Cobalt(III) complexes with 2-acetylpyridine-derived Schiff bases: Studies investigating ligand release upon reduction

Garcia, Camila V.; Parrilha, Gabrieli L.; Rodrigues, Bernardo L.; Barbeira, Paulo Jorge Sanches; Clarke, Ryan M.; Storr, Tim; Beraldo, Heloísa

doi:10.1016/j.poly.2016.12.024

Cited by 21 publications

(8 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cobalt(III)‐mustard agents, complexes containing Marimastat (a matrix metalloproteinase MMP inhibitor), and epidermal growth factor receptor (EGFR) inhibitor are considered the most successful examples, although they have failed to some extent during in vivo experiments. Besides these, complexes of curcumin, hydroxyquinoline, Schiff bases and coumarins have also been investigated.…”

Section: Introductionmentioning

confidence: 99%

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

et al. 2019

View full text Add to dashboard Cite

The search for new Co III -based drug delivery systems has attracted considerable attention in recent years. In this work, two cobalt complexes with general formula [Co(L)Am](ClO 4 ) n were synthesized, in which L -= (ethyl-3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate), a coumarin--keto ester ligand, and Am is the auxiliary amine TPA (tris-(2-pyridylmethyl)amine) or Py 2 en (2-pyridylmethyl)-1,2diamine). Complexation reactions yielded [Co II (L)TPA]ClO 4 (1) and [Co III (L)Py 2 en](ClO 4 ) 2 (2), and the Co III complex (2) was investigated as a potential hypoxia-activated prodrug prototype.[a]

show abstract

Section: Introductionmentioning

confidence: 99%

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Among the metal ion redox couples explored, those of the cobalt(III)/cobalt(II) and copper(II)/copper(I) couples are the most commonly exploited for the development of redox-activated prodrugs. Cobalt(III) complexes, which have been investigated as both hypoxia-targeting agents and as enzyme inhibitors, − are kinetically inert due to their low-spin d 6 electron configuration. Reduction to cobalt(II) yields a labile d 7 complex, facilitating the loss of ligands within the coordination sphere.…”

Section: Introductionmentioning

confidence: 99%

Bis(thiosemicarbazone) Complexes of Cobalt(III). Synthesis, Characterization, and Anticancer Potential

et al. 2017

View full text Add to dashboard Cite

Nine bis(thiosemicarbazone) (BTSC) cobalt(III) complexes of the general formula [Co(BTSC)(L)]NO were synthesized, where BTSC = diacetyl bis(thiosemicarbazone) (ATS), pyruvaldehyde bis(thiosemicarbazone) (PTS), or glyoxal bis(thiosemicarbazone) (GTS) and L = ammonia, imidazole (Im), or benzylamine (BnA). These compounds were characterized by multinuclear NMR spectroscopy, mass spectrometry, cyclic voltammetry, and X-ray crystallography. Their stability in phosphate-buffered saline was investigated and found to be highly dependent on the nature of the axial ligand, L. These studies revealed that complex stability is primarily dictated by the axial ligand following the sequence NH > Im > BnA. The cellular uptake and cytotoxicity in cancer cells were also determined. Both the cellular uptake and cytotoxicity were significantly affected by the nature of the equatorial BTSC. Complexes of ATS were taken up much more effectively than those of PTS and GTS. The cytotoxicity of the complexes was correlated to that of the free ligand. Cell uptake and cytotoxicity were also determined under hypoxic conditions. Only minor differences in the hypoxia activity and uptake were observed. Treatment of the cancer cells with the copper-depleting agent tetrathiomolybdate decreased the cytotoxic potency of the complexes, indicating that they may operate via a copper-dependent mechanism. These results provide a structure-activity relationship for this class of compounds, which may be applied for the rational design of new cobalt(III) anticancer agents.

show abstract

“…These complexes have also been studied as reductionactivated prodrugs. 81,95 Despite these previous investigations, few studies have systematically evaluated the general activity of the [Co(Schiff base)(L) 2 ] + scaffold. In this study, a small set of [Co(Schiff base)(L) 2 ] + complexes was prepared and thoroughly investigated.. Two families of Co(III) Schiff base complexes, bearing either ammonia (NH 3 ) or 3-fluorobenzylamine (3F-BnNH 2 ) axial ligands, were studied.…”

Section: Discussionmentioning

confidence: 99%

“…The longer distances observed for [Co(tfacen)(NH 3 ) 2 ] + may be a result of the strong electron donating character of the axial NH 3 ligand, which decreases the Lewis acidity of the metal center. 81 In comparing the axial ligand distances, this trend is the opposite. Namely, the axial Co-N distances of [Co(tfacen)(3F-BnNH 2 ) 2 ] + (1.972 Å) are † Electronic Supplementary Information (ESI) Available: physical characterization data for all complexes, representative ligand exchange plots, Eyring plots, and cytotoxicity data.…”

Section: X-ray Crystallographymentioning

confidence: 98%

Physical properties, ligand substitution reactions, and biological activity of Co(iii)-Schiff base complexes

et al. 2019

View full text Add to dashboard Cite

show abstract

Cobalt(III) complexes with 2-acetylpyridine-derived Schiff bases: Studies investigating ligand release upon reduction

Cited by 21 publications

References 44 publications

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

Bis(thiosemicarbazone) Complexes of Cobalt(III). Synthesis, Characterization, and Anticancer Potential

Physical properties, ligand substitution reactions, and biological activity of Co(iii)-Schiff base complexes

Contact Info

Product

Resources

About