Synthesis and characterization of multi-functional linear-dendritic block copolymer for intracellular delivery of antitumor drugs

International Journal of Pharmaceutics

Volumn 452, Issue 1-2, 2013, Pages 563-573

  Qiao, Hongzhi ^a   Li, Juan ^a   Wang, Yang ^a   Ping, Qineng ^a   Wang, Guangji ^a   Gu, Xiaochen ^b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Cellular uptake; Linear dendritic block copolymers; pH sensitive; Pharmacokinetics; Specific drug targeting

Indexed keywords

COPOLYMER; CREMOPHOR; DOCETAXEL; DRUG CARRIER; POLYAMIDOAMINE B POLY(DEXTRO,LEVO LACTIC ACID); UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DENDRIMER; LACTIC ACID; MICELLE; PAMAM STARBURST; POLYLACTIC ACID; POLYMER; TAXOID;

ANIMAL EXPERIMENT; ANIMAL MODEL; AQUEOUS SOLUTION; ARTICLE; BIOCOMPATIBILITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; CYTOTOXICITY; DECOMPOSITION; DRUG ABSORPTION; DRUG CLEARANCE; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG RELEASE; DRUG SYNTHESIS; DRUG TARGETING; FLUORESCENCE MICROSCOPY; HEMOLYSIS; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROPHOBICITY; IN VITRO STUDY; MICELLE; MOLECULAR WEIGHT; NONHUMAN; PARTICLE SIZE; POLYMERIZATION; PRIORITY JOURNAL; RAT; SURFACE PROPERTY; SURFACE TENSION; THERMOGRAVIMETRY; TUMOR MICROENVIRONMENT; ZETA POTENTIAL; ANIMAL; CELL CULTURE; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; ERYTHROCYTE; MCF 7 CELL LINE; PATHOLOGY; SPRAGUE DAWLEY RAT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; CELLS, CULTURED; DENDRIMERS; DRUG DELIVERY SYSTEMS; ERYTHROCYTES; HEMOLYSIS; HUMANS; LACTIC ACID; MCF-7 CELLS; MICELLES; POLYMERS; RATS; RATS, SPRAGUE-DAWLEY; TAXOIDS;

EID: 84892374932     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2013.05.003     Document Type: Article

References (43)

1. Aliabadi, H.M., Mahmud, A., Sharifabadi, A.D., Lavasanifar, A., 2005. Micelles of methoxy poly(ethylene oxide)-b-poly(ε-caprolactone) as vehicles for the solubilization and controlled delivery of cyclosporine A. J. Control. Release 104, 301-311. (Pubitemid 40724931)
2. Ambade, A.V., Savariar, E.N., Thayumanavan, S., 2005. Dendrimeric micelles for controlled drug release and targeted delivery. Mol. Pharmacol. 2, 264-272. (Pubitemid 41186402)
3. Bae, Y., Fukushima, S., Harada, A., Kataoka, K., 2003. Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change. Angew. Chem. Int. Ed. Engl. 42, 4640-4643. (Pubitemid 37271305)
4. Bhadra, D., Bhadra, S., Jain, S., Jain, N.K., 2003. A PEGylated dendritic nanoparticulate carrier of fluorouracil. Int. J. Pharm. 257, 111-124. (Pubitemid 36507038)
5. Chamorro, C., Boerman, M.A., Arnusch, C.J., Breukink, E., Pieters, R.J., 2012. Enhancing membrane disruption by targeting and multivalent presentation of antimicrobial peptides. Biochim. Biophys. Acta (BBA): Biomembranes 1818, 2171-2174.
6. Chang, C., Wei, H., Wu, D., Yang, B., Chen, N., Cheng, S.X., Zhang, X.Z., Zhuo, R.X., 2011. Thermo-responsive shell cross-linked PMMA-b-P(NIPAAm-co-NAS) micelles for drug delivery. Int. J. Pharm. 420, 333-340.
7. De Jesús, O.L.P., Henrik, R., Gagne, L., Fréchet, J.M.J., Szoka@@Jr., F.C., 2002. Polyester dendritic systems for drug delivery applications: in vitro and in vivo evaluation. Bioconjugate Chem. 13, 453-461.
8. Domański, D., Klajnert, B., Bryszewska, M., 2004. Influence of PAMAM dendrimers on human red blood cells. Bioelectrochemistry 63, 189-191. (Pubitemid 38534218)
9. Eichman, J.D., Bielinska, A.U., Kukowska-Latallo, J.F., BakerJr, J.R., 2000. The use of PAMAM dendrimers in the efficient transfer of genetic material into cells. Pharm. Sci. Technol. Today 3, 232-245. (Pubitemid 30462197)
10. Esfand, R., Tomalia, D.A., 2001. Poly(amidoamine)(PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications. Drug Discov. Today 6, 427-436. (Pubitemid 32328297)
11. Goldberg, D.S., Vijayalakshmi, N., Swaan, P.W., Ghandehari, H., 2011. G3.5 PAMAM dendrimers enhance transepithelial transport of SN38 while minimizing gastrointestinal toxicity. J. Control. Release 150, 318-325.
12. Ho, K.S., Aman, A.M., Al-awar, R.S., Shoichet, M.S., 2012. Amphiphilic micelles of poly(2-methyl-2-carboxytrimethylene carbonate-co-D,L-lactide)-graft- poly(ethylene glycol) for anti-cancer drug delivery to solid tumours. Biomaterials 33, 2223-2229.
13. Huo, M., Zhang, Y., Zhou, J., Zou, A., Yu, D., Wu, Y., Li, J., Li, H., 2010. Synthesis and characterization of low-toxic amphiphilic chitosan derivatives and their application as micelle carrier for antitumor drug. Int. J. Pharm. 394, 162-173.
14. Immordino, M.L., Brusa, P., Arpicco, S., Stella, B., Dosio, F., Cattel, L., 2003. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing docetaxel. J. Control. Release 91, 417-429. (Pubitemid 36980659)
15. Iyer, J., Fleming, K., Hammond, P.T., 1998. Synthesis and solution properties of new linear-dendritic diblock copolymers. Macromolecules 31, 8757-8765. (Pubitemid 128563550)
16. Jain, A.K., Goyal, A.K., Mishra, N., Vaidya, B., Mangal, S., Vyas, S.P., 2010. PEG-PLA-PEG block copolymeric nanoparticles for oral immunization against hepatitis B. Int. J. Pharm. 387, 253-262.
17. Jansen, J.F.G.A., Meijer, E.W., de Brabander-van Den Berg, E.M.M., 1995. The dendritic box: shape-selective liberation of encapsulated guests. J. Am. Chem. Soc. 117, 4417-4418.
18. Jevprasesphant, R., Penny, J., Jalal, R., Attwood, D., McKeown, N.B., D'Emanuele, A., 2003. The influence of surface modification on the cytotoxicity of PAMAM dendrimers. Int. J. Pharm. 252, 263-266. (Pubitemid 36126635)
19. Kailasan, A., Yuan, Q., Yang, H., 2010. Synthesis and characterization of thermoresponsive polyamidoamine-polyethylene glycol-poly(D,L-lactide) core-shell nanoparticles. Acta Biomater. 6, 1131-1139.
20. Kim, S.C., Kim, D.W., Shim, Y.H., Bang, J.S., Oh, H.S., Kim, S.W., Seo, M.H., 2001. In vivo evaluation of polymeric micellar paclitaxel formulation: toxicity and efficacy. J. Control. Release 72, 191-202. (Pubitemid 32522357)
21. Kitchens, K.M., Foraker, A.B., Kolhatkar, R.B., Swaan, P.W., Ghandehari, H., 2007. Endocytosis and interaction of poly(amidoamine) dendrimers with Caco-2 cells. Pharm. Res. 24, 2138-2145. (Pubitemid 47493582)
22. Kukowska-Latallo, J.F., Candido, K.A., Cao, Z., Nigavekar, S.S., Majoros, I.J., Thomas, T.P., Balogh, L.P., Khan, M.K., Baker, J.R., 2005. Nanoparticle targeting of anticancer drug improves therapeutic response in animal model of human epithelial cancer. Cancer Res. 65, 5317-5324. (Pubitemid 40827344)
