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

doi:10.1007/s11706-019-0469-9

Frontiers of Materials Science

2019, Vol. 13

Issue (3): 296-304 https://doi.org/10.1007/s11706-019-0469-9

本期目录

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

Weiwei FAN(

), Jilu WANG, Jiajun FENG, Yong WANG

Hubei Collaborative Innovation Center of Targeted Antitumor Drug, College of Chemical Engineering and Pharmacy, Jingchu University of Technology, Jingmen 448000, China

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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.

Key words： carboxymethylated chitosan nanoparticles benzoic-imine ionic cross-linking acid-sensitivity

收稿日期: 2019-05-04 出版日期: 2019-09-29

Corresponding Author(s): Weiwei FAN

引用本文:

. [J]. Frontiers of Materials Science, 2019, 13(3): 296-304.
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.

链接本文:

https://academic.hep.com.cn/foms/CN/10.1007/s11706-019-0469-9
https://academic.hep.com.cn/foms/CN/Y2019/V13/I3/296

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1	D Wang, Y Jin, X Zhu, et al.. Synthesis and applications of stimuli-responsive hyperbranched polymers. Progress in Polymer Science, 2017, 64: 114–153 https://doi.org/10.1016/j.progpolymsci.2016.09.005
2	S Ganta, H Devalapally, A Shahiwala, et al.. A review of stimuli-responsive nanocarriers for drug and gene delivery. Journal of Controlled Release, 2008, 126(3): 187–204 https://doi.org/10.1016/j.jconrel.2007.12.017 pmid: 18261822
3	C Lu, M W Urban. Stimuli-responsive polymer nano-science: Shape anisotropy, responsiveness, applications. Progress in Polymer Science, 2017, 78: 24–46 https://doi.org/10.1016/j.progpolymsci.2017.07.005
4	H Sun, C P Kabb, M B Sims, et al.. Architecture-transformable polymers: Reshaping the future of stimuli-responsive polymers. Progress in Polymer Science, 2019, 89: 61–75 https://doi.org/10.1016/j.progpolymsci.2018.09.006
5	M Wei, Y Gao, X Li, et al.. Stimuli-responsive polymers and their applications. Polymer Chemistry, 2017, 8(1): 127–143 https://doi.org/10.1039/C6PY01585A
6	M A C Stuart, W T S Huck, J Genzer, et al.. Emerging applications of stimuli-responsive polymer materials. Nature Materials, 2010, 9(2): 101–113 https://doi.org/10.1038/nmat2614 pmid: 20094081
7	S Mura, J Nicolas, P Couvreur. Stimuli-responsive nanocarriers for drug delivery. Nature Materials, 2013, 12(11): 991–1003 https://doi.org/10.1038/nmat3776 pmid: 24150417
8	L Rashidi, K Khosravi-Darani. The applications of nanotechnology in food industry. Critical Reviews in Food Science and Nutrition, 2011, 51(8): 723–730 https://doi.org/10.1080/10408391003785417 pmid: 21838555
9	D Fukumura, R K Jain. Tumor microvasculature and microenvironment: targets for anti-angiogenesis and normalization. Microvascular Research, 2007, 74(2‒3): 72–84 PMID:17560615 https://doi.org/10.1016/j.mvr.2007.05.003
10	H L O’Mary, A M Aldayel, S A Valdes, et al.. 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 https://doi.org/10.1021/acs.molpharmaceut.7b00024 pmid: 28463518
11	J Z Du, X J Du, C Q Mao, et al.. Tailor-made dual pH-sensitive polymer-doxorubicin nanoparticles for efficient anticancer drug delivery. Journal of the American Chemical Society, 2011, 133(44): 17560–17563 https://doi.org/10.1021/ja207150n pmid: 21985458
12	X Z Yang, J Z Du, S Dou, et al.. Sheddable ternary nanoparticles for tumor acidity-targeted siRNA delivery. ACS Nano, 2012, 6(1): 771–781 https://doi.org/10.1021/nn204240b pmid: 22136582
13	K Jiang, T Chi, T Li, et al.. 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 https://doi.org/10.1039/C7NR01677H pmid: 28660943
