITY; SOLVENTS; TECHNOLOGY, PHARMACEUTICAL;

EID: 84922394219     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2014.04.021     Document Type: Article

References (35)

1. T. Arumugam, V. Ramachandran, K.F. Fournier, H. Wang, L. Marquis, J.L. Abbruzzese, G.E. Gallick, C.D. Logsdon, Mc Conkey, D.J. Choi, and W Epithelial to mesenchymal transition contributes to drug resistance in pancreatic cancer Cancer Research 69 2009 5820 5828
2. D.M. Bender, J. Bao, A.H. Dantzig, W.D. Diseroad, K.L. Law, N.A. Magnus, J.A. Peterson, E.J. Perkins, Y.J. Pu, and S.M. Reutzel-Edens Synthesis, crystallization, and biological evaluation of an orally active prodrug of gemcitabine Journal of Medicinal Chemistry 52 2009 6958 6961
3. L. Bildstein, C. Dubernet, V. Marsaud, H. Chacun, V. Nicolas, C. Gueutin, A. Sarasin, H. Benech, S. Lepetre-Mouelhi, and D. Desmaele Transmembrane diffusion of gemcitabine by a nanoparticulate squalenoyl prodrug: an original drug delivery pathway Journal of Controlled Release 147 2010 163 170
4. H.r. Burris, M.J. Moore, J. Andersen, M.R. Green, M.L. Rothenberg, M.R. Modiano, M.C. Cripps, R.K. Portenoy, A.M. Storniolo, and P. Tarassoff Improvements in survival and clinical benefit with gemcitabine as first-line therapy for patients with advanced pancreas cancer: a randomized trial Journal of Clinical Oncology 15 1997 2403 2413 (Pubitemid 27251144)
5. W.-G. Chung, M.A. Sandoval, B.R. Sloat, D.S. Lansakara-P, and Z. Cui Stearoyl gemcitabine nanoparticles overcome resistance related to the over-expression of ribonucleotide reductase subunit M1 Journal of Controlled Release 157 2012 132 140
6. P. Couvreur, B. Stella, L.H. Reddy, H. Hillaireau, C. Dubernet, D. Desmaële, S. Lepêtre-Mouelhi, F. Rocco, N. Dereuddre-Bosquet, and P. Clayette Squalenoyl nanomedicines as potential therapeutics Nano Letters 6 2006 2544 2548 (Pubitemid 46076946)
7. S.N. Deming Multiple-criteria optimization Journal of Chromatography A 550 1991 15 25
8. G. Gaucher, M.-H. Dufresne, V.P. Sant, N. Kang, D. Maysinger, and J.-C. Leroux Block copolymer micelles: preparation, characterization and application in drug delivery Journal of Controlled Release 109 2005 169 188 (Pubitemid 41742123)
9. J. Gong, M. Chen, Y. Zheng, S. Wang, and Y. Wang Polymeric micelles drug delivery system in oncology Journal of Controlled Release 159 2012 312 323
10. Y. Harada, T. Yamamoto, M. Sakai, T. Saiki, K. Kawano, Y. Maitani, and M. Yokoyama Effects of organic solvents on drug incorporation into polymeric carriers and morphological analyses of drug-incorporated polymeric micelles International Journal of Pharmaceutics 404 2011 271 280
11. M.L. Immordino, P. Brusa, F. Rocco, S. Arpicco, M. Ceruti, and L. Cattel Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs Journal of Controlled Release 100 2004 331 346 (Pubitemid 39572916)
12. D.-W. Kim, S.-Y. Kim, H.-K. Kim, S.-W. Kim, S. Shin, J. Kim, K. Park, M. Lee, and D. Heo Multicenter phase II trial of genexol-PM, a novel cremophor-free, polymeric micelle formulation of paclitaxel, with cisplatin in patients with advanced non-small-cell lung cancer Annals of Oncology 18 2007 2009 2014 (Pubitemid 350286241)
13. A. Lamprecht, N. Ubrich, M. Hombreiro Perez, C.-M. Lehr, M. Hoffman, and P. Maincent Influences of process parameters on nanoparticle preparation performed by a double emulsion pressure homogenization technique International Journal of Pharmaceutics 196 2000 177 182 (Pubitemid 30105738)
14. C.-P. Lee, and M.-N.L. Huang D-optimal designs for second-order response surface models with qualitative factors Journal of Data Science 9 2011 139 153
15. S.C. Lee, K.M. Huh, J. Lee, Y.W. Cho, R.E. Galinsky, and K. Park Hydrotropic polymeric micelles for enhanced paclitaxel solubility: in vitro and in vivo characterization Biomacromolecules 8 2007 202 208 (Pubitemid 46140493)
16. J. Leiro, M. Siso, M. Ortega, M. Santamarina, and M. Sanmartin A factorial experimental design for investigation of the effects of temperature, incubation time, and pathogen-to-phagocyte ratio on in vitro phagocytosis by turbot adherent cells Comparative Biochemistry and Physiology Part C: Pharmacology, Toxicology and Endocrinology 112 1995 215 220 (Pubitemid 26004663)
