Efficacious hepatoma-targeted nanomedicine self-assembled from galactopeptide and doxorubicin driven by two-stage physical interactions

Journal of Controlled Release

Volumn 169, Issue 3, 2013, Pages 193-203

  Ding, Jianxun ^a,c   Xiao, Chunsheng ^a   Li, Yuce ^a,c   Cheng, Yilong ^a,c   Wang, Nannan ^a,b   He, Chaoliang ^a   Zhuang, Xiuli ^a   Zhu, Xiaojuan ^b   Chen, Xuesi ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b NORTHEAST NORMAL UNIVERSITY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Antitumor drug delivery; Hepatoma targetability; Malignancy therapy; Nanomedicine; Polypeptide

Indexed keywords

CELLS; CHEMOTHERAPY; CYTOLOGY; MEDICAL NANOTECHNOLOGY; MOLECULAR BIOLOGY; POLYPEPTIDES; RING OPENING POLYMERIZATION; SELF ASSEMBLY;

ANTITUMOR DRUG DELIVERIES; ASIALOGLYCOPROTEIN RECEPTORS; CONFOCAL LASER SCANNING MICROSCOPY; DRUG DELIVERY APPLICATIONS; HEPATOMA-TARGETABILITY; MALIGNANCY THERAPY; MICELLAR NANOPARTICLES; PHYSICAL INTERACTIONS;

TARGETED DRUG DELIVERY;

ACID ANHYDRIDE; ASIALOGLYCOPROTEIN RECEPTOR; AZIDAMFENICOL; DOXORUBICIN; GALACTOSE; GLUTAMIC ACID; LIGAND; NANOPARTICLE; POLYPEPTIDE;

ACIDITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CHEMOTHERAPY; CELL STRAIN HEPG2; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; CYCLOADDITION; DRUG DELIVERY SYSTEM; DRUG RELEASE; ENDOCYTOSIS; FEMALE; FLOW CYTOMETRY; HEPATOMA CELL; HISTOCOMPATIBILITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LIVER CELL CARCINOMA; MOUSE; NANOMEDICINE; NONHUMAN; PRIORITY JOURNAL; RING OPENING METATHESIS POLYMERIZATION; TISSUES;

EID: 84881600960     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2012.12.006     Document Type: Article

References (52)

