Redox-stimuli responsive micelles from DOX-encapsulating polycaprolactone-g-chitosan oligosaccharide

Carbohydrate Polymers

Volumn 112, Issue , 2014, Pages 746-752

  Guerry, Alexandre ^a,b   Cottaz, Sylvain ^a,b   Fleury, Etienne ^c,d,e   Bernard, Julien ^c,d,e   Halila, Sami ^a,b  

^a UNIV GRENOBLE ALPES   (France)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^c UNIVERSITÉ DE LYON   (France)

^d UNIVERSITÉ DE LYON   (France)

^e CNRS   (France)

Author keywords

Chitosan oligosaccharide; Copolymers; Drug delivery; Micelles; Polycaprolactone; Redox stimuli responsive

Indexed keywords

BIODEGRADABILITY; BIODEGRADABLE POLYMERS; CHITOSAN; CONTROLLED DRUG DELIVERY; COPOLYMERS; DRUG DELIVERY; GRAFTING (CHEMICAL); OLIGOSACCHARIDES; PHYSIOLOGICAL MODELS; POLYCAPROLACTONE; RHODIUM COMPOUNDS; SULFUR COMPOUNDS; TARGETED DRUG DELIVERY;

AMPHIPHILIC GRAFT COPOLYMERS; CHITOSAN OLIGOSACCHARIDE; GRAFTED COPOLYMERS; INTRACELLULAR GLUTATHIONE LEVELS; MODIFIED CHITOSAN; STIMULI-RESPONSIVE; STIMULI-RESPONSIVE MICELLES; SYNTHETIC POLYMERS;

MICELLES;

CHITOSAN; DOXORUBICIN; GLUTATHIONE; MICELLE; NANOPARTICLE; OLIGOSACCHARIDE; POLYCAPROLACTONE; POLYESTER;

CHEMISTRY; DRUG DELIVERY SYSTEM; METABOLISM; MICELLE; OXIDATION REDUCTION REACTION;

CHITOSAN; DOXORUBICIN; DRUG DELIVERY SYSTEMS; GLUTATHIONE; MICELLES; NANOPARTICLES; OLIGOSACCHARIDES; OXIDATION-REDUCTION; POLYESTERS;

EID: 84904326840     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2014.06.052     Document Type: Article

References (32)