17. Q. Li, Y.-Z. Du, H. Yuan, X.-G. Zhang, J. Miao, F.-D. Cui, and F.-Q. Hu Synthesis of lamivudine stearate and antiviral activity of stearic acid-g-chitosan oligosaccharide polymeric micelles delivery system European Journal of Pharmaceutical Sciences 41 2010 498 507
18. L. Mu, T. Elbayoumi, and V. Torchilin Mixed micelles made of poly(ethylene glycol)-phosphatidylethanolamine conjugate and d-α-tocopheryl polyethylene glycol 1000 succinate as pharmaceutical nanocarriers for camptothecin International Journal of Pharmaceutics 306 2005 142 149 (Pubitemid 41643148)
19. Myhren F., Borretzen B., Dalen A., Sandvold M.L., 2004. Gemcitabine derivatives. EP Patent 0,986,570.
20. N. Nasongkla, E. Bey, J. Ren, H. Ai, C. Khemtong, J.S. Guthi, S.-F. Chin, A.D. Sherry, D.A. Boothman, and J. Gao Multifunctional polymeric micelles as cancer-targeted, MRI-ultrasensitive drug delivery systems Nano Letters 6 2006 2427 2430 (Pubitemid 46076928)
21. N. Nishiyama, and K. Kataoka Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery Pharmacology & Therapeutics 112 2006 630 648 (Pubitemid 44592613)
22. T. Oguri, H. Achiwa, H. Muramatsu, H. Ozasa, S. Sato, S. Shimizu, H. Yamazaki, T. Eimoto, and R. Ueda The absence of human equilibrative nucleoside transporter 1 expression predicts nonresponse to gemcitabine-containing chemotherapy in non-small cell lung cancer Cancer Letters 256 2007 112 119 (Pubitemid 47333332)
23. D.E. Owens III, and N.A. Peppas Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles International Journal of Pharmaceutics 307 2006 93 102 (Pubitemid 41773257)
24. J. Panyam, D. Williams, A. Dash, D. Leslie-Pelecky, and V. Labhasetwar Solid-state solubility influences encapsulation and release of hydrophobic drugs from PLGA/PLA nanoparticles Journal of Pharmaceutical Sciences 93 2004 1804 1814 (Pubitemid 38823706)
25. L.H. Reddy, C. Dubernet, S.L. Mouelhi, P.E. Marque, D. Desmaele, and P. Couvreur A new nanomedicine of gemcitabine displays enhanced anticancer activity in sensitive and resistant leukemia types Journal of Controlled Release 124 2007 20 27 (Pubitemid 350103730)
26. R. Siegel, D. Naishadham, and A. Jemal Cancer statistics CA: A Cancer Journal for Clinicians 62 2012 10 29
27. B.R. Sloat, M.A. Sandoval, D. Li, W.-G. Chung, D.S. Lansakara-P, P.J. Proteau, K. Kiguchi, Di Giovanni, J. Cui, and Z In vitro and in vivo anti-tumor activities of a gemcitabine derivative carried by nanoparticles International Journal of Pharmaceutics 409 2011 278 288
28. A.M. Storniolo, S.R. Allerheiligen, and H.L. Pearce Preclinical, pharmacologic, and phase I studies of gemcitabine Seminars in Oncology 24 1997 S7-2-S7-7
29. X.-M. Tao, -c. J, -b. J, Q. Feng, -y. S, L.-R. Zhang, and Q. Zhang Enhanced anticancer activity of gemcitabine coupling with conjugated linoleic acid against human breast cancer in vitro and in vivo European Journal of Pharmaceutics and Biopharmaceutics 82 2012 401 409
30. M. Vandana, and S.K. Sahoo Long circulation and cytotoxicity of PEGylated gemcitabine and its potential for the treatment of pancreatic cancer Biomaterials 31 2010 9340 9356
31. Y. Wang, L. Yu, L. Han, X. Sha, and X. Fang Difunctional pluronic copolymer micelles for paclitaxel delivery: synergistic effect of folate-mediated targeting and pluronic-mediated overcoming multidrug resistance in tumor cell lines International Journal of Pharmaceutics 337 2007 63 73 (Pubitemid 46756036)
32. Z. Wei, J. Hao, S. Yuan, Y. Li, W. Juan, X. Sha, and X. Fang Paclitaxel-loaded pluronic P123/F127 mixed polymeric micelles: formulation, optimization and in vitro characterization International Journal of Pharmaceutics 376 2009 176 185
33. R.Z. Xiao, Z.W. Zeng, G.L. Zhou, J.J. Wang, F.Z. Li, and A.M. Wang Recent advances in PEG-PLA block copolymer nanoparticles International Journal of Nanomedicine 5 2010 1057
34. H.S. Yoo, and T.G. Park Biodegradable polymeric micelles composed of doxorubicin conjugated PLGA-PEG block copolymer Journal of Controlled Release 70 2001 63 70 (Pubitemid 32144793)
35. S. Zhu, D.S. Lansakara-P, X. Li, and Z. Cui Lysosomal delivery of a lipophilic gemcitabine prodrug using novel acid-sensitive micelles improved its antitumor activity Bioconjugate Chemistry 23 2012 966 980