PCL Copolymer Research Articles

Semiaromatic Polyester-Ethers with Tunable Degradation Profiles.

Poly(ε-caprolactone) (PCL) is a widely utilized polymer within the biomedical field; however, one of its limitations is the multi-year long degradation profile. Herein, we report a semiaromatic polyester-ether (SAEE) PCL copolymer using a salicylic acid-based monomer which can disrupt the semicrystalline nature of the bulk material. The molar percentage of incorporation correlated to a linear decrease in melting and crystallization temperature, until a totally amorphous solid was seen at 37 mol %. Alongside this, mechanical analysis elucidated a softer, more extensible material with E' decreasing from 292 to 222 to 43.8 MPa for PCL to 10 to 22 mol % SAEE, respectively. Accelerated basic degradation studies (2 M NaOH) exhibited total mass loss after 16 weeks for 6 mol % compared to only 38% mass loss for PCL over the same period. Overall, by varying the SAEE mol %, we show the ability to finely tune the thermal, mechanical, and degradation profiles of PCL copolymers while maintaining an advantageous biological profile.

Melt electrowriting of a biocompatible photo-crosslinkable poly(D,L-lactic acid)/poly(ε-caprolactone)-based material with tunable mechanical and functionalization properties.

The use of polymeric biomaterials to create tissue scaffolds using additive manufacturing techniques is a well-established practice, owing to the incredible rapidity and complexity in design that modern 3D printing methods can provide. One frontier approach is melt electrowriting (MEW), a technique that takes advantage of electrohydrodynamic phenomena to produce fibers on the scale of 10's of microns with designs capable of high resolution and accuracy. Poly(ε-caprolactone) (PCL) is a material that is commonly used in MEW due to its favorable thermal properties, high stability, and biocompatibility. However, one of the drawbacks of this material is that it lacks the necessary chemical groups which allow covalent crosslinking of additional elements onto its structure. Attempts to functionalise PCL structures therefore often rely on the functional units to be applied externally via coatings or integrally mixed elements. Both can be extremely useful depending on their applications, but can add extra difficulties into the use of the resulting structures. Coatings require careful design and application to prevent rapid degradation, while elements mixed into the polymer melt must deal with the possibilities of phase separation and changes to MEW properties of the unadulterated polymer. With this in mind, this study sought to imbibe functionality to MEW-printed scaffolds using the approach of adding functional units directly, via covalent bonding of functional groups to the polymer itself. To this end, this study employs a recently developed class of polymers called acrylate-endcapped urethane-based polymers (AUPs). The polymer backbone of the specific AUP used consists of a poly(D,L-lactic acid) (PDLLA)/PCL copolymer chain, which is functionalized with 6 acrylate groups, 3 at either end. Through blending of the AUP with PCL, various concentrations of this mixture were used with MEW to produce scaffolds that possessed acrylate groups on their surface. Using UV crosslinking, these groups were tagged with Fluorescein-o-Acrylate to verify that PDLLA/PCL AUP/PCL blends facilitate the direct covalent bonding of external agents directly onto the MEW material. Blending of the AUP with PCL increases the scaffold's stiffness and ultimate strength. Finally, blends were proven to be highly biocompatible, with cells attaching and proliferating readily at day 3 and 7 post seeding. Through this work, PDLLA/PCL AUP/PCL blends clearly demonstrated as a biocompatible material that can be processed using MEW to create functionalised tissue scaffolds.

Relaxation behaviour and free volume of bio-based Poly(trimethylene terephthalate)-block-poly(caprolactone) copolymers as revealed by Broadband Dielectric and Positron Annihilation Lifetime Spectroscopies

Broadband Dielectric (BDS) and Positron Annihilation Lifetime Spectroscopies (PALS) have been used to investigate the relaxation behaviour of novel bio-based aliphatic-aromatic block copolymers based on poly (trimethylene terephthalate) (PTT) and poly (caprolactone) (PCL). Copolymerization increases the ability to crystallize of the PTT-block-PCL copolymers in relation to PTT due to a decrease of the glass transition (Tg) temperatures as the amount PCL increases since PCL acts as plasticizer. The dielectric relaxation of the PTT-block -PCL copolymers is dominated by that of PTT being characterized by a α relaxation process above Tg and a bimodal β relaxation below Tg. The faster mode of the β relaxation has been assigned to the bond between the ester oxygen and the aliphatic carbon of the PTT block and the slower β mode has been attributed to the bond between the aromatic ring carbon to the ester carbon also in the PTT block. Both modes for the copolymers appear to be faster than those of PTT at comparable temperatures while for the copolymer series a nearly similar subglass dynamics is observed. Since free volume values for PTT and PTT-block-PCL (75/25) as measured by PALS are very similar and those for the copolymers increase with PCL content this effect is likely to be attributed to change in the flexibility of the polymeric chain upon going from PTT to the copolymers rather than to a free volume dependence confirming the local nature, i.e. non cooperative, of the β relaxation. The weak dependence of the β relaxation dynamics with PCL content for the copolymers suggests that this relaxation is mainly related to the PTT block. The α relaxation becomes faster the higher the PCL content is following the decrease of the Tg with increasing PCL content. This effect is supported by the free volume and o-Ps annihilation life time for the block copolymers measured by PALS at room temperature revealing an increase of both magnitudes with PCL content. By scaling free volume and o-Ps annihilation life time with Troom-Tg, being Tg the corresponding glass transition temperature for every copolymer, a characteristic sigmoidal variation with temperature is observed.

Highly Stretchable, Ultratough, and Multifunctional Poly(vinyl chloride)-Based Plastics via a Green, Star-Shaped Macromolecular Additive

As one of the most prolifically produced plastics in the world, poly(vinyl chloride) (PVC) suffers from mechanical brittleness and low toughness. Compared with traditional phthalate-type plasticizers, poly(e-caprolactone) (PCL)-based plasticizers are especially attractive due to their “green” nature and capabilities to achieve improved physical properties. Herein, a stretchable and ultratough PVC-based plastic was achieved by a star-shaped PCL copolymer with a rigid, amino-containing, branched polylactide (N-BPLA) core and a soft PCL shell, that is, RN-SPCLs. With an optimal feed ratio of the CL monomer and N-BPLA core, the RN-SPCL2 can efficiently lower the glass transition temperature (Tg) of PVC plastics, achieving the transition from the “glassy” to “rubbery” state at ambient temperature. The obtained RN-SPCL2/PVC not only shows high extensibility, that is, 453%, but also maintains close to 80% of tensile strength of neat PVC, that is, 30.1 MPa, which is much higher than the previously reported plasticized PVCs. Its overall toughness reaches 92.7 MJ/m³, being more than 50-fold higher than neat PVC and 2 to 3 times higher than linear PCL or dibutyl phthalate plasticized PVCs. The important role of star-shaped architecture with a rigid core and flexible PCL shell for RN-SPCL2 in achieving highly stretchable and ultratough PVC plastics is systematically investigated. More interestingly, the as-prepared RN-SPCLs also endow PVC plastics with photoluminescence property and allow homogeneous dispersion of nanosized TiO₂ for significantly enhancing the anti-UV capability.

Water-responsive shape memory PLLA via incorporating PCL-(PMVS-s-PAA)-PCL-PTMG-PCL-(PMVS-s-PAA)-PCL

Poly(L-lactide) (PLLA) was one of the most well-known biodegradable polyesters. Although its thermo-responsive shape memory (SM) function has been studied by proper program, high transformation temperature is not suitable in some biomedical applications. Water-responsive SM polymer is an alternative choice and exhibits great potential because it is harmless to the cells and tissues of organisms. In the work, a novel PCL-(PMVS-s-PAA)-PCL-PTMG-PCL-(PMVS-s-PAA)-PCL copolymer was devised as an additive to endow PLLA with water-responsive SM capability. The incorporated PLLA was characterized by cross-section, water contact angle, differential scanning calorimetry (DSC) and dynamic mechanical analysis (DMA). Inserted PTMG segment and assisted ambient temperature were contributed to its SM behaviors. The shape fixation ratio and shape recovery ratio were 92.0% and 94.2%, respectively. The schematic diagram between internal microstructures and macroscopic properties was proposed. At the same time, the incorporated PLLA showed excellent toughness. So the obtained SM material would be promising for medical and biomimetic fields.

DDAB cationic lipid-mPEG, PCL copolymer hybrid nano-carrier synthesis and application for delivery of siRNA targeting IGF-1R into breast cancer cells.

