Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids
| Autor: | Kastriot Ademi, Cristina Paiva de Sousa, Pedro I. S. Maia, Victor M. Deflon, Edson Rodrigues-Filho, N.F.G. Serrano, Zia Ud Din |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Chalcone biology 010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Active site Alanine carboxypeptidase Aromaticity Crystal structure Triclinic crystal system COMPOSTOS ALICÍCLICOS 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology biology.protein Conformational isomerism Spectroscopy Monoclinic crystal system |
| Zdroj: | Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP |
| Popis: | In this work the screening of 20 unsymmetrical chalcone and curcuminoids analogues in regard of their antimicrobial properties was conducted. Electron donating groups in the aromatic rings in the chalcone and curcuminoid derivatives produced higher antimicrobial effect. Compounds 1, 9 and 15 exhibited good activity against Escherichia coli and Staphylococcus aureus. These compounds were further evaluated against nine micro-organisms of pathological interest. Pharmmaper was used for target fishing of compounds against important bacterial targets. Molecular Docking helped to verify the results of these compounds against the selected bacterial target d -alanyl- d -alanine carboxypeptidase (PDB ID: 1PW1). The crystal structure of ligand and docked conformers in the active site of 1PW1 were analyzed. As a result structure-activity relationships are proposed. Structures of compounds 14 and 16 were obtained through single crystals X-ray diffraction studies. Compound 14 crystallizes in monoclinic space group P21/c with unit cell dimensions a = 13.1293(3) A, b = 17.5364(4) A, c = 15.1433(3) A, β = 95.6440(10), V = 3469.70(13) A3 and Z = 8. Compound 16 crystallizes in triclinic space group Pī with unit cell dimensions a = 6.8226(4) A, b = 7.2256(4) A, c = 18.1235(12) A, β = 87.322(4), V = 850.57(9) A3 and Z = 2. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|