Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives
The molecular structures of three 1,3‐diphenyl‐4‐(trichloro‐lλ4‐tellanyl)but‐2‐en‐1‐one derivatives (1–3), show similar coordination geometries defined by methylene-C, three chloride and carbonyl-O atoms. In each case, the resulting CCl3O donor set defines a square-pyramid with the vacant space opp...
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Elsevier
2021
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| Online Access: | http://eprints.sunway.edu.my/1790/ http://eprints.sunway.edu.my/1790/1/Tiekink%20journal%20of%20molecular%20structure%201244%20%282021%29%20130935.pdf |
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| author | Maganhi, Stella H. Caracelli, Ignez Zukerman-Schpector, Julio Cunha, Rodrigo L.O.R. Veja-Teijido, M. A. Tiekink, Edward R. T. * |
| author_facet | Maganhi, Stella H. Caracelli, Ignez Zukerman-Schpector, Julio Cunha, Rodrigo L.O.R. Veja-Teijido, M. A. Tiekink, Edward R. T. * |
| author_sort | Maganhi, Stella H. |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The molecular structures of three 1,3‐diphenyl‐4‐(trichloro‐lλ4‐tellanyl)but‐2‐en‐1‐one derivatives (1–3), show similar coordination geometries defined by methylene-C, three
chloride and carbonyl-O atoms. In each case, the resulting CCl3O donor set defines a square-pyramid with the vacant space opposite the methylene-C atom occupied by a
lone-pair of electrons. Each of the molecules dimerises in the crystal via weak intermolecular Te…Cl interactions so a distorted ψ-pentagonal-bipyramidal geometry ensues. Previous work has shown these compounds to inhibit cathepsin S to varying extents, with 2, having 2-methoxy substituents in the 2-position of rings, being particularly effective. Molecular docking calculations of cathepsin S with ligands 1'–3' (i.e. cations derived from 1–3 by removal of one of the tellurium-bound chloride atoms) showed the higher experimental second order inactivation rate of 2, compared with the other two ligands, is explained by the observation that the ligand occludes the entrance to the channel thereby blocking access to the catalytic Cys25 site and also because 2' occupies part of the crucial subsite S3 of the protein. |
| first_indexed | 2025-11-14T21:18:32Z |
| format | Article |
| id | sunway-1790 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:18:32Z |
| publishDate | 2021 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-17902021-12-31T03:42:49Z http://eprints.sunway.edu.my/1790/ Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives Maganhi, Stella H. Caracelli, Ignez Zukerman-Schpector, Julio Cunha, Rodrigo L.O.R. Veja-Teijido, M. A. Tiekink, Edward R. T. * QD Chemistry The molecular structures of three 1,3‐diphenyl‐4‐(trichloro‐lλ4‐tellanyl)but‐2‐en‐1‐one derivatives (1–3), show similar coordination geometries defined by methylene-C, three chloride and carbonyl-O atoms. In each case, the resulting CCl3O donor set defines a square-pyramid with the vacant space opposite the methylene-C atom occupied by a lone-pair of electrons. Each of the molecules dimerises in the crystal via weak intermolecular Te…Cl interactions so a distorted ψ-pentagonal-bipyramidal geometry ensues. Previous work has shown these compounds to inhibit cathepsin S to varying extents, with 2, having 2-methoxy substituents in the 2-position of rings, being particularly effective. Molecular docking calculations of cathepsin S with ligands 1'–3' (i.e. cations derived from 1–3 by removal of one of the tellurium-bound chloride atoms) showed the higher experimental second order inactivation rate of 2, compared with the other two ligands, is explained by the observation that the ligand occludes the entrance to the channel thereby blocking access to the catalytic Cys25 site and also because 2' occupies part of the crucial subsite S3 of the protein. Elsevier 2021 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1790/1/Tiekink%20journal%20of%20molecular%20structure%201244%20%282021%29%20130935.pdf Maganhi, Stella H. and Caracelli, Ignez and Zukerman-Schpector, Julio and Cunha, Rodrigo L.O.R. and Veja-Teijido, M. A. and Tiekink, Edward R. T. * (2021) Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives. Journal of Molecular Structure, 1244. p. 130935. ISSN 0022-2860 http://doi.org/10.1016/j.molstruc.2021.130935 doi:10.1016/j.molstruc.2021.130935 |
| spellingShingle | QD Chemistry Maganhi, Stella H. Caracelli, Ignez Zukerman-Schpector, Julio Cunha, Rodrigo L.O.R. Veja-Teijido, M. A. Tiekink, Edward R. T. * Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives |
| title | Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives |
| title_full | Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives |
| title_fullStr | Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives |
| title_full_unstemmed | Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives |
| title_short | Crystal structures and docking studies in cathepsin S of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives |
| title_sort | crystal structures and docking studies in cathepsin s of bioactive 1,3‐diphenyl‐4‐(trichloro‐λ4‐tellanyl)but‐2‐en‐1‐one derivatives |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1790/ http://eprints.sunway.edu.my/1790/ http://eprints.sunway.edu.my/1790/ http://eprints.sunway.edu.my/1790/1/Tiekink%20journal%20of%20molecular%20structure%201244%20%282021%29%20130935.pdf |