The triphenyltin(VI) complexes of NSAIDs and derivatives. Synthesis, crystal structure and antiproliferative activity. Potent anticancer agents
| Autor: | Dimitra Kovala-Demertzi, Alexandra Primikiri, Vaso Dokorou |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
Mefenamic acid
Stereochemistry Molecular Conformation Antineoplastic Agents Crystal structure Crystallography X-Ray Biochemistry Inorganic Chemistry chemistry.chemical_compound Mefenamic Acid Mice Structure-Activity Relationship Coordination Complexes Cell Line Tumor medicine Organotin Compounds Animals Humans Carboxylate Benzoic acid Coordination geometry Cell Proliferation Anti-Inflammatory Agents Non-Steroidal Esters Flufenamic Acid Trigonal bipyramidal molecular geometry Flufenamic acid chemistry Drug Design Drug Screening Assays Antitumor Selectivity medicine.drug |
| Zdroj: | Journal of inorganic biochemistry. 105(2) |
| ISSN: | 1873-3344 |
| Popis: | The novel triphenyltin(IV) esters of flufenamic acid ( 1 ), Hflu, [Ph 3 Sn(flu)] ( 2 ), and of [2-(2,3-dichlorophenylamino)benzoic acid] ( 3) , Hdcpa, [Ph 3 Sn(dcpa)] ( 4 ) have been structurally characterized by means of vibrational and 1 H, 13 C NMR spectroscopic studies. The crystal and molecular structures of [SnPh 3 (dcpa)(DMSO)] 4a are described. The molecular structure of 4a reveals that the Sn atom has a distorted trigonal bipyramidal coordination geometry with equatorial phenyl groups and the carboxylate and dimethylsulfoxide oxygen atoms occupying axial positions. The crystal structure of 4a is self-assembled by C–H---π and π–π stacking interactions. The in vitro cytotoxic activity of 1 – 4 and of the related non-steroidal anti-inflammatory drugs, NSAIDs, [2-(2,6-dimethylphenylamino)benzoic acid], Hdmpa ( 5 ), [Ph 3 Sn(dmpa)] ( 6 ), [2-(2,3-dimethylphenylamino)benzoic acid], mefenamic acid, Hmef ( 7 ) and [Ph 3 Sn(mef)] ( 8 ) has been evaluated against the cancer cell lines MCF-7, T-24, A-549 and L-929. The ligands exhibited very poor cytotoxic activity against the four cancer cell lines. Complex 6 exhibits the highest activity and selectivity against A-549 and MCF-7 cancer cell lines and complex 8 the highest activity and selectivity against T-24 cancer cell line. The cytotoxic results indicate that coupling of Hdmpa and Hmef with R 3 Sn(IV) metal center results in complexes with important biological properties and remarkable cytotoxic activity, since they display IC 50 values in a μΜ range better to that of the antitumor drug cis-platin. Complexes 6 and 8 are considered as excellent antitumor compounds and the results of this study represent the discovery of triphenyltin(IV)esters as a potential novel class of anticancer agents. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect