Biodegradable Oxamide‐Phenylene‐Based Mesoporous Organosilica Nanoparticles with Unprecedented Drug Payloads for Delivery in Cells

Croissant, Jonas G.; Fatieiev, Yevhen; Julfakyan, Khachatur; Lü, Jie; Emwas, Abdul‐Hamid; Anjum, Dalaver H.; Omar, Haneen; Tamanoi, Fuyuhiko; Zink, Jeffrey I.; Khashab, Niveen M.

doi:10.1002/chem.201601714

Cited by 88 publications

(78 citation statements)

References 43 publications

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“…Polymer‐based stimuli‐responsive materials have been the subject of significant and sustained research owing to their potential for a range of applications, for example, drug delivery, sensing, smart coatings . Much effort has been devoted to the development of systems that are responsive to biological changes such as pH, temperature, redox activity, or enzyme levels . For this purpose, thiol‐disulfide chemistry is of considerable interest, as it confers covalent stabilization of structures through reversible cross‐linking.…”

Section: Methodsmentioning

confidence: 99%

Poly(Pentafluorophenyl Methacrylate)‐Based Nano‐Objects Developed by Photo‐PISA as Scaffolds for Post‐Polymerization Functionalization

Couturaud

Georgiou

Varlas

et al. 2018

Macromol. Rapid Commun.

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The preparation of a functional fluorine-containing block copolymer using reversible addition-fragmentation chain-transfer dispersion polymerization in DMSO as a "platform/scaffold" is explored. The nanostructures, comprised of poly(ethyleneglycol)-b-poly(pentafluorophenyl methacrylate) or PEG-b-P(PFMA), are formulated via photo-initiated polymerization-induced self-assembly (PISA) followed by post-polymerization modification using different primary amines. A combination of light scattering and microscopy techniques are used to characterize the resulting morphologies. It is found that upon varying the degree of polymerization of the core-forming block of PFMA, only uniform spheres (with textured surfaces) are obtained. These nanostructures are subsequently modified by cross-linking using a non-responsive and a redox-responsive diamine, thus imparting stability to the particles in water. In response to intracellular glutathione (GSH) concentration, destabilization of the micelles occurs as evidenced by dynamic light scattering. The well-defined size, inherent reactivity of the nanoparticles toward nucleophiles, and GSH-responsiveness of the nanospheres make them ideal scaffolds for drug delivery to intracellular compartments with reductive environments.

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Section: Methodsmentioning

confidence: 99%

Poly(Pentafluorophenyl Methacrylate)‐Based Nano‐Objects Developed by Photo‐PISA as Scaffolds for Post‐Polymerization Functionalization

Couturaud

Georgiou

Varlas

et al. 2018

Macromol. Rapid Commun.

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“…[1][2][3][4][5][6][7][8][9][10][11] The absence of particle biodegradability prevents almost always the approval of the food and drug administration (FDA) and other regulatory agencies to enter the pharmaceutical market. Non-degradable nanomaterials are indeed raising concerns of toxicity due to their uncontrolled bio-accumulation.…”

Section: Introductionmentioning

confidence: 99%

“…The degraded products of biodegradable nanoparticles (NPs) should also to be biocompatible. Biodegradable nanomaterials include various polymer, [6] liposome, [12,13] silicon, [14,15] organically-doped silica, [2,3,5] and calcium phosphate nanosystems. [16,17] In addition, nano-objects of hydrodynamic diameter (HD) below 10 nm are excreted by the body via the renal clearance route which prevents the toxicity associated with the bio-accumulation of particles.…”

Section: Introductionmentioning

confidence: 99%

Biodegradable Magnetic Silica@Iron Oxide Nanovectors with Ultra-Large Mesopores for High Protein Loading, Magnetothermal Release, and Delivery

Omar

Croissant

Alamoudi

et al. 2017

Journal of Controlled Release

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Abstract:The delivery of large cargos of diameter above 15 nm for biomedical applications has proved challenging since it requires biocompatible, stably-loaded, and biodegradable nanomaterials. In this study, we describe the design of biodegradable silica-iron oxide hybrid nanovectors with large mesopores for large protein delivery in cancer cells. The mesopores of the nanomaterials spanned from 20 to 60 nm in diameter and post-functionalization allowed the electrostatic immobilization of large proteins (e.g. mTFP-Ferritin, ~534 kDa). Half of the content of the nanovectors was based with iron oxide nanophases which allowed the rapid biodegradation of the carrier in fetal bovine serum and a magnetic responsiveness. The nanovectors released large protein cargos in aqueous solution under acidic pH or magnetic stimuli. The delivery of large proteins was then autonomously achieved in cancer cells via the silica-iron oxide nanovectors, which is thus a promising for biomedical applications.

