Reduction/pH dual-sensitive PEGylated hyaluronan nanoparticles for targeted doxorubicin delivery

Carbohydrate Polymers

Volumn 98, Issue 1, 2013, Pages 181-188

  Xu, Minghui ^a   Qian, Junmin ^a   Suo, Aili ^a   Wang, Hongjie ^a   Yong, Xueqing ^a   Liu, Xuefeng ^a   Liu, Rongrong ^a  

^a XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

Doxorubicin; Hyaluronic acid; Nanoparticle; PEGylation; Reduction pH dual sensitivity; Targeted drug delivery

Indexed keywords

ALDEHYDES; CHEMOTHERAPY; ETHYLENE GLYCOL; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYALURONIC ACID; NANOPARTICLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; POLYOLS;

DOXORUBICIN; HEPATOCELLULAR CARCINOMA; INTRACELLULAR DELIVERY; INTRACELLULAR LEVELS; PEGYLATION; REDUCTIVE AMINATION; SPHERICAL NANOPARTICLES; TARGETED DELIVERY;

TARGETED DRUG DELIVERY;

3,3' THIODIPROPIONIC ACID; DOXORUBICIN; DRUG CARRIER; GALACTOSAMINE; HYALURONIC ACID; MACROGOL DERIVATIVE; NANOPARTICLE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CELL STRAIN HEPG2; CHEMISTRY; ENDOCYTOSIS; HUMAN; INTRACELLULAR SPACE; METABOLISM; OXIDATION REDUCTION REACTION; PEGYLATION; PH; REDUCTION/PH DUAL-SENSITIVITY; TARGETED DRUG DELIVERY;

DOXORUBICIN; HYALURONIC ACID; NANOPARTICLE; PEGYLATION; REDUCTION/PH DUAL-SENSITIVITY; TARGETED DRUG DELIVERY;

DOXORUBICIN; DRUG CARRIERS; ENDOCYTOSIS; GALACTOSAMINE; HEP G2 CELLS; HUMANS; HYALURONIC ACID; HYDROGEN-ION CONCENTRATION; INTRACELLULAR SPACE; NANOPARTICLES; OXIDATION-REDUCTION; POLYETHYLENE GLYCOLS; PROPIONATES;

EID: 84879477796     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2013.05.077     Document Type: Article

References (51)

1. Adams, M. L., Lavasanifar, A., & Kwon, G. S. (2003). Amphiphilic block copolymers for drug delivery. Journal of Pharmaceutical Sciences, 92(7), 1343-1355. (Pubitemid 36792748)
2. Akinc, A., Anderson, D. G., Lynn, D. M., & Langer, R. (2003). Synthesis of poly(betaamino ester)s optimized for highly effective gene delivery. Bioconjugate Chemistry, 14(5), 979-988. (Pubitemid 37152958)
3. Asayama, S., Nogawa, M., Takei, Y., Akaike, T., & Maruyama, A. (1998). Synthesis of novel polyampholyte comb-type copolymers consisting of a poly(l-lysine) backbone and hyaluronic acid side chains for a DNA carrier. Bioconjugate Chemistry, 9(4), 476-481. (Pubitemid 28338762)
4. Bae, Y., Fukushima, S., Harada, A., & Kataoka, K. (2003). Design of environmentsensitive supramolecular assemblies for intracellular drug delivery: Polymeric micelles that are responsive to intracellular pH change. Angewandte Chemie International Edition, 42(38), 4640-4643. (Pubitemid 37271305)
5. Bae, Y., Nishiyama, N., Fukushima, S., Koyama, H., Yasuhiro, M., & Kataoka, K. (2005). Preparation and biological characterization of polymeric micelle drug carriers with intracellular pH-triggered drug release property: Tumor permeability, controlled subcellular drug distribution, and enhanced in vivo antitumor efficacy. Bioconjugate Chemistry, 16(1), 122-130. (Pubitemid 40129685)
6. Bhattarai, N., Ramay, H. R., Gunn, J., Matsen, F. A., & Zhang, M. Q. (2005). PEG-grafted chitosan as an injectable thermosensitive hydrogel for sustained protein release. Journal of Controlled Release, 103(3), 609-624. (Pubitemid 40471019)
7. Cerritelli, S., Velluto, D., & Hubbell, J. A. (2007). PEG-SS-PPS: Reduction-sensitive disulfide block copolymer vesicles for intracellular drug delivery. Biomacromolecules, 8(6), 1966-1972. (Pubitemid 47009977)
8. Cheng, R., Feng, F., Meng, F. H., Deng, C., Feijen, J., & Zhong, Z. Y. (2011). Glutathioneresponsive nano-vehicles as a promising platform for targeted intracellular drug and gene delivery. Journal of Controlled Release, 152(1), 2-12.
9. Cho, H. J., Yooh, H. Y., Koo, H., Ko, S. H., Shim, J. S., Lee, J. H., et al. (2011). Self-assembled nanoparticles based on hyaluronic acid-ceramide (HA-CE) and Pluronic (R) for tumor-targeted delivery of docetaxel. Biomaterials, 32(29), 7181-7190.
10. Cho, H. J., Yoon, I. S., Yoon, H. Y., Koo, H., Jin, K. Y., Ko, S. H., et al. (2012). Polyethylene glycol-conjugated hyaluronic acid-ceramide self-assembled nanoparticles for targeted delivery of doxorubicin. Biomaterials, 33(4), 1190-1200.
11. Choi, K. Y., Min, K. H., Yoon, H. Y., Kim, K., Park, J. H., Kwon, I. C., et al. (2011). PEGylation of hyaluronic acid nanoparticles improves tumor targetability in vivo. Biomaterials, 32(7), 1880-1889.
12. Dong, L., Xia, S. H., Wu, K., Huang, Z., Chen, H. A., Chen, J. N., et al. (2010). A pH/Enzyme-responsive tumor-specific delivery system for doxorubicin. Biomaterials, 31(24), 6309-6316.
13. Dong, Y. C., & Feng, S. S. (2004). Methoxy poly(ethylene glycol)-poly(lactide) (MPEGPLA) nanoparticles for controlled delivery of anticancer drugs. Biomaterials, 25(14), 2843-2849.
14. Duncan, R. (2003). The dawning era of polymer therapeutics. Nature Reviews Drug Discovery, 2(5), 347-360. (Pubitemid 37361705)
15. Engstromlaurent, A., Loof, L., Nyberg, A., & Schroder, T. (1985). Increased serum levels of hyaluronate in liver-disease. Hepatology, 5(4), 638-642. (Pubitemid 15029737)
16. Ferlay, J., Shin, H. R., Bray, F., Forman, D., Mathers, C., & Parkin, D. M. (2010). Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008. International Journal of Cancer, 127(12), 2893-2917.
17. Fox, M. E., Szoka, F. C., & Frechet, J. M. J. (2009). Soluble polymer carriers for the treatment of cancer: The importance of molecular architecture. Accounts of Chemical Research, 42(8), 1141-1151.
