Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes
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...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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2018
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| Online Access: | http://eprints.sunway.edu.my/752/ http://eprints.sunway.edu.my/752/1/Tiekink%20Crystallographic%20and%20docking.pdf |
| _version_ | 1848801891230679040 |
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| author | Caracelli, Ignez Maganhi, Stella H. de Oliveira Cardoso, Josiane Cunha, Rodrigo L.O.R. Vega-Teijido, Mauricio Angel Zukerman-Schpector, Julio Tiekink, Edward R. T. * |
| author_facet | Caracelli, Ignez Maganhi, Stella H. de Oliveira Cardoso, Josiane Cunha, Rodrigo L.O.R. Vega-Teijido, Mauricio Angel Zukerman-Schpector, Julio Tiekink, Edward R. T. * |
| author_sort | Caracelli, Ignez |
| building | SU Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T21:14:39Z |
| format | Article |
| id | sunway-752 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:14:39Z |
| publishDate | 2018 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-7522020-10-07T09:20:50Z http://eprints.sunway.edu.my/752/ Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes Caracelli, Ignez Maganhi, Stella H. de Oliveira Cardoso, Josiane Cunha, Rodrigo L.O.R. Vega-Teijido, Mauricio Angel Zukerman-Schpector, Julio Tiekink, Edward R. T. * QD Chemistry 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. 2018 Article PeerReviewed text en http://eprints.sunway.edu.my/752/1/Tiekink%20Crystallographic%20and%20docking.pdf Caracelli, Ignez and Maganhi, Stella H. and de Oliveira Cardoso, Josiane and Cunha, Rodrigo L.O.R. and Vega-Teijido, Mauricio Angel and Zukerman-Schpector, Julio and Tiekink, Edward R. T. * (2018) Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes. Zeitschrift für Kristallographie - Crystalline Materials, 233 (2). pp. 113-124. ISSN 2194-4946 http://doi.org/10.1515/zkri-2017-2079 doi:10.1515/zkri-2017-2079 |
| spellingShingle | QD Chemistry Caracelli, Ignez Maganhi, Stella H. de Oliveira Cardoso, Josiane Cunha, Rodrigo L.O.R. Vega-Teijido, Mauricio Angel Zukerman-Schpector, Julio Tiekink, Edward R. T. * Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes |
| title | Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes |
| title_full | Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes |
| title_fullStr | Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes |
| title_full_unstemmed | Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes |
| title_short | Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes |
| title_sort | crystallographic and docking (cathepsins b, k, l and s) studies on bioactive halotelluroxetanes |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/752/ http://eprints.sunway.edu.my/752/ http://eprints.sunway.edu.my/752/ http://eprints.sunway.edu.my/752/1/Tiekink%20Crystallographic%20and%20docking.pdf |