Online citations, reference lists, and bibliographies.
← Back to Search

Redox-Sensitive Micelles Based On O,N-Hydroxyethyl Chitosan-Octylamine Conjugates For Triggered Intracellular Delivery Of Paclitaxel.

Meirong Huo, Y. Liu, L. Wang, Tingjie Yin, C. Qin, Y. Xiao, L. Yin, Ji-yong Liu, J. Zhou
Published 2016 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
A redox-sensitive micellar system constructed from an O,N-hydroxyethyl chitosan-octylamine (HECS-ss-OA) conjugate with disulfide linkages between the hydrophobic alkyl chains and hydrophilic chitosan backbone was synthesized for triggered intracellular delivery of hydrophobic paclitaxel (PTX). In aqueous environments, conjugates formed micelles with high PTX loading (>30%). Mechanistically, the sensitivity of HECS-ss-OA micelles to reducing environments was investigated using the parameters of in vitro release and particle size. Intracellular release of nile red fluorescence alongside cytotoxicity studies further confirmed the potency of redox-sensitive micelles for intracellular drug delivery compared with redox-insensitive micelles. Additionally, an in vivo study confirmed the efficacy of PTX-loaded micelles in tumor-bearing mice with superior antitumor efficacy and diminished systemic toxicity when compared with the redox-insensitive micelles and a PTX solution. These results demonstrate the potential of redox-sensitive HECS-ss-OA micelles for intracellular trafficking of lipophilic anticancer drugs.
This paper references
10.3109/03639045.2014.913613
Deoxycholic acid-grafted PEGylated chitosan micelles for the delivery of mitomycin C
X. Zhang (2015)
10.4155/tde.14.69
Polymeric nano-micelles: versatile platform for targeted delivery in cancer.
Salma Y. Mohamed (2014)
10.3109/10717544.2013.853708
Synthesis and characterization of chitosan quaternary ammonium salt and its application as drug carrier for ribavirin
Sidong Li (2014)
10.1021/bm5017755
Bioreducible shell-cross-linked hyaluronic acid nanoparticles for tumor-targeted drug delivery.
H. Han (2015)
10.1016/j.ijpharm.2010.05.001
Synthesis and characterization of low-toxic amphiphilic chitosan derivatives and their application as micelle carrier for antitumor drug.
Meirong Huo (2010)
10.1021/bm301424r
Polymer micelle with pH-triggered hydrophobic-hydrophilic transition and de-cross-linking process in the core and its application for targeted anticancer drug delivery.
Jianquan Fan (2012)
10.1016/0003-2697(73)90169-3
A sensitive method for localization of disulfide containing peptides in column effluents.
A. Habeeb (1973)
10.1021/bm5017805
Self-assembling polymer micelle/clay nanodisk/doxorubicin hybrid injectable gels for safe and efficient focal treatment of cancer.
Koji Nagahama (2015)
10.1016/j.micron.2008.01.001
Hydrophobic characterization of intracellular lipids in situ by Nile Red red/yellow emission ratio.
G. Diaz (2008)
10.1016/j.colsurfb.2013.04.023
Fabrication and reduction-sensitive behavior of polyion complex nano-micelles based on PEG-conjugated polymer containing disulfide bonds as a potential carrier of anti-tumor paclitaxel.
Haitao Huang (2013)
10.1517/17425247.2014.893292
Novel self-assembled micelles based on palmitoyl-trimethyl-chitosan for efficient delivery of harmine to liver cancer
Yong-yan Bei (2014)
10.1021/jp310677p
pH-responsive mechanism of a deoxycholic acid and folate comodified chitosan micelle under cancerous environment.
Daiqin Chen (2013)
10.1021/nl902709m
Polymeric nanoparticle-based activatable near-infrared nanosensor for protease determination in vivo.
S. Lee (2009)
10.1016/j.ijpharm.2012.08.042
Polymeric micelles and alternative nanonized delivery vehicles for poorly soluble drugs.
Y. Lu (2013)
10.1016/J.JCONREL.2004.12.009
Thermosensitive and biodegradable polymeric micelles for paclitaxel delivery.
O. Soga (2005)
10.1021/acs.molpharmaceut.5b00280
Well-Defined Redox-Sensitive Polyethene Glycol-Paclitaxel Prodrug Conjugate for Tumor-Specific Delivery of Paclitaxel Using Octreotide for Tumor Targeting.
Tingjie Yin (2015)
10.1016/j.biomaterials.2012.05.052
Somatostatin receptor-mediated tumor-targeting drug delivery using octreotide-PEG-deoxycholic acid conjugate-modified N-deoxycholic acid-O, N-hydroxyethylation chitosan micelles.
Meirong Huo (2012)
10.1002/anie.201006038
A smart polysaccharide/drug conjugate for photodynamic therapy.
S. Park (2011)
10.1021/CM2031569
Polymeric conjugates for drug delivery.
N. Larson (2012)
10.1016/j.msec.2014.09.008
In vitro drug release and biological evaluation of biomimetic polymeric micelles self-assembled from amphiphilic deoxycholic acid-phosphorylcholine-chitosan conjugate.
Minming Wu (2014)
10.1007/s11095-011-0555-x
Comparative Investigations on In Vitro Serum Stability of Polymeric Micelle Formulations
T. Miller (2011)
10.1016/J.CARBPOL.2010.10.073
Formation, microstructure, biodistribution and absence of toxicity of polymeric micelles formed by N-octyl-N,O-carboxymethyl chitosan
Meirong Huo (2011)
10.1016/S0959-8049(01)00171-X
Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation.
H. Gelderblom (2001)
10.1021/la404493n
Dual-stimuli-responsive micelle of an ABC triblock copolymer bearing a redox-cleavable unit and a photocleavable unit at two block junctions.
Juan Xuan (2014)
10.1021/BC9900338
Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate.
Y. Luo (1999)
10.1002/APP.34968
A convenient scheme for synthesizing reduction‐sensitive chitosan‐based amphiphilic copolymers for drug delivery
Cao Mo-yuan (2012)
10.1155/2015/987404
A Redox-Sensitive Micelle-Like Nanoparticle Self-Assembled from Amphiphilic Adriamycin-Human Serum Albumin Conjugates for Tumor Targeted Therapy
L. Chen (2015)
10.1016/j.biomaterials.2015.05.022
Co-delivery of hydrophobic paclitaxel and hydrophilic AURKA specific siRNA by redox-sensitive micelles for effective treatment of breast cancer.
Tingjie Yin (2015)
10.3978/j.issn.2223-4292.2012.05.01
Polysaccharide-based near-infrared fluorescence nanoprobes for cancer diagnosis.
Kyeongsoon Park (2012)
10.1517/17425247.2012.681299
Amphiphilic polymeric micelles as the nanocarrier for peroral delivery of poorly soluble anticancer drugs
Y. Tian (2012)
10.1021/bm100158p
Pharmacokinetics and biodegradation mechanisms of a versatile carboxymethyl derivative of chitosan in rats: in vivo and in vitro evaluation.
Wen Dong (2010)
10.1016/j.colsurfb.2014.06.068
Crosslinked triblock copolymeric micelle for redox-responsive drug delivery.
Yin Lv (2014)
10.1016/j.jconrel.2015.06.013
The studies about doxorubicin-loaded p(N-isopropyl-acrylamide-co-butyl methylacrylate) temperature-sensitive nanogel dispersions on the application in TACE therapies for rabbit VX2 liver tumor.
K. Qian (2015)
10.1016/S0008-6215(00)00182-8
Characterization of doubly substituted polysaccharide derivatives.
A. Senso (2000)
10.1016/j.ijbiomac.2014.10.052
Chitosan-based nanoparticles for tumor-targeted drug delivery.
M. Prabaharan (2015)
10.1016/J.BIOMATERIALS.2007.11.029
Pharmacokinetics, biodistribution, efficacy and safety of N-octyl-O-sulfate chitosan micelles loaded with paclitaxel.
C. Zhang (2008)
10.1016/j.biomaterials.2011.11.022
Redox-sensitive micelles self-assembled from amphiphilic hyaluronic acid-deoxycholic acid conjugates for targeted intracellular delivery of paclitaxel.
J. Li (2012)
10.3109/03639045.2014.935390
Co-delivery of paclitaxel and α-tocopherol succinate by novel chitosan-based polymeric micelles for improving micellar stability and efficacious combination therapy
J. Emami (2015)
10.1098/rsta.2012.0309
Cationic amphiphilic drugs self-assemble to the core–shell interface of PEGylated phospholipid micelles and stabilize micellar structure
J. Wang (2013)
10.1021/acs.biomac.5b00840
Squalenoylation of Chitosan: A Platform for Drug Delivery?
E. Lepeltier (2015)
10.1016/j.colsurfb.2013.10.032
Polymeric micelles with small lipophilic moieties for drug delivery.
D. Li (2014)
10.1016/J.POLYMER.2013.11.035
Preparation of reduction-triggered degradable microcapsules for intracellular delivery of anti-cancer drug and gene
Fuli Feng (2014)
10.1021/mp500723k
Ligand-directed stearic acid grafted chitosan micelles to increase therapeutic efficacy in hepatic cancer.
Y. Yang (2015)
10.1021/cr300358b
Disulfide-cleavage-triggered chemosensors and their biological applications.
M. H. Lee (2013)
10.1021/bm4004805
Intracellular drug delivery nanocarriers of glutathione-responsive degradable block copolymers having pendant disulfide linkages.
Behnoush Khorsand (2013)
10.1088/0957-4484/26/11/115101
Triggered-release polymeric conjugate micelles for on-demand intracellular drug delivery.
Yanwu Cao (2015)
10.1016/j.carbpol.2014.12.039
Synthesis and characterization of pH-responsive N-naphthyl-N,O-succinyl chitosan micelles for oral meloxicam delivery.
