Adaptive binding and selection of compressed 1,ω-diammonium-alkanes via molecular encapsulation in water

Dumitrescu, Dan; Legrand, Yves‐Marie; Petit, Eddy; Lee, Arie van der; Barboiu, Mihail

doi:10.1039/c4sc03945a

Cited by 17 publications

(15 citation statements)

References 42 publications

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“…Recent crystal structures of 4PSA in complex with guanidine and diaminoalkanes provideh ints as to how this ligand might simultaneously interactw ith up to four cationic side chains. [53] 4PSA had minimal effects on the "lysineb elt"; this suggested that the adjacent Asp and Glur esidues repelled the charge-dense anion.…”

Section: Discussionmentioning

confidence: 98%

“…Ligand 4PSA, the smallest and simplest of the four, was the most specific, with a binding site focused on the “arginine face” at which favourable hydrophobic, salt‐bridge and cation–π interactions may form. Recent crystal structures of 4PSA in complex with guanidine and diaminoalkanes provide hints as to how this ligand might simultaneously interact with up to four cationic side chains . 4PSA had minimal effects on the “lysine belt”; this suggested that the adjacent Asp and Glu residues repelled the charge‐dense anion.…”

Section: Discussionmentioning

confidence: 99%

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Protein Camouflage: Supramolecular Anion Recognition by Ubiquitin

et al. 2016

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Progress in the field of bio-supramolecular chemistry, the bottom-up assembly of protein-ligand systems, relies on a detailed knowledge of molecular recognition. To address this issue, we have characterised complex formation between human ubiquitin (HUb) and four supramolecular anions. The ligands were: pyrenetetrasulfonic acid (4PSA), p-sulfonato-calix[4]arene (SCLX4), bisphosphate tweezers (CLR01) and meso-tetrakis (4-sulfonatophenyl)porphyrin (TPPS), which vary in net charge, size, shape and hydrophobicity. All four ligands induced significant changes in the HSQC spectrum of HUb. Chemical shift perturbations and line-broadening effects were used to identify binding sites and to quantify affinities. Supporting data were obtained from docking simulations. It was found that these weakly interacting ligands bind to extensive surface patches on HUb. A comparison of the data suggests some general indicators for the protein-binding specificity of supramolecular anions. Differences in binding were observed between the cavity-containing and planar ligands. The former had a preference for the arginine-rich, flexible C terminus of HUb.

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Section: Discussionmentioning

confidence: 98%

Section: Discussionmentioning

confidence: 99%

Protein Camouflage: Supramolecular Anion Recognition by Ubiquitin

et al. 2016

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“…The shielding effects of PTSG{3} and PTSG{3}{4} are the largest observed among all the guests: the upfield shifts of H a and H b from PTS 4− are 0.12 and 0.20 ppm, and the aromatic protons H 1 , H 2 , H 3 or H 4 , H 5 , and H 6 from the serotonin ( 3 ) guest are 0.78, 0.66, 0.72, 0.59, 0.71, and 0.51 ppm, respectively. It is also worth noting that the shielding effects observed in the present case are larger than those previously observed for the non‐aromatic hosts . This indicates much better encapsulation, probably due to the stronger and combined π–π, H‐bonding, and electrostatic interactions between PTS 4− platforms and the biogenic amine guests 1 – 4 .…”

Section: Methodsmentioning

confidence: 99%

“…For PTSG{1},t he CÀH/p and p-p interactions between the PTS 4À À (3)g uest are 0.78, 0.66, 0.72, 0.59, 0.71, and0 .51 ppm, respectively.I ti s also worth noting that the shielding effects observed in the present case are larger than those previously observedf or the non-aromatic hosts. [10,11] This indicates much better encapsulation, probably due to the stronger and combined p-p,Hbonding, and electrostatic interactions between PTS 4À À platforms andt he biogenic amine guests 1-4.…”

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confidence: 96%

“Pyrene Box” Cages for the Confinement of Biogenic Amines

Feng

Lee

Legrand

et al. 2017

Chemistry A European J

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The complete structure of non-crystalline compounds can be determined by confining them in crystalline structures. The reduced motional degrees of freedom of encapsulated guests can be obtained through their anchoring to the host cages, which results in the reduction of a significant amount of disorder. The "pyrene box" cages that easily crystallize from aqueous solutions are recommended to achieve complete structure elucidation of compounds of biological interest. In this study, the "pyrene box" cages have been used for the in situ encapsulation of biogenic amines: histamine, dopamine, and serotonin. NMR spectroscopy illustrates that these systems are stable in aqueous solution. The X-ray single-crystal structure analysis reveals that the pyrene box/biogenic amine systems are stabilized through combined interactions, strongly contributing to in situ fixation and accurate determination of their crystal structures.

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“…The packing in the solid state and conformational changes of the flexible alkyldiaminium cations in different systems have been recently investigated both in solution (Dumitrescu et al, 2014(Dumitrescu et al, , 2015Fang et al, 2016) and in the solid state (Lemmerer & Billing, 2012;Visi et al, 2006;Song et al, 2002). A Cambridge Structural Database (Allen, 2002) overview of structures with 1,4-butanediaminium and 1,6-hexanediaminium cations was carried out by Paul and Kubicki in 2008(Paul & Kubicki, 2009.…”

Section: Introductionmentioning

confidence: 99%

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

Brozdowska

Chojnacki

2017

Acta Crystallogr Sect B

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A series of diaminium thiosulfates, derivatives of diamines: NHCHCH(CH)NH (1) and NH(CH)NH, n = 3-6 [(2)-(5)] and thiosulfuric acid were prepared and their structures determined by single-crystal X-ray diffraction analysis. Compounds (1), (2) and (4) turned out to be hydrates. The crystal structure of 1,2-propylenediaminium thiosulfate is chiral and exhibits spontaneous resolution. Crystals for both enantiomers [(1a) and (1b)] were obtained with high enantiometric excess and examined. An extended network of strong, charge-assisted hydrogen bonding of the N-H...O type (also O-H...O and O-H...S for hydrates) is most likely the main factor defining crystal packing and the variable conformation of the cations. The formation of chiral hydrogen-bond motifs - distorted cubans - seems to induce the formation of chiral solid-state structure from achiral components in the case of (4). Diaminium thiosulfates with an odd number of C atoms in the alkyl chain [compounds (1), (2) and (4)] form three-dimensional supramolecular networks, while in the case of diaminium salts with an even number of C atoms [(3) and (5)], two-dimensional layers of hydrogen-bond domains are observed. The aminium thiosulfates were also characterized by elemental analysis, NMR and Fourier transform (FT)-IR spectroscopy. The conformations of α,ω-alkyldiaminium cations in the solid state are discussed and rationalized by DFT calculations.

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Adaptive binding and selection of compressed 1,ω-diammonium-alkanes via molecular encapsulation in water

Abstract: Alkane chains may be encapsulated inside rigid crystalline capsules, adopting specific conformations of different levels of compression that are sufficiently kinetically stable under the confined conditions, to allow a conventional structure determination by X-ray diffraction.

Cited by 17 publications

References 42 publications

Protein Camouflage: Supramolecular Anion Recognition by Ubiquitin

Protein Camouflage: Supramolecular Anion Recognition by Ubiquitin

“Pyrene Box” Cages for the Confinement of Biogenic Amines

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

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