Host–Guest Allosteric Control of an Artificial Phosphatase

Czescik, Joanna; Lyu, Yanchao; Neuberg, Samuele; Scrimin, Paolo; Mancin, Fabrizio

doi:10.1021/jacs.9b12699

Cited by 22 publications

(19 citation statements)

References 24 publications

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“…Therefore, the corresponding second‐order rate constant ( k 2 = k cat / K M ) was calculated as 109±3 M −1 s −1 which is more than 15000 times higher than that of the mononuclear metal complex catalyst with a TACN head ( k 2 =0.007 M −1 s −1 ) thus lacking structural elements capable of bringing the two metal ions in close proximity [10a] . It is also far higher than the value reported for a dinuclear Zn 2+ complex ( k 2 of 0.25 M −1 s −1 ), [17] for vesicular assemblies with similar alkyl chain length ( k 2 of 5.7 M −1 s −1 ), [8b] and even for the inclusion complex formed by γ‐cyclodextrin (γ‐CD) and a bimetallic Zn 2+ complex ( k 2 of 3.6 M −1 s −1 ) [16a] . Interestingly, the k 2 ‐value of this system is comparable to, or even higher than, those reported for monolayer‐passivated Au nanoparticles containing TACN‐Zn 2+ complexes ( k 2 of 81.6 M −1 s −1 and 4.4 M −1 s −1 ) [10a,18] .…”

Section: Figurementioning

confidence: 81%

Self‐Assembled Multivalent Ag‐SR Coordination Polymers with Phosphatase‐Like Activity

Cao

Yao

Prins

et al. 2021

Chemistry A European J

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We show herein the phosphatase‐like catalytic activity of coordination polymers obtained after adding Ag+‐ions to thiols bearing hydrophobic alkyl chains terminated with a 1,4,7‐triazacyclononane (TACN) group. The subsequent addition of Zn2+ ‐ions to the self‐assembled polymers resulted in the formation of multivalent metal coordination polymers capable of catalysing the transphosphorylation of an RNA‐model compound (2‐hydroxypropyl‐4‐nitrophenyl phosphate, HPNPP) with high reactivity. Analysis of a series of metal ions showed that the highest catalytic activity was obtained when Ag+‐ions were used as the first metal ions to construct the backbone of the coordination polymer through interaction with the ‐SH group followed by Zn2+‐ions as the second metal ions complexed by the TACN‐macrocycle. Furthermore, it was demonstrated that the catalytic activity could be modulated by changing the length of the hydrophobic alkyl chain.

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Section: Figurementioning

confidence: 81%

Self‐Assembled Multivalent Ag‐SR Coordination Polymers with Phosphatase‐Like Activity

Cao

Yao

Prins

et al. 2021

Chemistry A European J

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“…Still, to this date such responsive catalysts remain very rare, have a narrow application scope or rely on extensive synthetic efforts [5] . Recently, there have been reports of regulation of the activity of synthetic catalysts [6] by supramolecular encapsulation including rotaxanes, [7–9] resorcin[4]arene, [10–12] cyclodextrin [13] and cucurbit[7]uril [14–18] which is of high interest because it enables precise, reversible and responsive control over reaction rates by adjusting the amount of available catalyst in situ. Among them, cucurbit[7]uril (CB[7]) is a widely applied molecular container, a cyclic glycoluril heptamer that binds strongly to small neutral and cationic compounds [19–21] .…”

Section: Introductionmentioning

confidence: 99%

Tuneable Control of Organocatalytic Activity through Host–Guest Chemistry

Trausel

Helm

et al. 2021

Angew Chem Int Ed

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Dynamic regulation of chemical reactivity is important in many complex chemical reaction networks,s uch as cascade reactions and signal transduction processes.S ignal responsive catalysts could play acrucial role in regulating these reaction pathways.R ecently,s upramolecular encapsulation was reported to regulate the activities of artificial catalysts.W e present ahost-guest chemistry strategy to modulate the activity of commercially available synthetic organocatalysts.T he molecular container cucurbit[7]uril was successfully applied to change the activity of four different organocatalysts and one initiator,enabling up-or down-regulation of the reaction rates of four different classes of chemical reactions.I nm ost cases CB[7] encapsulation results in catalyst inhibition, however in one case catalyst activation by binding to CB[7] was observed. The mechanism behind this unexpected behavior was explored by NMR binding studies and pKa measurements.The catalytic activity can be instantaneously switched during operation, by addition of either supramolecular host or competitive binding molecules,and the reaction rate can be predicted with akinetic model. Overall, this signal responsive system proves apromising tool to control catalytic activity.

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“…This phenomena can increase the solubility in water, stability, and bioavailability of host-guest complexes [ 3 , 4 , 5 ]. Due to their properties, CDs are applied in medicinal chemistry: drug-delivery systems [ 6 , 7 ], sensors [ 8 ], chiral chromatography [ 9 ], and enzyme mimics [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrins-Peptides/Proteins Conjugates: Synthesis, Properties and Applications

2021

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Cyclodextrins (CDs) are a family of macrocyclic oligosaccharides mostly composed of six, seven, or eight α-D-glucopyranose units with α-1,4-glycosidic bonds to form toroidal structures. The CDs possess a hydrophilic exterior and hydrophobic interior with the ability to form an inclusion complex, especially with hydrophobic molecules. However, most existing studies are about conjugation CDs with peptide/protein focusing on the formation of new systems. The CD-peptide/protein can possess new abilities; particularly, the cavity can be applied in modulation properties of more complexed proteins. Most studies are focused on drug delivery, such as targeted delivery in cell-penetrating peptides or co-delivery. The co-delivery is based mostly on polylysine systems; on the other hand, the CD-peptide allows us to understand biomolecular mechanisms such as fibryllation or stem cell behaviour. Moreover, the CD-proteins are more complexed systems with a focus on targeted therapy; these conjugates might be controllable with various properties due to changes in their stability. Finally, the studies of CD-peptide/protein are promising in biomedical application and provide new possibilities for the conjugation of simple molecules to biomolecules.

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Host–Guest Allosteric Control of an Artificial Phosphatase

Cited by 22 publications

References 24 publications

Self‐Assembled Multivalent Ag‐SR Coordination Polymers with Phosphatase‐Like Activity

Self‐Assembled Multivalent Ag‐SR Coordination Polymers with Phosphatase‐Like Activity

Tuneable Control of Organocatalytic Activity through Host–Guest Chemistry

Cyclodextrins-Peptides/Proteins Conjugates: Synthesis, Properties and Applications

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