1. X. Xu, H. Yuan, J. Chang, B. He, Z. Gu, Cooperative hierarchical self-assembly of peptide dendrimers and linear polypeptides into nanoarchitectures mimicking viral capsids, Angew. Chem. Int. Ed. 51 (2012) 3130-3133.
2. W.J. Syu, H.P. Yu, C.Y. Hsu, Y.C. Rajan, Y.H. Hsu, Y.C. Chang, W.Y. Hsieh, C.H. Wang, P.S. Lai, Improved photodynamic cancer treatment by folate-conjugated polymeric micelles in a KB xenografted animal model, Small 8 (2012) 2060-2069.
3. J. Yue, S. Liu, R. Wang, X. Hu, Z. Xie, Y. Huang, X. Jing, Transferrin-conjugated micelles: enhanced accumulation and antitumor effect for transferrin-receptor-overexpressing cancer models, Mol. Pharm. 9 (2012) 1919-1931.
4. W. Wang, J.X. Ding, C.S. Xiao, Z.H. Tang, D. Li, J. Chen, X.L. Zhuang, X.S. Chen, Synthesis of amphiphilic alternating polyesters with oligo(ethylene glycol) side chains and potential use for sustained release drug delivery, Biomacromolecules 12 (2011) 2466-2474.
5. J. Ding, C. Xiao, C. He, M. Li, D. Li, X. Zhuang, X. Chen, Facile preparation of a cationic poly(amino acid) vesicle for potential drug and gene co-delivery, Nanotechnology 22 (2011) 494012.
6. D. Li, J.X. Ding, Z.H. Tang, H. Sun, X.L. Zhuang, J.Z. Xu, X.S. Chen, In vitro evaluation of anticancer nanomedicines based on doxorubicin and amphiphilic Y-shaped copolymers, Int. J. Nanomedicine 7 (2012) 2687-2697.
7. S. Hama, S. Utsumi, Y. Fukuda, K. Nakayama, Y. Okamura, H. Tsuchiya, K. Fukuzawa, H. Harashima, K. Kogure, Development of a novel drug delivery system consisting of an antitumor agent tocopheryl succinate, J. Control. Release 161 (2012) 843-851.
8. K.B. Tan, L.U. Ling, R.M. Bunte, W.J. Chng, G.N.C. Chiu, In vivo efficacy of a novel liposomal formulation of safingol in the treatment of acute myeloid leukemia, J. Control. Release 160 (2012) 290-298.
9. A.N. Koo, K.H. Min, H.J. Lee, S.U. Lee, K. Kim, I. Chan Kwon, S.H. Cho, S.Y. Jeong, S.C. Lee, Tumor accumulation and antitumor efficacy of docetaxel-loaded core-shell-corona micelles with shell-specific redox-responsive cross-links, Biomaterials 33 (2012) 1489-1499.
10. R. Yang, F. Meng, S. Ma, F. Huang, H. Liu, Z. Zhong, Galactose-decorated cross-linked biodegradable poly(ethylene glycol)-b-poly(epsilon-caprolactone) block copolymer micelles for enhanced hepatoma-targeting delivery of paclitaxel, Biomacromolecules 12 (2011) 3047-3055.
11. R.P. Johnson, Y.I. Jeong, E. Choi, C.W. Chung, D.H. Kang, S.O. Oh, H. Suh, I. Kim, Biocompatible poly(2-hydroxyethyl methacrylate)-b-poly(L-histidine) hybrid materials for pH-sensitive intracellular anticancer drug delivery, Adv. Funct. Mater. 22 (2012) 1058-1068.
12. Y.C. Wang, X.Q. Liu, T.M. Sun, M.H. Xiong, J. Wang, Functionalized micelles from block copolymer of polyphosphoester and poly(epsilon-caprolactone) for receptor-mediated drug delivery, J. Control. Release 128 (2008) 32-40.
13. K. Letchford, H.M. Burt, Copolymer micelles and nanospheres with different in vitro stability demonstrate similar paclitaxel pharmacokinetics, Mol. Pharm. 9 (2012) 248-260.
14. J. Cheng, J.X. Ding, Y.C. Wang, J. Wang, Synthesis and characterization of star-shaped block copolymer of poly(ε-caprolactone) and poly(ethyl ethylene phosphate) as drug carrier, Polymer 49 (2008) 4784-4790.
15. H. Sun, B. Guo, R. Cheng, F. Meng, H. Liu, Z. Zhong, Biodegradable micelles with sheddable poly(ethylene glycol) shells for triggered intracellular release of doxo-rubicin, Biomaterials 30 (2009) 6358-6366.
16. G. Gaucher, M.H. Dufresne, V.P. Sant, N. Kang, D. Maysinger, J.C. Leroux, Block co-polymer micelles: preparation, characterization and application in drug delivery, J. Control. Release 109 (2005) 169-188. (Pubitemid 41742123)
