Amphiphilic Chitosan Derivatives Research Articles

Cholic acid modified N-(2-hydroxy)-propyl-3-trimethylammonium chitosan chloride for superoxide dismutase delivery

A series of novel amphiphilic chitosan derivatives, cholic acid modified N-(2-hydroxy)-propyl-3-trimethylammonium chitosan chloride (HTCC-CA) with different quaternization degrees and cholic acid substitutions were synthesized in this study. HTCC-CA is biocompatible and forms particles in aqueous solution. The binding with superoxide dismutase (SOD) at pH 6.8 destroys the original aggregates of HTCC-CA and produces smaller SOD/HTCC-CA complex nanoparticles via electrostatic and hydrophobic interactions. The SOD loading efficiency and loading capacity of HTCC-CA can reach to more than 90% and 45%, respectively. Confocal laser scanning microscopy observation and flow cytometry analysis reveal that SOD/HTCC-CA complex nanoparticles greatly enhance the cellular internalization of the loaded SOD. The SOD activities and malonaldehyde concentrations in the serum and organs of the rats, administrated intravenously with free SOD, free HTCC-CA, and SOD/HTCC-CA nanoparticles, were assayed to evaluate the antioxidant efficiency in vivo. The results demonstrate that free HTCC-CA is effective to scavenge superoxide radicals in the blood circulation and SOD/HTCC-CA nanoparticles have better antioxidant efficiency than free SOD as well as free HTCC-CA.

Hydrophobic effect of amphiphilic derivatives of chitosan on the antifungal activity against Aspergillus flavus and Aspergillus parasiticus.

Low molecular weight amphiphilic derivatives of chitosan were synthesized, characterized and their antifungal activities against Aspergillus flavus and Aspergillus parasiticus were tested. The derivatives were synthesized using as starting material a deacetylated chitosan sample in a two step process: the reaction with propyltrimethyl-ammonium bromide (Pr), followed by reductive amination with dodecyl aldehyde. Aiming to evaluate the effect of the hydrophobic modification of the derivatives on the antifungal activity against the pathogens, the degree of substitution (DS1) by Pr groups was kept constant and the proportion of dodecyl (Dod) groups was varied from 7 to 29% (DS2). The derivatives were characterized by 1H-NMR and FTIR and their antifungal activities against the pathogens were tested by the radial growth of the colony and minimum inhibitory concentration (MIC) methods. The derivatives substituted with only Pr groups exhibited modest inhibition against A. flavus and A. parasiticus, like that obtained with deacetylated chitosan. Results revealed that the amphiphilic derivatives grafted with Dod groups exhibited increasing inhibition indexes, depending on polymer concentration and hydrophobic content. At 0.6 g/L, all amphiphilic derivatives having from 7.0 to 29% of Dod groups completely inhibited fungal growth and the MIC values were found to decrease from 4.0 g/L for deacetylated chitosan to 0.25–0.50 g/L for the derivatives. These new derivatives open up the possibility of new applications and avenues to develop effective biofungicides based on chitosan.

Facile synthesis of amphiphilic chitosan‐g‐poly(lactic acid) derivatives and the study of their controlled drug release

We report here a simple and green procedure for the synthesis of amphiphilic chitosan (CS) derivatives with poly(lactic acid) (PLA) side chains, without the use of high pure lactide, high temperatures, or large amounts of organic solvent. The chemical structure and physical properties of these CS derivatives were characterized by Fourier transform infrared spectroscopy, 1H‐NMR, thermogravimetric analysis, and X‐ray diffraction. The formation and characteristics of polymeric micelles based on these CS derivatives were studied by fluorescence spectroscopy and dynamic light scattering. The critical aggregation concentration in water varied from 0.048 to 0.021 mg/mL, and the mean diameter was in the range 169.8–260.7 nm in aqueous solution at 25°C when the PLA grafting percentage increased from 92 to 132%. Transmission electron microscopy showed that the micelles exhibited a nanospheric morphology within a size range of 60–120 nm. For the resulting micellar aggregates, the drug loading and in vitro drug‐release characteristics were studied with indomethacin as the model drug. We found that such micellar aggregates could be potentially used as nanocarriers for drug delivery. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 130: 908‐915, 2013

<I>In Vitro</I> Cell Culture Evaluation and <I>In Vivo</I> Efficacy of Amphiphilic Chitosan for Oral Insulin Delivery