To use siRNA molecule as a therapeutic agent in gene silencing, an efficient delivery system is necessary. Stability and clearance by reticuloendothelial of siRNA still remains the major challenges for clinical application. Herein, we could develop new lipid-polymer hybrid nanoparticles (LPHNP) as a siRNA carrier to silence insulin-like growth factor type I (IGF-1R) gene overexpression in MCF-7 human breast cancer cell line. Dimethyldioctadecylammonium bromide-methoxy poly(ethylene glycol)-poly (ε-caprolactone) (DDAB-mPEG-PCL) LPHNPs were synthesized using a single step nanoprecipitation method and characterized by dynamic light scattering (DLS) and atomic force microscopy (AFM) microscope. Cytotoxicity of the nanoparticles was assessed in the MCF7 cell line using 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. Desired LPHNP-siRNA complex was determined using different Nitrogen:Phosphate ratio (N/P) ratios and gel retardation. To determine the encapsulation efficiency of siRNA (%) in LPHNP, its absorbance was measured. The effect of the siRNA-LPHNP complex on IGF-1R silencing was assessed by reverse transcription-polymerase chain reaction (RT-PCR) RESULTS: LPHNP was synthesized using a single-step sonication method with a size below 100nM. The viability of cells treated with hybrid nanoparticles was significantly greater than the corresponding cationic lipid (P < 0.01). As demonstrated by gel retardation assay, efficient siRNA binding to LPHNP occurred at N/P equal to 40 and siRNA encapsulation efficiency was found to be 95% ± 4 at this ratio. LPHNP-IGF-1R siRNA complex could be able to down-regulate the target more efficiently when it compared with the corresponded controls (P < 0.001). In conclusion, our results suggest that DDAB cationic lipid and mPEG-PCL copolymer hybrid nanoparticle may be a good candidate for efficient siRNA delivery.

Synthesis of PCL–PEG–PCL Triblock Copolymer via Organocatalytic Ring-Opening Polymerization and Its Application as an Injectable Hydrogel—An Interdisciplinary Learning Trial

Biocompatible and biodegradable block copolymers composed of poly(ethylene glycol) (PEG) and aliphatic polyester are a class of promising biomaterials. Herein, a teaching experiment was designed to furnish undergraduates with a reliable method to synthesize an amphiphilic poly(e-caprolactone)-PEG-poly(e-caprolactone) (PCL–PEG–PCL) triblock copolymer via ring-opening polymerization of e-caprolactone using PEG as the macroinitiator and diphenyl phosphate as the green organocatalyst; the concentrated solution of synthetic polymer in water was then demonstrated as an injectable thermogel with a sol–gel transition upon heating. Ten students serving as volunteers successfully synthesized PCL–PEG–PCL copolymer, and then analyzed their specimens using various techniques including proton-nuclear magnetic resonance spectroscopy, gel permeation chromatography, differential scanning calorimetry, and X-ray diffraction and learned the principles of instruments. Finally, students prepared an aqueous polymer solution, and observed its interesting spontaneous physical gelation upon heating via the tube-inverting approach and dynamic rheological analysis. The experimental features captured the students’ attention and made them more enthusiastic participants. This newly designed teaching experiment afforded senior undergraduates an excellent opportunity to consolidate basic concepts and principles in books with practical experimental sessions in the field of polymer chemistry, analytical chemistry, and materials science.

Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release.

Polymeric micelles (PMs) have been used to improve the poor aqueous solubility, slow absorption and non-selective biodistribution of chemotherapeutic agents (CAs), albeit, they suffer from disassembly and premature release of payloads in the bloodstream. To alleviate the thermodynamic instability of PMs, different core crosslinking approaches were employed. Herein, we synthesized the poly(ethylene oxide)-b-poly((2-aminoethyl)diselanyl)ethyl l-aspartamide)-b-polycaprolactone (mPEG-P(LA-DSeDEA)-PCL) copolymer which self-assembled into monodispersed nanoscale, 156.57 ± 4.42 nm, core crosslinked micelles (CCMs) through visible light-induced diselenide metathesis reaction between the pendant selenocystamine moieties. The CCMs demonstrated desirable doxorubicin (DOX)-loading content (7.31%) and encapsulation efficiency (42.73%). Both blank and DOX-loaded CCMs (DOX@CCMs) established appreciable colloidal stability in the presence of bovine serum albumin (BSA). The DOX@CCMs showed redox-responsive drug releasing behavior when treated with 5 and 10 mM reduced glutathione (GSH) and 0.1% H2O2. Unlike the DOX-loaded non-crosslinked micelles (DOX@NCMs) which exhibited initial burst release, DOX@CCMs demonstrated a sustained release profile in vitro where 71.7% of the encapsulated DOX was released within 72 h. In addition, the in vitro fluorescent microscope images and flow cytometry analysis confirmed the efficient cellular internalization of DOX@CCMs. The in vitro cytotoxicity test on HaCaT, MDCK, and HeLa cell lines reiterated the cytocompatibility (≥82% cell viability) of the mPEG-P(LA-DSeDEA)-PCL copolymer and DOX@CCMs selectively inhibit the viabilities of 48.85% of HeLa cells as compared to 15.75% of HaCaT and 7.85% of MDCK cells at a maximum dose of 10 µg/mL. Overall, all these appealing attributes make CCMs desirable as nanocarriers for the delivery and controlled release of DOX in tumor cells.