17. A. Guaragna, A. Chiaviello, C. Paolella, D. D'Alonzo, G. Palumbo, G. Palumbo, Synthesis and evaluation of folate-based chlorambucil delivery systems for tumor-targeted chemotherapy, Bioconjug. Chem. 23 (2012) 84-96.
18. X. Hu, R. Wang, J. Yue, S. Liu, Z. Xie, X. Jing, Targeting and anti-tumor effect of folic acid-labeled polymer-doxorubicin conjugates with pH-sensitive hydrazone linker, J. Mater. Chem. 22 (2012) 13303-13310.
19. T. Noh, Y.H. Kook, C. Park, H. Youn, H. Kim, E.T. Oh, E.K. Choi, H.J. Park, C. Kim, Block copolymer micelles conjugated with anti-EGFR antibody for targeted delivery of anticancer drug, J. Polym. Sci. A Polym. Chem. 46 (2008) 7321-7331.
20. A. Taheri, R. Dinarvand, F. Ahadi, M.R. Khorramizadeh, F. Atyabi, The in vivo antitumor activity of LHRH targeted methotrexate-human serum albumin nanoparticles in 4T1 tumor-bearing BALB/c mice, Int. J. Pharm. 431 (2012) 183-189.
21. A. Ray, N. Larson, D.B. Pike, M. Grüner, S. Naik, H. Bauer, A. Malugin, K. Greish, H. Ghandehari, Comparison of active and passive targeting of docetaxel for prostate cancer therapy by HPMA copolymer-RGDfK conjugates, Mol. Pharm. 8 (2011) 1090-1099.
22. Y. Bae, W.D. Jang, N. Nishiyama, S. Fukushima, K. Kataoka, Multifunctional polymeric micelles with folate-mediated cancer cell targeting and pH-triggered drug releasing properties for active intracellular drug delivery, Mol. Biosyst. 1 (2005) 242-250. (Pubitemid 41442434)
23. J. Vega, S. Ke, Z. Fan, S. Wallace, C. Charsangavej, C. Li, Targeting doxorubicin to epidermal growth factor receptors by site-specific conjugation of C225 to poly(L-glutamic acid) through a polyethylene glycol spacer, Pharm. Res. 20 (2003) 826-832. (Pubitemid 36515318)
24. H.F. Liang, T.F. Yang, C.T. Huang, M.C. Chen, H.W. Sung, Preparation of nanoparticles composed of poly(γ-glutamic acid)-poly(lactide) block copolymers and evaluation of their uptake by HepG2 cells, J. Control. Release 105 (2005) 213-225.
25. Y.I. Jeong, S.J. Seo, I.K. Park, H.C. Lee, I.C. Kang, T. Akaike, C.S. Cho, Cellular recognition of paclitaxel-loaded polymeric nanoparticles composed of poly(γ-benzyl L-glutamate) and poly(ethylene glycol) diblock copolymer endcapped with galactose moiety, Int. J. Pharm. 296 (2005) 151-161. (Pubitemid 40693384)
26. G. Kwon, M. Naito, M. Yokoyama, T. Okano, Y. Sakurai, K. Kataoka, Block copolymer micelles for drug delivery: loading and release of doxorubicin, J. Control. Release 48 (1997) 195-201. (Pubitemid 27401978)
27. M. Yokoyama, S. Fukushima, R. Uehara, K. Okamoto, K. Kataoka, Y. Sakurai, T. Okano, Characterization of physical entrapment and chemical conjugation of adriamycin in polymeric micelles and their design for in vivo delivery to a solid tumor, J. Control. Release 50 (1998) 79-92. (Pubitemid 28044103)
28. T.J. Deming, Synthetic polypeptides for biomedical applications, Prog. Polym. Sci. 32 (2007) 858-875. (Pubitemid 47202019)
29. Y. Bae, K. Kataoka, Intelligent polymeric micelles from functional poly(ethylene glycol)-poly(amino acid) block copolymers, Adv. Drug Deliv. Rev. 61 (2009) 768-784.
30. C. Sanson, C. Schatz, J.F. Le Meins, A. Soum, J. Thevenot, E. Garanger, S. Lecommandoux, A simple method to achieve high doxorubicin loading in biodegradable polymersomes, J. Control. Release 147 (2010) 428-435.
31. J. Ding, C. Xiao, Z. Tang, X. Zhuang, X. Chen, Highly efficient "grafting from," an α-helical polypeptide backbone by atom transfer radical polymerization, Macromol. Biosci. 11 (2011) 192-198.
32. J. Ding, C. Xiao, L Zhao, Y Cheng, L M.a., Z. Tang, X. Zhuang, X. Chen, Poly(L-glutamic acid) grafted with oligo(2-(2-(2-methoxyethoxy)ethoxy) ethyl methacrylate): thermal phase transition, secondary structure, and self-assembly, J. Polym. Sci. A Polym. Chem. 49 (2011) 2665-2676.
