Cooperative Binding and Stepwise Encapsulation of Drug Molecules by Sulfonylcalixarene-Based Metal-Organic Supercontainers

Sheng, Tianlu; Fan, Xinxia; Zheng, Ganhong; Dai, Fulong; Chen, Xiaoming

doi:10.3390/molecules25112656

Cited by 15 publications

(8 citation statements)

References 33 publications

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“…Their applications in guest encapsulation and recognition, − catalysis, − and biomedical settings − have been widely investigated. Taking advantage of both the intrinsic and extrinsic porosity ,,− of coordination containers, they have been demonstrated to be excellent candidates for the storage and separation of small molecules . However, use of coordination containers for radioactive iodine capture has not been extensively documented. , We have in recent years been investigating a new class of coordination containers derived from the assembly of sulfonylcalix[4]arene-based container precursors, divalent metal ions (e.g., Co 2+ , Ni 2+ , Zn 2+ , etc.…”

Section: Introductionmentioning

confidence: 99%

Iodine Adsorption via Porous Molecular Solids Based on Coordination Containers Derived from Naphthalene-1,8-dicarboxylate

Liu

Sheng

et al. 2022

Crystal Growth & Design

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Efficient methods to sequester the radioactive iodine element are urgently needed in the nuclear and environmental industries. Nanoporous solid adsorbents based on container molecules are particularly suited for achieving iodine sequestration due to their uniquely tunable intrinsic and extrinsic porous structure. In the present work, we describe the design and synthesis of two new coordination containers based on a sulfonylcalixarene precursor and naphthalene-1,8-dicarboxylate linker and demonstrate their promising application for iodine adsorption and release. We show that, in addition to the more common C−H•••π hydrogen bonding and hydrophobic interactions, another less appreciated type of noncovalent interaction, namely, a dual Br•••π binding motif, can be introduced through the modification of the dicarboxylate linker with a bromine substituent to strengthen the crystal packing and maintain the solid-state porosity of the molecular containers. These synthetic coordination containers not only exhibit an excellent adsorption capacity for iodine vapor at a solid−gas interface but also show an effective iodine capture ability from a hexane solution through a solid−liquid interface. Importantly, the adsorption of iodine by these porous molecular solids displays remarkable reversibility and recyclability, indicating their promising practical utility for iodine capture and release.

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Section: Introductionmentioning

confidence: 99%

Iodine Adsorption via Porous Molecular Solids Based on Coordination Containers Derived from Naphthalene-1,8-dicarboxylate

Liu

Sheng

et al. 2022

Crystal Growth & Design

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“…Based on UV-Vis spectroscopy spectra for complexes formed at pH 9.0, 9.5, and 10.0 in the DOX concentration range of 53–430 μM, the titration data were fitted to this model using the nonlinear regression method within the SigmaPlot Version 10.0 software. The DOX binding constants to the G4.0 PAMAM molecule were determined using the Hill equation [ 27 , 44 , 45 ]:

where

A ( = A obs – A 0 ) is the change in absorbance,

A max is the maximum change in absorbance, [ L ] 0 is the initial guest concentration, n is the Hill coefficient, and K a is the association constant [ 44 ].…”

Section: Resultsmentioning

confidence: 99%

Effect of Alkaline Conditions on Forming an Effective G4.0 PAMAM Complex with Doxorubicin

Szota

Jachimska

2023

Pharmaceutics

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In this study, special attention was paid to the correlation between the degree of ionization of the components and the effective formation of the complex under alkaline conditions. Using UV-Vis, 1H NMR, and CD, structural changes of the drug depending on the pH were monitored. In the pH range of 9.0 to 10.0, the G4.0 PAMAM dendrimer can bind 1 to 10 DOX molecules, while the efficiency increases with the concentration of the drug relative to the carrier. The binding efficiency was described by the parameters of loading content (LC = 4.80–39.20%) and encapsulation efficiency (EE = 17.21–40.16%), whose values increased twofold or even fourfold depending on the conditions. The highest efficiency was obtained for G4.0PAMAM-DOX at a molar ratio of 1:24. Nevertheless, regardless of the conditions, the DLS study indicates system aggregation. Changes in the zeta potential confirm the immobilization of an average of two drug molecules on the dendrimer’s surface. Circular dichroism spectra analysis shows a stable dendrimer-drug complex for all the systems obtained. Since the doxorubicin molecule can simultaneously act as a therapeutic and an imaging agent, the theranostic properties of the PAMAM-DOX system have been demonstrated by the high fluorescence intensity observable on fluorescence microscopy.

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“…Representing a new class of self-assembled supramolecular nanocarriers, metal-organic supercontainers (MOSCs) based on sulfonylcalix[4]arenes have been designed and synthesized in the past decade 22 - 25 . The multiple binding domains, favorable biocompatibility, stable chemical properties and suitable molecular size for cellular internalization make MOSCs a desirable drug delivery system 24 , 26 - 29 . Recently, we reported a magnesium-based MOSC for the enhanced treatment of joint inflammation, which co-loaded target agents and drug molecules in the exo- and endo -cavities, respectively 30 .…”

Section: Introductionmentioning

confidence: 99%

Mitochondria-targeted supramolecular coordination container encapsulated with exogenous itaconate for synergistic therapy of joint inflammation

Chen¹,

Li²,

Cao³

et al. 2022

Theranostics

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Rationale: Inflammatory macrophages and osteoclasts (OCs) play critical roles in joint inflammation, which feature the excessive production of reactive oxygen species (ROS), resulting in synovial inflammation and bone erosion. Scavenging ROS, especially by modulating mitochondrial metabolic activity, could be a desirable strategy for the management of inflammatory joints. This study aimed to develop a mitochondria-targeted supramolecular drug delivery system with exogenous and endogenous ROS-scavenging activities for the treatment of joint inflammation. Methods: In this study, we utilized a zinc-based metal-organic supercontainer (MOSC) as a proton sponge and electron reservoir with outstanding proton binding capacity, extracellular ROS-scavenging ability, and biocompatibility to establish an efficient supramolecular nanocarrier for endo/lysosomal escape and mitochondrial targeting. 4-Octyl itaconate (4-OI), an itaconate derivative, served as the loaded guest for the construction of a synergistic therapeutic system for inflammatory macrophages and OCs. Results: After the effective encapsulation of 4-OI, 4-OI@Zn-NH-pyr not only exhibited potent ROS-scavenging capacity, but also reduced ROS production by mediating mitochondrial respiration in inflammatory macrophages. Regarding its anti-inflammatory efficacy, 4-OI@Zn-NH-pyr ameliorated the inflammatory reaction by activating nuclear factor erythroid 2-related factor 2 (Nrf2), thus increasing the production of antioxidants, apart from the inhibition of NF-κB pathways. Additionally, receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclast differentiation and function was remarkably suppressed by 4-OI@Zn-NH-pyr. Consistent with in vitro observations, 4-OI@Zn-NH-pyr efficiently inhibited synovial inflammation and subchondral bone destruction in an acute arthritis model. Conclusion: By using MOSCs that are highly reactive to ROS as drug-loaded matrices for the first time, this study provides an avenue for the management of severe joint inflammation by designing synergistic supramolecular drug-delivery systems with subcellular targeting and ROS-scavenging capacity.

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Cooperative Binding and Stepwise Encapsulation of Drug Molecules by Sulfonylcalixarene-Based Metal-Organic Supercontainers

Cited by 15 publications

References 33 publications

Iodine Adsorption via Porous Molecular Solids Based on Coordination Containers Derived from Naphthalene-1,8-dicarboxylate

Iodine Adsorption via Porous Molecular Solids Based on Coordination Containers Derived from Naphthalene-1,8-dicarboxylate

Effect of Alkaline Conditions on Forming an Effective G4.0 PAMAM Complex with Doxorubicin

Mitochondria-targeted supramolecular coordination container encapsulated with exogenous itaconate for synergistic therapy of joint inflammation

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