Novel nanoparticles generated by polymeric amphiphiles with π-π conjugated small molecules for anti-tumor drug delivery

Journal of Biomedical Nanotechnology

Volumn 9, Issue 8, 2013, Pages 1336-1344

  Deng, Xin ^a   Xu, Xianghui ^a   Lai, Yusi ^a   He, Bin ^a   Gu, Zhongwei ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

stacking; Cellular internalization; Doxorubicin; Drug delivery; Nanoparticles

Indexed keywords

CELLULAR INTERNALIZATION; CONJUGATED SMALL MOLECULES; DOXORUBICIN; DRUG LOADED NANOPARTICLE; HYDROPHOBIC INTERACTIONS; HYDROPHOBIC POLYMER CHAINS; METHOXYPOLYETHYLENE GLYCOL; SELF-ASSEMBLY NANOPARTICLES;

AMINO ACIDS; AMPHIPHILES; CONJUGATED POLYMERS; DRUG DELIVERY; DRUG INTERACTIONS; ENCAPSULATION; HYDROGEN BONDS; HYDROPHOBICITY; MOLECULES; MOTION PICTURE EXPERTS GROUP STANDARDS; NANOPARTICLES; POLYETHYLENE GLYCOLS; POLYMERS; SELF ASSEMBLY;

SYNTHESIS (CHEMICAL);

AMPHOPHILE; ANTINEOPLASTIC AGENT; DOXORUBICIN; MACROGOL DERIVATIVE; METHOXY POLY(ETHYLENE GLYCOL); N (9 FLUORENYLMETHOXYCARBONYL)PHENYLALANINE; NANOCARRIER; PHENYLALANINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL INTERACTION; CONTROLLED STUDY; HYDROGEN BOND; HYDROPHOBICITY; IN VITRO STUDY; PARTICLE SIZE; STATIC ELECTRICITY;

ANTINEOPLASTIC AGENTS; DOXORUBICIN; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; DRUG EVALUATION, PRECLINICAL; HEP G2 CELLS; HUMANS; MODELS, BIOLOGICAL; NANOCONJUGATES; NANOPARTICLES; POLYETHYLENE GLYCOLS; POLYMERS; SURFACE-ACTIVE AGENTS;

EID: 84880864762     PISSN: 15507033     EISSN: 15507041     Source Type: Journal    
DOI: 10.1166/jbn.2013.1626     Document Type: Article

References (52)