33. W. Tansey, S. Ke, X.Y. Cao, M.J. Pasuelo, S. Wallace, C. Li, Synthesis and characterization of branched poly(L-glutamic acid) as a biodegradable drug carrier, J. Control. Release 94 (2004) 39-51. (Pubitemid 37542376)
34. Z. Wang, S.F. Yu, X. Gu, G.L Wu, Y.N. Wang, H. Gao, J.B. Ma, Synthesis of poly(ethylene glycol)-poly(glutamic acid)-poly(alanine acid) triblock copolymer and the pH-sensitive drug delivery of nanoparticles therefrom, Acta Polym Sin. 6 (2012) 599-605.
35. C. Li, Poly(L-glutamic acid) - anticancer drug conjugates, Adv. Drug Deliv. Rev. 54 (2002) 695-713. (Pubitemid 35247523)
36. J. Ding, X. Zhuang, C. Xiao, Y. Cheng, L. Zhao, C. He, Z. Tang, X. Chen, Preparation of photo-cross-linked pH-responsive polypeptide nanogels as potential carriers for controlled drug delivery, J. Mater. Chem. 21 (2011) 11383-11391.
37. Y. Cheng, C. He, C. Xiao, J. Ding, X. Zhuang, X. Chen, Versatile synthesis of temperature-sensitive polypeptides by click grafting of oligo(ethylene glycol), Polym. Chem. 2 (2011) 2627-2634.
38. C. Xiao, C. Zhao, P. He, Z. Tang, X. Chen, X. Jing, Facile synthesis of glycopolypeptides by combination of ring-opening polymerization of an alkyne-substituted N-carboxyanhydride and click "Glycosylation,", Macromol. Rapid Commun. 31 (2010) 991-997.
39. J. Ding, C. He, C. Xiao, J. Chen, X. Zhuang, X. Chen, pH-responsive drug delivery systems based on clickable poly(L-glutamic acid)-grafted comb copolymers, Macromol. Res. 20 (2012) 292-301.
40. F. Shi, J. Ding, C. Xiao, X. Zhuang, C. He, L. Chen, X. Chen, Intracellular microenvi-ronment responsive PEGylated polypeptide nanogels with ionizable cores for efficient doxorubicin loading and triggered release, J. Mater. Chem. 22 (2012) 14168-14179.
41. G. Minotti, Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity, Pharmacol. Rev. 56 (2004) 185-229. (Pubitemid 38720829)
42. R. Palchaudhuri, P.J. Hergenrother, DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action, Curr. Opin. Biotechnol. 18 (2007) 497-503.
43. J. Ding, F. Shi, C. Xiao, L Lin, L. Chen, C. He, X. Zhuang, X. Chen, One-step preparation of reduction-responsive poly(ethylene glycol)-poly (amino acid)s nanogels as efficient intracellular drug delivery platforms, Polym. Chem 2 (2011) 2857-2864
44. D. Schmaljohann, Thermo- and pH-responsive polymers in drug delivery, Adv. Drug Deliv. Rev. 58 (2006) 1655-1670. (Pubitemid 44830149)
45. A.R. Kolatkar, W.I. Weis, Structural basis of galactose recognition by C-type animal lectins, J. Biol. Chem. 271 (1996) 6679-6685. (Pubitemid 26104097)
46. M. Hashida, H. Hirabayashi, M. Nishikawa, Y. Takakura, Targeted delivery of drugs and proteins to the liver via receptor-mediated endocytosis, J. Control. Release 46 (1997) 129-137. (Pubitemid 27110893)
47. K.C. Partlow, G.M. Lanza, S.A. Wickline, Exploiting lipid raft transport with membrane targeted nanoparticles: a strategy for cytosolic drug delivery, Biomaterials 29 (2008) 3367-3375.
48. X. Dong, CA. Mattingly, M.T. Tseng, M.J. Cho, Y. Liu, V.R. Adams, R.J. Mumper, Doxorubicin and paclitaxel-loaded lipid-based nanoparticles overcome multidrug resistance by inhibiting p-glycoprotein and depleting ATP, Cancer Res. 69 (2009) 3918-3926.
49. A.A. Gabizon, Liposome circulation time and tumor targeting - implications for cancer-chemotherapy, Adv. Drug Deliv. Rev. 16 (1995) 285-294.
50. R.J. Cersosimo, Oxaliplatin-associated neuropathy: a review, Ann. Pharmacother. 39 (2005) 128-135. (Pubitemid 40052388)
51. E. Sanchez Marta, H.G. Maria Fe, G. Anciano Jara, A. Olea Ascension, Oxaliplatin-induced neurotoxicity, Aten. Farm. 13 (2011) 280-293.
52. L. Samuel, J. Cummings, P. Shaw, Daunorubicin cardiotoxicity in childhood cancer, Lancet 352 (1998) 1150.