Microwave‐assisted in situ polymerization of polycaprolactone/boron nitride composites with enhanced thermal conductivity and mechanical properties

AbstractPolycaprolactone/boron nitride (PCL/BN) composites were prepared by microwave‐assisted ring‐opening polymerization of ε‐caprolactone (ε‐CL). In order to improve the dispersibility and interfacial interaction between BN fillers and PCL matrix, hydroxyl functional BN (mBN) was first prepared to be used as a macroinitiator for ε‐CL. Then BN grafted PCL (BN‐g‐PCL) copolymers were obtained via the in situ method, which acted as in situ compatibilizers in the PCL/BN composites. Various techniques were applied to characterize the mBN and PCL/BN composites. The Fourier transform infrared spectroscopy results confirm the structure of the BN‐g‐PCL copolymer. Field emission SEM graphs exhibit that, for the PCL/mBN composites, the mBN presents a homogeneous dispersion in the matrix and interfacial adhesion between the PCL and mBN is improved. These are beneficial for enhancing the thermal conductivity of the PCL/mBN composites. Notably, the PCL/mBN composite with 5 wt% mBN loading achieves the highest thermal conductivity of 0.55 W m−1 K−1, which is 2.75 times higher than that of pure PCL, 0.20 W m−1 K−1. This indicates that the excellent dispersion and interfacial adhesion could lead to the construction of continuous thermal conductive paths at a low BN loading and reduce the heat loss caused by phonon scattering in the interface. Furthermore, mBN could help to improve the mechanical properties of the composite. On adding 5 wt% mBN, the tensile strength and tensile modulus of the composite are 1.58 and 2.05 times higher, respectively, than those of PCL. © 2020 Society of Chemical Industry

Nanoparticles decorated with folate based on a site-selective αCD-rotaxanated PEG-b-PCL copolymer for targeted cancer therapy

NPs fabricated from a mixture of PEG-b-PCL and selectively rotaxanated Fol-PEG(αCD)-PCL showed internalisation in KB cells through an active targeting mechanism.

Investigating the Mechanical Behavior of PGA/PCL Copolymer Surgical Suture Material Using Multiple-Beam Interference Microscopy

The article aims to investigate the mechanical behavior of polyglycolic acid PGA/polycaprolactone PCL copolymer surgical suture material. A suture fibre-drawing device was designed and calibrated to be attached with the multiple-beam interferometric technique. Multiple-beam interferometric technique of the Fizeau type, in transmission, was used to investigate the optical properties. The designed drawing device was used to stretch the suture fibre sample at different draw ratios to investigate the mechanical properties. Different values of stresses were applied by utilizing the suture fibre-drawing device. The influence of the applied stresses on the physical and structural properties was studied. The stress-strain curve, optical orientation factor, refractive indices, refractive index profiles, orientation angle, Young’s modulus, elastic shear modulus and compressibility were investigated for the PGA/PCL suture materials at different draw ratios. The behavior of the stress-strain curve of PGA/PCL suture materials takes the J-shape which agreed with the behavior of soft tissue. Illustrations using microinterferograms and graphs are given.

Influence of poly(ε-caprolactone) end-groups on the temperature-induced macroscopic gelation of Pluronic in aqueous media

