Biomaterials Science
·
2015
·Vol. 3
·期 7
·1134-1146
·
IF 3.831
Jiaolong Lv,Huanli Sun,Yan Zou,Fenghua Meng,Aylvin A. Dias,Marc Hendriks,Jan Feijen,Zhiyuan Zhong
Novel reductively degradable α-amino acid-based poly(ester amide)-graft-galactose (SSPEA-Gal) copolymers were designed and developed to form smart nano-vehicles for active hepatoma-targeting doxorubicin (DOX) delivery. SSPEA-Gal copolymers were readily synthesized via solution polycondensation reaction of di-p-toluenesulfonic acid salts of bis-L-phenylalanine 2,2-thiodiethanol diester and bis-vinyl sulfone functionalized cysteine hexanediol diester with dinitrophenyl ester of adipic acid, followed by conjugating with thiol-functionalized galactose (Gal-SH) via the Michael addition reaction. SSPEA-Gal formed unimodal nanoparticles (PDI = 0.10 − 0.12) in water, in which average particle sizes decreased from 138 to 91 nm with increasing Gal contents from 31.6 wt% to 42.5 wt%. Notably, in vitro drug release studies showed that over 80% DOX was released from SSPEA-Gal nanoparticles within 12 h under an intracellular mimicking reductive conditions, while low DOX release (<20%) was observed for reduction-insensitive PEA-Gal nanoparticles under otherwise the same conditions and SSPEA-Gal nanoparticles under non-reductive conditions. Notably, SSPEA-Gal nanoparticles exhibited high specificity to asialoglycoprotein receptor (ASGP-R)-overexpressing HepG2 cells. MTT assays using HepG2 cells showed that DOX-loaded SSPEA-Gal had a low half maximal inhibitory concentration (IC50) of 1.37 μg mL−1, approaching that of free DOX. Flow cytometry and confocal laser scanning microscopy studies confirmed the efficient uptake of DOX-loaded SSPEA-Gal nanoparticles by HepG2 cells as well as fast intracellular DOX release. Importantly, SSPEA-Gal and PEA-Gal nanoparticles were non-cytotoxic to HepG2 and MCF-7 cells up to a tested concentration of 1.0 mg mL−1. These tumor-targeting and reduction-responsive degradable nanoparticles have appeared as an interesting multi-functional platform for advanced drug delivery.
研究领域:
生物材料学
·
药物递送系统
·
肿瘤治疗
✓ 已验证
DOI
PubMed
高影响因子
Polymer Chemistry
·
2019
·Vol. 11
·期 6
·1211-1219
·
IF 4.76
Fu-Rong Zeng,Jing Xu,Lin-Hao Sun,Jimei Ma,Hong Jiang,Zi-Long Li
Poly(ester amide)s (PEAs) attract considerable attention owing to their intriguing properties. However, the establishment of precise structure–property relationship for PEAs is hindered by the ambiguous primary structures of these biologically important polymers. Herein, we propose polyesterification as an efficient strategy for the synthesis of copolymers of ε-caprolactone (CLo) and ε-caprolactam (CLa). Two sorts of AB-type monomers bearing halogen and carboxylic acid terminal groups, namely 6-bromohexanoic acid (1) and 6-(6-bromohexanamido)hexanoic acid (2), underwent nucleophilic substitution in a step-growth manner to furnish P(CLo) (P0) and P(CLo-alt-CLa) (P5), respectively. Moreover, random copolymers P1–P4 were also synthesized by copolymerization of 1 and 2 in predetermined feed ratios. Thermal properties, crystal structure, surface wettability, thermal responsiveness and degradation profiles of P0–P5 along with P(CLa) (P6) were investigated. The melting ranges of polymers P0–P6 become narrowed if the structural regularity is pronounced, and the melting temperatures (Tms) are fundamentally determined by chemical composition and sequence distribution. The crystal structures and morphologies of P0–P6 are influenced by their chemical compositions, and the unit cell changes from orthorhombic to α-monoclinic while increasing the molar fraction of the CLa unit. Moreover, alternating copolymer P5 shows upper critical solution temperature (UCST) behavior in dimethyl sulfoxide (DMSO).
