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

Author(s)

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]

Affiliation

^[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

• Document type: Journal article
• Source: ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS; v. 231, n. 6, p. 321-328, JUN 2016.
• Web of Science Citations: 3

Abstract

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)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 12/22524-9 - Synthesis, characterization and docking studies of controlled drug delivery systems for drugs and potential drugs using chitosan as a carrier
• Grantee: Stella Hernandez Maganhi
• Support Opportunities: Scholarships in Brazil - Post-Doctoral