The overall goal of this paper was to enhance the bioavailability of orally delivered insulin. A mucoadhesive amphiphilic chitosan derivative, lauroyl sulphated chitosan (LSCS) was used as the oral carrier for insulin. Trans epithelial electrical resistance experiment was performed on Caco-2 cell monolayers and observed a reduction of TEER after the incubation with the particles. The insulin transport experiment was done with excised rat intestinal tissue using an Ussing chamber and observed an enhanced transport of insulin due to the effect of LSCS. Following oral administration of FITC-insulin loaded LSCS in SD rats; the qualitative biodistribution of the administered drug was investigated using a fluorescence microscopy. The results showed the time dependent distribution of insulin through gastro intestinal tract (GIT). The efficacy of insulin-loaded LSCS sub micro particles (LSCS-ins) was investigated in diabetic rats by measuring the blood glucose level and found to be an effective reduction of the blood glucose level after oral administration of LSCS-ins. The pharmacological availability was found to be 2.5-fold and had a longer pharmacological activity compared with that of native insulin via oral and subcutaneous (sc) routes. The enhanced oral bioavailability of insulin may be associated with a higher release rate in the intestinal juice, enhanced absorption by improved permeability and increased residence time in the intestinal cavity. Thus, encapsulating insulin in LSCS matrix is a promising carrier for sustained and controlled drug delivery with improved bioavailability of insulin for diabetic patients.

Self-assembled nanoparticles based on amphiphilic chitosan derivative and hyaluronic acid for gene delivery

The present work described nanoparticles (NPs) made of oleoyl-carboxymethy-chitosan (OCMCS)/hyaluronic acid (HA) using coacervation process as novel potential carriers for gene delivery. An N/P ratio of 5 and OCMCS/HA weight ratio of 4 were the optimal conditions leading to the smallest (164.94nm), positive charged (+14.2mV) and monodispersed NPs. OCMCS-HA/DNA (OHD) NPs showed higher in vitro DNA release rates and increased cellular uptake by Caco-2 cells due to the HA involved in NPs. The MTT survival assay indicated no significant cytotoxicity. The transfection efficiency of OHD NPs was 5-fold higher than OCMCS/DNA (OD) NPs; however, it decreased significantly in the presence of excess free HA. The results indicated that OHD NPs internalized in Caco-2 cells were mediated by the hyaluronan receptor CD44. The data obtained in the present research gave evidence of the potential of OHD NPs for the targeting and further transfer of genes to the epithelial cells.

Synthesis and characterization of low-toxicity N-caprinoyl-N-trimethyl chitosan as self-assembled micelles carriers for osthole

Novel amphiphilic chitosan derivatives (N-caprinoyl-N-trimethyl chitosan [CA-TMC]) were synthesized by grafting the hydrophobic moiety caprinoyl (CA) and hydrophilic moiety trimethyl chitosan to prepare carriers with good compatibility for poorly soluble drugs. Based on self-assembly, CA-TMC can form micelles with sizes ranging from 136 nm to 212 nm. The critical aggregation concentration increased from 0.6 mg • L−1 to 88 mg • L−1 with decrease in the degree of CA substitution. Osthole (OST) could be easily encapsulated into the CA-TMC micelles. The highest entrapment efficiency and drug loading of OST-loaded CA-TMC micelles(OST/CA-TMC) were 79.1% and 19.1%, respectively. The antitumor efficacy results show that OST/CA-TMC micelles have significant antitumor activity on Hela and MCF-7 cells, with a 50% of cell growth inhibition (IC50) of 35.8 and 46.7 μg. mL−1, respectively. Cell apoptosis was the main effect on cell death of Hela and MCF-7 cells after OST administration. The blank micelles did not affect apoptosis or cell death of Hela and MCF-7 cells. The fluorescence imaging results indicated that OST/CA-TMC micelles could be easily uptaken by Hela and MCF-7 cells and could localize in the cell nuclei. These findings suggest that CA-TMC micelles are promising carriers for OST delivery in cancer therapy.

Surface modification of quantum dots and magnetic nanoparticles with PEG-conjugated chitosan derivatives for biological applications

AbstractIn this paper, amphiphilic chitosan derivatives (N-octyl-N-mPEG-chitosan, mPEG = poly(ethylene glycol) monomethyl ether; OPEGC) were successfully synthesised via the Schiff base reduction reaction of chitosan and mPEG-aldehyde, or octanal, with chitosan acting as the backbone of the grafted copolymers, and mPEG-aldehyde providing the hydrophilic chain or octanal providing the hydrophobic alkyl chain. The synthesis was confirmed by characterisation employing Fourier transform infrared spectroscopy (FTIR) and 1H NMR. In the subsequent procedure, water-soluble quantum dots (QDs) and iron(II,III) oxide (IO) nanoparticles, widely used as nanoprobes in medical applications, were produced by the incorporation of QDs or IO inside the polymeric micelle core. Finally, the optical properties of QDs incorporated into OPEGC (OPEGC@QDs) were characterised by UV-VIS spectroscopy, fluorescence spectroscopy, cell viability was obtained through MTT, and the morphology of their assembly formed in water were observed by atomic force microscope (AFM) and transmission electron microscope (TEM) and the QDs content of OPEGC@QDs was calculated following thermo gravimetric analysis (TGA). In addition, the properties of IO incorporated into OPEGC (OPEGC@IO) were characterised by vibrating sample magnetometry (VSM), FT-IR, MTT, TGA, AFM, and TEM. The results indicated that the OPEGC composite nanoparticles with size narrowly distributed, good water solubility, and low cytotoxicity were prepared here, which represented a high quantum yield or good super-paramagnetism.

Positively Charged Amphiphilic Chitosan Derivative for the Transscleral Delivery of Rapamycin

We explored the potential of an amphiphilic chitosan derivative to facilitate the transscleral delivery of rapamycin, a potential multitherapeutic agent with poor water solubility. The amphiphilic chitosan derivative, O-octanoyl-chitosan-polyethylene glycol (OChiPEG) graft copolymer, was analyzed using Fourier-transform infrared spectroscopy (FT-IR). OChiPEG micelles were prepared via the thin film method and characterized for their size using dynamic light scattering (DLS), zeta potential using laser Doppler velocimetry (LDV), morphology using transmission electron microscopy (TEM), drug entrapment efficiency (EE), and drug loading (DL) efficiency using reversed-phase high performance liquid chromatography (RP-HPLC), critical micelle concentration (CMC) using spectrofluorometry, and thermal properties using differential scanning calorimetry (DSC) and x-ray powder diffraction (XRPD). Scleral permeation and retention of rapamycin from the drug-loaded micelles were determined in porcine sclera clamped in Ussing chambers, using RP-HPLC. Conjugation of hydrophilic and hydrophobic groups to chitosan was confirmed using FT-IR. Rapamycin-loaded micelles of particle size 40.6 nm and zeta potential + 6.84 mV were prepared successfully. These carriers exhibited a high EE and DL of 85.6 and 16.3%, respectively, and a CMC of 16.6 μM. OChiPEG micelles showed a high rapamycin scleral retention (14.8 ± 0.81 μg/g) with successful transscleral permeation (5.57 ± 1.04 × 10(-8) cm(2) · s(-1)). Positively charged OChiPEG micelles loaded with rapamycin were prepared successfully. These showed a high scleral retention and successful permeation of rapamycin, and therefore may be useful for the topical delivery of other hydrophobic agents.

A novel ultrasound-triggered drug vehicle with multimodal imaging functionality

A novel remotely triggered drug vehicle having multimodal imaging functionality was developed. It exhibits magnetic resonance (MR) imaging, ultrasound (US) imaging, encapsulation of a hydrophobic agent and US-triggered release behavior. Lipophilic superparamagnetic iron oxide (SPIO) nanoparticles were self-assembled with an amphiphilic chitosan derivative, carboxymethyl hexanoyl chitosan (CHC), to form superparamagnetic CHC/SPIO micelles and then loaded with camptothecin (a hydrophobic anticancer agent). The superparamagnetic micelles were then conjugated with albumin-based microbubbles (MBs) to form superparamagnetic micelle-decorated MBs (CHC/SPIO-decorated MBs). The albumin MBs and CHC/SPIO-decorated MBs both demonstrated in vitro concentration-dependent US imaging contrast. Interestingly, the in vitro US contrast was enhanced by decoration. In vivo US images showed that the B-mode contrast of the proposed vehicles could be clearly observed in the veins and arteries of Sprague–Dawley rats. Moreover, the proposed vehicle exhibited significant US-triggered release behavior under therapeutic US sonication at a frequency of 1MHz and power density of 2.4Wcm−2 for 30min. However, similar behavior was not observed under diagnostic US bombardment at a frequency of 12MHz and mechanical index of 0.5. On the other hand, in vitro MR images of the CHC/SPIO-micelle-decorated MBs also revealed a significant concentration-dependent T2 (spin–spin relaxation time) contrast due to their decoration with superparamagnetic micelles. Most importantly, the r2∗-r2 value of the CHC/SPIO-decorated MBs decreased after therapeutic US bombardment for 30min. This might be considered as an index to probe destruction of the drug-loaded CHC/SPIO micelles.