18. Gewirtz, D. A. (1999). A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochemical Pharmacology, 57(7), 727-741. (Pubitemid 29094544)
19. Gu, F. X., Karnik, R., Wang, A. Z., Alexis, F., Levy-Nissenbaum, E., Hong, S., et al. (2007). Targeted nanoparticles for cancer therapy. Nano Today, 2(3), 14-21. (Pubitemid 46672835)
20. Han, J. H., Oh, Y. K., Kim, D. S., & Kim, C. K. (1999). Enhanced hepatocyte uptake and liver targeting of methotrexate using galactosylated albumin as a carrier. International Journal of Pharmaceutics, 188(1), 39-47.
21. Hanson, J. A., Li, Z. B., & Deming, T. J. (2010). Nonionic block copolypeptide micelles containing a hydrophobic rac-leucine core. Macromolecules, 43(15), 6268-6269.
22. Harris, J. M., Struck, E. C., Case, M. G., Paley, M. S., Vanalstine, J. M., & Brooks, D. E. (1984). Synthesis and characterization of poly(ethylene glycol) derivatives. Journal of Polymer Science Part A: Polymer Chemistry, 22(2), 341-352. (Pubitemid 14529695)
23. Jemal, A., Bray, F., Center, M. M., Ferlay, J., Ward, E., & Forman, D. (2011). Global cancer statistics. CA: A Cancer Journal for Clinicians, 61, 69-90.
24. Jones, D. P., Carlson, J. L., Samiec, P. S., Stemberg, P., Mody, V. C., Reed, R. L., et al. (1998). Glutathione measurement in human plasma: Evaluation of sample collection, storage and derivatization conditions for analysis of dansyl derivatives by HPLC. Clinica Chimica Acta, 275(2), 175-184. (Pubitemid 28323074)
25. Kawaguchi, H. (2000). Functional polymer microspheres. Progress in Polymer Science, 25(8), 1171-1210. (Pubitemid 32030196)
26. Koo, A. N., Lee, H. J., Kim, S. E., Chang, J. H., Park, C., Kim, C., et al. (2008). Disulfide-cross-linked PEG-poly(amino acid)s copolymer micelles for glutathione-mediated intracellular drug delivery. Chemical Communications, 48, 6570-6572.
27. Kuppusamy, P., Li, H. Q., Ilangovan, G., Cardounel, A. J., Zweier, J. L., Yamada, K., et al. (2002). Noninvasive imaging of tumor redox status and its modification by tissue glutathione levels. Cancer Research, 62(1), 307-312. (Pubitemid 34074020)
28. Lee, H., Mok, H., Lee, S., Oh, Y. K., & Park, T. G. (2007). Target-specific intracellular delivery of siRNA using degradable hyaluronic acid nanogels. Journal of Controlled Release, 119(2), 245-252. (Pubitemid 46754507)
29. Llovet, J. M., Ricci, S., Mazzaferro, V., Hilgard, P., Gane, E., Blanc, J. F., et al. (2008). Sorafenib in advanced hepatocellular carcinoma. New England Journal of Medicine, 359(4), 378-390.
30. Li, J., Huo, M. R., Wang, J., Zhou, J. P., Mohammad, J. M., Zhang, Y. L., et al. (2012). Redox-sensitive micelles self-assembled from amphiphilic hyaluronic aciddeoxycholic acid conjugates for targeted intracellular delivery of paclitaxel. Biomaterials, 33(7), 2310-2320.
31. Li, X. J., Qian, Y. F., Liu, T., Hu, X. L., Zhang, G. Y., You, Y. Z., et al. (2011). Amphiphilic multiarm star block copolymer-based multifunctional unimolecular micelles for cancer targeted drug delivery and MR imaging. Biomaterials, 32(27), 6595-6605.
32. Luo, Y., & Prestwich, G. D. (1999). Prestwich. Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate. Bioconjugate Chemistry, 10(5), 755-763. (Pubitemid 29456361)
33. Maeda, H., Wu, J., Sawa, T., Matsumura, Y., & Hori, K. (2000). Tumor vascular permeability and the EPR effect in macromolecular therapeutics: A review. Journal of Controlled Release, 65(1-2), 271-284. (Pubitemid 30122932)
34. Meng, F. H., Hennink, W. E., & Zhong, Z. Y. (2009). Reduction-sensitive polymers and bioconjugates for biomedical applications. Biomaterials, 30(12), 2180-2198.
