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

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 ste...

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Main Authors: Caracelli, Ignez, Zukerman-Schpector, Julio, Madureira, Lucas Sousa, Maganhi, Stella H., Stefani, Hélio A., Guadagnin, Rafael C., Tiekink, Edward R. T. *
Format: Article
Language:English
Published: De Gruyter 2016
Subjects:
QD Chemistry
Online Access:http://eprints.sunway.edu.my/654/1/Z.%20Kristallogr.%202016%20231%20321.pdf
http://eprints.sunway.edu.my/654/
http://dx.doi.org/10.1515/zkri-2016-1931
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spelling my.sunway.eprints.6542020-10-07T09:58:44Z http://eprints.sunway.edu.my/654/ Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound Caracelli, Ignez Zukerman-Schpector, Julio Madureira, Lucas Sousa Maganhi, Stella H. Stefani, Hélio A. Guadagnin, Rafael C. Tiekink, Edward R. T. * QD Chemistry 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. De Gruyter 2016 Article PeerReviewed text en http://eprints.sunway.edu.my/654/1/Z.%20Kristallogr.%202016%20231%20321.pdf Caracelli, Ignez and Zukerman-Schpector, Julio and Madureira, Lucas Sousa and Maganhi, Stella H. and Stefani, Hélio A. and Guadagnin, Rafael C. and Tiekink, Edward R. T. * (2016) Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound. Zeitschrift für Kristallographie - Crystalline Materials, 231 (6). pp. 321-328. ISSN 2194-4946 http://dx.doi.org/10.1515/zkri-2016-1931 doi:10.1515/zkri-2016-1931
institution Sunway University
building Sunway Campus Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Sunway University
content_source Sunway Institutional Repository
url_provider http://eprints.sunway.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Caracelli, Ignez
Zukerman-Schpector, Julio
Madureira, Lucas Sousa
Maganhi, Stella H.
Stefani, Hélio A.
Guadagnin, Rafael C.
Tiekink, Edward R. T. *
Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
description 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.
format Article
author Caracelli, Ignez
Zukerman-Schpector, Julio
Madureira, Lucas Sousa
Maganhi, Stella H.
Stefani, Hélio A.
Guadagnin, Rafael C.
Tiekink, Edward R. T. *
author_facet Caracelli, Ignez
Zukerman-Schpector, Julio
Madureira, Lucas Sousa
Maganhi, Stella H.
Stefani, Hélio A.
Guadagnin, Rafael C.
Tiekink, Edward R. T. *
author_sort Caracelli, Ignez
title Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
title_short Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
title_full Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
title_fullStr Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
title_full_unstemmed Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
title_sort crystallographic, dft and docking (cathepsin b) studies on an organotellurium(iv) compound
publisher De Gruyter
publishDate 2016
url http://eprints.sunway.edu.my/654/1/Z.%20Kristallogr.%202016%20231%20321.pdf
http://eprints.sunway.edu.my/654/
http://dx.doi.org/10.1515/zkri-2016-1931
_version_ 1680323390616895488
score 13.211869

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