Synthesis, photophysical properties and structures of organotin-Schiff bases utilizing aromatic amino acid from the chiral pool and evaluation of the biological perspective of a triphenyltin compound
| Autor: | Ulli Englert, Tushar S. Basu Baul, Nikhil Guchhait, Raveendra B. Mokhamatam, Michelangelo Scopelliti, Sunil K. Manna, Nerina Armata, Ruimin Wang, Andrew Duthie, Nune Raviprakash, Pelesakuo Kehie |
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| Přispěvatelé: | Basu Baul, T., Kehie, P., Duthie, A., Guchhait, N., Raviprakash, N., Mokhamatam, R., Manna, S., Armata, N., Scopelliti, M., Wang, R., Englert, U. |
| Rok vydání: | 2017 |
| Předmět: |
Models
Molecular Cell Survival Stereochemistry Antineoplastic Agents Crystal structure Chiral Schiff base Crystallography X-Ray 010402 general chemistry 01 natural sciences Biochemistry Inorganic Chemistry Amino Acids Aromatic Inhibitory Concentration 50 chemistry.chemical_compound Bromide Cell Line Tumor Ribose Organotin Compounds Humans Schiff Bases Spectroscopy X-ray crystallography Coordination geometry chemistry.chemical_classification Cyclodextrin 010405 organic chemistry Ligand A375 (human melanoma) cell line Tryptophan Stereoisomerism Photochemical Processes Organotin(IV) compound 0104 chemical sciences Molecular Docking Simulation Monomer chemistry Settore CHIM/03 - Chimica Generale E Inorganica Derivative (chemistry) |
| Zdroj: | Journal of Inorganic Biochemistry. 168:76-89 |
| ISSN: | 0162-0134 |
| DOI: | 10.1016/j.jinorgbio.2016.12.001 |
| Popis: | Five new organotin(IV) complexes of compositions [Me 2 SnL 1 ] ( 1 ), [Me 2 SnL 2 ] n ( 2 ), [Me 2 SnL 3 ] ( 3 ), [Ph 3 SnL 1 H] n ( 4 ) and [Ph 3 SnL 3 H] ( 5 ) (where L 1 = (2 S )-2-(( E )-(( Z )-4-hydroxypent-3-en-2-ylidene)amino)-3-(1 H -indol-3-yl)propanoate, L 2 = (2 S )-( E )-2-((2-hydroxybenzylidene)amino)-3-(1 H -indol-3-yl)propanoate and L 3 = (2 S )-( E )-2-((1-(2-hydroxyphenyl)ethylidene)amino)-3-(1 H -indol-3-yl)propanoate were synthesized and spectroscopically characterized. The crystal structures of 1 – 4 were determined. For the dimethyltin derivative 2 , a polymeric chain structure was observed as a result of a long Sn∙∙∙O contact involving the exocyclic carbonyl oxygen-atom from the tridentate ligand of a neighboring Sn-complex unit. The tin atom in this complex has a distorted octahedral coordination geometry, in which the long Sn-O bond is almost trans to the tridentate ligand nitrogen-atom. In contrast, the dimethyltin(IV) complexes 1 and 3 displayed discrete monomeric structures where the tin atom has distorted trigonal-bipyramidal geometry with the two coordinating L oxygen atoms defining the axial positions. On the other hand, 4 is a chain polymer in the solid state. The ligand-bridged Sn atoms adopt a trans -Ph 3 SnO 2 trigonal-bipyramidal configuration with equatorial phenyl groups. A carboxylato oxygen atom from one and the hydroxyl oxygen of the successive ligand in the chain occupy the axial positions. The solution structures were predicted by the use of 119 Sn NMR chemical shifts. The photophysical properties of the complexes were investigated in the solid and in solution. The triphenyltin(IV) compound 4 was tested in detail ex vivo against A375 (human melanoma) cell line, exhibiting an IC 50 value of 261 nM to induce cell death as assessed by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay without significant alteration of cytolysis as determined by lactate dehydrogenase (LDH) assay. Compound 4 -mediated potent cell death was also determined by Live and Dead assay and caspase-mediated cleavage of poly-ADP ribose polymerase (PARP). Potent cell death activity was not observed in primary cells, like blood-derived peripheral mononuclear cells (PBMC). Compound 4 inhibited the diphenyl hexatriene (DPH) binding to cells and decreased the micro viscosity in a dose-dependent manner. Additionally, the ability of 4 and cyclodextrin (CD) to interact was determined by molecular modelling. |
| Databáze: | OpenAIRE |
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