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Synthesis of pH-Sensitive and Self-Fluorescent Polymeric Micelles Derived From Rosin and Vegetable Oils via ATRP.

ABSTRACT: Preparation and application of sustainable polymers derived from renewable resources are of great significance. The aim of this study is to synthesize a kind of sustainable polymeric micelles from rosin and vegetable oils via atom transfer radical polymerization (ATRP) and to investigate the doxorubicin delivery properties of these micelles. Dehydroabietic acid-based poly lauryl methacrylate (DA-PLMA) with narrow PDI of 1.13 was prepared in a well-controlled process using rosin as an ATRP initiator. Thereafter, carboxylic groups were introduced to form poly methacrylic acid (PMAA) moieties in DA-PLMA polymer via acid hydrolysis. The resulted DA-PLMA-PMAA could self-assemble in water to form pH-dependent polymeric micelles with a diameter of ∼65 nm and PDI as low as 0.105. Owing to the existence of rosin, DA-PLMA-PMAA micelles also showed self-fluorescence properties. In addition, Dox-loaded micelles were prepared in aqueous solution with the drug-loading capacity as high as 16.0% and showed sustained-release characteristics. These results demonstrate great promise for designing polymeric micellar from rosin and vegetable oils.

SUBMITTER: Yu J

PROVIDER: S-EPMC8596564 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Synthesis of pH-Sensitive and Self-Fluorescent Polymeric Micelles Derived From Rosin and Vegetable Oils <i>via</i> ATRP.

Yu Juan J Xu Chaoqun C Lu Chuanwei C Liu Qian Q Wang Jifu J Chu Fuxiang F

Frontiers in bioengineering and biotechnology 20211102

Preparation and application of sustainable polymers derived from renewable resources are of great significance. The aim of this study is to synthesize a kind of sustainable polymeric micelles from rosin and vegetable oils <i>via</i> atom transfer radical polymerization (ATRP) and to investigate the doxorubicin delivery properties of these micelles. Dehydroabietic acid-based poly lauryl methacrylate (DA-PLMA) with narrow PDI of 1.13 was prepared in a well-controlled process using rosin as an ATRP ...[more]

PMID: 34805111

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Project description:Cancer cells are known to create an acidic microenvironment (the Warburg effect). At the same time, fluorescent dyes can be sensitive to pH, showing a sharp increase or decrease in fluorescence depending on pH. However, modern applications, such as confocal laser scanning microscopy (CLSM), set additional requirements for such fluorescent markers to be of practical use, namely, high quantum yield, low bleaching, minimal quenching in the cell environment, and minimal overlap with auto-fluorophores. R6G could be the perfect match for these requirements, but its fluorescence is not pH-dependent. We have attempted to develop an R6G conjugate with its FRET or PeT pair that would grant it pH sensitivity in the desired range (5.5-7.5) and enable the selective targeting of tumor cells, thus improving CLSM imaging. Covalent conjugation of R6G with NBD using a spermidine (spd) linker produced a pH-sensitive FRET effect but within the pH range of 7.0-9.0. Shifting this effect to the target pH range of 5.5-7.5 appeared possible by incorporating the R6G-spd-NBD conjugate within a "smart" polymeric micelle based on chitosan grafted with lipoic acid. In our previous studies, one could conclude that the polycationic properties of chitosan could make this pH shift possible. As a result, the micellar form of the NBD-spd-R6G fluorophore demonstrates a sharp ignition of fluorescence by 40%per1 pH unit in the pH range from 7.5 to 5. Additionally, "smart" polymeric micelles based on chitosan allow the label to selectively target tumor cells. Due to the pH sensitivity of the fluorophore NBD-spd-R6G and the selective targeting of cancer cells, the efficient visualization of A875 and K562 cells was achieved. CLSM imaging showed that the dye actively penetrates cancer cells (A875 and K562), while minimal accumulation and low fluorophore emission are observed in normal cells (HEK293T). It is noteworthy that by using "smart" polymeric micelles based on polyelectrolytes of different charges and structures, we create the possibility of regulating the pH dependence of the fluorescence in the desired interval, which means that these "smart" polymeric micelles can be applied to the visualization of a variety of cell types, organelles, and other structures.

Project description:Introduction: Chemotherapy is a common strategy for the treatment of osteosarcoma. However, its therapeutic efficacy is not ideal due to the low targeting, lowbioavailability, and high toxicity of chemotherapy drugs. Nanoparticles can improve the residence time of drugs at tumor sites through targeted delivery. This new technology can reduce the risk to patients and improve survival rates. To achieve this goal, we developed a pHsensitive charge-conversion polymeric micelle [mPEG-b-P(C7-co-CA) micelles] for osteosarcoma-targeted delivery of cinnamaldehyde (CA). Methods: First, an amphiphilic cinnamaldehyde polymeric prodrug [mPEG-b-P(C7-co-CA)] was synthesized through Reversible Addition-Fragmentation Chain Transfer Polymerization (RAFT) polymerization and post-modification, and self-assembled into mPEG-b-P(C7-co-CA) micelles in an aqueous solution. The physical properties of mPEG-b-P(C7-co-CA) micelles, such as critical micelle concentration (CMC), size, appearance, and Zeta potential were characterized. The CA release curve of mPEG-b-P(C7-co-CA) micelles at pH 7.4, 6.5 and 4.0 was studied by dialysis method, then the targeting ability of mPEG-b-P(C7-co-CA) micelles to osteosarcoma 143B cells in acidic environment (pH 6.5) was explored by cellular uptakeassay. The antitumor effect of mPEG-b-P(C7-co-CA) micelles on 143B cells in vitro was studied by MTT method, and the level of reactive oxygen species (ROS) in 143B cells after mPEG-b-P(C7-co-CA) micelles treatment was detected. Finally, the effects of mPEG-b-P(C7-co-CA) micelles on the apoptosis of 143B cells were detected by flow cytometry and TUNEL assay. Results: An amphiphilic cinnamaldehyde polymeric prodrug [mPEG-b-P(C7-co-CA)] was successfully synthesized and self-assembled into spheric micelles with a diameter of 227 nm. The CMC value of mPEG-b-P(C7-co-CA) micelles was 25.2 mg/L, and it showed a pH dependent release behavior of CA. mPEG-b-P(C7-co-CA) micelles can achieve chargeconversion from a neutral to a positive charge with decreasing pHs. This charge-conversion property allows mPEG-b-P(C7-co-CA) micelles to achieve 143B cell targeting at pH 6.5. In addition, mPEG-b-P(C7-co-CA) micelles present high antitumor efficacy and intracellular ROS generation at pH 6.5 which can induce 143B cell apoptosis. Discussion: mPEG-b-P(C7-co-CA) micelles can achieve osteosarcoma targeting effectively and enhance the anti-osteosarcoma effect of cinnamaldehyde in vitro. This research provides a promising drug delivery system for clinical application and tumor treatment.

Dataset Information

Synthesis of pH-Sensitive and Self-Fluorescent Polymeric Micelles Derived From Rosin and Vegetable Oils via ATRP.

Publications

Synthesis of pH-Sensitive and Self-Fluorescent Polymeric Micelles Derived From Rosin and Vegetable Oils <i>via</i> ATRP.

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