1. K. W. Leong and R. Langer, Polymeric controlled drug delivery. Adv. Drug Delivery Rev. 1, 199 (1988).
2. R. Langer, Polymer-controlled drug delivery systems. Acc. Chem. Res. 26, 537 (1993).
3. C. Gong, C. Wang, Y. Wang, Q. Wu, D. Zhang, F. Luo, and Z. Qian, Efficient inhibition of colorectal peritoneal carcinomatosis by drug loaded micelles in thermosensitive hydrogel composites. Nanoscale 4, 3095 (2012).
4. X. Peng, J. Wang, H. Song, D. Cui, L. Li, J. Li, L. Lin, J. Zhou, and Y. Liu, Optimized preparation of celastrol-loaded polymeric nanomicelles using rotatable central composite design and response surface methodology. J. Biomed. Nanotechnol. 8. 491 (2012).
5. J. S. Lee and J. Feijen, Polymersomes for drug delivery: Design, formation and characterization. J. Control Release 161, 473 (2012).
6. K. Wang, X. Xu, Y. Wang, X. Yan, G. Guo, M. Huang, F. Luo, X. Zhao, Y. Wei, and Z. Qian, Synthesis and characterization of poly(methoxyl ethylene glycol-caprolactone-co-methacrylic acid-copoly(ethylene glycol) methyl ether methacrylate) pH-sensitive hydrogel for delivery of dexamethasone. Int. J. Pharm. 389, 130 (2010).
7. H. Yuan, K. Luo, Y. Lai, Y. Pu, B. He, G. Wang, Y. Wu, and Z. Gu, A novel poly(l-glutamic acid) dendrimer based drug delivery system with both pH-sensitive and targeting functions. Mol. Pharm. 7, 953 (2010).
8. M. Gou, K. Men, H. Shi, M. Xiang, J. Zhang, J. Song, J. Long, Y. Wan, F. Luo, X. Zhao, and Z. Qian, Curcumin-loaded biodegradable polymeric micelles for colon cancer therapy in vitro and in vivo. Nanoscale 3, 1558 (2011).
9. K. Fukushima, R. C. Pratt, F. Nederberg, J. P. K. Tan, Y. Y. Yang, R. M. Waymouth, and J. L. Hedrick, Organocatalytic approach to amphiphilic comb-block copolymers capable of stereocomplexation and self-assembly. Biomacromolecules 9, 3051 (2008).
10. V. Percec, D. A. Wilson, P. Leowanawat, C. J. Wilson, A. D. Hughes, M. S. Kaucher, D. A. Hammer, D. H. Levine, A. J. Kim, F. S. Bates, K. P. Davis, T. P. Lodge, M. L. Klein, R. H. DeVane, E. Aqad, B. M. Rosen, A. O. Argintaru, M. J. Sienkowska, K. Rissanen, S. Nummelin, and J. Ropponen, Self-assembly of janus dendrimers into uniform dendrimersomes and other complex architectures. Science 328, 1009 (2010).
11. S. Chen, X.-Z. Zhang, S.-X. Cheng, R.-X. Zhuo, and Z.-W. Gu, Functionalized amphiphilic hyperbranched polymers for targeted drug delivery. Biomacromolecules 9, 2578 (2008).
12. Z. Li, M. A. Hillmyer, and T. P. Lodge, Morphologies of multicompartment micelles formed by ABC miktoarm star terpolymers. Langmuir 22, 9409 (2006).
13. M. Gou, X. Zheng, K. Men, J. Zhang, B. Wang, L. Lv, X. Wang, Y. Zhao, F. Luo, L. Chen, X. Zhao, Y. Wei, and Z. Qian, Self-assembled hydrophobic honokiol loaded MPEG-PCL diblock copolymer micelles. Pharm. Res. 26, 2164 (2009).
14. B. Xue, Y. Wang, X. Tang, P. Xie, Y. Wang, F. Luo, C. Wu, and Z. Qian, Biodegradable Self-assembled MPEG-PCL micelles for hydrophobic oridonin delivery in vitro. J. Biomed. Nanotechnol. 8, 80 (2012).
15. J. Fan, G. Fang, X. Wang, F. Zeng, Y. Xiang, and S. Wu, Targeted anticancer prodrug with mesoporous silica nanoparticles as vehicles. Nanotechnology 22, 455102 (2011).
16. M. Gou, H. Shi, G. Men, Z. Zheng, Z. Li, F. Luo, Z. Qian, X. Zhao, and Y. Wei, Improving anticancer activity and reducing systemic toxicity of doxorubicin by self-assembled polymeric micelles. Nanotechnology 22, 095102 (2011).
17. C. Gong, S. Shi, P. Dong, B. Kan, M. Gou, X. Wang, X. Li, F. Luo, X. Zhao, Y.Wei, and Z. Qian, Synthesis and characterization of PEGPCL-PEG thermosensitive hydrogel. Int. J. Pharm. 365, 89 (2009).
18. Y. Shen, E. Jin, B. Zhang, C. J. Murphy, M. Sui, J. Zhao, J. Wang, J. Tang, M. Fan, E. Van Kirk, and W. J. Murdoch, Prodrugs forming high drug loading multifunctional nanocapsules for intracellular cancer drug delivery. J. Am. Chem. Soc. 132, 4259 (2010).
19. Y. Lai, Y. Long, Y. Lei, X. Deng, B. He, M. Sheng, M. Li, and Z. Gu, A novel micelle of coumarin derivative monoend-functionalized PEG for anti-tumor drug delivery: In vitro and in vivo study. J. Drug Target. 20, 246 (2011).
20. R. Liu, D. Li, B. He, X. Xu, M. Sheng, Y. Lai, G. Wang, and Z. Gu, Anti-tumor drug delivery of pH-sensitive poly(ethylene glycol)-poly(L-histidine- )-poly(L-lactide) nanoparticles. J. Control Release 152, 49 (2011).
21. S. H. Kim, J. P. K. Tan, F. Nederberg, K. Fukushima, J. Colson, C. Yang, A. Nelson, Y.-Y. Yang, and J. L. Hedrick, Hydrogen bonding-enhanced micelle assemblies for drug delivery. Biomaterials 31, 8063 (2010).
22. X. Xu, H. Yuan, J. Chang, B. He, and Z. Gu, Cooperative hierarchical self-assembly of peptide dendrimers and linear polypeptides into nanoarchitectures mimicking viral capsids. Angew. Chem. 124, 3184 (2012).
23. J. Zhang, and P. X. Ma, Core-shell structured nanoassemblies based on β-cyclodextrin containing block copolymer and poly(β-benzyl l-aspartate) via host-guest complexation. Polymer 52, 4928 (2011).
24. X. Zhang, Z. Chen, and F. Würthner, Morphology control of fluorescent nanoaggregates by co-self-assembly of wedge- and dumbbell-shaped amphiphilic perylene bisimides. J. Am. Chem. Soc. 129, 4886 (2007).
25. X. Yan, M. Zhang, P. Wei, B. Zheng, X. Chi, X. Ji, and F. Huang, pH-responsive assembly and disassembly of a supramolecular cryptand-based pseudorotaxane driven by [small pi]-[small pi] stacking interaction. Chem. Commun. 47, 9840 (2011).
26. K. L. Niece, J. D. Hartgerink, J. J. J. M. Donners, and S. I. Stupp, Self-assembly combining two bioactive peptide-amphiphile molecules into nanofibers by electrostatic attraction. J. Am. Chem. Soc. 125, 7146 (2003).
27. C. Wang, S. Yin, S. Chen, H. Xu, Z. Wang, and X. Zhang, Controlled self-assembly manipulated by charge-transfer interactions: From tubes to vesicles. Angew. Chem. 120, 9189 (2008).
28. R. Liu, B. He, D. Li, Y. Lai, J. Z. Tang, and Z. Gu, Stabilization of pH-sensitive mPEG-PH-PLA nanoparticles by stereocomplexation between enantiomeric polylactides. Macromol. Rapid Commun. 33, 1061 (2012).
29. C. Tu, L. Zhu, P. Li, Y. Chen, Y. Su, D. Yan, X. Zhu, and G. Zhou, Supramolecular polymeric micelles by the host-guest interaction of star-like calix[4]arene and chlorin e6 for photodynamic therapy. Chem. Commun. 47, 6063 (2011).
30. Z. Liu, X. Sun, N. Nakayama-Ratchford, and H. Dai, Supramolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery. ACS Nano 1, 50 (2007).
31. X. Shuai, H. Ai, N. Nasongkla, S. Kim, and J. Gao, Micellar carriers based on block copolymers of poly(-caprolactone) and poly(ethylene glycol) for doxorubicin delivery. J. Control Release 98, 415 (2004).
32. J. Mao, P. Ni, Y. Mai, and D. Yan, Multicompartment micelles from hyperbranched star-block copolymers containing polycations and fluoropolymer segment. Langmuir 23, 5127 (2007).
33. T. Ouchi, H. Miyazaki, H. Arimura, F. Tasaka, A. Hamada, and Y. Ohya, Formation of polymeric micelles with amino surfaces from amphiphilic AB-type diblock copolymers composed of poly(glycolic acid lysine) segments and polylactide segments. J. Polym. Sci., Part A: Polym. Chem. 40, 1426 (2002).
34. Y. Chen and C.-M. Dong, pH-sensitive supramolecular polypeptide-based micelles and reverse micelles mediated by hydrogen-bonding interactions or host-guest chemistry: Characterization and in vitro controlled drug release. J. Phys. Chem. B 114, 7461 (2010).
35. Y. Zhou and D. Yan, Supramolecular self-assembly of giant polymer vesicles with controlled sizes. Angew. Chem. Int. Ed. 43, 4896 (2004).
36. J.-Z. Du, L.-Y. Tang, W.-J. Song, Y. Shi, and J. Wang, Evaluation of polymeric micelles from brush polymer with poly(ε-caprolactone)-b- poly(ethylene glycol) side chains as drug carrier. Biomacromolecules 10, 2169 (2009).
