A biomimetic strategy for the selective recognition of organophosphates in 100% water: synergies of electrostatic interactions, cavity embedment and metal coordination

Collin, Solène; Giraud, Nicolas; Dumont, Élise; Reinaud, Olivia

doi:10.1039/c9qo00263d

“…29,30 In this regard, we have developed a family of molecular receptors displaying a nitrogenous binding site, the access to which is controlled by a calix [6]arene-based polyaromatic cavity. [31][32][33] These supramolecular systems have led to the elaboration of molecular probes, [34][35][36] transmembrane transporters, 37,38 selectors for stationary phases 39 or mimics of enzymatic pockets. 40 Host-guest molecular switches were obtained as well, using acid-base [41][42][43][44][45][46] or electrochemical stimuli.…”

Section: Introductionmentioning

confidence: 99%

A 4-state acid–base controlled molecular switch based on a host–guest system

Leener

¹

,

Over

²

,

Reinaud

³

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Wang,

Zhang

et al. 2023

Angewandte Chemie

0

View full text Add to dashboard Cite

Precise binding towards structurally similar substrates is a common feature of biomolecular recognition. However, achieving such selectivity—especially in distinguishing subtle differences in substrates—with synthetic hosts can be quite challenging. Herein, we report a novel design strategy involving the combination of different rigid skeletons to adjust the distance between recognition sites within the cavity, which allows for the highly selective recognition of hydrogen‐bonding complementary substrates, such as 4‐chromanone. X‐ray single‐crystal structures and density functional theory calculations confirmed that the distance of endo‐functionalized groups within the rigid cavity is crucial for achieving high binding selectivity through hydrogen bonding. The thermodynamic data and molecular dynamics simulations revealed a significant influence of the hydrophobic cavity on the binding affinity. The new receptor possesses both high selectivity and high affinity, which provide valuable insights for the design of customized receptors.

show abstract

Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Wang,

Zhang

et al. 2023

View full text Add to dashboard Cite

Precise binding towards structurally similar substrates is a common feature of biomolecular recognition. However, achieving such selectivity—especially in distinguishing subtle differences in substrates—with synthetic hosts can be quite challenging. Herein, we report a novel design strategy involving the combination of different rigid skeletons to adjust the distance between recognition sites within the cavity, which allows for the highly selective recognition of hydrogen‐bonding complementary substrates, such as 4‐chromanone. X‐ray single‐crystal structures and density functional theory calculations confirmed that the distance of endo‐functionalized groups within the rigid cavity is crucial for achieving high binding selectivity through hydrogen bonding. The thermodynamic data and molecular dynamics simulations revealed a significant influence of the hydrophobic cavity on the binding affinity. The new receptor possesses both high selectivity and high affinity, which provide valuable insights for the design of customized receptors.

show abstract

A biomimetic strategy for the selective recognition of organophosphates in 100% water: synergies of electrostatic interactions, cavity embedment and metal coordination

Abstract: A biomimetic receptor allows selective recognition of organophosphates in water thanks to multipoint recognition associating coordination, electrostatics and cavity hosting.

Cited by 7 publications

References 37 publications

A 4-state acid–base controlled molecular switch based on a host–guest system

A 4-state acid–base controlled molecular switch based on a host–guest system

Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Contact Info

Product

Resources

About