4.7 Article

Influence of 2-(diisopropylamino)ethyl methacrylate on acid-triggered hydrolysis of cyclic benzylidene acetals and their importance in efficient drug delivery

Journal

POLYMER CHEMISTRY
Volume 6, Issue 37, Pages 6671-6679

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5py00734h

Keywords

-

Funding

  1. National Natural Science Foundation of China [81371667, 81471727]
  2. Specialized Research Fund for the Doctoral Program of Higher Education [20120032110013]

Ask authors/readers for more resources

The ability to tune the degradation rate of a biodegradable polymer, which can achieve precise spatio-temporal control of drug delivery, is of considerable interest for biomedical applications. In this study, a series of amphiphilic copolymers, methoxy poly(ethyleneglycol)-b-poly((2,4,6-trimethoxybenzylidene-1,1,1-tris(hydroxymethyl) ethane methacrylate)-co-2-(diisopropylamino) ethyl methacrylate) (mPEG-b-P (TTMA-co-DPA), PETD) with different numbers of DPA units, were synthesized by Reversible Addition Fragmentation Chain Transfer (RAFT) copolymerization, in which DPA containing tertiary amines were introduced to adjust the hydrolysis behavior of cyclic benzylidene acetals (CBAs). The molecular structure and the chemical composition of PETD were characterized by H-1 NMR and gel permeation chromatography (GPC). PETD could self-assemble into stable nanoparticles with well-defined spherical morphology and displayed high drug loading capacity with doxorubicin (DOX) as the drug model. The hydrolysis behavior of CBAs in the PETD NPs was investigated by UV/vis spectroscopy under different pH values. Compared with PETD-0 bearing no DPA unit, the hydrolysis rate of PETD-3 with more DPA was faster, while PETD-1 with less DPA hydrolyzed much slower, which indicated that the introduction of DPA had an amphoteric effect on the hydrolysis behavior of CBAs under acidic conditions. In addition, the in vitro release of DOX was also investigated under different pH conditions and the result was in accordance with the hydrolysis result. Furthermore, the results of fluorescence microscopy demonstrated improved internalization of DOX-loaded PETD-3 NPs in HepG-2 cells with rapid DOX release intracellularly, which showed considerable cytotoxicity against HepG-2 cells.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Analytical

Structure of Self-assembled Peptide Determines the Activity of Aggregation-Induced Emission Luminogen-Peptide Conjugate for Detecting Alkaline Phosphatase

Liping Zhang, Yun Li, Ganen Mu, Lijun Yang, Chunhua Ren, Zhongyan Wang, Qingxiang Guo, Jianfeng Liu, Cuihong Yang

Summary: The unique fluorescence property of aggregation-induced emission luminogens (AIEgens) makes them ideal for constructing self-assembled peptide-based nanoprobes. This study reveals the key factors influencing the assembly and luminescence of AIEgen-peptides and proposes strategies for efficient assembly and luminescence. Additionally, AIEgen-peptide probes show good selectivity and sensitivity for alkaline phosphatase (ALP) detection. These insights are crucial for guiding the design of AIEgen-conjugated supramolecular materials, especially for applications in enzyme detection, biomarker imaging, diseases therapy, and other biomedical fields.

ANALYTICAL CHEMISTRY (2022)

Article Oncology

Paclitaxel-based supramolecular hydrogel loaded with mifepristone for the inhibition of breast cancer metastasis

Cui-Cui Zhao, Chuan-Gui Zhang, Xuan Sun, Qingxiang Guo, Jinjian Liu, Yan Liu, Ya-Nan Hao, Guowei Feng, Lijun Yang, Hong Liu, Jianfeng Liu

Summary: The study demonstrated that using paclitaxel-conjugated mifepristone-loaded hydrogel (PM-nano) can effectively inhibit breast cancer metastasis, showing good water solubility and biocompatibility. Additionally, PM-nano inhibits metastasis by impacting glucocorticoid receptor/receptor tyrosine kinase-like orphan receptor 1 and MMPs.

CANCER SCIENCE (2022)

Article Engineering, Biomedical

Bioinspired and Inflammation-Modulatory Glycopeptide Hydrogels for Radiation-Induced Chronic Skin Injury Repair

Zujian Feng, Yumin Zhang, Chunfang Yang, Xiang Liu, Yini Huangfu, Chuangnian Zhang, Pingsheng Huang, Anjie Dong, Jinjian Liu, Jianfeng Liu, Deling Kong, Weiwei Wang

Summary: A glycopeptide hydrogel inspired by extracellular matrix (ECM) has been designed to accelerate wound healing in radiation-induced skin injury (RSI) by modulating chronic inflammation. The hydrogel replicates ECM components and structure, scavenges reactive oxygen species (ROS), and polarizes macrophages to reduce inflammation. In mouse models, the hydrogel significantly reduces hyperplasia, promotes regeneration and angiogenesis, and decreases proinflammatory cytokine expression, making it superior to current treatment options.

ADVANCED HEALTHCARE MATERIALS (2023)

Article Environmental Sciences

Analyzing toxicological effects of AsIII and AsV to Chlamys farreri by integrating transcriptomic and metabolomic approaches

Huan Liu, Xiuhui Tian, Xianghong Gong, Dianfeng Han, Lihua Ren, Yanmei Cui, Fang Jiang, Junqiang Zhao, Jianqiang Chen, Lisheng Jiang, Yingjiang Xu, Huanjun Li

Summary: In this study, transcriptomics and metabolomics were used to investigate the genetic and metabolite changes and functional physiological disturbances in scallops exposed to inorganic arsenic. The omics results were supported by physiological indicators and cell apoptosis analysis, confirming the toxic effects of inorganic arsenic. The study reveals that inorganic arsenic disrupts the physiological functions of bivalves by interfering with cell growth and small molecule metabolism, providing new insights into the toxic effects of environmental pollutants on marine organisms.

MARINE POLLUTION BULLETIN (2023)

Article Chemistry, Multidisciplinary

Tumor-Specific Peroxynitrite Overproduction Disrupts Metabolic Homeostasis for Sensitizing Melanoma Immunotherapy

Lijun Yang, Dianyu Wang, Haixue Jia, Cuihong Yang, Yumin Zhang, Hui Li, Jinjian Liu, Jianfeng Liu

Summary: Tumor cells use metabolic reprogramming to create an immunosuppressive tumor microenvironment (TME) and evade the immune system. This study develops a tumor-specific peroxynitrite nanogenerator that disrupts metabolic homeostasis in melanoma cells. The produced peroxynitrite induces a decrease in metabolites in the tricarboxylic acid cycle and reduces lactate production. Mechanistically, peroxynitrite impairs glucose metabolism by affecting the activity of glyceraldehyde-3-phosphate dehydrogenase. These metabolic alterations reverse the immunosuppressive TME and promote antitumor immune responses. When combined with anti-PD-L1, the nanogenerator inhibits both primary and metastatic melanomas without causing toxicity. This research provides a new strategy for enhancing immunotherapy sensitivity.

ADVANCED MATERIALS (2023)

Article Chemistry, Multidisciplinary

Cancer Stem-Like Cells-Oriented Surface Self-Assembly to Conquer Radioresistance

Qian Wang, Hongmei Cao, Xiaoxue Hou, Dianyu Wang, Zhilong Wang, Yue Shang, Shuqin Zhang, Jinjian Liu, Chunhua Ren, Jianfeng Liu

Summary: A surface-induced self-assembly system (CA-Pt) is developed to overcome hypoxic cancer stem cell-mediated radioresistance by deep penetration, amplified CAIX inhibition, and enhanced cellular uptake. It effectively relieves the hypoxic and acidic microenvironment, promotes the differentiation of hypoxic CSCs, and enhances the DNA damage induced by radiotherapy. This study provides a universal treatment strategy for overcoming tumor radioresistance.

ADVANCED MATERIALS (2023)

Article Green & Sustainable Science & Technology

Aminated Polyacrylonitrile Nanofiber Membrane for Effective In Situ Bivalent Cadmium Contaminated Kaolin Remediation

Botao Jia, Ning Yang, Xianwen Zhang, Gan Wang, Peichen Wang, Junqiang Zhao, Li Chen, Yiping Zhao

Summary: An aminated polyacrylonitrile (PAN) nanofiber membrane was fabricated for the in situ remediation of Cd(II) contaminated soil. The membrane showed potential as a permeable reactive barrier (PRB) combined with electrokinetics (EK) for the remediation of potentially toxic metal contaminated soil.

