Application of functionalized magnetic silica nanoparticles for selective induction of three coumarin metastable polymorphs

doi:10.1016/j.cjche.2022.05.008

中国化学工程学报 ›› 2022, Vol. 50 ›› Issue (10): 155-167.DOI: 10.1016/j.cjche.2022.05.008

• Separation Science and Engineering • 上一篇下一篇

Application of functionalized magnetic silica nanoparticles for selective induction of three coumarin metastable polymorphs

Yiqing Chen¹, Xin Huang^1,2, Suping Ding¹, Yaoguang Feng¹, Na Wang^1,2, Hongxun Hao^1,2,3

1 National Engineering Research Center of Industrial Crystallization Technology, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2 Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China;
3 School of Chemical Engineering and Technology, Hainan University, Haikou 570228, China

收稿日期:2022-03-17 修回日期:2022-05-22 出版日期:2022-10-28 发布日期:2023-01-04
通讯作者: Xin Huang,E-mail:x_huang@tju.edu.cn;Hongxun Hao,E-mail:hongxunhao@tju.edu.cn
基金资助:
The authors are very grateful for financial support from the National Natural Science Foundation of China (21908159) and the Tianjin Natural Science Foundation (18JCZDJC38100).

Application of functionalized magnetic silica nanoparticles for selective induction of three coumarin metastable polymorphs

Yiqing Chen¹, Xin Huang^1,2, Suping Ding¹, Yaoguang Feng¹, Na Wang^1,2, Hongxun Hao^1,2,3

1 National Engineering Research Center of Industrial Crystallization Technology, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2 Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China;
3 School of Chemical Engineering and Technology, Hainan University, Haikou 570228, China

Received:2022-03-17 Revised:2022-05-22 Online:2022-10-28 Published:2023-01-04
Contact: Xin Huang,E-mail:x_huang@tju.edu.cn;Hongxun Hao,E-mail:hongxunhao@tju.edu.cn
Supported by:
The authors are very grateful for financial support from the National Natural Science Foundation of China (21908159) and the Tianjin Natural Science Foundation (18JCZDJC38100).

摘要/Abstract

摘要： The precise control of active pharmaceutical ingredient (API) crystal nucleation and polymorphism is a key consideration in pharmaceutical manufacturing. In this study, tunable nanoparticles were developed to regulate the nucleation process of coumarin. Magnetic silica nanoparticles with four different functional groups (—NH₂, —COOH, —SH, —NCO) were prepared and coated on the substrate for inducing the crystallization of coumarin. Confined melt crystallization and microspacing sublimation crystallization methods were used to investigate the regulation mechanism. The results indicated that three metastable forms of coumarin can be obtained as pure components based on the combined influence of crystallization methods and functionalized nanoparticles. Form II could be selectively obtained by microspacing sublimation crystallization on Fe₃O₄@SiO₂—SH substrates, and Form IV could be obtained by confined melt crystallization on Fe₃O₄@SiO₂—NCO substrates. Form III could be obtained by further heating Form IV crystals to 52 ℃ on Fe₃O₄@SiO₂—NCO substrates. Moreover, the polarized light microscopy results also indicated that the introduction of nanoparticles could also increase the stability of the metastable crystalline forms of coumarin. Finally, the diffusion and surface dynamics during nanoparticle induced crystallization were comparatively investigated and the corresponding polymorphic selectivity mechanism was proposed.

关键词: Polymorph, Functional nanoparticles, Surface interactions, Heterogeneous nucleation

Abstract: The precise control of active pharmaceutical ingredient (API) crystal nucleation and polymorphism is a key consideration in pharmaceutical manufacturing. In this study, tunable nanoparticles were developed to regulate the nucleation process of coumarin. Magnetic silica nanoparticles with four different functional groups (—NH₂, —COOH, —SH, —NCO) were prepared and coated on the substrate for inducing the crystallization of coumarin. Confined melt crystallization and microspacing sublimation crystallization methods were used to investigate the regulation mechanism. The results indicated that three metastable forms of coumarin can be obtained as pure components based on the combined influence of crystallization methods and functionalized nanoparticles. Form II could be selectively obtained by microspacing sublimation crystallization on Fe₃O₄@SiO₂—SH substrates, and Form IV could be obtained by confined melt crystallization on Fe₃O₄@SiO₂—NCO substrates. Form III could be obtained by further heating Form IV crystals to 52 ℃ on Fe₃O₄@SiO₂—NCO substrates. Moreover, the polarized light microscopy results also indicated that the introduction of nanoparticles could also increase the stability of the metastable crystalline forms of coumarin. Finally, the diffusion and surface dynamics during nanoparticle induced crystallization were comparatively investigated and the corresponding polymorphic selectivity mechanism was proposed.

Key words: Polymorph, Functional nanoparticles, Surface interactions, Heterogeneous nucleation

Yiqing Chen, Xin Huang, Suping Ding, Yaoguang Feng, Na Wang, Hongxun Hao. Application of functionalized magnetic silica nanoparticles for selective induction of three coumarin metastable polymorphs[J]. 中国化学工程学报, 2022, 50(10): 155-167.

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Application of functionalized magnetic silica nanoparticles for selective induction of three coumarin metastable polymorphs

Application of functionalized magnetic silica nanoparticles for selective induction of three coumarin metastable polymorphs

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