Diorganotin(IV) complexes with 2-furancarboxylic acid hydrazone derivative of benzoylacetone : synthesis, X-ray structure, antibacterial activity, DNA cleavage and molecular docking
Articolo
Data di Pubblicazione:
2015
Citazione:
Diorganotin(IV) complexes with 2-furancarboxylic acid hydrazone derivative of benzoylacetone : synthesis, X-ray structure, antibacterial activity, DNA cleavage and molecular docking / T. Sedaghat, Y. Ebrahimi, L. Carlucci, D.M. Proserpio, V. Nobakht, H. Motamedi, M.R. Dayer. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - 794:(2015), pp. 223-230. [10.1016/j.jorganchem.2015.06.034]
Abstract:
Two new diorganotin(IV) complexes, Me2SnL and Ph2SnL, have been synthesized from the reaction of
Me2SnCl2 and Ph2SnCl2 with the hydrazone H2L [H2L ¼ (Furan-2-yl) (5-hydroxy-3-methyl-5-phenyl-4,5-
dihydro-1H-pyrazol-1-yl)-methanone] derived from furan-2-carbohydrazide and benzoylacetone. The
new compounds have been characterized by elemental and spectroscopic analyses. The crystal structures
of the monohydrate form of the ligand and of the Me2SnL derivative have been also determined by X-ray
crystallography. Experimental evidences confirm the existence of the hydrazone ligand exclusively in
cyclic form in both solution and solid state. On coordination to tin the hydrazone undergoes a ring
opening reaction and a doubly deprotonation to act as a tridentate ligand via imine nitrogen and enolic
oxygens. The tin atom in the complexes is five coordinate with geometry between square-pyramidal and
trigonal-bipyramidal. The in vitro antibacterial activity of ligand and its complexes has been evaluated
against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli
and Pseudomonas aeruginosa) bacteria. The interaction between compounds with bacterial DNA was also
studied by molecular docking. Our findings indicate that diphenyltin(IV) complex, by binding to DNA via
minor groove to TATA sequence in genes upstream, has good activities along with the standard antibacterial
drugs. Our agarose-gel electrophoresis experiments show that the ligand exert DNA cleavage,
while Me2SnL and Ph2SnL did not.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Organotin(IV); Hydrazone; Diketone; Antibacterial activity; DNA cleavage; Molecular docking
Elenco autori:
T. Sedaghat, Y. Ebrahimi, L. Carlucci, D.M. Proserpio, V. Nobakht, H. Motamedi, M.R. Dayer
Link alla scheda completa: