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Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound

  • Ignez Caracelli EMAIL logo , Julio Zukerman-Schpector , Lucas Sousa Madureira , Stella H. Maganhi , Hélio A. Stefani , Rafael C. Guadagnin and Edward R.T. Tiekink EMAIL logo
Published/Copyright: April 20, 2016
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 6

Abstract

Some biologically active organotellurium compounds exhibit inhibitory potency against cathepsin B. In this study, an alkyl derivative, viz. [CH3(CH2)2C(I)=C(H)](nBu)TeI2, 1, has been structurally characterised by X-ray crystallography and shown to be coordinated within a C2I2 donor set. When the stereochemically active lone pair of electrons is taken into account, a distorted trigonal bipyramidal geometry results with the iodide atoms in axial positions. Both intra- and inter-molecular Te···I interactions are also noted. If all interactions are considered, the coordination geometry is based on a Ψ-pentagonal bipyramidal geometry. An unusual feature of the structure is the curving of the functionalised C5 chain. This feature has been explored by DFT methods and shown to arise as a result of close C–H···I interactions. A docking study (cathepsin B) was performed to understand the inhibition mechanism and to compare the new results with previous observations. Notably, 1 has the same pose exhibited by analogous biologically active compounds with aryl groups. Thus, the present study suggests that (alkyl)2TeX2 compounds should also be evaluated for biological activity.

Keywords: crystal structure analysis; DFT; docking; organotellurium; X-ray diffraction

Acknowledgments

The Brazilian agencies National Council for Scientific and Technological Development (CNPq-306121/2013-2 to IC, 305626/2013-2 to JZS and 308.320/2010-7 to HAS) and São Paulo Research Foundation (FAPESP-Grants 2012/00424-2 to HAS and 12/22524-9 to SHM) are acknowledged for financial support.

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2016-1931) offers supplementary material, available to authorized users.

Received: 2016-2-5
Accepted: 2016-3-7
Published Online: 2016-4-20
Published in Print: 2016-6-1

©2016 by De Gruyter

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Ni4 and Ni3Ga clusters as building units in Ca3Ni4Ga4 and Sr3Ni3□Ga4
  5. Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
  6. Organic and Metalorganic Crystal Structures
  7. Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis
  8. Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay
  9. Nanoscratching meets nanoindentation
  10. Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate
  11. Investigation of the crystal structures and Hirshfeld surfaces of three closely related N-(2-fluorobenzoyl)-arylsulfonamides
https://doi.org/10.1515/zkri-2016-1931
Keywords for this article
crystal structure analysis; DFT; docking; organotellurium; X-ray diffraction

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Ni4 and Ni3Ga clusters as building units in Ca3Ni4Ga4 and Sr3Ni3□Ga4
  5. Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
  6. Organic and Metalorganic Crystal Structures
  7. Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis
  8. Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay
  9. Nanoscratching meets nanoindentation
  10. Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate
  11. Investigation of the crystal structures and Hirshfeld surfaces of three closely related N-(2-fluorobenzoyl)-arylsulfonamides
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