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

Autor(es)

Caracelli, Ignez ^[1] ; Zukerman-Schpector, Julio ^[2] ; Madureira, Lucas Sousa ^[2] ; Maganhi, Stella H. ^[1] ; Stefani, Helio A. ^[3] ; Guadagnin, Rafael C. ^[4] ; Tiekink, Edward R. T. ^[5]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos, BioMat, Dept Fis, CP 676, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Fed Sao Carlos, Lab Cristalog Estereodinam & Modelagem Mol, Dept Quim, CP 676, BR-13565905 Sao Carlos, SP - Brazil

^[3] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP - Brazil

^[4] Univ Fed Sao Paulo, Inst & Ciencias Ambientais, Quim & Farmaceut, Diadema, SP - Brazil

^[5] Sunway Univ, Fac Sci & Technol, Ctr Crystalline Mat, Bandar Sunway 47500, Selangor Darul - Malaysia

• Tipo de documento: Artigo Científico
• Fonte: ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS; v. 231, n. 6, p. 321-328, JUN 2016.
• Citações Web of Science: 3

Resumo

Some biologically active organotellurium compounds exhibit inhibitory potency against cathepsin B. In this study, an alkyl derivative, viz. {[}CH3(CH2)(2)C(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 center dot center dot center dot I interactions are also noted. If all interactions are considered, the coordination geometry is based on Psi-pentagonal bipyramidal geometry. An unusual feature of the structure is the curving of the functionalised C-5 chain. This feature has been explored by DFT methods and shown to arise as a result of close C-H center dot center dot center dot 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)(2)TeX2 compounds should also be evaluated for biological activity. (AU)

• Processo FAPESP: 12/00424-2 - Síntese de pequenas bibliotecas empregando organotrifluoroboratos de potássio em reações de Suzuki-Miyaura
• Beneficiário: Helio Alexandre Stefani
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 12/22524-9 - Síntese, caracterização e estudos de docking de sistemas de liberação controlada de fármacos e potenciais fármacos utilizando quitosana como carreador
• Beneficiário: Stella Hernandez Maganhi
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado