Silver(I) complexes with 2,6-diacetylpyridine-bis(benzoylhydrazones): Antifungal activity and interaction with DNA

• Published in: Polyhedron Vol. 138; pp. 270 - 276
• Main Authors: Santos, Ane F., Ferreira, Isabella P., Pinheiro, Carlos B., Takahashi, Jacqueline A., Teixeira, Letícia R., Beraldo, H.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 14.12.2017; Elsevier
• Subjects: Antifungal activity; Bis(benzoylhydrazones); Chemistry; Chemistry, Inorganic & Nuclear; Crystal structures; Crystallography; Interaction with DNA; Physical Sciences; Science & Technology; Silver(I) complexes; Crystal structures; Antifungal activity; Interaction with DNA; Silver(I) complexes; Bis(benzoylhydrazones); CELLS; ANTIBACTERIAL; BISMUTH(III) COMPLEXES; IONS; 2-BENZOYLPYRIDINE-DERIVED HYDRAZONES; IN-VITRO; AGENTS; BINDING-PROPERTIES; DERIVATIVES
• ISSN: 0277-5387
• DOI: 10.1016/j.poly.2017.09.019

[AgHL]NO3 complexes (1–4), HL=2,6-diacetylpyridine bis(benzoylhydrazone) (1) and its bis(para-methylbenzoylhydrazone) (2), bis(para-chlorobenzoylhydrazone) (3), and bis(para-nitrobenzoylhydrazone) (4) derivatives were obtained. While the parent ligand revealed to be inactive, complex (2) was as active as miconazole nitrate against Candida albicans. Complexes (1–4) strongly interact with calf thymus DNA by an intercalative mode. [Display omitted] Complexes [Ag(H2-2,6AcPh)]NO3 (1), [Ag(H2-2,6AcpCH3Ph)]NO3 (2), [Ag(H2-2,6AcpClPh)]NO3·2H2O (3) and [Ag(H2-2,6AcpNO2Ph)]NO3 (4) were obtained with 2,6-diacetylpyridine bis(benzoylhydrazone) (H2-2,6AcPh) and its bis(para-methylbenzoylhydrazone) (H2-2,6AcpCH3Ph), bis(para-chlorobenzoylhydrazone) (H2-2,6AcpClPh), and bis(para-nitrobenzoylhydrazone) (H2-2,6AcpNO2Ph) derivatives. Complexes (1–4) were characterized by microanalyses, molar conductivities, and by means of their infrared and NMR spectra. The crystal structures of (2) and (3) were determined. The bis(benzoylhydazones) were inactive or poorly active against yeast and filamentous fungal strains. In several cases the antimicrobial activity increased upon coordination to silver(I). While the parent ligand revealed to be inactive, complex (2) proved to be as active as miconazole nitrate against Candida albicans. Although the bis(benzoylhydrazones) showed no antifungal activity, complex (1) proved to be as active as nystatin against Penicillium citrinium. In addition, complexes (1) and (2) proved to be as or more effective than nystatin against Aspergillus parasiticus. The silver(I) complexes strongly interact with calf thymus DNA by an intercalative mode.