37. J. P. K. Tan, S. H. Kim, F. Nederberg, K. Fukushima, D. J. Coady, A. Nelson, Y. Y. Yang, and J. L. Hedrick, Delivery of anticancer drugs using polymeric micelles stabilized by hydrogen-bonding urea groups. Macromol. Rapid Commun. 31, 1187 (2010).
38. X. Wang, G. Wu, C. Lu, W. Zhao, Y. Wang, Y. Fan, H. Gao, and J. Ma, A novel delivery system of doxorubicin with high load and pH-responsive release from the nanoparticles of poly(α,β-aspartic acid) derivative. Eur. J. Pharm. Sci. 47, 256 (2012).
39. H. Yin and Y. H. Bae, Physicochemical aspects of doxorubicin-loaded pH-sensitive polymeric micelle formulations from a mixture of poly(l-histidine)-b-poly(l-lactide)-b-poly(ethylene glycol). Eur. J. Pharm. Biopharm. 71, 223 (2009).
40. L. Qiu, L. Zhang, C. Zheng, and R. Wang, Improving physicochemical properties and doxorubicin cytotoxicity of novel polymeric micelles by poly(-caprolactone) segments. J. Pharm. Sci. 100, 2430 (2011).
41. D. Depan, J. Shah, and R. D. K. Misra, Controlled release of drug from folate-decorated and graphene mediated drug delivery system: Synthesis, loading efficiency, and drug release response. Mater. Sci. Eng.: C 31, 1305 (2011).
42. D. M. Guldi, M. Marcaccio, D. Paolucci, F. Paolucci, N. Tagmatarchis, D. Tasis, E. Vázquez, and M. Prato, Single-wall carbon nanotube-ferrocene nanohybrids: Observing intramolecular electron transfer in functionalized SWNTs. Angew. Chem. 115, 4338 (2003).
43. H. Murakami, T. Nomura, and N. Nakashima, Noncovalent porphyrin-functionalized single-walled carbon nanotubes in solution and the formation of porphyrin-nanotube nanocomposites. Chem. Phys. Lett. 378, 481 (2003).
44. N. Nakayama-Ratchford, S. Bangsaruntip, X. Sun, K. Welsher, and H. Dai, Noncovalent functionalization of carbon nanotubes by fluorescein-polyethylene glycol: Supramolecular conjugates with pH-dependent absorbance and fluorescence. J. Am. Chem. Soc. 129, 2448 (2007).
45. W. Huang, W. Wang, P. Wang, Q. Tian, C. Zhang, C. Wang, Z. Yuan, M. Liu, H. Wan, and H. Tang, Glycyrrhetinic acid-modified poly(ethylene glycol)-b-poly(γ-benzyl l-glutamate) micelles for liver targeting therapy. Acta Biomater. 6. 3927 (2010).
46. Y. Lee, S. Y. Park, H. Mok, and T. G. Park, Synthesis, characterization, antitumor activity of pluronic mimicking copolymer micelles conjugated with doxorubicin via acid-cleavable linkage. Bioconjug. Chem. 19, 525 (2007).
47. Y. Sun, X. Yan, T. Yuan, J. Liang, Y. Fan, Z. Gu, and X. Zhang, Disassemblable micelles based on reduction-degradable amphiphilic graft copolymers for intracellular delivery of doxorubicin. Biomaterials 31, 7124 (2010).
48. H. S. Yoo, J. E. Oh, K. H. Lee, and T. G. Park, Biodegradable nanoparticles containing doxorubicin-PLGA conjugate for sustained release. Pharm. Res. 16, 1114 (1999).
49. M. Talelli, M. Iman, A. K. Varkouhi, C. J. F. Rijcken, R. M. Schiffelers, T. Etrych, K. Ulbrich, C. F. van Nostrum, T. Lammers, G. Storm, and W. E. Hennink, Core-crosslinked polymeric micelles with controlled release of covalently entrapped doxorubicin. Biomaterials 31, 7797 (2010).
50. O. Hovorka, M. Št'astný, T. Etrych, V. Šubr, J. Strohalm, K. Ulbrich, and B. Říhová, Differences in the intracellular fate of free and polymer-bound doxorubicin. J. Control. Release 80, 101 (2002).
51. X. Yang, J. J. Grailer, S. Pilla, D. A. Steeber, and S. Gong. Tumortargeting, pH-responsive, and stable unimolecular micelles as drug nanocarriers for targeted cancer therapy. Bioconjug. Chem. 21, 496 (2010).
52. H.-C. Tsai, W.-H. Chang, C.-L. Lo, C.-H. Tsai, C.-H. Chang, T.-W. Ou, T.-C. Yen, and G.-H. Hsiue, Graft and diblock copolymer multifunctional micelles for cancer chemotherapy and imaging. Biomaterials 31, 2293 (2010).