14	C Y Sun, S Shen, C F Xu, et al.. Tumor acidity-sensitive polymeric vector for active targeted siRNA delivery. Journal of the American Chemical Society, 2015, 137(48): 15217–15224 https://doi.org/10.1021/jacs.5b09602 pmid: 26571079
15	S D Li, L Huang. 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	G Prencipe, S M Tabakman, K Welsher, et al.. PEG branched polymer for functionalization of nanomaterials with ultralong blood circulation. Journal of the American Chemical Society, 2009, 131(13): 4783–4787 https://doi.org/10.1021/ja809086q pmid: 19173646
17	C Zhao, H Deng, J Xu, et al.. “Sheddable” PEG-lipid to balance the contradiction of PEGylation between long circulation and poor uptake. Nanoscale, 2016, 8(20): 10832–10842 https://doi.org/10.1039/C6NR02174C pmid: 27167180
18	Q Jin, Y Deng, X Chen, et al.. Rational design of cancer nanomedicine for simultaneous stealth surface and enhanced cellular uptake. ACS Nano, 2019, 13(2): 954–977 https://doi.org/10.1021/acsnano.8b07746 pmid: 30681834
19	F Fan, Y Yu, F Zhong, et al.. Design of tumor acidity-responsive sheddable nanoparticles for fluorescence/magnetic resonance imaging-guided photodynamic therapy. Theranostics, 2017, 7(5): 1290–1302 https://doi.org/10.7150/thno.18557 pmid: 28435466
20	B Romberg, W E Hennink, G Storm. Sheddable coatings for long-circulating nanoparticles. Pharmaceutical Research, 2008, 25(1): 55–71 https://doi.org/10.1007/s11095-007-9348-7 pmid: 17551809
21	S D Li, L Huang. Stealth nanoparticles: high density but sheddable PEG is a key for tumor targeting. Journal of Controlled Release, 2010, 145(3): 178–181 https://doi.org/10.1016/j.jconrel.2010.03.016 pmid: 20338200
22	L Bugnicourt, C Ladavière. Interests of chitosan nanoparticles ionically cross-linked with tripolyphosphate for biomedical applications. Progress in Polymer Science, 2016, 60: 1–17 https://doi.org/10.1016/j.progpolymsci.2016.06.002
23	L Qi, Z Xu, X Jiang, et al.. Preparation and antibacterial activity of chitosan nanoparticles. Carbohydrate Research, 2004, 339(16): 2693–2700 https://doi.org/10.1016/j.carres.2004.09.007 pmid: 15519328
24	V V S R Karri, G Kuppusamy, S V Talluri, et al.. Curcumin loaded chitosan nanoparticles impregnated into collagen-alginate scaffolds for diabetic wound healing. International Journal of Biological Macromolecules, 2016, 93(Pt B): 1519–1529 https://doi.org/10.1016/j.ijbiomac.2016.05.038 pmid: 27180291
25	A M Piras, G Maisetta, S Sandreschi, et al.. 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) https://doi.org/10.3389/fmicb.2015.00372 pmid: 25972852
26	B He, F Wu, L Fan, et al.. 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 https://doi.org/10.1016/j.ejphar.2018.02.024 pmid: 29462593
27	X F Liu, Y L Guan, D Z Yang, et al.. Antibacterial action of chitosan and carboxymethylated chitosan. Journal of Applied Polymer Science, 2001, 79(7): 1324–1335 https://doi.org/10.1002/1097-4628(20010214)79:7<1324::AID-APP210>3.0.CO;2-L
28	V C Dumont, A A P Mansur, S M Carvalho, et al.. 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 https://doi.org/10.1016/j.msec.2015.10.018 pmid: 26652373
29	M Dash, F Chiellini, R M Ottenbrite, et al.. Chitosan — A versatile semi-synthetic polymer in biomedical applications. Progress in Polymer Science, 2011, 36(8): 981–1014 https://doi.org/10.1016/j.progpolymsci.2011.02.001
30	S A Agnihotri, N N Mallikarjuna, T M Aminabhavi. Recent advances on chitosan-based micro- and nanoparticles in drug delivery. Journal of Controlled Release, 2004, 100(1): 5–28 https://doi.org/10.1016/j.jconrel.2004.08.010 pmid: 15491807