研究领域:
高分子化学
·
材料科学
·
生物医学工程
✓ 已验证
DOI
高影响因子
MACROMOLECULES
·
2018
·
IF 5.914
Jian Zhang,Yu-Huan Wu,Jia-Chen Wang,Fu-Sheng Du,Zi-Chen Li
We describe a straightforward synthetic strategy for a new family of functional poly(ester–amide)s (PEAs) with tertiary ester linkages via the Passerini multicomponent polymerization (Passerini-MCP) of a diacid (A2), 1,6-diisocyanohexane (B2), and four kinds of electron-deficient ketones. First, Passerini three-component reactions (Passerni-3CR) of hexanoic acid and tert-butyl isocyanide with nine kinds of ketones were investigated to evaluate the reactivities of these ketones toward Passerni-3CR. Four electron-deficient ketones, 1,1,1-trifluoroacetone (1), 1,1,1-trifluoroacetophenone (2), ethyl pyruvate (3), and 2,3-butanedione (4), were found to be excellent oxo-compounds for this Passerini-3CR. Then, the Passerini-MCP of A2 and B2 with 1, 2, 3, and 4 in CH2Cl2 was performed to generate polymers P1–P4 with tertiary ester linkages and different electron-withdrawing substituents. Polymer P5 was also prepared by the Passerini-MCP of A2 and B2 with phenylacetaldehyde (5) for comparison. Size exclusion chromatography (SEC) verified the high molecular weights (Mn up to 30.6 kDa) of these polymers. The structures of these polymers were confirmed by 1H NMR, 13C NMR, 19F NMR, and matrix-assisted laser desorption ionization mass spectroscopy. Thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC) revealed that P1–P4 are less stable than polymer P5, and they are amorphous with variable glass transition temperatures (Tg) depending on the side groups. Hydrolytic degradation of P1, P4, and P5 in a mixture of acetonitrile and phosphate buffer (different pH) was investigated, and at the same pH, the degradation follows the order of P4 > P1 > P5. The static water contact angles of thin films formed by these polymers decreased from 96° (P1) to 78° (P2), 50° (P3), and finally to 32° (P4). Tensile properties of polymer P3 and P4 were characterized by dynamic mechanical analysis (DMA). P4 displayed a high tensile stress of 25 MPa with the elongation up to 200%.
研究领域:
高分子化学
·
材料科学
·
生物医学工程
✓ 已验证
DOI
高影响因子
JOURNAL OF POLYMER RESEARCH
·
2021
·Vol. 28
·期 8
·1-9
·
IF 3.097
He Tingwei,Liu Tao,Huang Junyao,Wang Xueli,He Yong,Ma Bomou
In this work, a novel poly(ester amide)s (PEAs) was designed and synthesized from dimethyl terephthalate (DMT), 3-amino-1-propanol (AP) and adipic acid (AA). Firstly, the aromatic diol monomer (BHTT) was synthesized by DMT and AP, it was characterized by 1 H NMR, 13 C NMR, FT-IR and DSC, respectively. Then, the BHTT and AA were used to synthesize the semi-aromatic PEAs with alternating structure by melt polymerization. The effects of polymerization temperature and time on the crystallization, thermal stability and amide transesterification of PEAs were fully investigated. It was found that the prepared PEAs are semi-crystalline polymer with melting point around 154–165 °C and decomposition temperature around 377–392 °C. Most important, the chemical structure of PEAs synthesized under different conditions was explored by 1 H NMR, 13 C NMR and DEPT spectra, which confirms the occurrence of amide transesterification during the melt polymerization process.
研究领域:
高分子化学
·
材料科学
✓ 已验证
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2024
·
IF 7.1
Huihui Gao,Xiankun Wu,Jingjing Fan,Zhongkai Wang
Replacing traditional petroleum-based plastics with degradable biobased plastics has become one of the significant strategies to address energy shortages and environmental issues. Nevertheless, it still remains a scientific challenge to develop biobased plastics with ultrastrong mechanical strength and superior recyclability. Here, the catalytic conversion of Sapium sebiferum oil (SSO) to 9,10-dihydroxy-octadecanoic acid (C18-OH) monomer is first designed. Simultaneously, a novel biobased plastic, namely, PEA, is fabricated by a dual network through one-pot melt-polymerization, which exhibits mechanical performance higher than most commercial plastics and other reported PEAs. Benefiting from the synergy of the dynamic nature of H-bonds and hydroxy-ester bonds as well as the flexibility of the long aliphatic chain, the PEAs exhibit exceptional repairability and reprocessability. More importantly, PEAs can be efficiently degraded into the original reagents and the cross-linked materials can be reconstructed by the recovered monomers without losing the pristine performance. Additionally, abundant polar groups provide excellent adhesion properties for PEAs with a high shear strength of 10.29 ± 0.21 MPa. This work unveils an elegant and efficient synthetic route to fabricate impressively robust and chemically recyclable materials as promising alternatives to conventional plastics.
研究领域:
材料科学
·
环境科学
·
有机化学
✓ 已验证
DOI
高影响因子
Regenerative Biomaterials
·
2021
·Vol. 8
·期 2
·
IF 6.353
Zhang Jianhua,Hu Junfei,Chen Baoshu,Zhao Tianbao,Gu Zhipeng
Wound healing dressing is increasingly needed in clinical owing to the large quantity of skin damage annually. Excessive reactive oxygen species (ROS) produced through internal or external environmental influences can lead to lipid peroxidation, protein denaturation, and even DNA damage, and ultimately have harmful effects on cells. Aiming to sufficiently contact with the wound microenvironment and scavenge ROS, superabsorbent poly (acrylic acid) and antioxidant poly (ester amide) (PAA/PEA) hybrid hydrogel has been developed to enhance wound healing. The physical and chemical properties of hybrid hydrogels were studied by Fourier-transform infrared (FTIR) absorption spectrum, compression, swelling, degradation, etc. Besides, the antioxidant properties of hybrid hydrogels can be investigated through the free radical scavenging experiment, and corresponding antioxidant indicators have been tested at the cellular level. Hybrid hydrogel scaffolds supported the proliferation of human umbilical vein endothelial cells and fibroblasts, as well as accelerated angiogenesis and skin regeneration in wounds. The healing properties of wounds in vivo were further assessed on mouse skin wounds. Results showed that PAA/PEA hybrid hydrogel scaffolds significantly accelerated the wound healing process through enhancing granulation formation and re-epithelialization. In summary, these superabsorbent and antioxidative hybrid hydrogels could be served as an excellent wound dressing for full-thickness wound healing.
研究领域:
生物材料学
·
医学
·
组织工程学
✓ 已验证
DOI
高影响因子
HIGH PERFORMANCE POLYMERS
·
2024
·
IF 1.8
Yaqing Wen,Ge Zhu,Jie Li,Xingzhong Fang,Guofei Chen
Two series of novel poly(ester-amide-imide)s (PEsAIs) with pendant phthalimide side group were synthesized by copolymerization of phthalimide-hydroquinone bis(trimellitate anhydride) (PI-TAHQ), p-phthaloyl chloride (TPC) and other fluorinated monomers using the two-step method. These PEsAIs had glass transition temperatures (Tgs) in the range of 228 °C–296°C and coefficients of thermal expansion (CTEs) of 18–55 ppm·K−1. These films had good mechanical properties with tensile modulus of 3.7–5.7 GPa, tensile strengths of 92–153 MPa and elongations at break of 2.2%–8.3%. All films displayed good transparency with transmittances at 400 nm (T400nm) of 43%–79% and transmittances at 850 nm (T850nm) exceeding 89%, and these PEsAIs were amorphous. Especially, PEsAI-d-60 presented the best comprehensive performance with Tg of 296°C, low CTE of 18 ppm·K−1 and high transmittance (T400nm of 79%, T850nm of 91%), which exhibited the potential of this novel poly(ester-amide-imide) containing pendant phthalimide substituent in optical transparent materials.
研究领域:
材料科学
·
高分子化学
✓ 已验证
DOI
高影响因子
JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART B-APPLIED BIOMATERIALS
·
2016
·Vol. 105
·期 6
·1369-1378
·
IF 2.881
Bing Wang,Jun Dong,Lijing Niu,Wenyan Chen,Dongliang Chen,Chengyi Shen,Jiang Zhu,Xiaoming Zhang
Electrospun membranes of poly(p-dioxanone-co- l -phenylalanine) (PDPA) hold potential as an anti-adhesion material. Since adjustable degradation properties are important for anti-adhesion materials, in this study, the in vitro and in vivo degradation processes of PDPA electrospun membranes were investigated in detail. The morphological analysis of these membranes revealed the main degradation conditions of PDPA membranes. The weight remaining and molecular weight variation showed that the overall degradation rate of the membranes could be adjusted by modulating the molecular structure of the PDPAs. Especially, α-chymotrypsin could catalyze the degradation process of PDPAs. Based on these results, the in vitro degradation mechanism was demonstrated, and confirmed by 1 H NMR of the hydrolysis products. Finally, the in vivo degradation and biocompatibility of different PDPAs were investigated. The kinetic study showed that the in vitro and in vivo molecular weight loss of PDPAs have the first-order characteristics. The in vivo degradation rate of the most Phe-containing PDPA-3 is the slowest, and this result relates to the biocompatibilities of PDPAs. © 2016 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater, 105B: 1369–1378, 2017.
研究领域:
生物材料学
·
组织工程
·
高分子科学
·
生物医学工程
·
药物递送
·
再生医学
·
生物降解
✓ 已验证
DOI
高影响因子
Cell Reports Physical Science
·
2022
·
IF 7.832
Yongliang Ding,Cheng Liu,Xi Zhou,Zhiyou Wang,Juan He,Feng Jiang,Zhongkai Wang
Summary Biobased eco-plastics are an emerging class of sustainable materials. However, the synthesis of mechanically strong polymer materials usually needs high-purity monomers derived from biomass, which is not “green” during production. On the other hand, the recycling of plastics is highly desired for environmental protection. Here, we present a robust and facile strategy to design and prepare mechanically strong polyester amides (PEAs) from low-grade plant oils that can be treated as real eco-plastics. Low-grade C21 diacid (C21) derived from plant oils was chosen as the main monomer to synthesize mechanically strong PEAs via a one-pot condensation polymerization process. The resulting PEAs can be processed like thermoplastics. More importantly, the PEAs can undergo sustainable recycling, including physical recycling, hydro recycling, and composite recycling, without sacrificing their performance. The marriage of low monomer purity, thermoplastic-like behavior, and sustainable recycling can provide vital opportunities for developing novel eco-plastics to compete with traditional plastics.
研究领域:
材料科学
·
可持续化学
·
聚合物科学
·
环境科学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）