Temperature-induced gelation of amphiphilic copolymers in aqueous media has attracted a great deal of interest in recent years. We have investigated phase behavior, gelation, rheology, and structure of modified versions of the water-soluble copolymer of type PEO-PPO-PEO (Pluronic, F127) with short (PCL(5)) or long (PCL(11)) poly(caprolactone) blocks at both ends. By visual inspection of the studied semidilute and concentrated polymer samples at various temperatures, gelation and phase separation could be mapped and the length of the PCL blocks had a strong impact on the observed features. By using oscillatory shear experiments, the gel points of the systems were determined and an interesting anomaly of the complex viscosity was observed at high frequencies where the moieties were kinetically arrested. This irregularity was strengthened for the PCL(11) copolymer and this was ascribed to bridging of the micelles due to the long PCL blocks. The mesoscopic structure of the systems was studied by using small angle neutron scattering. The position and amplitude of the observed correlation peak, which discloses vital intermicellar correlations in the scattering function depends on temperature, concentration, and the length of the PCL blocks. Frequently the scattering function could be portrayed by a spherical core-shell micelle model with hard sphere interaction between them. The estimated aggregation number (Nagg) was substantially affected by the PCL content of the polymer and a significant influence of polymer concentration and temperature on the value of Nagg was found.

Correction: Methotrexate-conjugated mPEG–PCL copolymers: a novel approach for dual triggered drug delivery

Correction for ‘Methotrexate-conjugated mPEG–PCL copolymers: a novel approach for dual triggered drug delivery’ by Kobra Rostamizadeh et al., New J. Chem., 2018, 42, 5937–5945.

Fe3O4 magnetic nanoparticles coated with a copolymer: a novel reusable catalyst for one-pot three-component synthesis of 2-amino-4H-chromene

In this paper, an efficient method for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives is described. The method uses Fe3O4 magnetic nanoparticles coated with poly (e-caprolactone)/poly (ethylene glycol)/poly (e-caprolactone) (MNPs-Fe3O4/PCL–PEG–PCL) as a biodegradable and green catalyst under solvent-free conditions. The catalyst was prepared from PCL–PEG–PCL copolymer and MNPs-Fe3O4 and characterized by FT-IR, X-ray diffraction and SEM spectroscopy. Most aromatic aldehydes bearing electron-withdrawing or electron donating groups reacted successfully with malononitrile and dimedone under solvent-free conditions at 80 °C. The corresponding chromenes were isolated in good to excellent yields and the structures of them were confirmed by 1H NMR and IR spectroscopy. The catalyst could be recovered using an external magnet without a considerable loss in its catalytic activity. Moreover, some advantages of this method are simplicity of procedure, easy separation of the catalyst, high yields, efficiency, stability and non-toxicity of the catalyst, short reaction times, and environmentally benign conditions.

Interaction of antitumoral drug erlotinib with biodegradable triblock copolymers: a molecular modeling study

Combination of molecular dynamics simulations and miscibility calculations was used to investigate erlotinib drug delivery systems based on poly-e-caprolactone–polyethylene glycol–poly-e-caprolactone (PCL–PEG–PCL) and poly-e-caprolactone–polyglycolic acid–poly-e-caprolactone (PCL–PGA–PCL) biodegradable copolymers. The molecular modeling strategy involving visual observation of models, concentration profile analysis, Flory–Huggins χ parameter, cohesive energy density, and mean square displacement calculations reproduced experimental evidence of erlotinib release from PCL–PEG–PCL matrix successfully. Increasing portion of PCL in PCL–PEG–PCL copolymer led to dissolution of erlotinib aggregates recorded in visual and concentration profile analyses. Higher portion of PCL led to higher cohesive energy density and lower mean square displacement values. Success of this strategy in reproduction of experimental data made an opportunity to utilize the same modeling design in prediction of erlotinib release from similar but not yet experimentally tested PCL–PGA–PCL matrix. In this case, agglomeration of erlotinib molecules and stronger cohesive energy density values were observed.

Facile Optimization and Evaluation of PEG-PCL Block Copolymeric Nanoparticles for Anticancer Drug Delivery Using Copolymer Hybrids and Histoculture Drug Response Assays.

The traditional method of optimizing poly(ethyleneglycol)-polycaprolactone (PEG-PCL) copolymers for drug delivery requires high reaction temperatures, long reaction times, and various organic reagents. Furthermore, the in vivo evaluations of the antitumor effects of these drug delivery systems are time consuming, with animal sacrifice, and negative environmental effects. In this paper, nanoparticles (NPs) prepared from PEG-PCL/PCL hybrids were obtained by mixing PEG-PCL and PCL copolymer in different proportions and used to deliver cisplatin, a widely used anticancer drug. Histoculture drug response assay (HDRA), a predictive method typically used to evaluate chemosensitivity, was applied to evaluate the in vivo antitumor potencies of the NPs. The PEG-PCL and PCL proportions of the PEG-PCL/PCL hybrid were found to affect the NP diameter, drug loading content, encapsulation efficiency, stability, in vitro release properties, in vitro cytotoxicity, and antitumor effect in HDRA. The optimal NPs exhibited a satisfactory antitumor effect along with comparatively low side effects during an in vivo study in a murine model. The results reveal that PEG-PCL/PCL hybrids and HDRA can be used to conveniently and easily optimize and evaluate NPs prepared from block copolymers.