SYNTHESIS OF AMPHIPHILIC CHITOSAN DERIVATIVES AND THEIR APPLICATION IN ENCAPSULATION OF QDs

Amphiphilic chitosan derivatives(N-octyl-N-mPEG-chitosan,OPEGC)were successfully synthesized via sequential Schiff base reduction reaction of chitosan with mPEG-aldehyde and n-octanal,with chitosan acting as the backbone of the grafted copolymers,and mPEG-aldehyde providing hydrophilic chain and n-octanal providing hydrophobic alkyl chain,respectively,thereby hydrophobic moiety inclining to segregate into the core of the polymeric micelles,while hydrophilic moiety forming a stabilizing interface between the hydrophobic core and the external medium.The structure of grafted copolymers with both hydrophilic and hydrophobic composition simultaneously was confirmed by characterization employing FTIR and 1H-NMR.In the subsequent procedure,water-soluble quantum dots(QDs),widely used as nanoprobe for medical application,were achieved by incorporation of QDs inside the polymeric micelle core through the hydrophobic interaction between the acyl chain ligand capped on the QDs and the hydrophobic inner core of the polymeric micelles.The size and distribution of the polymeric micelle was determined by dynamic light scattering(DLS),as well the effect of the amount of alkyl chains on the size of the hollow polymeric micelles.The result showed that with grafting level increasing,the size of these nanoparticles diminished accordingly.Moreover,critical micelle concentration(CMC) was determined based on I3/I1 derived from emission spectrum afforded by fluorescence spectroscopy with pyrene as fluorescent probe,with the value of CMC 2.032×10-2mg/mL.At last,the optical properties of OPEGC/QDs were characterized by UV-Vis spectroscopy,fluorescence spectroscopy and the morphology of their assembly formed in water was observed by TEM.The results indicated that the OPEGC/QDs nanoparticles with narrow size distribution were prepared here,which represented good water solubility and high quantum yield.

Removal of cationic dyes from aqueous solutions using N-benzyl-O-carboxymethylchitosan magnetic nanoparticles

Magnetic nanoparticles prepared with iron oxides and N-benzyl-O-carboxymethylchitosan, an amphiphilic chitosan derivative, were prepared through the incorporation method and characterized by Fourier infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), transmission electron microscopy (TEM), Mössbauer spectroscopy, and magnetization measurements. The γ-Fe2O3 nanoparticles proved to be spherical and well crystallized, and some aggregation behavior was observed. The particles containing the polymer presented saturation magnetization of 18.4emug−1 and roughly superparamagnetic behavior. The material was used to adsorb three cationic dyes from aqueous solution (methylene blue, crystal violet, and malachite green). The adsorption process preferably followed the Langmuir–Freundlich isotherm and pseudo-second-order kinetic model. The removal of the dyes was optimized using a 32 factorial design, and the initial dye concentration proved to be more influential in dye adsorption than the temperature of the system.

Stable nanomicelles based on chitosan derivative: In vitro antiplatelet aggregation and adhesion properties

Amphiphilic chitosan derivative (SA-chitosan), water insoluble chitosan modified with salicylic acid (SA), possessed both antiplatelet aggregation and adhesion properties. Chemical structure was characterized by FTIR and 1H NMR. The SA substitution degree calculated by 1H NMR was 70.8%. SA-chitosan can form micelles (size: 292 ± 2 nm). The Critical aggregation concentration (CAC) value (1.216 × 10−4 mg/mL) and zeta potential (52 mV) indicated that they had excellent dispersion stability. TEM image suggested that the micelles were almost spherical. The result of in vitro antiplatelet activity revealed that the potential platelet aggregation inhibitory activity by different agonists was in a dose-dependent manner. At low SA-chitosan concentrations, antiplatelet aggregation capability of SA-chitosan was better than that of low-dose aspirin. The platelet adhesion test showed significant difference between the effect of SA-chitosan and that of the control group (p < 0.05). These results indicated that SA-chitosan can be potentially used as an antiplatelet aggregation and adhesion agent.

Synthesis and characterization of amphiphilic chitosan derivatives as a nano-carrier for paclitaxel delivery

Synthesis and characterization of amphiphilic chitosan derivatives as a nano-carrier for paclitaxel delivery

Preparation and characterization of micelles of oligomeric chitosan linked to all-trans retinoic acid

New amphiphilic chitosan derivatives of all trans retinoic acid–chitosan (RA–chitosan) with different molar feeding ratios of all trans retinoic acid (ATRA) were synthesized. The degree of ATRA substitution ranged from 8.72% to 18.78%. The RA–chitosan formed micelles with an average size of 142.14–208.4 nm, and zeta potential of +27.25 to 34.48 mV. The critical association concentration (CAC) was found to range from 1.3 × 10−2 to 2.13 × 10−2 mg ml−1. Upon evaluation, the RA–chitosan shows no significant cytotoxicity on Hela and HepG2 cells. Analysis of micelles loaded with ATRA revealed that the size of micelles decreased by increasing loaded drug content while zeta potential did not change. ATRA was released slowly over 3-day period, and drug content had no effect on the release rate. These phenomena make RA–chitosan micelles as a candidate for drug carrier.

Submicroparticles composed of amphiphilic chitosan derivative for oral insulin and curcumin release applications

Amphiphilic polymers for dual drug delivery have been a focus of research in recent years. We have previously developed and characterized Lauroyl sulphated chitosan (LSCS). Here biological characterizations like mucoadhesion, cytotoxicity, calcium binding, tight junction opening and enzymatic degradation studies were performed to understand its applicability. In vitro drug release properties of both hydrophilic insulin and hydrophobic curcumin were carried out. The biological activity and stability of released insulin were also studied. The stability studies of encapsulated curcumin and uptake studies have also been carried out. LSCS showed strong mucoadhesion and 100% of non-toxicity. LSCS could transiently open tight junctions between Caco-2 cells and thus increase the paracellular permeability. LSCS enhanced calcium binding properties and decreased enzymatic degradation rate retaining insulin activity. LSCS could protect curcumin from photodegradation and could also enter into the cells. From release studies, LSCS was found to be a suitable candidate for both drugs.

Vesicle formation with amphiphilic chitosan derivatives and a conventional cationic surfactant in mixed systems

The self-assembly behavior of mixed systems consisting of amphiphilic chitosan derivatives Cn-OCMCS (n=4, 6, 8) and the conventional cationic surfactant cetyltrimethylammonium bromide (CTAB) is investigated. Transmission electron microscopy (TEM), dynamic light scattering (DLS), small-angle X-ray diffraction (XRD), UV–vis spectra, and zeta potential measurements have been utilized to characterize the microstructures of Cn-OCMCS/CTAB mixtures in aqueous solutions. Spherical vesicles are formed spontaneously in the Cn-OCMCS (n=4, 6, 8)/CTAB mixed systems, and the increased hydrophobic chain length of Cn-OCMCS enhances the ability to form vesicles. The addition of NaBr with higher concentrations to the vesicle system transforms vesicles into micelles, and an increase in temperature decreases the vesicle size. The results indicate that the main driving forces controlling vesicle formation may be attributed to the strong electrostatic interactions as well as the hydrophobic interactions, and also the hydrogen bonding between Cn-OCMCS molecules.

Synthesis of a Novel Amphiphilic Quaternized Chitosan and Its Distribution in Rats

A novel amphiphilic chitosan derivative, N-[(2-hydroxy-3-N,N-dimethylhexadecyl ammonium)propyl]chitosan chloride (N-CQCs), was prepared with a degree of substitution (DS) of 15.58%. N-CQCs was positively charged and its zeta potential was +28.4 mV. The introduction of a long carbon chain with a quaternary ammonium salt group into the chitosan backbone enabled N-CQCs to be lipotropic and hydrophilic. According to the hypothesis of the hypocholesterolemic effect of N-CQCs, its organ distribution in rats was investigated 48 h after administration via gavage using fluorescein isothiocyanate labeling. N-CQCs showed lower cytotoxicity. The plasma half-life of N-CQCs in rats was 48 h and the plasma AUC0–48 h P was 371.70 μg/ml per h, suggesting that N-CQCs remained in body for a long time. The results also showed that the accumulation in adipose tissue and gastrointestinal tract was higher than in thymus, kidney, liver and spleen at 48 h after administration. It could be presumed that N-CQCs play an important part in the metabolic process of body fat. Adipose tissue and gastrointestinal tract were the probable interaction sites of N-CQCs and body fat.

