Nanomedicine has had a profound impact on the treatment of many diseases especially cancer. However, synthesis of multifunctional nanoscale drug carriers often requires multistep coupling and purification reactions, which can pose major scale-up challenges. Here we leveraged bioinspired oxidation-triggered polymerization of catechols to synthesize nanoparticles (NPs) from the plant polyphenol quercetin (QCT) loaded with a hydrophobic anti-cancer drug, curcumin, and functionalized with poly(ethylene glycol) (PEG) for steric stabilization in one reaction step.NPs were formed by base-catalyzed oxidative self-polymerization of QCT in the presence of curcumin and thiol-terminated PEG upon mixing in a universal solvent (dimethyl sulfoxide), followed by self-assembly with the gradual addition of water. Dynamic light scattering and X-ray photoelectron spectroscopy were used to confirm NP PEGylation. Drug loading was verified by UV-Vis spectroscopy. Curcumin-loaded NPs were efficiently internalized by CT26 murine colon cancer cells as determined by flow cytometry and confocal microscopy. NPs also demonstrated sustained release and potent cytotoxicity in vitro. Moreover, in vivo imaging of CT26 tumorbearing Balb/c mice following tail vein injection of DiR-labeled QCT NPs showed steady tumor accumulation of the NPs up to 24 h. This was further supported by significant tumor uptake of curcumin-loaded QCT NPs as measured by flow cytometry analysis of tumor homogenates. Our findings present a greener synthetic route for the fabrication of drug-loaded surface functionalized NPs from poorly water-soluble plant polyphenols such as QCT as promising anti-cancer delivery systems.
Plant polyphenols have received considerable attention in recent years due to their ability to undergo oxidation-triggered self-polymerization, forming biocompatible versatile coatings and templated nanoparticles (NPs) that can be leveraged for a variety of biomedical applications. Here we show for the first time that untemplated NPs can be conveniently synthesized from the abundant plant polyphenol quercetin (QCT) simply by incubation with an oxidizing agent in a universal organic solvent, followed by self-assembly upon gradual addition of water. The process yielded NPs of around 180–200 nm in size with a range of colors that resembled light to medium-brown skin tones. The NPs were characterized by UV-Vis, FT-IR, and 1H-NMR spectroscopy and by dynamic light scattering and transmission electron microscopy to understand their physicochemical properties. Antioxidant and cell viability assays were also conducted to demonstrate the NPs’ free-radical scavenging activity and biocompatibility, altogether providing valuable insights into the structure and function of this emerging class of nanomaterials to guide future biomedical applications.
Plant polyphenols have attracted attention in recent years due to their ability to undergo oxidative coupling reactions enabled by the presence of multiple phenolic hydroxyl groups, forming chemically versatile coatings and biocompatible nanoparticles (NPs) for various applications. The aim of this study was to investigate whether coffee bean aqueous extracts, which are known to be rich in polyphenols, could serve as a natural source of NP building blocks. Extracts were prepared by heating ground Arabica beans of varying roasting degrees in water with or without the addition of sodium metaperiodate or copper sulfate as an oxidizing agent, followed by filtration. NP formation was verified by dynamic light scattering and transmission electron microscopy, which revealed the presence of nano-sized particles with varying sizes and polydispersities as a function of the coffee type and oxidizing agent used. NP colors ranged from light to medium to dark brown, and particle sizes were between 44 and 250 nm with relatively low polydispersity indices. In vitro antioxidant assays showed that oxidizing agent-treated coffee NPs had lower antioxidant potency compared to air-oxidized NPs, but the free-radical scavenging activity was still retained. Coffee NPs exhibited no antimicrobial activity against common bacterial and fungal strains. Cell viability assays demonstrated that the NPs were biocompatible in human dermal fibroblasts, while exhibiting antiproliferative activity against MCF7 breast cancer cells, particularly copper sulfate-oxidized NPs. This study presents a facile and economical method to produce template-free antioxidant NPs that may be explored for various applications such as drug delivery and cosmetics.
Thymoquinone (TQ) is a water-insoluble natural compound isolated from Nigella sativa that has demonstrated promising chemotherapeutic activity. The purpose of this study was to develop a polymeric nanoscale formulation for TQ to circumvent its delivery challenges. TQ-encapsulated nanoparticles (NPs) were fabricated using methoxy poly(ethylene glycol)-b-poly(ε-caprolactone) (mPEG-PCL) copolymers by the nanoprecipitation technique. Formulation variables included PCL chain length and NP architecture (matrix-type nanospheres or reservoir-type nanocapsules). The formulations were characterized in terms of their particle size, polydispersity index (PDI), drug loading efficiency, and drug release. An optimized TQ NP formulation in the form of oil-filled nanocapsules (F2-NC) was obtained with a mean hydrodynamic diameter of 117 nm, PDI of 0.16, about 60% loading efficiency, and sustained in vitro drug release. The formulation was then tested in cultured human cancer cell lines to verify its antiproliferative efficacy as a potential anticancer nanomedicine. A pilot pharmacokinetic study was also carried out in healthy mice to evaluate the oral bioavailability of the optimized formulation, which revealed a significant increase in the maximum plasma concentration (Cmax) and a 1.3-fold increase in bioavailability compared to free TQ. Our findings demonstrate that the versatility of polymeric NPs can be effectively applied to design a nanoscale delivery platform for TQ that can overcome its biopharmaceutical limitations.
Glucose oxidase was immobilized on conventional multi-well plates via bioinspired polyphenol chemistry for convenient colorimetric quantitation of glucose.
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