Facile preparation of acid/CO2 stimuli-responsive sheddable nanoparticles based on carboxymethylated chitosan

Weiwei FAN, Jilu WANG, Jiajun FENG, Yong WANG

PDF(1152 KB)
PDF(1152 KB)
Front. Mater. Sci. ›› 2019, Vol. 13 ›› Issue (3) : 296-304. DOI: 10.1007/s11706-019-0469-9
RESEARCH ARTICLE
RESEARCH ARTICLE

Facile preparation of acid/CO2 stimuli-responsive sheddable nanoparticles based on carboxymethylated chitosan

Author information +
History +

Abstract

The present study describes the facile preparation of acid/CO2 stimuli-responsive sheddable nanoparticles based on carboxymethylated chitosan (CMCS). Commercially available CMCS was grafted with monomethoxy polyethylene glycol (mPEG) chains via an acid/CO2 responsive linker, i.e., benzoic-imine, and then was used for the cross-linking with CaCl2. With a high CMCS concentration up to 7 mg/mL, stable nanoparticles were successfully prepared. The particle size grew slightly with increasing the molecular weight of mPEG. When the concentration of CaCl2 and the feed ratio of CMCS to mPEG increased, the particle size decreased at first and then increased after reaching a minimum size. When the particles were stimulated by CO2 or acid, benzoic-imine cleaved quickly, and mPEG fell off the nanoparticles simultaneously, and then flocculation and precipitation occurred. These sheddable nanoparticles might have potential application in the biomedical field including the intelligent drug delivery system.

Keywords

carboxymethylated chitosan / nanoparticles / benzoic-imine / ionic cross-linking / acid-sensitivity

Cite this article

Download citation ▾
Weiwei FAN, Jilu WANG, Jiajun FENG, Yong WANG. Facile preparation of acid/CO2 stimuli-responsive sheddable nanoparticles based on carboxymethylated chitosan. Front. Mater. Sci., 2019, 13(3): 296‒304 https://doi.org/10.1007/s11706-019-0469-9