35. Min, K. H., Kim, J. H., Bae, S. M., Shin, H., Kim, M. S., Park, S., et al. (2010). Tumoral acidic pH-responsive MPEG-poly(beta-amino ester) polymeric micelles for cancer targeting therapy. Journal of Controlled Release, 144(2), 259-266.
36. Neradovic, D., van Nostrum, C. F., & Hennink, W. E. (2001). Thermoresponsive polymeric micelles with controlled instability based on hydrolytically sensitive N-isopropylacrylamide copolymers. Macromolecules, 34(22), 7589-7591. (Pubitemid 33074518)
37. Oh, E. J., Kang, S. W., Kim, B. S., Jiang, G., Cho, I. H., & Hahn, S. K. (2008). Control of the molecular degradation of hyaluronic acid hydrogels for tissue augmentation. Journal of Biomedical Materials Research, 86A(3), 685-693.
38. Ong, G. L., Ettenson, D., Sharkey, R. M., Marks, A., Baumal, R., Goldenberg, D. M., et al. (1991). Galactose-conjugated antibodies in cancer therapy: Properties and principles of action. Cancer Research, 51(6), 1619-1626.
39. Parveen, S., Misra, R., & Sahoo, S. K. (2012). Nanoparticles: A boon to drug delivery, therapeutics, diagnostics and imaging. Nanomedicine: Nanotechnology, Biology and Medicine, 8(2), 147-166.
40. Peer, D., Karp, J. M., Hong, S., FarokHzad, O. C., Margalit, R., & Langer, R. (2007). Nanocarriers as an emerging platform for cancer therapy. Nature Nanotechnology, 2(12), 751-760. (Pubitemid 350223348)
41. Pham, M. C., Oulahyane, M., Mostefai, M., & Chehimi, M. M. (1998). Multiple internal reflection FT-IR spectroscopy (MIRFTIRS) study of the electrochemical synthesis and the redox process of poly(1,5-diaminonaphthalene). Synthetic Metals, 93(2), 89-96. (Pubitemid 128393122)
42. Pouyani, T., & Prestwich, G. D. (1994). Functionalized derivatives of hyaluronic acid oligosaccharides: Drug carriers and novel biomaterials. Bioconjugate Chemistry, 5(4), 339-347.
43. Renuga Devi, T. S., & Gayathri, S. (2010). FTIR and FT-Raman spectral analysis of paclitaxel drugs. International Journal of Pharmaceutical Sciences Review and Research, 2(2), 106-110.
44. Sakamoto, M., Takeda, J., Yamada, Y., & Tonami, H. (1970). Reversible crosslinking in cellulose. II. Mono-and bifunctional reactions of bis-isocyanatoethyl disulfide with cotton. Journal of Applied Polymer Science, 14(4), 865-878.
45. Shen, Z. Y., Wei, W., Tanaka, H., Kohama, K., Ma, G. H., Dobashi, T., et al. (2011). A galactosamine-mediated drug delivery carrier for targeted liver cancer therapy. Pharmaceutical Research, 64(4), 410-419.
46. Shuai, X. T., Ai, H., Nasongkla, N., Kim, S., & Gao, J. M. (2004). Micellar carriers based on block copolymers of poly(e-caprolactone) and poly(ethylene glycol) for doxorubicin delivery. Journal of Controlled Release, 98(3), 415-426. (Pubitemid 39093952)
47. Stern, R., Asari, A. A., & Sugahara, K. N. (2006). Hyaluronan fragments: An information-rich system. European Journal of Cell Biology, 85(8), 699-715. (Pubitemid 44070579)
48. Sun, H. L., Guo, B. N., Cheng, R., Meng, F. H., Liu, H. Y., & Zhong, Z. Y. (2009). Biodegradable micelles with sheddable poly(ethylene glycol) shells for triggered intracellular release of doxorubicin. Biomaterials, 30(31), 6358-6366.
49. Teramura, Y., Kaneda, Y., & Iwata, H. (2007). Islet-encapsulation in ultra-thin layerby- layer membranes of poly(vinyl alcohol) anchored to poly(ethylene glycol)- lipids in the cell membrane. Biomaterials, 28(32), 4818-4825. (Pubitemid 47285341)
50. Wu, D. Q., Lu, B., Chang, C., Chen, C. S., Wang, T., Zhang, Y. Y., et al. (2009). Galactosylated fluorescent labeled micelles as a liver targeting drug carrier. Biomaterials, 30(7), 1363-1371.
51. Zhang, J., & Misra, R. D. K. (2007). Magnetic drug-targeting carrier encapsulated with thermosensitive smart polymer: Core-shell nanoparticle carrier and drug release response. Acta Biomaterialia, 3(6), 838-850. (Pubitemid 47382675)