Covalent Organic Framework Material Bearing Phloroglucinol Building Units as a Potent Anticancer Agent

Abstract

Covalent organic frameworks (COFs) having periodicity in pores of nanoscale dimensions can be suitably designed for the organic building units bearing reactive functional groups at their surfaces. Thus, they are an attractive option as an anticancer agent to overcome the limitations of chemotherapy. Herein, we first report a new porous biodegradable nitrogen containing COF material, EDTFP-1 (ethylenedianiline-triformyl phloroglucinol), synthesized using 4,4'-ethylenedianiline and 2,4,6-triformylphloroglucinol via Schiff base condensation reaction. EDTFP-1 exhibited 3D-hexagonal porous structure with average pores of ca. 1.5 nm dimension. Here, we have explored the anticancer potentiality of EDTFP-1. Result demonstrated an enhanced cytotoxicity was observed against four cancer cells HCT 116, HepG2, A549, and MIA-Paca2 with significant lower IC on HCT116 cells. Additionally, EDTFP-1-induced cell death was associated with the characteristic apoptotic changes like cell membrane blebbing, nuclear DNA fragmentation, externalization of phosphatidylserine from the cell membrane followed by a loss of mitochondrial membrane potential as well as modulation of pro and antiapoptotic proteins. Further, the result depicted a direct correlation between the generations of ROS with mitochondrial-dependent apoptosis through the involvement of p53 phosphorylation upon EDTFP-1 induction, suggesting this COF material is a novel chemotherapeutic agent for cancer treatment.

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“…The blots were detected using a chromogenic substrate, nitro blue tetrazolium/5-bromo-4-chloro-3-indolyl-phosphate, and the photographs were taken using a Chemidoc XR Imager (Bio-Rad Laboratories Inc., Hercules, CA, USA). 31 The relative density of each blot was measured using ImageJ software. 27,32 Determination of proinflammatory cytokine level IL 1-beta (IL-1β), IL-2, IL-6, IL-10, and tumor necrosis factor-alpha (TNF-α) concentrations in the renal tissue samples were analyzed by using commercially available kits from eBiosciences (Santa Clara, CA, USA).…”

Covalent Organic Frameworks: From Materials Design to Biomedical Application

“…Apart from carrying anti-cancer drugs, functional COFs can kill tumor cells by themselves. Bhaumik and co-workers reported an interesting work in which phloroglucinol contained COFs were used as anticancer agents [ 328 ]. They applied 2,4,6-triformylphloroglucinol and 4,4’-ethylenedianiline to construct nanofiber like COFs (EDTFP-1) with a diameter of 22–30 nm (as shown in Figure 12 a).…”

“… Schematic representations of the preparation of EDTFP-1 ( a ) and its induced apoptotic pathway ( b ). Reproduced with permission from [ 328 ]. Copyright American Chemical Society, 2017.…”

Impedimetric Detection of Ammonia and Low Molecular Weight Amines in the Gas Phase with Covalent Organic Frameworks

“…These materials have a high surface area, and due to the strength of the covalent bond, they exhibit excellent stability in aqueous solution, acidic media, and also at high temperatures and corrosive environments [28]. These properties make COFs suitable for gas storage, energy storage, water treatments, cancer treatment, fuel cells, catalysts, and explosives sensors [29][30][31][32][33][34][35][36]. The synthesis of COFs can be carried out by several methods, including solvothermal, dropwise, microwave, sonochemistry, and mechanochemistry [37][38][39][40].…”