Abstract
SummaryCovalent organic frameworks (COFs), an emerging class of organic porous materials, have attracted intense attention due to their versatile applications. However, the deliberate fabrication of COF-based nanomaterials for nanomedical application remains challenging due to difficulty in their size- and structure-controlled synthesis and poor aqueous dispersibility. Herein, we report two boron-dipyrromethene (BODIPY)-decorated nanoscale COFs (NCOFs), which were prepared by the Schiff-base condensation of the free end –CHO (bonding defects in COFs) on the established imine-based NCOFs with the amino-substituted organic photosensitizer BODIPY via “bonding defects functionalization” approach. Thus BODIPY has been successfully nanocrystallized via the NCOF platform, and can be used for photodynamic therapy (PDT) to treat tumors. These NCOF-based PDT agents featured nanometer size (∼110 nm), low dark toxicity, and high phototoxicity as evidenced by in vitro and in vivo experiments. Moreover, the “bonding defects functionalization” approach might open up new avenues for the fabrication of additional COF-based platforms for biomedical treatment.
Highlights
As is known, cancer is one of the greatest threats to human health (Fitzmaurice et al, 2018; Siegel et al, 2019)
Recent studies revealed that organic PSs can be readily nanocrystallized via nanoscale metal-organic framework (NMOF) platform by either one-pot (Guan et al, 2018b; Lu et al, 2014) or post-synthetic modification (PSM) (Kan et al, 2018; Nian et al, 2017; Wang et al, 2016)
We report, the first of its kind, two BODIPY-decorated nanoscale COFs (NCOFs), which were generated from the NCOF LZU-1 (1) (Ding et al, 2011) and two amino-decorated BODIPY molecules, termed BODIPY-2I (2) and BODIPY-2H (4), by the bonding defects functionalization (BDF) approach under the given conditions (Figure 1A)
Summary
Cancer is one of the greatest threats to human health (Fitzmaurice et al, 2018; Siegel et al, 2019). Compared with chemotherapy and radiotherapy, PDT generates less collateral damage to normal tissues, because 1O2 is produced only in the illuminated area where the PS accumulates In this context, some organic dyes, such as boron-dipyrromethene (BODIPY)- and porphyrin-based species (Bertrand et al, 2018; Durantini et al, 2018; Josefsen and Boyle, 2012; Rajora et al, 2017), have been demonstrated to be the highly effective PSs owing to their high extinction coefficient and low dark toxicity in this minimally invasive cancer treatment. Nanocrystallization of the organic PSs significantly improves their endocytosis-based cellular uptake (Mosquera et al, 2018; Yoon and Rossi, 2018), and augments their cancer therapeutic efficacy
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