31	V Kamat, I Marathe, V Ghormade, et al.. Synthesis of monodisperse chitosan nanoparticles and in situ drug loading using active microreactor. ACS Applied Materials & Interfaces, 2015, 7(41): 22839–22847 https://doi.org/10.1021/acsami.5b05100 pmid: 26448128
32	M Bodnar, J F Hartmann, J Borbely. Synthesis and study of cross-linked chitosan-N-poly(ethylene glycol) nanoparticles. Biomacromolecules, 2006, 7(11): 3030–3036 https://doi.org/10.1021/bm0605053 pmid: 17096528
33	M Bodnar, J F Hartmann, J Borbely. Preparation and characterization of chitosan-based nanoparticles. Biomacromolecules, 2005, 6(5): 2521–2527 https://doi.org/10.1021/bm0502258 pmid: 16153088
34	L Li, D Chen, Y Zhang, et al.. Magnetic and fluorescent multifunctional chitosan nanoparticles as a smart drug delivery system. Nanotechnology, 2007, 18(40): 405102 https://doi.org/10.1088/0957-4484/18/40/405102
35	T Shiomi, T Tsunoda, A Kawai, et al.. Formation of cage-like hollow spherical silica via a mesoporous structure by calcination of lysozyme-silica hybrid particles. Chemical Communications, 2007, (42): 4404–4406 https://doi.org/10.1039/b709534a pmid: 17957301
36	T Shiomi, T Tsunoda, A Kawai, et al.. 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 https://doi.org/10.1002/smll.200800834 pmid: 19040212
37	L Li, E S G Choo, X Tang, et al.. 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 https://doi.org/10.1039/B817937A pmid: 19214322
38	Y Lu, Y Zhao, L Yu, et al.. Hydrophilic Co@Au yolk/shell nanospheres: synthesis, assembly, and application to gene delivery. Advanced Materials, 2010, 22(12): 1407–1411 https://doi.org/10.1002/adma.200903298 pmid: 20437492
39	S Peng, C Wu. Light scattering study of the formation and structure of partially hydrolyzed poly(acrylamide)/calcium(II) complexes. Macromolecules, 1999, 32(3): 585–589 https://doi.org/10.1021/ma9809031
40	A Zhu, S Dai, L Li, et al.. Salt effects on aggregation of O-carboxymethyl chitosan in aqueous solution. Colloids and Surfaces B: Biointerfaces, 2006, 47(1): 20–28 https://doi.org/10.1016/j.colsurfb.2005.11.020 pmid: 16387481
41	D J Sullivan, M Cruz-Romero, T Collins, et al.. Synthesis of monodisperse chitosan nanoparticles. Food Hydrocolloids, 2018, 83: 355–364 https://doi.org/10.1016/j.foodhyd.2018.05.010
42	N Song, M Ding, Z Pan, et al.. Construction of targeting-clickable and tumor-cleavable polyurethane nanomicelles for multifunctional intracellular drug delivery. Biomacromolecules, 2013, 14(12): 4407–4419 https://doi.org/10.1021/bm401342t pmid: 24219322
43	J Gu, W P Cheng, J Liu, et al.. pH-triggered reversible “stealth” polycationic micelles. Biomacromolecules, 2008, 9(1): 255–262 https://doi.org/10.1021/bm701084w pmid: 18095651
44	J W Kim, F V Cochran, J R Cochran. 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 https://doi.org/10.1021/ja508416e pmid: 25486381
45	M Malhotra, C Tomaro-Duchesneau, S Saha, et al.. Development and characterization of chitosan‒PEG‒TAT nanoparticles for the intracellular delivery of siRNA. International Journal of Nanomedicine, 2013, 8: 2041–2052 pmid: 23723699
46	Y S Lin, N Abadeer, C L Haynes. Stability of small mesoporous silica nanoparticles in biological media. Chemical Communications, 2011, 47(1): 532–534 https://doi.org/10.1039/C0CC02923H pmid: 21082109
47	R Z Xiao, Z W Zeng, G L Zhou, et al.. Recent advances in PEG‒PLA block copolymer nanoparticles. International Journal of Nanomedicine, 2010, 5: 1057–1065 pmid: 21170353

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