Cation-Induced π-Stacking

Bosch, Eric; Barnes, Charles L.; Brennan, Nathan L.; Eakins, Galen L.; Breyfogle, Bryan E.

doi:10.1021/jo800343f

Cited by 27 publications

(9 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cationic-π and π-π-stacking are considered as natural key non-covalent interactions [80]. They are important as solitary effects, but also their interplay omnipresent in many biological systems [81].…”

Section: Resultsmentioning

confidence: 99%

A Complete Assessment of Dopamine Receptor- Ligand Interactions through Computational Methods

Bueschbell

Barreto²,

Preto³

et al. 2019

Molecules

View full text Add to dashboard Cite

Background: Selectively targeting dopamine receptors (DRs) has been a persistent challenge in the last years for the development of new treatments to combat the large variety of diseases involving these receptors. Although, several drugs have been successfully brought to market, the subtype-specific binding mode on a molecular basis has not been fully elucidated. Methods: Homology modeling and molecular dynamics were applied to construct robust conformational models of all dopamine receptor subtypes (D1-like and D2-like). Fifteen structurally diverse ligands were docked. Contacts at the binding pocket were fully described in order to reveal new structural findings responsible for selective binding to DR subtypes. Results: Residues of the aromatic microdomain were shown to be responsible for the majority of ligand interactions established to all DRs. Hydrophobic contacts involved a huge network of conserved and non-conserved residues between three transmembrane domains (TMs), TM2-TM3-TM7. Hydrogen bonds were mostly mediated by the serine microdomain. TM1 and TM2 residues were main contributors for the coupling of large ligands. Some amino acid groups form electrostatic interactions of particular importance for D1R-like selective ligands binding. Conclusions: This in silico approach was successful in showing known receptor-ligand interactions as well as in determining unique combinations of interactions, which will support mutagenesis studies to improve the design of subtype-specific ligands.

show abstract

Section: Resultsmentioning

confidence: 99%

A Complete Assessment of Dopamine Receptor- Ligand Interactions through Computational Methods

Bueschbell

Barreto²,

Preto³

et al. 2019

Molecules

View full text Add to dashboard Cite

show abstract

“…Our work was inspired by the helical metal complexes reported by Bosch et al., and by our previous work on [N−I−N] + halogen bonds (Figure ). Examples of halogen bonding helices are sparse, and most have only been confirmed in the solid state.…”

Section: Figurementioning

confidence: 99%

Halogen Bonding Helicates Encompassing Iodonium Cations

et al. 2019

View full text Add to dashboard Cite

The first halonium‐ion‐based helices were designed and synthesized using oligo‐aryl/pyridylene‐ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X‐ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT calculations. The helical complexes possess potential synthetic utility, as demonstrated by their ability to induce iodocyclization of 4‐penten‐1‐ol.

show abstract

“…Our work was inspired by the helical metal complexes reported by Bosch et al, [16] and by our previous work on [NÀ IÀN] + halogen bonds ( Figure 1). Examples of halogen bonding helices are sparse, [6b, 17] and most have only been confirmed in the solid state.Anoteworthy exception is the work of Massena et al,w ho have produced solution-stable,a nioninduced, halogen-bonding triple helices.…”

mentioning

confidence: 99%