CLEAN-SOIL AIR WATER (2023)

Article Engineering, Biomedical

Bio-Inspired Antioxidant Heparin-Mimetic Peptide Hydrogel for Radiation-Induced Skin Injury Repair

Yusen Hao, Hui Li, Jiajun Guo, Dan Wang, Jiamin Zhang, Jinjian Liu, Cuihong Yang, Yumin Zhang, Guoliang Li, Jianfeng Liu

Summary: Radiotherapy is an important cancer treatment method, but it can cause adverse reactions and injuries to the skin. This study designed an antioxidant heparin-mimetic peptide hydrogel (K16) for repairing radiation-induced skin injuries (RISI). The K16 hydrogel can scavenge excess reactive oxygen species (ROS), prevent radiation damage to DNA, promote cell proliferation, migration, and angiogenesis, and eliminate inflammation at the wound site. In vivo experiments demonstrated that the K16 hydrogel inhibits wound degradation, reduces inflammation, and promotes wound healing. Therefore, the K16 hydrogel has great potential for application in repairing radiation-induced skin injuries.

ADVANCED HEALTHCARE MATERIALS (2023)

Article Engineering, Biomedical

EISA in Tandem with ICD to Form In Situ Nanofiber Vaccine for Enhanced Tumor Radioimmunotherapy

Hongjing Luo, Hongmei Cao, Haixue Jia, Yuna Shang, Jinjian Liu, Han Gui, Cuihong Yang, Chunhua Ren, Zhongyan Wang, Jianfeng Liu

Summary: Radiotherapy can remodel the tumor microenvironment by inducing immunogenic cell death and inflammation, but it is not effective in generating a systemic antitumor immune response. This study presents a novel strategy to create in situ peptide-based nanovaccines using enzyme-induced self-assembly, in combination with immunogenic cell death. The nanovaccine enhances antigen accumulation in the lymph nodes and cross-presentation by antigen-presenting cells, and promotes the repolarization of macrophages and reduces regulatory T cells and myeloid-derived suppressor cells. The combination of nanovaccines and radiotherapy significantly improves the therapeutic effect on tumors, providing a promising strategy for tumor radioimmunotherapy.

ADVANCED HEALTHCARE MATERIALS (2023)

Article Environmental Sciences

Amantadine Toxicity in Apostichopus japonicus Revealed by Proteomics

Junqiang Zhao, Jianqiang Chen, Xiuhui Tian, Lisheng Jiang, Qingkui Cui, Yanqing Sun, Ningning Wu, Ge Liu, Yuzhu Ding, Jing Wang, Yongchun Liu, Dianfeng Han, Yingjiang Xu

Summary: This study investigated the toxicity of amantadine on sea cucumbers, showing that it can induce oxidative stress and histopathological changes in the intestinal tissues of Apostichopus japonicus. Proteomics analysis revealed alterations in metabolic pathways, including increased energy production, activation of NF-kappa B pathway, and inhibition of protein synthesis and growth. These findings provide a theoretical basis for further research on amantadine toxicity.

TOXICS (2023)

Article Engineering, Chemical

Superwetting membrane by co-deposition technique using a novel N-oxide zwitterionic polymer assisted by bioinspired dopamine for efficient oil-water separation

Jing Yang, Ligang Lin, Fengling Tang, Junqiang Zhao

Summary: In this study, a novel N-oxide zwitterionic polymer (PTMAO) was developed with ultralow fouling property and superior hydrophilicity, inspired by the secretion of trimethylamine-N-oxide (TMAO) by saltwater fish. A zwitterionic polymer network was formed using a biomimetic co-deposition technique of dopamine (DA) and PTMAO. The fabricated membrane exhibited excellent superhydrophilicity and underwater superoleophobicity, achieving high efficiency of oil-water separation performance under ultra-low-pressure conditions.

SEPARATION AND PURIFICATION TECHNOLOGY (2023)

Article Chemistry, Multidisciplinary

Preparation and Characterization of a High Perm-selectivity Poly(amide/ester)Nanofiltration Membrane Using a Poly(vinylidene fluoride)Substrate

Yang Yanfu, Wang Qiqi, Zhang Hui, Zhang Qinglei, Zhao Junqiang, Zhao Yiping, Chen Li

Summary: Using PVDF as a substrate material, a block copolymer PHMH with hydrophilic and hydrophobic segments was used to modify the PVDF substrate. The modified substrate had smaller surface pore size, increased porosity and hydrophilicity. The nanofiltration membrane prepared from PVDF/PHMH exhibited higher surface roughness, hydrophilicity and lower molecular weight cut-off, with a rejection rate of 96.0% for Na2SO4 and a permeation flux of 304 L·m(-2)·h(-1)·MPa-1.

CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE (2023)

Article Chemistry, Multidisciplinary

Achieving higher hierarchical structures by cooperative assembly of tripeptides with reverse sequences

Zhongyan Wang, Yuna Shang, Hongjing Luo, Cuihong Yang, Zhimou Yang, Chunhua Ren, Jianfeng Liu

Summary: This study presents a novel strategy of achieving higher hierarchical structures through cooperative self-assembly of hydrophobic tripeptides with reverse sequences, showing a low-to-high hierarchical structure transformation. The cooperation between different sequences also allows different morphological transitions, promoting a more compact molecular arrangement by creating more hydrogen bond interactions and in-register π-π stacking in the anti-parallel β-sheet conformation. This work provides a handy approach for controlled hierarchical assembly and the development of various functional bionanomaterials.

NANOSCALE (2023)

Article Engineering, Biomedical

Extensor Digitorum Communis Compartments With a Double Compensation Synergy Strategy for Constant Force Control of the Index Finger

Zhixian Gao, Yehong Zhang, Yun Zhao, Yinping Wei, Shiyang Lv, Zhenpeng Shao, Zongya Zhao, Chang Wang, Xuezhi Zhou, Junqiang Zhao, Wensheng Hou, Yi Yu

Summary: This study aimed to investigate how neuromuscular compartments within a forearm multi-tendon muscle cooperate to achieve constant finger force. Through electromyography signal analysis, the study found a coordination strategy across EDC compartments during sustained index finger extension, involving an auxiliary pattern compensating for the intensity and stability of the primary pattern. These findings provide new insights into constant force control of prosthetic hands.

IEEE TRANSACTIONS ON NEURAL SYSTEMS AND REHABILITATION ENGINEERING (2023)

Article Chemistry, Multidisciplinary

Cancer Stem-Like Cells-Oriented Surface Self-Assembly to Conquer Radioresistance

Qian Wang, Hongmei Cao, Xiaoxue Hou, Dianyu Wang, Zhilong Wang, Yue Shang, Shuqin Zhang, Jinjian Liu, Chunhua Ren, Jianfeng Liu

Summary: This study reports a CAIX-targeted induced in situ self-assembly system on the surface of hypoxic cancer stem-like cells (CSCs), which relieves the hypoxic and acidic microenvironment and promotes CSC differentiation to overcome tumor radiotherapy resistance. The constructed peptide-based drug delivery system exhibits deep penetration, amplified CAIX inhibition, and enhanced cellular uptake, showing potential as a universal treatment strategy for overcoming tumor radioresistance.

ADVANCED MATERIALS (2023)

Article Polymer Science

A dual action coumarin-camptothecin polymer for light responsive drug release and photodynamic therapy

Paige A. Shaw, Maxime Klausen, Mark Bradley

Summary: A light-responsive polymer capable of controlled release of camptothecin and generation of reactive oxygen species (ROS) was developed, which exhibited high cancer cell killing activity through both camptothecin release and ROS generation.

POLYMER CHEMISTRY (2024)

Article Polymer Science

Facile synthesis of N-phenoxycarbonyl amino acids by a two-phase reaction for direct polymerization

Donghui Zhang, Shiqi Liu, Zhihao Cai, Weizhe Luo, Guojian Liu, Runhui Liu

Summary: A straightforward and efficient method for synthesizing NPC monomers has been developed in this study, which enhances the availability of NPC monomers and facilitates the synthesis of polypeptides.

POLYMER CHEMISTRY (2024)