23. Le Garrec, D., Gori, S., Luo, L., Lessard, D., Smith, D., Yessine, M.A., Ranger, M., Leroux, J.C., 2004. Poly(N-vinylpyrrolidone)-block-poly(D,L-lactide) as a new polymeric solubilizer for hydrophobic anticancer drugs: in vitro and in vivo evaluation. J. Control. Release 99, 83-101. (Pubitemid 39165736)
24. Lee, E.S., Gao, Z., Kim, D., Park, K., Kwon, I.C., Bae, Y.H., 2008. Super pH-sensitive multifunctional polymeric micelle for tumor pH-specific TAT exposure and multidrug resistance. J. Control. Release 129, 228-236.
25. Lee, J., Cho, E.C., Cho, K., 2004. Incorporation and release behavior of hydrophobic drug in functionalized poly(D,L-lactide)-block-poly(ethylene oxide) micelles. J. Control. Release 94, 323-335. (Pubitemid 38117144)
26. Li, Y., Li, Q., Li, F., Zhang, H., Jia, L., Yu, J., Fang, Q., Cao, A., 2006. Amphiphilic poly(L-lactide)-b-dendritic poly(L-lysine) s synthesized with a metal-free catalyst and new dendron initiators: chemical preparation and characterization. Biomacromolecules 7, 224-231. (Pubitemid 43154498)
27. Liu, M., Kono, K., Fréchet, J.M.J., 2000. Water-soluble dendritic unimolecular micelles: their potential as drug delivery agents. J. Control. Release 65, 121-131. (Pubitemid 30122921)
28. Loh, X.J., Tan, Y.X., Li, Z., Teo, L.S., Goh, S.H., Li, J., 2008. Biodegradable thermogelling poly(ester urethane)s consisting of poly(lactic acid) - thermodynamics of micellization and hydrolytic degradation. Biomaterials 29, 2164-2172.
29. Malik, N., Wiwattanapatapee, R., Klopsch, R., Lorenz, K., Frey, H., Weener, J., Meijer, E., Paulus, W., Duncan, R., 2000. Dendrimers: relationship between structure and biocompatibility in vitro, and preliminary studies on the biodistribution of 125I-labelled polyamidoamine dendrimers in vivo. J. Control. Release 65, 133-148. (Pubitemid 30122922)
30. Matsumura, Y., Maeda, H., 1986. A New concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res. 46, 6387-6392. (Pubitemid 17221789)
31. Nguyen, P.M., Hammond, P.T., 2006. Amphiphilic linear-dendritic triblock copolymers composed of poly(amidoamine) and poly(propylene oxide) and their micellar-phase and encapsulation properties. Langmuir 22, 7825-7832. (Pubitemid 44373460)
32. Orienti, I., Zuccari, G., Falconi, M., Teti, G., Illingworth, N.A., Veal, G.J., 2012. Novel micelles based on amphiphilic branched PEG as carriers for fenretinide. Nanomed. Nanotechnol. Biol. Med. 8, 880-890.
33. Ostacolo, L., Marra, M., Ungaro, F., Zappavigna, S., Maglio, G., Quaglia, F., Abbruzzese, A., Caraglia, M., 2010. In vitro anticancer activity of docetaxel-loaded micelles based on poly(ethylene oxide)-poly(epsilon- caprolactone) block copolymers: do nanocarrier properties have a role? J. Control. Release 148, 255-263.
34. Perumal, O.P., Inapagolla, R., Kannan, S., Kannan, R.M., 2008. The effect of surface functionality on cellular trafcking of dendrimers. Biomaterials 29, 3469-3476.
35. Poon, Z., Lee, J.A., Huang, S., Prevost, R.J., Hammond, P.T., 2011. Highly stable, ligand-clustered "patchy" micelle nanocarriers for systemic tumor targeting. Nanomed. Nanotechnol. Biol. Med. 7, 201-209.
36. Sethuraman, V.A., Bae, Y.H., 2007. TAT peptide-based micelle system for potential active targeting of anti-cancer agents to acidic solid tumors. J. Control. Release 118, 216-224. (Pubitemid 46350711)
37. Svenson, S., Tomalia, D.A., 2005. Dendrimers in biomedical applications - reflections on the field. Adv. Drug. Deliv. Rev 57, 2106-2129. (Pubitemid 41759389)
38. Tomalia, D.A., Naylor, A.M., Goddard III, W.A., 1990. Starburst dendrimers: molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter. Angew. Chem. Int. Ed. Engl. 29, 138-175. (Pubitemid 20142204)
39. van Tellingen, O., Beijnen, J.H., Verweij, J., Scherrenburg, E.J., Nooijen, W.J., Sparreboom, A., 1999. Rapid esterase-sensitive breakdown of polysorbate 80 and its impact on the plasma pharmacokinetics of docetaxel and metabolites in mice. Clin. Cancer Res. 5, 2918-2924. (Pubitemid 29493971)
40. Wurm, F., Frey, H., 2011. Linear-dendritic block copolymers: the state of the art and exciting perspectives. Prog. Polym. Sci. 36, 1-52.
41. Zhao, Y., Shuai, X., Chen, C., Xi, F., 2003. Synthesis and characterization of star-shaped poly(L-lactide)s initiated with hydroxyl-terminated poly(amidoamine) (PAMAM-OH) dendrimers. Chem. Mater. 15, 2836-2843.
42. Zhao, Y.L., Li, J., Yu, H., Wang, G.J., Liu, W., 2012. Synthesis and characterization of a novel polydepsipeptide contained tri-block copolymer (mPEG-PLLA-PMMD) as self-assembly micelle delivery system for paclitaxel. Int. J. Pharm. 430, 282-291.
43. Zsóka, W., Judit, C., Csaba, R., László, R., János, S., Zoltán, R., 2011. Complement activation by polyethoxylated pharmaceutical surfactants: Cremophor-EL, Tween-80 and Tween-20. Eur. J. Pharm. Sci. 45, 492-498.