Details

Autor(en) / Beteiligte

• Kovala-Demertzi, Dimitra
• Dokorou, Vaso
• Primikiri, Alexandra
• Vargas, Richy
• Silvestru, Cristian
• Russo, Umberto
• Demertzis, Mavroudis A.

Titel

Organotin meclofenamic complexes: Synthesis, crystal structures and antiproliferative activity of the first complexes of meclofenamic acid – Novel anti-tuberculosis agents

Ist Teil von

• Journal of inorganic biochemistry, 2009-05, Vol.103 (5), p.738-744

Ort / Verlag

United States: Elsevier Inc

Erscheinungsjahr

2009

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• The complexes [Me 2(Meclo)SnOSn(Meclo)Me 2] 2 ( 2) and [Ph 3Sn(Meclo)] ( 3) where HMeclo is meclofenamic acid, N-(2,6-dichloro- m-tolylanthranilic acid)], have been prepared and structurally characterized by means of vibrational, 1H and 13C NMR spectroscopies. The crystal structure of complexes ( 2) and ( 3) have been determined by X-ray crystallography. Three distannoxane rings are present to the dimeric tetraorganodistannoxane of planar ladder arrangement of ( 2). The structure is centro symmetric and features a central rhombus Sn 2O 2 unit two additional tin atoms linked at the oxygen atoms. Five- and six-coordinated tin centers are present in the dimer distannoxane. X-ray analysis of ( 3) revealed a penta-coordinated structure containing Ph 3Sn coordinated to the chelated carboxylato group. The polar imino hydrogen atom participates in intra-molecular hydrogen bonds. Complexes ( 2) and ( 3) are self-assembled via π → π, C–H–π, stacking interactions and intra-molecular hydrogen bonds. Meclofenamic acid and [Ph 3Sn(Meclo)] have been evaluated for antiproliferative activity in vitro against three human cancer cell lines: MCF-7 (human breast cancer cell line), T24 (bladder cancer cell line), A-549 (non-small cell lung carcinoma) and a mouse L-929 (a fibroblast-like cell line cloned from strain L). The [Ph 3Sn(Meclo)] complex exhibited high cytotoxic activity against all the cancer cell lines. Meclofenamic and [Ph 3Sn(Meclo)] were tested for anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv. The [Ph 3Sn(Meclo)] complex was found to be a promising anti-mycobacterial lead compound, displaying high activity against M. tuberculosis H37Rv.