IQUIR   05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
congresos y reuniones científicas
Título:
Antifungal, phyto, cyto and genotoxic properties of two complexes of sulfadimethoxine (H-SDM) with Ag(I). Synthesis and characterization of [Ag3SDM(SCN)2].
Autor/es:
MOSCONI, N.; MONTI, L.; M. VEGA; WILLIAMS PATRICIA A.M.; B. TOPLIKAR; SVETAZ L. ; RAIMONDI M. ; RIZZOTTO, M.
Lugar:
Concón
Reunión:
Congreso; 14a Conferencia Latinoamericana de Físico-Química Orgánica; 2017
Institución organizadora:
Pontificia Universidad Católica de Chile
Resumen:
The treatment of infectious diseases is still an important and challenging current problem. The interest in metal?sulfanilamide derivatives was stimulated by the successful introduction of a Ag(I) sulfadiazine complex, yet in current use, to prevent bacterial infections during burn treatment of both humans and animals. H-SDM (Fig. 1) is used in medicine, most frequently veterinary, to treat many infections, such as respiratory, urinary, etc. Here we report the synthesis, characterization by elemental analysis (Carlo Erba EA1108 elemental analyzer), FTIR (4,000-400 cm-1, using the KBr pellet technique) and NMR (1H NMR, 300.1 MHz; 13C NMR, 50.3 MHz) of the heterolepticcomplex [Ag3(SCN)2SDM], named as Ag-SDM-SCN and biological properties (lipophilicity, antifungal, phyto, cyto and genotoxicity) of Ag-SDM-SCN and the homoleptic one: Ag-SDM, following previously reported procedures1,2. Elemental analysis of the obtained white powder gave satisfactory results for [Ag3(SDM)(SCN)2], Ag3C14H13N6O4S3, calculated MM: 749.10 g mol-1. 1H NMR spectra show that the sulfonamide moiety loses its acidic proton in both complexes, in agreement with the FTIR results. Infrared spectrum (Fig. 2) suggests that silver interacted with the N atom of the aromatic ring, generating changes in the methoxy groups vibrations. The thiocyanate group in the complex absorbed at 754 cm-1 and 2086 cm-1 (as a single band), as would be expected if coordination occurred through the N atom of the thiocyanate ligand, discarding S- and bridging coordinations. Lipophilicity: log Koctanol/water values were 0.80, 0.84, 0.85 and 0.94 for H-SDM, NaSDM, Ag-SDM and Ag-SDM-SCN respectively, similarly to another sulfa-metal complexes2. Minimal inhibitory and minimal fungicidal concentrations of the complexes were determined against the following fungi: Candida albicans ATCC 10231; Candida tropicalis C 131; Cryptococcus neoformans ATCC 32264; Aspergillus flavus ATCC 9170; Aspergillus fumigatus ATCC 26934; Aspergillus niger ATCC 9029; Microsporum gypseum C 115; Trichophyton rubrum C 113; Trichophyton mentagrophytes ATCC 9972. (ATCC: American Type Culture Collection; C: CEREMIC, FCByF, UNR) Both complexes showed a moderate antifungal activity with all the assayed fungi, mainly against the yeasts. None of the tested fungi was inhibit by the free ligand. No genotoxicity or cytotoxicity was observed for both complexes in the Allium cepa test, which is auspicious for further study of these complexes as potential drugs.