A sustainable lecithin-based ligand for the bio-functionalization of iron and hybrid metal organic frameworks (MOFs) nanoparticles with the sugar mannose†

IF 9.3 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Green Chemistry Pub Date : 2024-10-22 DOI:10.1039/d4gc03743j

Camilla M. Cova , Víctor Ramos , Alberto Escudero , Juan P. Holgado , Noureddine Khiar , Alessio Zuliani

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Abstract

The functionalization of nanoparticles with specific ligands, such as antibodies, peptides, and small molecules, plays a critical role in achieving targeted delivery, enhancing biocompatibility, and controlling drug release. However, to date, practically no attention has been paid to the design of green ligands. Herein, an innovative approach to develop a sustainable ligand for nanoparticle functionalization is reported. Its synthesis involved a photochemical thio–ene “click” reaction between the natural compounds phosphatidylcoline, the main component of lecithin, and cysteine, followed by a reductive amination with mannose, a sugar of growing interest for biomedical targeting, in a continuous flow hydrogenation reactor. Comprehensive characterization techniques, including nuclear magnetic resonance (NMR), mass spectrometry (MS), Fourier-transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS) and elemental analysis, confirmed the structure and properties of the novel ligand. The environmental sustainability of the ligand was evaluated determining some green metrics using the EATOS software. The obtained E-factor was compared with a conventional PEG-based ligand. The newly developed lecithin-derived ligand was successfully used to functionalize diverse NP platforms, including the MOFs MIL-101(Fe), PCN-222, UiO-66, and iron nanoparticles (in the form of akaganeite), demonstrating its potential in nanomedicine applications.

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一种基于卵磷脂的可持续配体，用于铁和混合金属有机框架（MOFs）纳米粒子与甘露糖的生物功能化

用特定配体（如抗体、肽和小分子）对纳米颗粒进行功能化，在实现靶向递送、增强生物相容性和控制药物释放方面起着至关重要的作用。然而，迄今为止，人们对绿色配体的设计几乎没有关注。本文报告了一种开发可持续纳米颗粒功能化配体的创新方法。该配体的合成涉及天然化合物磷脂酰胆碱（卵磷脂的主要成分）与半胱氨酸之间的光化学硫代烯 "点击 "反应，然后在连续流氢化反应器中与甘露糖（一种在生物医学靶向领域日益受到关注的糖类）进行还原胺化反应。核磁共振（NMR）、质谱（MS）、傅立叶变换红外光谱（FTIR）、X 射线光电子能谱（XPS）和元素分析等综合表征技术证实了这种新型配体的结构和性质。通过使用 EATOS 软件确定一些绿色指标，对配体的环境可持续性进行了评估。获得的 E 因子与传统的 PEG 配体进行了比较。新开发的卵磷脂配体被成功地用于功能化各种 NP 平台，包括 MOFs MIL-101(Fe)、PCN-222、UiO-66 和铁纳米颗粒（akaganeite 形式），证明了其在纳米医学应用方面的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Green Chemistry 化学-化学综合

CiteScore

16.10

自引率

7.10%

发文量

677

审稿时长

1.4 months

期刊介绍： Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.