Protection and Transformation of Natural Products within Aqueous Metal‐Organic Cages

Cruz-Nava, Sofía; Valencia-Loza, Sergio de Jesús; Percástegui, Edmundo G.

doi:10.1002/ejoc.202200844

Cited by 8 publications

(3 citation statements)

References 90 publications

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“…This dramatic stabilization can be explained by the encapsulationinduced isolation of MC from the aqueous phase. Such encapsulation-induced enhancement of hydrolytic stability has previously been reported for a range of species otherwise prone to hydrolysis, 61 ranging from white phosphorus 13 to cyclic di(lactic acid). 62 Notably, however, these molecules were encapsulated within small-window cages, similar to B.…”

Section: Encapsulation Of Spiropyrans Within D 2h -Symmetric Cage a A...supporting

confidence: 55%

Altering the Properties of Spiropyran Switches Using Coordination Cages with Different Symmetries

et al. 2022

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Molecular confinement effects can profoundly alter the physicochemical properties of the confined species. A plethora of organic molecules were encapsulated within the cavities of supramolecular hosts, and the impact of the cavity size and polarity was widely investigated. However, the extent to which the properties of the confined guests can be affected by the symmetry of the cage�which dictates the shape of the cavity�remains to be understood. Here we show that cage symmetry has a dramatic effect on the equilibrium between two isomers of the encapsulated spiropyran guests. Working with two Pd-based coordination cages featuring similarly sized but differently shaped hydrophobic cavities, we found a highly selective stabilization of the isomer whose shape matches that of the cavity of the cage. A T d -symmetric cage stabilized the spiropyrans' colorless form and rendered them photochemically inert. In contrast, a D 2hsymmetric cage favored the colored isomer, while maintaining reversible photoswitching between the two states of the encapsulated spiropyrans. We also show that the switching kinetics strongly depend on the substitution pattern on the spiropyran scaffold. This finding was used to fabricate a time-sensitive information storage medium with tunable lifetimes of the encoded messages.

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Section: Encapsulation Of Spiropyrans Within D 2h -Symmetric Cage a A...supporting

confidence: 55%

Altering the Properties of Spiropyran Switches Using Coordination Cages with Different Symmetries

et al. 2022

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“…Apart from the selective formation of unsaturated groups, the cage-anchored MCs also display high activity toward the stereoselective hydrogenation reaction, in which a pair of isomers are generated as the products. 46 Pt@Cu-MOC (average size: 1.11 nm) reported by Zhao's group exhibited supereminent stereoselectivity and conversion for hydrogenation of a-pinene to cis-pinane under mild conditions. 47 The success was attributed to the coordinatively unsaturated metal sites that can activate targeted chemical bonds and lower the reaction energy barrier during the reaction.…”

Section: Thermocatalysismentioning

confidence: 98%

The marriage of porous cages and metal clusters for advanced catalysis

Yang

Chen

et al. 2023

Mater. Chem. Front.

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“…However, the biomedical applications of molecular cages are still in their infancy [61][62][63][64][65]. In the context of drug delivery, molecular cages can play a pivotal role as protective systems from the surrounding media, increasing drug stability [66,67].…”

Section: Biological Applicationsmentioning

confidence: 99%

Water-Soluble Molecular Cages for Biological Applications

Montà-González,

Ortiz-Gómez,

López-Lima

et al. 2024

Molecules

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The field of molecular cages has attracted increasing interest in relation to the development of biological applications, as evidenced by the remarkable examples published in recent years. Two key factors have contributed to this achievement: First, the remarkable and adjustable host–guest chemical properties of molecular cages make them highly suitable for biological applications. This allows encapsulating therapeutic molecules to improve their properties. Second, significant advances have been made in synthetic methods to create water-soluble molecular cages. Achieving the necessary water solubility is a significant challenge, which in most cases requires specific chemical groups to overcome the inherent hydrophobic nature of the molecular cages which feature the organic components of the cage. This can be achieved by either incorporating water-solubilizing groups with negative/positive charges, polyethylene glycol chains, etc.; or by introducing charges directly into the cage structure itself. These synthetic strategies allow preparing water-soluble molecular cages for diverse biological applications, including cages’ anticancer activity, anticancer drug delivery, photodynamic therapy, and molecular recognition of biological molecules. In the review we describe selected examples that show the main concepts to achieve water solubility in molecular cages and some selected recent biological applications.

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Protection and Transformation of Natural Products within Aqueous Metal‐Organic Cages

Cited by 8 publications

References 90 publications

Altering the Properties of Spiropyran Switches Using Coordination Cages with Different Symmetries

Altering the Properties of Spiropyran Switches Using Coordination Cages with Different Symmetries

The marriage of porous cages and metal clusters for advanced catalysis

Water-Soluble Molecular Cages for Biological Applications

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