Thisirak Woraphatphadung (2015)
10.1083/JCB.100.3.965
Nile red: a selective fluorescent stain for intracellular lipid droplets
P. Greenspan (1985)



This paper is referenced by
10.1002/adtp.202000129
Stimuli‐Responsive Biomaterials for Vaccines and Immunotherapeutic Applications
Noah Pacifici (2020)
10.1016/j.colsurfb.2017.07.063
Drug-loaded pH-responsive polymeric micelles: Simulations and experiments of micelle formation, drug loading and drug release.
Qiu Li (2017)
10.1016/j.addr.2018.05.007
Reduction‐sensitive polymeric nanomedicines: An emerging multifunctional platform for targeted cancer therapy
H. Sun (2018)
10.1016/j.msec.2016.11.030
Internal stimuli-responsive nanocarriers for drug delivery: Design strategies and applications.
Mengrui Liu (2017)
10.1016/j.jconrel.2017.04.043
Smart chemistry-based nanosized drug delivery systems for systemic applications: A comprehensive review.
T. Ramasamy (2017)
10.3390/pharmaceutics10040245
N-(2-Hydroxy)-propyl-3-trimethylammonium, O-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin
D. S. Silva (2018)
10.1016/j.jddst.2020.101523
Stimuli-responsive polymeric micelles for the delivery of paclitaxel
Hao-tong Yang (2020)
10.2217/nnm-2020-0022
pH-responsive PEG-chitosan/iron oxide hybrid nanoassemblies for low-power-assisted PDT/PTT combination therapy.
Guiyang Zhang (2020)
10.1016/j.jconrel.2017.12.033
Amphiphilic polysaccharides as building blocks for self‐assembled nanosystems: molecular design and application in cancer and inflammatory diseases
Xiaoye Yang (2018)
10.1016/j.jcis.2017.02.033
Redox-sensitive self-assembled nanoparticles based on alpha-tocopherol succinate-modified heparin for intracellular delivery of paclitaxel.
Xiaoye Yang (2017)
10.2147/IJN.S201110
Hyaluronic acid-decorated redox-sensitive chitosan micelles for tumor-specific intracellular delivery of gambogic acid
Wei Xu (2019)
10.1007/s12272-017-0995-x
Emerging potential of stimulus-responsive nanosized anticancer drug delivery systems for systemic applications
H. B. Ruttala (2018)
10.1016/j.msec.2018.12.105
Current applications of electrospun polymeric nanofibers in cancer therapy.
Sharjeel Abid (2019)
10.1016/j.msec.2017.03.024
Combinatorial delivery of superparamagnetic iron oxide nanoparticles (γFe2O3) and doxorubicin using folate conjugated redox sensitive multiblock polymeric nanocarriers for enhancing the chemotherapeutic efficacy in cancer cells.
Chetan Nehate (2017)
10.1016/j.ijbiomac.2019.12.145
Chitosan-based advanced materials for docetaxel and paclitaxel delivery: Recent advances and future directions in cancer theranostics.
M. Ashrafizadeh (2019)
10.1039/c6dt04308a
Facile fabrication of a magnetically smart PTX-loaded Cys-Fe3O4/CuS@BSA nano-drug for imaging-guided chemo-photothermal therapy.
L. Ren (2017)
10.1016/J.CARBPOL.2019.03.064
Redox-sensitive micelles based on retinoic acid modified chitosan conjugate for intracellular drug delivery and smart drug release in cancer therapy.
Tingting Luo (2019)
10.1021/ACSAMI.6B09604
Enhanced Cellular Internalization and On-Demand Intracellular Release of Doxorubicin by Stepwise pH-/Reduction-Responsive Nanoparticles.
F. Li (2016)
10.1007/s13233-018-6113-1
Anticancer Effect of Intracellular-Delivered Doxorubicin Using a Redox-Responsive LMWSC-g-Lipoic Acid Micelles
Jun-Hyuk Anh (2018)
10.1016/B978-0-08-101914-6.00001-6
Biocomposites in therapeutic application: Current status and future
Sabyasachi Maiti (2017)
10.1007/s00289-018-2488-6
Photo-responsive polymeric micelles bearing ammonium salts cross-linked for efficient drug delivery
Lili Yu (2018)
10.1002/MACP.201600234
Acid-Labile Copolymer Micelles Cross-Linked by a Twin Ortho Ester Cross-Linking Agent: Synthesis, Characterization, and Evaluation
X. Wang (2016)
10.3390/polym12061397
Stimuli-Responsive Polymeric Nanocarriers for Drug Delivery, Imaging, and Theragnosis
S. Das (2020)
10.1080/10717544.2018.1451571
Development of redox-responsive theranostic nanoparticles for near-infrared fluorescence imaging-guided photodynamic/chemotherapy of tumor
Xiaoye Yang (2018)
10.2147/IJN.S155383
Paclitaxel-loaded redox-sensitive nanoparticles based on hyaluronic acid-vitamin E succinate conjugates for improved lung cancer treatment
Yu Song (2018)
10.1016/J.CARBPOL.2019.115004
Advances in chitosan-based nanoparticles for oncotherapy.
E. Zhang (2019)
Semantic Scholar Logo Some data provided by SemanticScholar