References

[1]
Wang D, Jin Y, Zhu X, . Synthesis and applications of stimuli-responsive hyperbranched polymers. Progress in Polymer Science, 2017, 64: 114–153
CrossRef Google scholar
[2]
Ganta S, Devalapally H, Shahiwala A, . A review of stimuli-responsive nanocarriers for drug and gene delivery. Journal of Controlled Release, 2008, 126(3): 187–204
CrossRef Pubmed Google scholar
[3]
Lu C, Urban M W. Stimuli-responsive polymer nano-science: Shape anisotropy, responsiveness, applications. Progress in Polymer Science, 2017, 78: 24–46
CrossRef Google scholar
[4]
Sun H, Kabb C P, Sims M B, . Architecture-transformable polymers: Reshaping the future of stimuli-responsive polymers. Progress in Polymer Science, 2019, 89: 61–75
CrossRef Google scholar
[5]
Wei M, Gao Y, Li X, . Stimuli-responsive polymers and their applications. Polymer Chemistry, 2017, 8(1): 127–143
CrossRef Google scholar
[6]
Stuart M A C, Huck W T S, Genzer J, . Emerging applications of stimuli-responsive polymer materials. Nature Materials, 2010, 9(2): 101–113
CrossRef Pubmed Google scholar
[7]
Mura S, Nicolas J, Couvreur P. Stimuli-responsive nanocarriers for drug delivery. Nature Materials, 2013, 12(11): 991–1003
CrossRef Pubmed Google scholar
[8]
Rashidi L, Khosravi-Darani K. The applications of nanotechnology in food industry. Critical Reviews in Food Science and Nutrition, 2011, 51(8): 723–730
CrossRef Pubmed Google scholar
[9]
Fukumura D, Jain R K. Tumor microvasculature and microenvironment: targets for anti-angiogenesis and normalization. Microvascular Research, 2007, 74(2‒3): 72–84PMID:17560615
CrossRef Google scholar
[10]
O’Mary H L, Aldayel A M, Valdes S A, . Acid-sensitive sheddable PEGylated, mannose-modified nanoparticles increase the delivery of betamethasone to chronic inflammation sites in a mouse model. Molecular Pharmaceutics, 2017, 14(6): 1929–1937
CrossRef Pubmed Google scholar
[11]
Du J Z, Du X J, Mao C Q, . Tailor-made dual pH-sensitive polymer-doxorubicin nanoparticles for efficient anticancer drug delivery. Journal of the American Chemical Society, 2011, 133(44): 17560–17563
CrossRef Pubmed Google scholar
[12]
Yang X Z, Du J Z, Dou S, . Sheddable ternary nanoparticles for tumor acidity-targeted siRNA delivery. ACS Nano, 2012, 6(1): 771–781
CrossRef Pubmed Google scholar
[13]
Jiang K, Chi T, Li T, . A smart pH-responsive nano-carrier as a drug delivery system for the targeted delivery of ursolic acid: suppresses cancer growth and metastasis by modulating P53/MMP-9/PTEN/CD44 mediated multiple signaling pathways. Nanoscale, 2017, 9(27): 9428–9439
CrossRef Pubmed Google scholar
[14]
Sun C Y, Shen S, Xu C F, . Tumor acidity-sensitive polymeric vector for active targeted siRNA delivery. Journal of the American Chemical Society, 2015, 137(48): 15217–15224
CrossRef Pubmed Google scholar
[15]
Li S D, Huang L. Nanoparticles evading the reticuloendothelial system: Role of the supported bilayer. Biochimica et Biophysica Acta- Biomembranes, 2009, 1788(10): 2259‒2266 doi:10.1016/j.bbamem.2009.06.022
[16]
Prencipe G, Tabakman S M, Welsher K, . PEG branched polymer for functionalization of nanomaterials with ultralong blood circulation. Journal of the American Chemical Society, 2009, 131(13): 4783–4787
CrossRef Pubmed Google scholar
[17]
Zhao C, Deng H, Xu J, . “Sheddable” PEG-lipid to balance the contradiction of PEGylation between long circulation and poor uptake. Nanoscale, 2016, 8(20): 10832–10842
CrossRef Pubmed Google scholar
[18]
Jin Q, Deng Y, Chen X, . Rational design of cancer nanomedicine for simultaneous stealth surface and enhanced cellular uptake. ACS Nano, 2019, 13(2): 954–977
CrossRef Pubmed Google scholar
[19]
Fan F, Yu Y, Zhong F, . Design of tumor acidity-responsive sheddable nanoparticles for fluorescence/magnetic resonance imaging-guided photodynamic therapy. Theranostics, 2017, 7(5): 1290–1302
CrossRef Pubmed Google scholar
[20]
Romberg B, Hennink W E, Storm G. Sheddable coatings for long-circulating nanoparticles. Pharmaceutical Research, 2008, 25(1): 55–71
CrossRef Pubmed Google scholar
[21]
Li S D, Huang L. Stealth nanoparticles: high density but sheddable PEG is a key for tumor targeting. Journal of Controlled Release, 2010, 145(3): 178–181
CrossRef Pubmed Google scholar
[22]
Bugnicourt L, Ladavière C. Interests of chitosan nanoparticles ionically cross-linked with tripolyphosphate for biomedical applications. Progress in Polymer Science, 2016, 60: 1–17
CrossRef Google scholar
[23]
Qi L, Xu Z, Jiang X, . Preparation and antibacterial activity of chitosan nanoparticles. Carbohydrate Research, 2004, 339(16): 2693–2700
CrossRef Pubmed Google scholar
[24]
Karri V V S R, Kuppusamy G, Talluri S V, . Curcumin loaded chitosan nanoparticles impregnated into collagen-alginate scaffolds for diabetic wound healing. International Journal of Biological Macromolecules, 2016, 93(Pt B): 1519–1529
CrossRef Pubmed Google scholar
[25]
Piras A M, Maisetta G, Sandreschi S, . Chitosan nanoparticles loaded with the antimicrobial peptide temporin B exert a long-term antibacterial activity in vitro against clinical isolates of Staphylococcus epidermidis. Frontiers in Microbiology, 2015, 6: 372 (10 pages)