Characterization of polymer micelles with hemocompatibility based on N-succinyl-chitosan grafting with long chain hydrophobic groups and loading aspirin

Blood compatibility exerts an essential role in designing medical materials. The negative surface charge possessed by N-succinyl-chitosan (SCCS) has the benefit of being nonthrombogenic. To enhance the self-aggregation of SCCS, 2-hydroxy-3-(octadecyloxy)propyl groups (HOP) were employed as hydrophobic groups on SCCS to synthesise amphiphilic chitosan derivatives (HOPSCCS). The degree of succinyl substitution (DS) significantly influenced the water solubility of SCCS. Due to the intermolecular electrostatic attraction, SCCS (H-DS39.1) was water-insoluble, while SCCS (H-DS67.51, 78.6) were water-soluble. The substitution degree of HOP was 0.99–4.05%. The size of HOPSCCS micelles mainly ranged from 117 nm to 194 nm, and their critical micelle concentrations (CMC) were in the range of 1.42–4.24 × 10−3 mg mL−1, and their surface had a negative charge ranging from −27.0 mV to −35.6 mV, suggesting that they possessed excellent stability and dispersion stability which was beneficial to prolong their circulation half-life and reduce the frequency of drug use. Aspirin was encapsulated into HOPSCCS, and the value of maximum drug loading capacity (LC) reached 18.5%, indicating that it can be an effective vehicle for aspirin and a good strategy for the use of aspirin. 1H NMR confirmed the aggregation behaviour of the micelles. Aspirin-loaded HOPSCCS, HOPSCCS/aspirin mixture and the influence of DS of SCCS on order structure were measured by FTIR. Thermal behaviour was determined by DTA/TG. Anticoagulant assays indicated that HOPSCCS had a slight anticoagulant property. Cell toxicity assessment, anticoagulant assays and hemolysis test suggested that HOPSCCS possessed low cytotoxicity and excellent hemocompatibility as a potential drug carrier for systemic administration and therapy of some blood diseases.

Micellar Solubilization and In Vitro Release of Silymarin in the self‐Aggregates of an Amphiphilic Derivative of Chitosan

AbstractSummary: The amphiphilic derivatives of chitosan, (2‐hydroxyl‐3‐butoxyl)‐propylcarboxymethyl‐chitosan (HBP‐CMCHS), can form micelles with the inner core of hydrophobic segments and the outer shell of hydrophilic segments. The typical poor water‐soluble drug silymarin was solubilized in the HBP‐CMCHS micellar by physical entrapped method. Results showed that the solubilizing capacity was enhanced by increasing the concentration of HBP‐CMCHS with the same dosage of silymarin. Silymarin‐loaded micellar system of HBP‐CMCHS was characterized by TEM and DLS. TEM photograph revealed that the micelles were spherical and silymarin was solubilized in the cores of the spherical polymeric micelles. DLS showed that after solubilization the size of the micelles became bigger. In vitro tests showed that silymarin was slowly released from micellar solution and the release lasted up to 40 h by means of the dialysis method.

Enhanced Oral Absorption of Paclitaxel in N-Deoxycholic Acid-N, O-Hydroxyethyl Chitosan Micellar System

The overall goal of this study was to develop a micellar system of paclitaxel (PTX) to enhance its oral absorption. An amphiphilic chitosan derivative, N-deoxycholic acid-N, O-hydroxyethyl chitosan (DHC), was synthesized and characterized by FTIR, (1)H NMR, elemental analysis, and X-ray diffraction (XRD) techniques. The degree of substitution (DS) of hydroxyethyl group and deoxycholic acid group ranged from 89.5-114.5% and 1.11-8.17%, respectively. The critical micelle concentration (CMC) values of DHC decreased from 0.26 to 0.16 mg/mL as the DS of deoxycholic acid group increased. PTX was successfully loaded in DHC micelles with a high drug loading (31.68 ± 0.14%) and entrapment efficiency (77.57 ± 0.51%). The particle size of PTX-loaded DHC micelles ranged from 203.35 ± 2.19 to 236.70 ± 3.40 nm as the DS of deoxycholic acid group increased. After orally administration of PTX-loaded DHC micelles, the bioavailability was threefold compared with that of an orally dosed Taxol®. The single-pass intestinal perfusion studies (SPIP) showed that the intestinal absorption of micelles was via endocytosis involving a saturable process and a p-glycoprotein (P-gp)-independent way. All these indicated that the DHC micelles might be a promising tool for oral delivery of poorly water-soluble drugs.