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

Caracelli, Ignez; Zukerman-Schpector, Júlio; Madureira, Lucas Sousa; Maganhi, Stella H.; Stefani, Hélio A.; Guadagnin, Rafael C.; Tiekink, Edward R. T.

doi:10.1515/zkri-2016-1931

Cited by 2 publications

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“…With the aim to understand how potential therapeutic agents based on tellurium inhibit cysteine proteases, significant effort has been made to elucidate their binding modes and correlate them with inhibitory data [47][48][49][50][51]. Continuing this research, the present work targets to explain trends in previous published inhibitory data of a series of halotelluroxetanes, Figure 1, against Cathepsins B, K, L and S. New crystallographic data are presented for 1 and 4, Figure 1, and docking studies of cationic ligands 1ꞌ-4ꞌ, i.e.…”

Section: Decane (1) (3e)-2-chloro-3-(chloromethylidene)-2-(4-methoxymentioning

confidence: 99%

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

Caracelli

Maganhi

Cardoso

et al. 2017

Zeitschrift Für Kristallographie - Crystalline Materials

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Abstract. The molecular structures of the halotelluroxetanes pMeOC6H4Te(X)[C(=C(H)Xꞌ)C(CH2)nO], X = Xꞌ = Cl and n = 6 (1) and X = Cl, Xꞌ = 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⋯(arene) interactions lead to supramolecular layers. Literature studies have shown these and related compounds (i.e. 2: X = Xꞌ = Cl and n = 5; 3: X = Xꞌ = 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 telluriumbound X atoms) 1ꞌ-3ꞌ (note 3ꞌ = 4ꞌ) 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 1ꞌ 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.

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Section: Decane (1) (3e)-2-chloro-3-(chloromethylidene)-2-(4-methoxymentioning

confidence: 99%

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

Caracelli

Maganhi

Cardoso

et al. 2017

Zeitschrift Für Kristallographie - Crystalline Materials

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1-Butyl-1-chloro-3-methyl-3H-2,1λ⁴-benzoxatellurole: crystal structure and Hirshfeld analysis

et al. 2017

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

Abstract: Some biologically active organotellurium compounds exhibit inhibitory potency against cathepsin B. In this study, an alkyl derivative, viz. [CH

Cited by 2 publications

References 42 publications

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

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

1-Butyl-1-chloro-3-methyl-3H-2,1λ⁴-benzoxatellurole: crystal structure and Hirshfeld analysis

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

Abstract: Some biologically active organotellurium compounds exhibit inhibitory potency against cathepsin B. In this study, an alkyl derivative, viz. [CH

Cited by 2 publications

References 42 publications

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

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

1-Butyl-1-chloro-3-methyl-3H-2,1λ4-benzoxatellurole: crystal structure and Hirshfeld analysis

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1-Butyl-1-chloro-3-methyl-3H-2,1λ⁴-benzoxatellurole: crystal structure and Hirshfeld analysis