CrossRef Pubmed Google scholar
[26]
He B, Wu F, Fan L, . Carboxymethylated chitosan protects Schwann cells against hydrogen peroxide-induced apoptosis by inhibiting oxidative stress and mitochondria dependent pathway. European Journal of Pharmacology, 2018, 825: 48–56
CrossRef Pubmed Google scholar
[27]
Liu X F, Guan Y L, Yang D Z, . Antibacterial action of chitosan and carboxymethylated chitosan. Journal of Applied Polymer Science, 2001, 79(7): 1324–1335
CrossRef Google scholar
[28]
Dumont V C, Mansur A A P, Carvalho S M, . Chitosan and carboxymethyl-chitosan capping ligands: Effects on the nucleation and growth of hydroxyapatite nanoparticles for producing biocomposite membranes. Materials Science and Engineering C, 2016, 59: 265–277
CrossRef Pubmed Google scholar
[29]
Dash M, Chiellini F, Ottenbrite R M, . Chitosan — A versatile semi-synthetic polymer in biomedical applications. Progress in Polymer Science, 2011, 36(8): 981–1014
CrossRef Google scholar
[30]
Agnihotri S A, Mallikarjuna N N, Aminabhavi T M. Recent advances on chitosan-based micro- and nanoparticles in drug delivery. Journal of Controlled Release, 2004, 100(1): 5–28
CrossRef Pubmed Google scholar
[31]
Kamat V, Marathe I, Ghormade V, . Synthesis of monodisperse chitosan nanoparticles and in situ drug loading using active microreactor. ACS Applied Materials & Interfaces, 2015, 7(41): 22839–22847
CrossRef Pubmed Google scholar
[32]
Bodnar M, Hartmann J F, Borbely J. Synthesis and study of cross-linked chitosan-N-poly(ethylene glycol) nanoparticles. Biomacromolecules, 2006, 7(11): 3030–3036
CrossRef Pubmed Google scholar
[33]
Bodnar M, Hartmann J F, Borbely J. Preparation and characterization of chitosan-based nanoparticles. Biomacromolecules, 2005, 6(5): 2521–2527
CrossRef Pubmed Google scholar
[34]
Li L, Chen D, Zhang Y, . Magnetic and fluorescent multifunctional chitosan nanoparticles as a smart drug delivery system. Nanotechnology, 2007, 18(40): 405102
CrossRef Google scholar
[35]
Shiomi T, Tsunoda T, Kawai A, . Formation of cage-like hollow spherical silica via a mesoporous structure by calcination of lysozyme-silica hybrid particles. Chemical Communications, 2007, (42): 4404–4406
CrossRef Pubmed Google scholar
[36]
Shiomi T, Tsunoda T, Kawai A, . Synthesis of a cagelike hollow aluminosilicate with vermiculate micro-through-holes and its application to ship-in-bottle encapsulation of protein. Small, 2009, 5(1): 67–71
CrossRef Pubmed Google scholar
[37]
Li L, Choo E S G, Tang X, . A facile one-step route to synthesize cage-like silica hollow spheres loaded with superparamagnetic iron oxide nanoparticles in their shells. Chemical Communications, 2009, (8): 938–940
CrossRef Pubmed Google scholar
[38]
Lu Y, Zhao Y, Yu L, . Hydrophilic Co@Au yolk/shell nanospheres: synthesis, assembly, and application to gene delivery. Advanced Materials, 2010, 22(12): 1407–1411
CrossRef Pubmed Google scholar
[39]
Peng S, Wu C. Light scattering study of the formation and structure of partially hydrolyzed poly(acrylamide)/calcium(II) complexes. Macromolecules, 1999, 32(3): 585–589
CrossRef Google scholar
[40]
Zhu A, Dai S, Li L, . Salt effects on aggregation of O-carboxymethyl chitosan in aqueous solution. Colloids and Surfaces B: Biointerfaces, 2006, 47(1): 20–28
CrossRef Pubmed Google scholar
[41]
Sullivan D J, Cruz-Romero M, Collins T, . Synthesis of monodisperse chitosan nanoparticles. Food Hydrocolloids, 2018, 83: 355–364
CrossRef Google scholar
[42]
Song N, Ding M, Pan Z, . Construction of targeting-clickable and tumor-cleavable polyurethane nanomicelles for multifunctional intracellular drug delivery. Biomacromolecules, 2013, 14(12): 4407–4419
CrossRef Pubmed Google scholar
[43]
Gu J, Cheng W P, Liu J, . pH-triggered reversible “stealth” polycationic micelles. Biomacromolecules, 2008, 9(1): 255–262
CrossRef Pubmed Google scholar
[44]
Kim J W, Cochran F V, Cochran J R. A chemically cross-linked knottin dimer binds integrins with picomolar affinity and inhibits tumor cell migration and proliferation. Journal of the American Chemical Society, 2015, 137(1): 6–9
CrossRef Pubmed Google scholar
[45]
Malhotra M, Tomaro-Duchesneau C, Saha S, . Development and characterization of chitosan‒PEG‒TAT nanoparticles for the intracellular delivery of siRNA. International Journal of Nanomedicine, 2013, 8: 2041–2052
Pubmed
[46]
Lin Y S, Abadeer N, Haynes C L. Stability of small mesoporous silica nanoparticles in biological media. Chemical Communications, 2011, 47(1): 532–534
CrossRef Pubmed Google scholar
[47]
Xiao R Z, Zeng Z W, Zhou G L, . Recent advances in PEG‒PLA block copolymer nanoparticles. International Journal of Nanomedicine, 2010, 5: 1057–1065
Pubmed

Acknowledgements

This work was supported by the Natureal Science Foundation of Hubei Province (2016CFB329), the Science and Technology Research Program of Hubei Provincial Department of Education (B2016260), and the Scientific Research and Technological Development Program of Jingmen City (YFYB2016021).

RIGHTS & PERMISSIONS

2019 Higher Education Press and Springer-Verlag GmbH Germany, part of Springer Nature
AI Summary AI Mindmap
PDF(1152 KB)

Accesses

Citations

Detail

Sections
Recommended

/