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“…12,13 In another study, it was shown that biodegradable SiO 2 NPs with unprecedented drug payloads could be fabricated by using enzyme-sensitive oxamide/phenylene-based organosilica precursors. 14 Furthermore, researchers have indicated the use of breakable disulfide-based silsesquioxane nanoparticles for in vitro two-photon imaging and drug delivery to cancer cells. 15–17 Vivero-Escoto et al have made degradable polysilsesquioxane nanoparticles using bis(trialkoxysilyl) derivatives of Gd(III) diethylenetriamine pentaacetate (Gd-DTPA) as efficient contrast agents for magnetic resonance imaging (MRI).…”

Section: Introductionmentioning

confidence: 99%

Redox-Responsive Polysulfide-Based Biodegradable Organosilica Nanoparticles for Delivery of Bioactive Agents

Moghaddam

Saikia

Yazdimamaghani

et al. 2017

ACS Appl. Mater. Interfaces

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Design and development of silica nanoparticles (SiO2 NPs) with a controlled degradation profile promises effective drug delivery with a predetermined carrier elimination profile. In this research, we fabricated a series of redox-responsive polysulfide-based biodegradable SiO2 NPs with low polydispersity and with variations in size (average diameters of 58 ± 7, 108 ± 11, 110 ± 9, 124 ± 9, and 332 ± 6 nm), porosity, and composition (disulfide vs tetrasulfide bonds). The degradation kinetics of the nanoparticles was analyzed in the presence of 8 mM glutathione (GSH), mimicking the intracellular reducing condition. Results indicate that porosity and core composition play the predominant roles in the degradation rate of these nanoparticles. The 108 nm mesoporous disulfide-based nanoparticles showed the highest degradation rate among all the synthesized nanoparticles. Transmission electron microscopy (TEM) reveals that nonporous nanoparticles undergo surface erosion, while porous nanoparticles undergo both surface and bulk erosion under reducing environment. The cytotoxicity of these nanoparticles in RAW 264.7 macrophages was evaluated. Results show that all these nanoparticles with the IC50 values ranging from 233 ± 42 to 705 ± 17 μg mL−1 do not have cytotoxic effect in macrophages at concentrations less than 125 μg mL−1. The degradation products of these nanoparticles collected within 15 days did not show cytotoxicity in the same macrophage cell line after 24 h of incubation. In vitro doxorubicin (DOX) release was examined in 108 nm mesoporous disulfide-based nanoparticles in the absence and presence of 8 mM GSH. It was shown that drug release depends on intracellular reducing conditions. Due to their ease of synthesis and scale up, robust structure, and the ability to control size, composition, release, and elimination, biodegradable SiO2 NPs provide an alternative platform for delivery of bioactive and imaging agents.

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Biodegradable Oxamide‐Phenylene‐Based Mesoporous Organosilica Nanoparticles with Unprecedented Drug Payloads for Delivery in Cells

Cited by 88 publications

References 43 publications

Poly(Pentafluorophenyl Methacrylate)‐Based Nano‐Objects Developed by Photo‐PISA as Scaffolds for Post‐Polymerization Functionalization

Poly(Pentafluorophenyl Methacrylate)‐Based Nano‐Objects Developed by Photo‐PISA as Scaffolds for Post‐Polymerization Functionalization

Biodegradable Magnetic Silica@Iron Oxide Nanovectors with Ultra-Large Mesopores for High Protein Loading, Magnetothermal Release, and Delivery

Redox-Responsive Polysulfide-Based Biodegradable Organosilica Nanoparticles for Delivery of Bioactive Agents

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