High-gravity technology intensified Knoevenagel condensation-Michael addition polymerization of poly (ethylene glycol)-poly (n-butyl cyanoacrylate) for blood-brain barrier delivery

doi:10.1016/j.cjche.2021.05.005

中国化学工程学报 ›› 2022, Vol. 46 ›› Issue (6): 94-103.DOI: 10.1016/j.cjche.2021.05.005

High-gravity technology intensified Knoevenagel condensation-Michael addition polymerization of poly (ethylene glycol)-poly (n-butyl cyanoacrylate) for blood-brain barrier delivery

Xingzheng Liu¹, Chuanbo Fu¹, Manting Wang¹, Jiexin Wang^1,2, Haikui Zou², Yuan Le^1,2, Jianfeng Chen^1,2

1 State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China;
2 Research Centre of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

收稿日期:2021-02-24 修回日期:2021-05-18 出版日期:2022-06-28 发布日期:2022-07-20
通讯作者: Haikui Zou,E-mail:zouhk@mail.buct.edu.cn;Yuan Le,E-mail:leyuan@mail.buct.edu.cn
基金资助:
This work was supported by National Key Research and Development Program of China (2016YFA0201701).

High-gravity technology intensified Knoevenagel condensation-Michael addition polymerization of poly (ethylene glycol)-poly (n-butyl cyanoacrylate) for blood-brain barrier delivery

Xingzheng Liu¹, Chuanbo Fu¹, Manting Wang¹, Jiexin Wang^1,2, Haikui Zou², Yuan Le^1,2, Jianfeng Chen^1,2

1 State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China;
2 Research Centre of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

Received:2021-02-24 Revised:2021-05-18 Online:2022-06-28 Published:2022-07-20
Contact: Haikui Zou,E-mail:zouhk@mail.buct.edu.cn;Yuan Le,E-mail:leyuan@mail.buct.edu.cn
Supported by:
This work was supported by National Key Research and Development Program of China (2016YFA0201701).

摘要/Abstract

摘要： Poly (ethylene glycol)-poly (n-butyl cyanoacrylate) (PEG-PBCA) is a remarkable drug delivery carrier for permeating blood-brain barrier. In this work, a novel high-gravity procedure was reported to intensify Knoevenagel condensation-Michael addition polymerization of PEG-PBCA. A series of PEG-PBCA containing different block ratios were synthesized with narrow molecular weight distribution of polydispersity indexes less than 1.1. Furthermore, the reaction time reduced 60% compared to conventional stirred tank reactor process. Chemical structures of as-prepared polymers were characterized. In vitro drug delivery performance was evaluated. The cytotoxicity of PEG-PBCA to brain microvessel endothelial cells (BMVEC) decreases with the extension of the PEG chain and the shortening of the PBCA chain. The polymer cellular uptake to BMVECs was better after improving hydrophilicity by PEG block. Results of blood-brain barrier permeability demonstrated that medium length of PBCA chain and short PEG chain are favorable for hydrophobic Nile red permeation, while long PEG chain and short PBCA chain are beneficial to delivery water-soluble doxorubicin hydrochloride (Dox). The average apparent permeability coefficient increased 1.7 and 0.25 times than that of raw Nile red and Dox, respectively. High-gravity intensified condensation polymerization should have great potential in brain drug delivery system.

关键词: High-gravity technology, Knoevenagel condensation-Michael addition polymerization, Poly (ethylene glycol)-poly (n-butyl cyanoacrylate), Blood-brain barrier, Polymerization, Reactors

Abstract: Poly (ethylene glycol)-poly (n-butyl cyanoacrylate) (PEG-PBCA) is a remarkable drug delivery carrier for permeating blood-brain barrier. In this work, a novel high-gravity procedure was reported to intensify Knoevenagel condensation-Michael addition polymerization of PEG-PBCA. A series of PEG-PBCA containing different block ratios were synthesized with narrow molecular weight distribution of polydispersity indexes less than 1.1. Furthermore, the reaction time reduced 60% compared to conventional stirred tank reactor process. Chemical structures of as-prepared polymers were characterized. In vitro drug delivery performance was evaluated. The cytotoxicity of PEG-PBCA to brain microvessel endothelial cells (BMVEC) decreases with the extension of the PEG chain and the shortening of the PBCA chain. The polymer cellular uptake to BMVECs was better after improving hydrophilicity by PEG block. Results of blood-brain barrier permeability demonstrated that medium length of PBCA chain and short PEG chain are favorable for hydrophobic Nile red permeation, while long PEG chain and short PBCA chain are beneficial to delivery water-soluble doxorubicin hydrochloride (Dox). The average apparent permeability coefficient increased 1.7 and 0.25 times than that of raw Nile red and Dox, respectively. High-gravity intensified condensation polymerization should have great potential in brain drug delivery system.

Key words: High-gravity technology, Knoevenagel condensation-Michael addition polymerization, Poly (ethylene glycol)-poly (n-butyl cyanoacrylate), Blood-brain barrier, Polymerization, Reactors

Xingzheng Liu, Chuanbo Fu, Manting Wang, Jiexin Wang, Haikui Zou, Yuan Le, Jianfeng Chen. High-gravity technology intensified Knoevenagel condensation-Michael addition polymerization of poly (ethylene glycol)-poly (n-butyl cyanoacrylate) for blood-brain barrier delivery[J]. 中国化学工程学报, 2022, 46(6): 94-103.

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High-gravity technology intensified Knoevenagel condensation-Michael addition polymerization of poly (ethylene glycol)-poly (n-butyl cyanoacrylate) for blood-brain barrier delivery

High-gravity technology intensified Knoevenagel condensation-Michael addition polymerization of poly (ethylene glycol)-poly (n-butyl cyanoacrylate) for blood-brain barrier delivery

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