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Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes

  • Ignez Caracelli EMAIL logo , Stella H. Maganhi , Josiane de Oliveira Cardoso , Rodrigo L.O.R. Cunha , Mauricio Angel Vega-Teijido , Julio Zukerman-Schpector and Edward R.T. Tiekink EMAIL logo
Published/Copyright: September 19, 2017
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 233 Issue 2

Abstract

The molecular structures of the halotelluroxetanes p-MeOC6H4Te(X)[C(=C(H)X′)C(CH2)nO], X=X′=Cl and n=6 (1) and X=Cl, X′=Br and n=5 (4), show similar binuclear aggregates sustained by {· · ·Te–O}2 cores comprising covalent Te–O and secondary Te· · ·O interactions. The resulting C2ClO2(lone-pair) sets define pseudo-octahedral geometries. In each structure, C–X· · ·π(arene) interactions lead to supramolecular layers. Literature studies have shown these and related compounds (i.e. 2: X=X′=Cl and n=5; 3: X=X′=Br and n=5) to inhibit Cathepsins B, K, L and S to varying extents. Molecular docking calculations have been conducted on ligands (i.e. cations derived by removal of the tellurium-bound X atoms) 1′–3′ (note 3′=4′) enabling correlations between affinity for sub-sites and inhibition. The common feature of all docked complexes was the formation of a Te–S covalent bond with cysteine residues, the relative stability of the ligands with an E-configuration and the formation of a C–O· · ·π interaction with the phenyl ring; for 1′ the Te–S covalent bond was weak, a result correlating with its low inhibition profile. At the next level differences are apparent, especially with respect to the interactions formed by the organic-ligand-bound halides. While these atoms do not form specific interactions in Cathepsins B and K, in Cathepsin L, these halides are involved in C–O· · ·X halogen bonds.

Keywords: halotelluroxetanes; crystal structure analysis; DFT; docking in Cathepsins; X-ray diffraction

Acknowledgements

The support of the Brazilian agencies the National Council for Scientific and Technological Development (CNPq-308480/2016-3 to IC, 305626/2013-2 to JZS), São Paulo Research Foundation (FAPESP-12/22524-9 to SHM) and the Coordination for the Improvement of Higher Education Personnel (CAPES) are acknowledged.

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Supplemental Material:

The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2017-2079).

Received: 2017-6-1
Accepted: 2017-8-19
Published Online: 2017-9-19
Published in Print: 2018-2-23

©2018 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Syntheses, crystal structures and photoluminescence properties of two rare-earth molybdates CsLn(MoO4)2 (Ln=Eu, Tb)
  5. Two superstructures of Ce3Rh4Ge4
  6. Organic and Metalorganic Crystal Structures
  7. Organic-inorganic hybrid materials from divalent metal cations and expanded N,N′-donor linkers
  8. Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes
  9. Radical scavenging potency of 2-(benzofuran-2-yl)-2-oxoethyl 3-(methyl/amino)benzoate: synthesis, crystal structure and Hirshfeld surface analysis
  10. Crystal structures and Hirshfeld surface analyses of halogen substituted azine derivatives, 1,4-bis(halophenyl)-2,3-diazabuta-1,3-dienes
  11. Proton-transfer compounds featuring the unusual 4-arsonoanilinium cation from the reaction of (4-aminophenyl)arsonic acid with strong organic acids
https://doi.org/10.1515/zkri-2017-2079
Keywords for this article
halotelluroxetanes; crystal structure analysis; DFT; docking in Cathepsins; X-ray diffraction

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Syntheses, crystal structures and photoluminescence properties of two rare-earth molybdates CsLn(MoO4)2 (Ln=Eu, Tb)
  5. Two superstructures of Ce3Rh4Ge4
  6. Organic and Metalorganic Crystal Structures
  7. Organic-inorganic hybrid materials from divalent metal cations and expanded N,N′-donor linkers
  8. Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes
  9. Radical scavenging potency of 2-(benzofuran-2-yl)-2-oxoethyl 3-(methyl/amino)benzoate: synthesis, crystal structure and Hirshfeld surface analysis
  10. Crystal structures and Hirshfeld surface analyses of halogen substituted azine derivatives, 1,4-bis(halophenyl)-2,3-diazabuta-1,3-dienes
  11. Proton-transfer compounds featuring the unusual 4-arsonoanilinium cation from the reaction of (4-aminophenyl)arsonic acid with strong organic acids
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