Magnetic interactions as a stabilizing factor of semiquinone species of lawsone by metal complexation

Valle-­Bourrouet, Grettel; Ugalde‐Saldívar, Víctor M.; Gómez, Martı́n; Ortiz‐Frade, Luis; González, Ignacio; Frontana, Carlos

doi:10.1016/j.electacta.2010.08.006

Cited by 28 publications

(22 citation statements)

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“…To date, a few reports describing the syntheses and properties of copper(II), nickel(II), cobalt(II), chromium(III), iron(II), manganese(II), and zinc(II) complexes of 1,4-naphthoquinone derivatives with various compositions [6–8]. …”

Section: Introductionmentioning

confidence: 99%

“…The hydroxyl-substitutions in the positions 2- (lawsone derivatives, HLaw) and 8- (juglone/plumbagin derivatives) open the possibility to utilize such 1,4-naphthoquinones as chelate ligands in transition metal complexes. To date, a few reports describing the syntheses and properties of copper(II), nickel(II), cobalt(II), chromium(III), iron(II), manganese(II), and zinc(II) complexes of 1,4-naphthoquinone derivatives with various compositions [ 6 – 8 ].…”

Section: Introductionmentioning

confidence: 99%

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In vitro and in vivo anti-inflammatory active copper(II)-lawsone complexes

et al. 2017

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We report in vitro and in vivo anti-inflammatory activities of a series of copper(II)-lawsone complexes of the general composition [Cu(Law)2(LN)x(H2O)(2-x)]·yH2O; where HLaw = 2-hydroxy-1,4-naphthoquinone, x = 1 when LN = pyridine (1) and 2-aminopyridine (3) and x = 2 when LN = imidazole (2), 3-aminopyridine (4), 4-aminopyridine (5), 3-hydroxypyridine (6), and 3,5-dimethylpyrazole (7). The compounds were thoroughly characterized by physical techniques, including single crystal X-ray analysis of complex 2. Some of the complexes showed the ability to suppress significantly the activation of nuclear factor κB (NF-κB) both by lipopolysaccharide (LPS) and TNF-alpha (complexes 3–7 at 100 nM level) in the similar manner as the reference drug prednisone (at 1 μM level). On the other hand, all the complexes 1–7 decreased significantly the levels of the secreted TNF-alpha after the LPS activation of THP-1 cells, thus showing the anti-inflammatory potential via both NF-κB moderation and by other mechanisms, such as influence on TNF-alpha transcription and/or translation and/or secretion. In addition, a strong intracellular pro-oxidative effect of all the complexes has been found at 100 nM dose in vitro. The ability to suppress the inflammatory response, caused by the subcutaneous application of λ-carrageenan, has been determined by in vivo testing in hind-paw edema model on rats. The most active complexes 1–3 (applied in a dose corresponding to 40 μmol Cu/kg), diminished the formation of edema simalarly as the reference drug indomethacine (applied in 10 mg/kg dose). The overall effect of the complexes, dominantly 1–3, shows similarity to anti-inflammatory drug benoxaprofen, known to induce intracellular pro-oxidative effects.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In vitro and in vivo anti-inflammatory active copper(II)-lawsone complexes

et al. 2017

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“…Stirring of 1 with M(CH 3 COO) 2 in EtOH at r.t. yield complex 281 . Stirring 1 with M(NO 3 ) 2 and pyridine in dry MeOH afforded coordination compound 282 . The one‐pot Mannich condensation between 1 , benzaldehyde, and 2‐aminomethylpyridine in EtOH yielded 2‐hydroxy‐3‐(phenyl((pyridin‐2‐ylmethyl)amino)methyl)naphthalen‐1,4‐dione ( 283 ).…”

Section: Reactivity Of Lawsonementioning

confidence: 99%

Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione)

Hamama

Hassanien

Zoorob

2017

Journal of Heterocyclic Chem

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“…esters and bifunctional chiral amine-derived squaramides (78) as catalysts that function through a hydrogen-bond mediated activation mechanism, and they obtained the chiral adducts in high yields and excellent enantioselectivities under mild conditions. This organocatalytic asymmetric Michael addition provides an efficient route to optically active functionalized naphthoquinones 79a-f…”

Section: Rsc Advances Accepted Manuscriptmentioning

confidence: 99%