Redox-responsive polymer-drug conjugates based on doxorubicin and chitosan oligosaccharide- g -stearic acid for cancer therapy

Molecular Pharmaceutics

Volumn 12, Issue 4, 2015, Pages 1193-1202

  Su, Yigang ^a   Hu, Yingwen ^a   Du, Yongzhong ^a   Huang, Xuan ^b   He, Jiabei ^a   You, Jian ^a   Yuan, Hong ^a   Hu, Fuqiang ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b JIAXING UNIVERSITY   (China)

Author keywords

chitosan; controlled release; drug resistance; polymer drug conjugates; redox responsive

Indexed keywords

CHITOSAN; DOXORUBICIN; DOXORUBICIN CONJUGATED STEARIC ACID GRAFTED CHITOSAN OLIGOSACCHARIDE; OLIGOSACCHARIDE; STEARIC ACID; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DISULFIDE; MICELLE; POLYMER; STEARIC ACID DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CANCER THERAPY; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG RELEASE; DRUG UPTAKE; IN VITRO STUDY; IN VIVO STUDY; MICELLE; MOUSE; NONHUMAN; PRIORITY JOURNAL; ANIMAL; BAGG ALBINO MOUSE; CHEMISTRY; CONFOCAL MICROSCOPY; DRUG RESISTANCE; DRUG SCREENING; HUMAN; IC50; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; MCF 7 CELL LINE; NEOPLASMS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUDE MOUSE; OXIDATION REDUCTION REACTION; PARTICLE SIZE;

ANIMALS; ANTINEOPLASTIC AGENTS; CHITOSAN; CHROMATOGRAPHY, LIQUID; DISULFIDES; DOXORUBICIN; DRUG DELIVERY SYSTEMS; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; MCF-7 CELLS; MICE; MICE, INBRED BALB C; MICE, NUDE; MICELLES; MICROSCOPY, CONFOCAL; NEOPLASMS; OLIGOSACCHARIDES; OXIDATION-REDUCTION; PARTICLE SIZE; POLYMERS; STEARIC ACIDS;

EID: 84926442369     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500710x     Document Type: Article

References (33)

1. Haag, R.; Kratz, F. Polymer therapeutics: concepts and applications Angew. Chem., Int. Ed. 2006, 45, 1198-215
2. Bildstein, L.; Dubernet, C.; Couvreur, P. Prodrug-based intracellular delivery of anticancer agents Adv. Drug Delivery Rev. 2011, 63, 3-23
3. Khandare, J.; Minko, T. Polymer-drug conjugates: Progress in polymeric prodrugs Prog. Polym. Sci. 2006, 31, 359-397
4. Santra, S.; Kaittanis, C.; Santiesteban, O. J.; Perez, J. M. Cell-specific, activatable, and theranostic prodrug for dual-targeted cancer imaging and therapy J. Am. Chem. Soc. 2011, 133, 16680-16688
5. Guo, X.; Shi, C.; Wang, J.; Di, S.; Zhou, S. pH-triggered intracellular release from actively targeting polymer micelles Biomaterials 2013, 34, 4544-4554
6. Etrych, T.; Kovář, L.; Strohalm, J.; Chytil, P.; Říhová, B.; Ulbrich, K. Biodegradable star HPMA polymer-drug conjugates: Biodegradability, distribution and anti-tumor efficacy J. Controlled Release 2011, 154, 241-248
7. Talelli, M.; Iman, M.; Varkouhi, A. K.; Rijcken, C. J.; Schiffelers, R. M.; Etrych, T.; Ulbrichb, K.; Nostrum, C. F.; Lammersa, T.; Storm, G.; Hennink, W. E. Core-crosslinked polymeric micelles with controlled release of covalently entrapped doxorubicin Biomaterials 2010, 31, 7797-7804
8. Law, B.; Tung, C. H. Proteolysis: a biological process adapted in drug delivery, therapy, and imaging Bioconjugate Chem. 2009, 20, 1683-1695
9. Johnson, J. A.; Lu, Y. Y.; Burts, A. O.; Xia, Y.; Durrell, A. C.; Tirrell, D. A.; Grubbs, R. H. Drug-loaded, bivalent-bottle-brush polymers by graft-through ROMP Macromolecules 2010, 43, 10326-10335
10. Kurtoglu, Y. E.; Navath, R. S.; Wang, B.; Kannan, S.; Romero, R.; Kannan, R. M. Poly(amidoamine) dendrimer-drug conjugates with disulfide linkages for intracellular drug delivery Biomaterials 2009, 30, 2112-2121
11. Navath, R. S.; Wang, B.; Kannan, S.; Romero, R.; Kannan, R. M. Stimuli-responsive star poly(ethylene glycol) drug conjugates for improved intracellular delivery of the drug in neuroinflammation J. Controlled Release 2010, 142, 447-456
12. Kuppusamy, P.; Li, H.; Ilangovan, G.; Cardounel, A. J.; Zweier, J. L.; Yamada, K.; Krishna, M. C.; Mitchell, J. B. Noninvasive imaging of tumor redox status and its modification by tissue glutathione levels Cancer Res. 2002, 62, 307-312
13. Hwang, C.; Sinskey, A. J.; Lodish, H. F. Oxidized redox state of glutathione in the endoplasmic reticulum Science 1992, 257, 1496-1502
14. Lee, M. H.; Yang, Z.; Lim, C. W.; Lee, Y. H.; Dongbang, S.; Kang, C.; Kim, J. S. Disulfide-cleavage-triggered chemosensors and their biological applications Chem. Rev. 2013, 113, 5071-5109
15. Takemura, G.; Fujiwara, H. Doxorubicin-induced cardiomyopathy from the cardiotoxic mechanisms to management Prog. Cardiovasc. Dis. 2007, 49, 330-352
16. Markman, J. L.; Rekechenetskiy, A.; Holler, E.; Ljubimova, J. Y. Nanomedicine therapeutic approaches to overcome cancer drug resistance Adv. Drug Delivery Rev. 2013, 65, 1866-1879
17. Hu, F. Q.; Zhao, M. D.; Yuan, H.; You, J.; Du, Y. Z.; Zeng, S. A novel chitosan oligosaccharide-stearic acid micelles for gene delivery: properties and in vitro transfection studies Int. J. Pharm. 2006, 315, 158-166
18. Li, J.; Huo, M.; Wang, J.; Zhou, J. P.; Mohammad, J. M.; Zhang, Y. L.; Zhu, Q. N.; Waddad, A. Y.; Zhang, Q. Redox-sensitive micelles self-assembled from amphiphilic hyaluronic acid-deoxycholic acid conjugates for targeted intracellular delivery of paclitaxel Biomaterials 2012, 33, 2310-2320
19. Yan, J.; Du, Y. Z.; Chen, F. Y.; You, J.; Yuan, H.; Hu, F. Q. Effect of Proteins with Different Isoelectric Points on the Gene Transfection Efficiency Mediated by Stearic Acid Grafted Chitosan Oligosaccharide Micelles Mol. Pharmaceutics 2013, 10, 2568-2577
20. Zhao, M. D.; Hu, F. Q.; Du, Y. Z.; Yuan, H.; Chen, F. Y.; Lou, Y. M.; Yu, H. Y. Coadministration of glycolipid-like micelles loading cytotoxic drug with different action site for efficient cancer chemotherapy Nanotechnology 2009, 20, 055102
21. You, J.; Wang, Z.; Du, Y. Z.; Yuan, H.; Zhang, P.; Zhou, J.; Liu, F.; Li, C.; Hu, F. Q. Specific tumor delivery of paclitaxel using glycolipid-like polymer micelles containing gold nanospheres Biomaterials 2013, 34, 4510-4519
22. Hu, F. Q.; Ren, G. F.; Yuan, H.; Du, Y. Z.; Zeng, S. Shell cross-linked stearic acid grafted chitosan oligosaccharide self-aggregated micelles for controlled release of paclitaxel Colloids Surf. B 2006, 50, 97-103
23. Kohori, F.; Yokoyama, M.; Sakai, K.; Okano, T. Process design for efficient and controlled drug incorporation into polymeric micelle carrier systems J. Controlled Release 2002, 78, 155-163
24. Nogusa, H.; Yano, T.; Okuno, S.; Hamana, H.; Inoue, K. Synthesis of carboxymethylpullulan-peptide-doxorubicin conjugates and their properties Chem. Pharm. Bull. 1995, 43, 1931-1936
25. Lee, K.; Kwon, I.; Kim, Y. H.; Jo, W.; Jeong, S. Preparation of chitosan self-aggregates as a gene delivery system J. Controlled Release 1998, 51, 213-220
26. Zhou, C.; Shen, P.; Cheng, Y. Quantitative study of the drug efflux kinetics from sensitive and MDR human breast cancer cells Biochim. Biophys. Acta 2007, 1770, 1011-1020
27. Tanaka, K.; Kitamura, N.; Chujo, Y. Heavy metal-free 19F NMR probes for quantitative measurements of glutathione reductase activity using silica nanoparticles as a signal quencher Bioorg. Med. Chem. 2012, 20, 96-100
28. Garsky, V. M.; Lumma, P. K.; Feng, D. M.; Wai, J.; Ramjit, H. G.; Sardana, M. K.; Oliff, A.; Jones, R. E.; DeFeo-Jones, D.; Freidinger, R. M. The synthesis of a prodrug of doxorubicin designed to provide reduced systemic toxicity and greater target efficacy J. Med. Chem. 2001, 44, 4216-4224
29. Zou, P.; Yu, Y.; Wang, Y. A.; Zhong, Y.; Welton, A.; Galbán, C.; Wang, S. M.; Sun, D. X. Superparamagnetic iron oxide nanotheranostics for targeted cancer cell imaging and pH-dependent intracellular drug release Mol. Pharmaceutics 2010, 7, 1974-1984
30. Ntziachristos, V.; Bremer, C.; Weissleder, R. Fluorescence imaging with near-infrared light: new technological advances that enable in vivo molecular imaging Eur. Radiol. 2003, 13, 195-208
31. Hu, F. Q.; Liu, L. N.; Du, Y. Z.; Yuan, H. Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles Biomaterials 2009, 30, 6955-6963
32. Holt, G. D.; Hart, G. W. The subcellular distribution of terminal n-acetylglucosamine moieties J. Biol. Chem. 1986, 17, 8049-8057
33. Holt, G. D.; Snow, C. M.; Senior, A.; Haltiwanger, R. S.; Gerace, L.; Hart, G. W. Nuclear pore complex glycoproteins contain cytoplasmically disposed o-Linked n-acetylglucosamine J. Cell Biol. 1987, 104, 1157-1164