Abstract
The novel zinc(II) µ-oxo-bridged-dimeric complex [Zn2(µ-O)2(BMIP)2] (BMIP = 1,3-bis(5-methoxy-1-methyl-1H-indol-3-yl)propane-1,3-dione), 1, was synthetized and fully characterized. The spectral data indicate a zincoxane molecular structure, with the BMIP ligand coordinating in its neutral form via its oxygen atoms. Structural changes in 1 in dimethylsulfoxide (DMSO) were evidenced by means of spectroscopic techniques including infrared absorption and nuclear magnetic resonance, showing DMSO entrance in the coordination sphere of the metal ion. The resulting complex [Zn2(µ-O)2(BMIP)2(DMSO)], 2, readily reacts in the presence of N-methyl-imidazole (NMI), a liquid-phase nucleoside mimic, to form [Zn2(µ-O)2(BMIP)2(NMI)], 3, through DMSO displacement. The three complexes show high thermal stability, demonstrating that 1 has high affinity for hard nucleophiles. Finally, with the aim of probing the suitability of this system as model scaffold for new potential anticancer metallodrugs, the interactions of 1 with calf thymus DNA were investigated in vitro in pseudo-physiological environment through UV-Vis absorption and fluorescence emission spectroscopy, as well as time-resolved fluorescence studies. The latter analyses revealed that [Zn2(µ-O)2(BMIP)2(DMSO)] binds to DNA with high affinity upon DMSO displacement, opening new perspectives for the development of optimized drug substances.
Highlights
Since the anticancer properties of cisplatin were first discovered by Rosenberg in1965 [1], many efforts have been focused on both finding more effective metallodrugs and reducing the severe side effects typical of the parent compound [2,3,4,5]
Reveals that the C=O stretching band is located at 1520 cm−1, strongly red-shifted compared to the homologous vibration at 1618 cm−1 detected for the BMIP free ligand
−1, strongly red-shifted compared reveals that the stretching band is located at cm to the homologous vibration at 1618 cm detected for the BMIP free ligand
Summary
Since the anticancer properties of cisplatin were first discovered by Rosenberg in. 1965 [1], many efforts have been focused on both finding more effective metallodrugs and reducing the severe side effects typical of the parent compound [2,3,4,5]. Β-diketone-based metal complexes are constantly catching interest [6,7] due to β-dicarbonyls’ structural simplicity and, in case of, e.g., curcuminoid compounds, intrinsic biological properties and natural availability [8]. Many ZnII complexes with good DNA-binding properties were synthetized, exploiting different types of bidentate ligands such as bis(thiosemicarbazone) [22], Pharmaceuticals 2021, 14, 760. Many ZnII complexes with good DNA-binding properties were synthetized, exploiting different types of bidentate ligands such as bis(thiosemicarbazone) [22], isoeuxanthone [23], 5,7-dihalo-8-substituted quinolones isoeuxanthone [23], [25]. Compound shows good affinity for hard nucleophiles, as it can readily expand sphere when dissolved in DMSO, forming the [Zn2(μ-O)2(BMIP)2(DMSO)] species,its.
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