Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer

Micelle is mainly used for drug delivery and is prepared from amphiphilic block copolymers. It can be formed into an obvious core-shell structure that can incorporate liposoluble drugs. However, micelles are not suitable for the encapsulation of water-soluble drugs, and it is also difficult to maint...

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Autores principales:	Lingling Qi, Chao Liu, Yingying Zhang, Zheao Zhang, Hongxia Duan, Heming Zhao, Xin Xin, Liqing Chen, Mingji Jin, Youyan Guan, Zhonggao Gao, Wei Huang
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	micelles mitomycin C bladder cancer π–π stacking hydrogen bonding interaction Pharmacy and materia medica RS1-441
Acceso en línea:	https://doaj.org/article/971cc920d2014b349bcfbca4aafc09cd
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spelling	oai:doaj.org-article:971cc920d2014b349bcfbca4aafc09cd2021-11-25T18:40:36ZDevelopment of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer10.3390/pharmaceutics131117761999-4923https://doaj.org/article/971cc920d2014b349bcfbca4aafc09cd2021-10-01T00:00:00Zhttps://www.mdpi.com/1999-4923/13/11/1776https://doaj.org/toc/1999-4923Micelle is mainly used for drug delivery and is prepared from amphiphilic block copolymers. It can be formed into an obvious core-shell structure that can incorporate liposoluble drugs. However, micelles are not suitable for the encapsulation of water-soluble drugs, and it is also difficult to maintain stability in the systemic circulation. To solve these problems, a type of polymer material, Fmoc-Lys-PEG and Fmoc-Lys-PEG-RGD, was designed and synthesized. These copolymers could self-assemble into micelles driven by π–π stacking and the hydrophobic interaction of 9-fluorenylmethoxycarbony (Fmoc) and, at the same time, form a framework for a hydrogen-bonding environment in the core. Mitomycin C (MMC), as a water-soluble drug, can be encapsulated into micelles by hydrogen-bonding interactions. The interaction force between MMC and the polymers was analyzed by molecular docking simulation and Fourier transform infrared (FTIR). It was concluded that the optimal binding conformation can be obtained, and that the main force between the MMC and polymers is hydrogen bonding. Different types of MMC nanoparticles (NPs) were prepared and the physicochemical properties of them were systematically evaluated. The pharmacodynamics of the MMC NPs in vitro and in vivo were also studied. The results show that MMC NPs had a high uptake efficiency, could promote cell apoptosis, and had a strong inhibitory effect on cell proliferation. More importantly, the as-prepared NPs could effectively induce tumor cell apoptosis and inhibit tumor growth and metastasis in vivo.Lingling QiChao LiuYingying ZhangZheao ZhangHongxia DuanHeming ZhaoXin XinLiqing ChenMingji JinYouyan GuanZhonggao GaoWei HuangMDPI AGarticlemicellesmitomycin Cbladder cancerπ–π stackinghydrogen bonding interactionPharmacy and materia medicaRS1-441ENPharmaceutics, Vol 13, Iss 1776, p 1776 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	micelles mitomycin C bladder cancer π–π stacking hydrogen bonding interaction Pharmacy and materia medica RS1-441
spellingShingle	micelles mitomycin C bladder cancer π–π stacking hydrogen bonding interaction Pharmacy and materia medica RS1-441 Lingling Qi Chao Liu Yingying Zhang Zheao Zhang Hongxia Duan Heming Zhao Xin Xin Liqing Chen Mingji Jin Youyan Guan Zhonggao Gao Wei Huang Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer
description	Micelle is mainly used for drug delivery and is prepared from amphiphilic block copolymers. It can be formed into an obvious core-shell structure that can incorporate liposoluble drugs. However, micelles are not suitable for the encapsulation of water-soluble drugs, and it is also difficult to maintain stability in the systemic circulation. To solve these problems, a type of polymer material, Fmoc-Lys-PEG and Fmoc-Lys-PEG-RGD, was designed and synthesized. These copolymers could self-assemble into micelles driven by π–π stacking and the hydrophobic interaction of 9-fluorenylmethoxycarbony (Fmoc) and, at the same time, form a framework for a hydrogen-bonding environment in the core. Mitomycin C (MMC), as a water-soluble drug, can be encapsulated into micelles by hydrogen-bonding interactions. The interaction force between MMC and the polymers was analyzed by molecular docking simulation and Fourier transform infrared (FTIR). It was concluded that the optimal binding conformation can be obtained, and that the main force between the MMC and polymers is hydrogen bonding. Different types of MMC nanoparticles (NPs) were prepared and the physicochemical properties of them were systematically evaluated. The pharmacodynamics of the MMC NPs in vitro and in vivo were also studied. The results show that MMC NPs had a high uptake efficiency, could promote cell apoptosis, and had a strong inhibitory effect on cell proliferation. More importantly, the as-prepared NPs could effectively induce tumor cell apoptosis and inhibit tumor growth and metastasis in vivo.
format	article
author	Lingling Qi Chao Liu Yingying Zhang Zheao Zhang Hongxia Duan Heming Zhao Xin Xin Liqing Chen Mingji Jin Youyan Guan Zhonggao Gao Wei Huang
author_facet	Lingling Qi Chao Liu Yingying Zhang Zheao Zhang Hongxia Duan Heming Zhao Xin Xin Liqing Chen Mingji Jin Youyan Guan Zhonggao Gao Wei Huang
author_sort	Lingling Qi
title	Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer
title_short	Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer
title_full	Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer
title_fullStr	Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer
title_full_unstemmed	Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer
title_sort	development of mitomycin c-loaded nanoparticles prepared using the micellar assembly driven by the combined effect of hydrogen bonding and π–π stacking and its therapeutic application in bladder cancer
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/971cc920d2014b349bcfbca4aafc09cd
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Development of Mitomycin C-Loaded Nanoparticles Prepared Using the Micellar Assembly Driven by the Combined Effect of Hydrogen Bonding and π–π Stacking and Its Therapeutic Application in Bladder Cancer

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