Functionalization of Reduced Graphene Oxide via Thiol–Maleimide “Click” Chemistry: Facile Fabrication of Targeted Drug Delivery Vehicles,ACS Applied Materials & Interfaces

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Functionalization of Reduced Graphene Oxide via Thiol–Maleimide “Click” Chemistry: Facile Fabrication of Targeted Drug Delivery Vehicles
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2017-09-21 00:00:00 , DOI: 10.1021/acsami.7b08433
Yavuz Oz , Alexandre Barras ₁ , Rana Sanyal ₂ , Rabah Boukherroub ₁ , Sabine Szunerits ₁ , Amitav Sanyal

Affiliation

Materials based on reduced graphene oxide (rGO) have shown to be amenable to noncovalent functionalization through hydrophobic interactions. The scaffold, however, does not provide sufficient covalent linkage given the low number of reactive carboxyl and alcohol groups typically available on the rGO. The integration of clickable groups, particularly the ones that can undergo efficient conjugation without any metal catalyst, would allow facile functionalization of these materials. This study reports on the noncovalent association of a maleimide-containing catechol (dopa-MAL) surface anchor onto the rGO. Thiol–maleimide chemistry allows thereafter the facile attachment of thiol-containing molecules under ambient metal-free conditions. Although the attachment of glutathione and 6-(ferrocenyl)hexanethiol was used as model thiols, the attachment of a cancer cell targeting cyclic peptide, c(RGDfC), opened the possibility of using the dopa-MAL-modified rGO as a targeted drug delivery system for doxorubicin (DOX). Although free DOX showed to be more effective at killing the human cervical cancer cells (HeLa) over human breast adenocarcinoma cancer cells (MDA-MB-231), the DOX-loaded rGO/dopa-MAL-c (RGDfC) nanostructure showed an opposite effect being notably more effective at targeting and killing the MDA-MB-231 cells. The effect is enhanced upon laser irradiation for 10 min at 2 W cm^–2. The facile fabrication and functionalization to readily obtain a functional material in a modular fashion make this clickable-rGO construct an attractive platform for various applications.

中文翻译：

通过硫醇-马来酰亚胺“点击”化学作用还原氧化石墨烯的功能：靶向药物输送载体的简便制备

基于还原性氧化石墨烯（rGO）的材料已显示可通过疏水相互作用进行非共价官能化。然而，考虑到rGO上通常可用的反应性羧基和醇基团数量少，该支架不能提供足够的共价键。可点击基团的整合，特别是那些可在没有任何金属催化剂的情况下进行有效共轭的基团，将可以使这些材料容易地官能化。这项研究报告了含马来酰亚胺的邻苯二酚（dopa-MAL）表面锚与rGO的非共价结合。巯基-马来酰亚胺化学反应之后，可以在无金属的环境下轻松连接含硫醇的分子。尽管使用了谷胱甘肽和6-（二茂铁基）己烷硫醇的连接物作为模型硫醇，癌细胞靶向环肽c（RGDfC）的附着打开了将dopa-MAL修饰的rGO用作阿霉素（DOX）靶向药物递送系统的可能性。尽管游离DOX在杀死人宫颈癌细胞（MDA-MB-231）方面比杀死人宫颈癌细胞（MDA-MB-231）更有效，但DOX加载的rGO / dopa-MAL-c（RGDfC）纳米结构却显示出相反的结果这种作用在靶向和杀死MDA-MB-231细胞方面更为有效。在2 W cm处进行10分钟激光照射后，效果会增强尽管游离DOX在杀死人宫颈癌细胞（MDA-MB-231）方面比杀死人宫颈癌细胞（MDA-MB-231）更有效，但DOX加载的rGO / dopa-MAL-c（RGDfC）纳米结构却显示出相反的结果这种作用在靶向和杀死MDA-MB-231细胞方面更为有效。在2 W cm下激光照射10分钟后，效果会增强尽管游离DOX在杀死人宫颈癌细胞（MDA-MB-231）方面比杀死人宫颈癌细胞（MDA-MB-231）更有效，但DOX加载的rGO / dopa-MAL-c（RGDfC）纳米结构却显示出相反的结果这种作用在靶向和杀死MDA-MB-231细胞方面更为有效。在2 W cm下激光照射10分钟后，效果会增强^–2。易于制造和功能化，以模块化方式轻松获得功能性材料，使该可单击的rGO可以为各种应用构建有吸引力的平台。

更新日期：2017-09-21

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