Signal-dependent reactivity of host-guest complexes controls supramolecular aggregate formation

Li, Guotai; Yu-cheng, Wan; Lewis, Reece W.; Fan, Boyu; Eelkema, Rienk

doi:10.1016/j.xcrp.2023.101309

Cited by 4 publications

(2 citation statements)

References 52 publications

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“…Further, we believe that the reduced cytotoxicity of these species, specifically DVP, compared to other commonly used reagents in CRNs, can act as an entry into interactions of synthetic CRNs with living systems. We are currently working on exploring further projects in the fields of host–guest chemistry, where we have recently demonstrated application in control over supramolecular aggregate formation, 108 triggered drug and catalyst release, transient materials, and beyond. We hope this overview can give researchers an understanding of the scope of applications and the reactivity of the involved species and aid in further discoveries based on novel CRNs that make use of this versatile chemistry.…”

Section: Discussionmentioning

confidence: 99%

Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Spitzbarth¹,

Eelkema²

2023

Chem. Commun.

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Section: Discussionmentioning

confidence: 99%

Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Spitzbarth¹,

Eelkema²

2023

Chem. Commun.

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“…Confinement of reagents on template molecules or in a confined molecular space has proven highly efficient to accelerate reactions and affect their outcomes. Molecules and reaction networks − have been developed that are able to process molecular input to create output following Boolean logic or, more recently, also through adaptation at the systems level . Additionally, the development of chemically fueled self-assembly processes has provided a tool to transiently activate chemical processes. − …”

Section: Introductionmentioning

confidence: 99%

Chemical Information Processing by a Responsive Chemical System

Gabrielli,

Goldin,

Chandrabhas

et al. 2024

J. Am. Chem. Soc.

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Nature has an extraordinary capacity to precisely regulate the chemical reactivity in a highly complex mixture of molecules that is present in the cell. External stimuli lead to transient up-and downregulation of chemical reactions and provide a means for a cell to process information arriving from the environment. The development of synthetic chemical systems with life-like properties requires strategies that allow likewise control over chemical reactivity in a complex environment. Here, we show a synthetic system that mimics the initial steps that take place when a natural signal transduction pathway is activated. Monophosphate nucleosides act as chemical triggers for the self-assembly of nanoreactors that upregulate chemical reactions between reagents present at low micromolar concentrations. Different nucleotides template different assemblies and hence activate different pathways, thus establishing a distinct connection between input and output molecules. Trigger-induced upregulation of chemical reactivity occurs for only a limited amount of time because the chemical triggers are gradually removed from the system by enzymes. It is shown that the same system transiently produces different output molecules depending on the chemical input that is provided.

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Dual pH and Ca²⁺‐Responsive PEG‐Modified Pillar[5]arene‐Based Supramolecular Nanodrug Delivery System: Excellent Cargo Encapsulation and Minimal Drug Toxicity

Shao,

Duan,

Huang

et al. 2024

Chemistry A European J

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Chemotherapy is one of the most employed strategies in clinical treatment of cancer. However, reducing medication adverse effects and improving the biological activity remains a significant issue for chemotherapy. We developed a pH and Ca2+‐responsive pillar[5]arene‐based supramolecular nanodrug delivery system (NDDS) WP5⊃EV@DOX to address the aforementioned challenges. The formation of this NDDS began with the spontaneous formation of supramolecular nanodrug carrier WP5⊃EV in water from PEG‐modified pillar[5]arene and the bipyridilium salt derivative EV through simple host‐guest interaction. Then the antitumor drug doxorubicin DOX was efficiently loaded with a high encapsulation rate of 84.6%. Cytotoxicity results indicated that the constructed nanoplatform not only reduced DOX toxicity and side effects on normal cell (293T), but also significantly enhanced the antitumor activity on cancer cell (HepG2). Moreover, in vivo experiments showed that WP5⊃EV@DOX had a longer half‐life and higher bioavailability in the blood of mice compared to the nake drug DOX, with increases to 212% and 179%, respectively. Therefore, WP5⊃EV@DOX has great potential in tumor therapy and provides a new idea for host‐guest drug delivery system.

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Signal-dependent reactivity of host-guest complexes controls supramolecular aggregate formation

Cited by 4 publications

References 52 publications

Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Chemical Information Processing by a Responsive Chemical System

Dual pH and Ca²⁺‐Responsive PEG‐Modified Pillar[5]arene‐Based Supramolecular Nanodrug Delivery System: Excellent Cargo Encapsulation and Minimal Drug Toxicity

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Signal-dependent reactivity of host-guest complexes controls supramolecular aggregate formation

Cited by 4 publications

References 52 publications

Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Chemical Information Processing by a Responsive Chemical System

Dual pH and Ca2+‐Responsive PEG‐Modified Pillar[5]arene‐Based Supramolecular Nanodrug Delivery System: Excellent Cargo Encapsulation and Minimal Drug Toxicity

Contact Info

Product

Resources

About

Dual pH and Ca²⁺‐Responsive PEG‐Modified Pillar[5]arene‐Based Supramolecular Nanodrug Delivery System: Excellent Cargo Encapsulation and Minimal Drug Toxicity