Methotrexate-conjugated mPEG–PCL copolymers: a novel approach for dual triggered drug delivery

A conjugate of the antitumor drug, methotrexate (MTX), with a diblock methoxypoly(ethylene glycol)–poly(caprolactone) (mPEG–PCL) copolymer was synthesized by the reaction of the mPEG–PCL copolymer with MTX in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine.

The effect of different thermal treatment on the physical properties of PGA/PCL copolymer suture material.

Samples of polyglycolic acid PGA/polycaprolactone PCL copolymer absorbable suture materials, which is called Poliglecaprone PGC copolymer suture, were thermally treated by two different processes. The first method is the direct heat exposure, from 20 to 38 °C, in the surrounding medium. Which is an environmental study. The other method is the annealing process at temperatures ranged from 65, 80, 100, 120, and 140 °C, for two different duration periods 60 and 120 min. This is an extensive technical study. The refractive indices of thermally treated PGA/PCL copolymer sutures were measured using multiple-beam Fizeau fringes. The birefringence profiles across the suture cross-sections were studied for different annealing conditions. The effect of heat on the polarizabilty per unit volume, dielectric properties, and suture diameter were investigated. The activation energy for the heating processes was calculated using Arrhenius equation. Microinterferograms are given for illustration.

Electrospinning of poly(lactic acid)/polycaprolactone blends: investigation of the governing parameters and biocompatibility

Abstract Blends of poly(lactic acid)/polycaprolactone (PLA/PCL) were electrospun under various conditions to study the influence of solution concentration, feed rate and voltage supply on the morphology of the nanofibers. To improve compatibility and to help produce fine electrospun nanofibers, an L-lactide/caprolactone (LACL) copolymer was introduced as a compatibilizer in the PLA/PCL blends. It was found that the solution concentration was a principal governing factor. The mean diameter of the fibers increased with the solution concentration, feed rate and voltage. Too high of a concentration and feed rate caused the fibers to stick to each other. A slow feed rate, 10% solution concentration, and 20 kV voltage were capable of producing thin, smooth and uniform fibers. Preliminary biocompatibility assays of the nanofibers were conducted with NIH 3T3 cells. The cells grown on the nanofiber blend exhibited spindle-like morphologies. The addition of PCL and LACL copolymer was found to improve the biocompatibility of PLA nanofibers, suggesting their potential application as cell culture scaffolds.

Co-delivery of hydrophilic and hydrophobic drugs by micelles: a new approach using drug conjugated PEG–PCLNanoparticles

Co-delivery strategy has been proposed to minimize the amount of each drug and to achieve the synergistic effect for cancer therapies. A conjugate of the antitumor drug, doxorubicin, with diblock methoxy poly (ethylene glycol)-poly caprolactone (mPEG-PCL) copolymer was synthesized by the reaction of mPEG–PCL copolymer with doxorubicin in the presence of p-nitrophenylchloroformate. The conjugated copolymer was characterized in vitro by 1H-NMR, FTIR, DSC and GPC techniques. Then, the doxorubicin conjugated mPEG–PCL(DOX–mPEG-PCL) was self-assembled into micelles in the presence of curcumin in aqueous solution. The resulting micelles were characterized further by various techniques such as dynamic light scattering (DLS) and atomic force microscopy (AFM).The encapsulation efficiency of doxorubicin and curcumin were 82.31 ± 3.32 and 78.15 ± 3.14%, respectively. The results revealed that the micelles formed by the DOX–mPEG-PCL with and without curcumin have spherical structure with average size of 116 and 134 nm respectively. The release behavior of curcumin and doxorubicin loaded to micelles were investigated in a different media. The release rate of micelles consisted of the conjugated copolymer was pH dependent as it was higher at lower pH than in neutral condition. Another feature of the conjugated micelles was a sustained release profile. The cytotoxicity of micelles were evaluated by MTT (3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide, atetrazole) assay on lung cancer A549 cell lines. In vitro cytotoxicity assay showed that the mPEG–PCL copolymer did not affect the growth of A549 cells. The cytotoxic activity of the micelles against A549 cells was greater than free doxorubicin and free curcumin.