1. P. Artusso, T. Lindmark, S.S. Davis, and L. Illum Effect of chitosan on the permeability of monolayers of intestinal epithelial cells (Caco-2) Pharmaceutical Research 11 1994 1358 1361 (Pubitemid 24287420)
2. H. Feng, and C.-M. Dong Preparation, characterization, and self-assembled properties of biodegradable chitosan-poly(l-lactide) hybrid amphiphiles Biomacromolecules 7 2006 3069 3075 (Pubitemid 46039962)
3. K.-J. Gao, G. Li, X. Lu, B.-Q. Wu, and J.-H. Fuhrhop Giant vesicle formation through self-assembly of chitooligosaccharide-based graft copolymers Chemical Communications 12 2008 1449 1451 (Pubitemid 351367577)
4. R. Gref, J. Rodrigues, and P. Couvreur Polysaccharides grafted with polyesters: Novel amphiphilic copolymers for biomedical applications Macromolecules 35 2002 9861 9867
5. A. Guerry, J. Bernard, E. Samain, E. Fleury, S. Cottaz, and S. Halila Aniline-catalyzed reductive amination as a powerful method for the preparation of reducing end-"clickable" chitooligosaccharides Bioconjugate Chemistry 24 2013 544 549
6. Y. Haijun, W. Wenshou, C. Xuesi, D. Chao, and J. Xiabin Synthesis and characterization of the biodegradable polycaprolactone-graft-chitosan amphiphilic copolymers Biopolymers 83 2006 233 242
7. A. Haradaa, and K. Kataoka Supramolecular assemblies of block copolymers in aqueous media as nanocontainers relevant to biological applications Progress in Polymer Science 31 2006 949 982 (Pubitemid 44738012)
8. S. Huanli, G. Bingnan, L. Xiaoqing, C. Ru, M. Fenghua, and L. Haiyan et al. Shell-sheddable micelles based on dextran-SS-poly(ε-caprolactone) diblock copolymer for efficient intracellular release of doxorubicin Biomacromolecules 11 2010 848 854
9. E. Kaditi, G. Mountrichas, S. Pispas, and C. Demetzos Block copolymers for drug delivery nano-systems Current Medicinal Chemistry 19 2012 5088 5100
10. B. Khorsand, G. Lapointe, C. Brett, and J.-K. Oh Intracellular drug delivery nanocarriers of glutathione-responsive degradable block copolymers having p disulfide linkages Biomacromolecules 14 2013 2103 2111
11. H.R. Kricheldorf, and S. Eggerstedt Macrocycles 2. Living macrocyclic polymerization of ε-caprolactone with 2,2-dibutyl-2-stanna-1,3-dioxepane as initiator Macromolecular Chemistry and Physics 199 1998 283 290 (Pubitemid 128479189)
12. M.H. Lee, Z. Yang, C.W. Lim, Y.H. Lee, S. Dongbang, and C. Kang et al. Disulfide-cleavage-triggered chemosensors and their biological applications Chemical Reviews 113 2013 5071 5109
13. J. Liu, X. Jiang, L. Xu, X. Wang, W.E. Hennink, and R. Zhuo Novel reduction-responsive cross-linked polyethylenimine derivatives by click chemistry for nonviral gene delivery Bioconjugate Chemistry 21 2010 1827 1835
14. D.S. Manickam, J. Li, D.A. Putt, Q.H. Zhou, C. Wu, and L.H. Lash et al. Effect of innate glutathione levels on activity of redox-responsive gene delivery vectors Journal of Controlled Release 141 2010 77 84
15. R.L. McCarley Redox-responsive delivery systems Annual Review of Analytical Chemistry 5 2012 391 411
16. L. Meng, W. Huang, D. Wang, X. Huang, X. Zhu, and D. Yan Chitosan-based nanocarriers with pH and light dual response for anticancer drug delivery Biomacromolecules 14 2013 2601 2610
17. X. Minghui, Q. Junmin, S. Aili, W. Hongjie, Y. Xueqing, and L. Xuefeng et al. Reduction/pH dual-sensitive PEGylated hyaluronan nanoparticles for targeted doxorubicin delivery Carbohydrate Polymers 98 2013 181 188
18. C. Moyuan, J. Haixia, Y. Weijuan, L. Peng, W. Liqun, and J. Hongliang A convenient scheme for synthesizing reduction-sensitive chitosan-based amphiphilic copolymers for drug delivery Journal of Applied Polymer Science 123 2012 3137 3144
19. S. Mura, J. Nicolas, and P. Couvreur Stimuli-responsive nanocarriers for drug delivery Nature Materials 12 2013 991 1003
20. R. Novoa-Carballal, R. Riguera, and E. Fernandez-Megia Chitosan-based systems for biopharmaceuticals: delivery, targeting and polymer therapeutics B. Sarmento, J. das Neves, Chapter 19: Chitosan copolymers for biopharmaceuticals 2012 John Wiley & Sons, Ltd.
21. X. Qu, A. Wirsen, and A.C. Albertsson Synthesis and characterization of pH-sensitive hydrogels based on chitosan and d,l-lactic acid Journal of Applied Polymer Science 74 1999 3193 3202 (Pubitemid 30538329)
22. I. Richard, M. Thibault, G. De Crescenzo, M.D. Bushmann, and M. Lavertu Ionization behavior of chitosan and chitosan-DNA polyplexes indicate that chitosan has a similar capability to induce a proton-sponge effect as PEI Biomacromolecules 14 2013 1732 1740
23. R. Riva, S. Schmeits, C. Jérôme, R. Jérôme, and P. Lecomte Combination of ring-opening polymerization and "click chemistry": Toward functionalization and grafting of poly(ε- caprolactone) Macromolecules 40 2007 796 803 (Pubitemid 46383725)
24. S. Sanyakamdhorn, D. Agudelo, and H.-A. Tajmir-Riahi Encapsulation of antitumor drug doxorubicin and its analogue by chitosan nanoparticles Biomacromolecules 14 2013 557 563
25. S.K. Shukla, A.K. Mishra, O.A. Arotiba, and B.B. Mamba Chitosan-based nanomaterials: A state-of-the-art review International Journal of Biological Macromolecules 59 2013 46 58
26. S. Sinha, P. Ilankumaran, and S. Chandrasekaran The prop-2-ynyloxy carbonyl function (POC): A new amino-protecting group removable from sulfur-containing peptides by ultrasonic irradiation with tetrathiomolybdate under mild and neutral conditions Tetrahedron Letters 40 1999 771 774 (Pubitemid 29059458)
27. I.A. Sogias, A.C. Williams, and V.V. Khutoryanskiy Why is chitosan mucoadhesive? Biomacromolecules 9 2008 1837 1842
28. Y.-C. Wang, F. Wang, T.-M. Sun, and J. Wang Redox-responsive nanoparticles from the single disulfide bond-bridged block copolymer as drug carriers for overcoming multidrugr in cancer cells Bioconjugate Chemistry 22 2011 1939 1945
29. L. Zhang, S. Wang, M. Zhang, and J. Sun Nanocarriers for oral drug delivery Journal of Drug Targeting 21 2013 515 527
30. Q. Zhang, N.R. Koa, and J.K. Oh Recent advances in stimuli-responsive degradable block copolymer micelles: Synthesis and controlled drug delivery applications Chemical Communications 48 2012 7542 7552
31. F.E. Ziegler, K.W. Fowler, W.B. Rodgers, and R.T. Wester Ambient-temperature Ullman reaction: 4,5,4′,5′-Tetramethoxy-1, 1′-biphenyl-2,2′-dicarboxaldehyde Organic Syntheses 65 1987 108 118
32. L. Zonghua, Z. Ziyong, Z. Changren, and J. Yanpeng Hydrophobic modifications of cationic polymers for gene delivery Progress in Polymer Science 35 2010 1144 1162