Effect of fluorine position on the coordinating ability of fluorosalicylic acids — An experimental study complemented with computations

Szabó-Plánka, Terézia; Gyurcsik, Béla; Pálinkó, István; Nagy, Nóra Veronika; Rockenbauer, Antal; Šípoš, Rastislav; Šíma, Jozef; Melnı́k, Milan

doi:10.1016/j.jinorgbio.2010.09.009

Cited by 7 publications

(1 citation statement)

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“…The good agreement between the measured and calculated values presume also that the complex structure formed in solution is kept upon freezing. Comparing the EPR parameters of CuL (go = 2.166 and Ao = 53 G) with those ofcopper(II)-fluorosalicylicacid analogoues (go = ~2.179-2.186 and Ao = ~35-38 G) [33], we can conclude that much higher go values and lower Ao values could be detected than for the different fluorosalicylic complexes. This indicates a sig nificantly higher ligand field for DQ715 as compared with fluorosalicylic acid, owing to the positive inductive effect of the pyridinic nitrogen in contrast with the negative inductive effect of the fluo rine.…”

Section: Cu(ii)-dq5 and Cu(ii)-dq715 Systemsmentioning

confidence: 83%

Hydroxypyridinecarboxylic acid derivatives influencing metal ion levels in the brain: Equilibrium complexation studies with Cu(II) and Zn(II)

Sija¹,

Nagy

Gandin

et al. 2014

Polyhedron

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The metal ion chelators 4-hydroxy-5-methyl-3-pyridinecarboxylic acid (DQ5) and 1,5-dimethyl-4-\ud hydroxy-3-pyridinecarboxylic acid (DQ715) and Cu(II) and Zn(II) were investigated with the aim to restore the homeostasis of the brain Cu(II) and Zn(II) in neurodegenerative diseases. The proton dissociation\ud constants of the ligands, the stability constants, and the coordination modes of the metal complexes formed were determined by pH-potentiometric, and spectral (UV–Vis and EPR or 1H NMR) methods. The results show that in slightly acidic and neutral pH range mono and bis complexes are formed through bidentate coordination of the ligands. The biological MTT-test reveals that the DQ715 ligand is able to\ud lower the cytotoxic effect of Cu(II) in human embryonic kidney HEK-293 cells. Our studies revealed, however, that none of the chelators were efficient enough to withdraw these metal ions from the amyloid aggregates

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Section: Cu(ii)-dq5 and Cu(ii)-dq715 Systemsmentioning

confidence: 83%

Hydroxypyridinecarboxylic acid derivatives influencing metal ion levels in the brain: Equilibrium complexation studies with Cu(II) and Zn(II)

Sija¹,

Nagy

Gandin

et al. 2014

Polyhedron

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Synthesis of Dipyridyl Ketone Isonicotinoyl Hydrazone Copper(II) Complex: Structure, Anticancer Activity and Anticancer Mechanism

2016

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In an effort to better understand the biological efficacy of the tridentate aroyl hydrazone Cu(II) complexes, the Cu(II) complex of di-2-pyridyl ketone isonicotinoyl hydrazone ligand (HL), {[Cu(L)(HO)]·HO·NO} (C1) was synthesized and characterized. Single crystal X-ray study reveals that complex C1 forms 1D zigzag chains in solid state. In water, the hydrolysis of the 1D zigzag chains was observed, and finally formation of monomeric species. In vitro studies revealed that complex C1 showed significantly more anticancer activity than the ligand alone. Investigation of the anticancer mechanisms of C1, confirmed that the Cu(II) complex exhibit a strong capacity to promote productions of reactive oxygen species (ROS), leading to caspase-dependent apoptotic cell death.

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Photophysics of Fe(III) complexes with fluorosalicylic acid isomers in aqueous solutions

Pozdnyakov

Melnikov

Šípoš

et al. 2016

Chemical Physics Letters

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Effect of fluorine position on the coordinating ability of fluorosalicylic acids — An experimental study complemented with computations

Cited by 7 publications

References 49 publications

Hydroxypyridinecarboxylic acid derivatives influencing metal ion levels in the brain: Equilibrium complexation studies with Cu(II) and Zn(II)

Hydroxypyridinecarboxylic acid derivatives influencing metal ion levels in the brain: Equilibrium complexation studies with Cu(II) and Zn(II)

Synthesis of Dipyridyl Ketone Isonicotinoyl Hydrazone Copper(II) Complex: Structure, Anticancer Activity and Anticancer Mechanism

Photophysics of Fe(III) complexes with fluorosalicylic acid isomers in aqueous solutions

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