A new packing motif for para-sulfonatocalix[4]arene: the solid state structure of the para-sulfonatocalix[4]arene d-arginine complex

Lazar, Adina N.; Silva, Éric Da; Navaza, A.; Barbey, Carole; Coleman, Anthony W.

doi:10.1039/b408863h

Cited by 57 publications

(65 citation statements)

References 14 publications

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“…For example, they can be functionalised to yield multivalent ligands that promote specific binding . Considering the propensity of sulfonato‐calix[4]arene (sclx 4 ) to encapsulate lysine or arginine we have focused our attention on this ligand. Previously, we demonstrated that the four‐fold symmetric sclx 4 can bind to several sites on cytochrome c .…”

Section: Introductionmentioning

confidence: 99%

Protein Recognition by Functionalized Sulfonatocalix[4]arenes

Doolan

Rennie

Crowley

2017

Chemistry A European J

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The interactions of two mono-functionalized sulfonatocalix[4]arenes with cytochrome c were investigated by structural and thermodynamic methods. The replacement of a single sulfonate with either a bromo or a phenyl substituent resulted in altered recognition of cytochrome c as evidenced by X-ray crystallography. The bromo-substituted ligand yielded a new binding mode in which a self-encapsulated calixarene dimer contributed to crystal packing. This ligand also formed a weak halogen bond with the protein. The phenyl-substituted ligand was bound to Lys4 of cytochrome c, in a 1.7 Å resolution crystal structure. A dimeric packing arrangement mediated by ligand-ligand contacts in the crystal suggested a possible assembly mechanism. The different protein recognition properties of these calixarenes are discussed.

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Section: Introductionmentioning

confidence: 99%

Protein Recognition by Functionalized Sulfonatocalix[4]arenes

Doolan

Rennie

Crowley

2017

Chemistry A European J

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“…Hence, neither SC4 and its derivatives nor C4diP show any inhibitory effects, this would imply that binding to more than one amino acid residue is required for enzyme inhibition. The solid-state structures of SC4 with Lys [40] or Arg [41] confirm that this system only binds a single amino acid. For the larger systems, SC6 and SC8 inhibitory effects occur for the SCNa molecules; this would be in line with binding to pharmacophore pockets 1 and 6, as shown in Figure 7 below.…”

Section: Discussionmentioning

confidence: 69%

Size and Flexibility Define the Inhibition of the H3N2 Influenza Endonuclease Enzyme by Calix[n]arenes

et al. 2019

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Inhibition of H3N2 influenza PA endonuclease activity by a panel of anionic calix[n]arenes and β-cyclodextrin sulfate has been studied. The joint experimental and theoretical results reveal that the larger, more flexible and highly water-soluble sulfonato-calix[n]arenes have high inhibitory activity, with para-sulfonato-calix[8]arene, SC8, having an IC50 value of 6.4 μM. Molecular docking calculations show the SC8 can interact at both the polyanion binding site and also the catalytic site of H3N2 influenza PA endonuclease.

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“…While there is considerable literature on the inclusion properties of SCX4 and SCX6, many of the papers focus on complexes with a potential biological importance [ 27 , 33 , 34 , 35 , 36 ]. Calixarene binding to the OP VX has been reported [ 19 ] and, as we have demonstrated, the formation of host–guest inclusion complexes of the OP nerve agent GD and commonly used simulants with SCX4 and SCX6 is clearly feasible.…”

Section: Resultsmentioning

confidence: 99%

Comparison of Binding Affinities of Water-Soluble Calixarenes with the Organophosphorus Nerve Agent Soman (GD) and Commonly-Used Nerve Agent Simulants

2018

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The formation of inclusion complexes of the water-soluble p-sulfonatocalix[n]arenes, where n = 4 or 6, with the Chemical Warfare Agent (CWA) GD, or Soman, and commonly used dialkyl methylphosphonate simulants has been studied by experimental solution NMR methods and by Molecular Mechanics (MMFF) and semi-empirical (PM6) calculations. Complex formation in non-buffered and buffered solutions is driven by the hydrophobic effect, and complex stoichiometry determined as 1:1 for all host:guest pairs. Low affinity complexes (Kassoc < 100 M−1) are observed for all guests, attributed to poor host–guest complementarity and the role of buffer cation species accounts for the low affinity of the complexes. Comparison of CWA and simulant behavior adds to understanding of CWA–simulant correlations and the challenges of simulant selection.

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A new packing motif for para-sulfonatocalix[4]arene: the solid state structure of the para-sulfonatocalix[4]arene d-arginine complex

Abstract: The solid-state structure of the complex of para-sulfonatocalix[4]arene with d-arginine, contains a water channel diagonal to a zigzag bilayer of the host, within the bilayer six crystallographically independent molecules of arginine are present, four being included in the calix cavities.

Cited by 57 publications

References 14 publications

Protein Recognition by Functionalized Sulfonatocalix[4]arenes

Protein Recognition by Functionalized Sulfonatocalix[4]arenes

Size and Flexibility Define the Inhibition of the H3N2 Influenza Endonuclease Enzyme by Calix[n]arenes

Comparison of Binding Affinities of Water-Soluble Calixarenes with the Organophosphorus Nerve Agent Soman (GD) and Commonly-Used Nerve Agent Simulants

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