Synthesis and cytotoxic activity of metallic complexes of lawsone

Oramas‐Royo, Sandra; Torrejón, Concepción; Cuadrado, Irene; Hernández-Molina, Rita; Hortelano, Sonsoles; Estévez‐Braun, Ana; Heras, Beatriz de las

doi:10.1016/j.bmc.2013.03.002

Cited by 48 publications

(20 citation statements)

References 25 publications

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“…Recently, the interesting antimicrobial activity of transition metal complexes (Cu, Co, Fe, Ni, Cr) of 5-amino-8-hydroxy-1,4-naphthoquinone derivatives was reported [9]. In addition, the anticancer potential of transition metal complexes (M = Cu, Ni, Co, Mn) of lawsone, and complexes (M = Cu, Co, Ni) of juglone and lapachol were studied [7, 10, 11]. The copper(II), nickel(II), cobalt(II), and manganese(II) aqua-complexes involving lawsone with the general composition [M(Law) 2 (H 2 O) 2 ] revealed interesting antiproliferative activities and the most active copper(II) complex showed the cytotoxicity against the RAW 264.7 cells, with IC 50 = 2.5 μM.…”

Section: Introductionmentioning

confidence: 99%

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%

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

et al. 2017

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“…Like other naphthoquinones [13,14], lapachol is a feasible ligand for the preparation of coordinating or organometallic compounds. In fact, there are some findings showing that lapachol-metal complexes are biologically more active than the free molecule [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Antiparasitic activities of novel ruthenium/lapachol complexes

Barbosa

Corrêa

Oliveira

et al. 2014

Journal of Inorganic Biochemistry

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The present study describes the synthesis, characterization, antileishmanial and antiplasmodial activities of novel diimine/(2,2′-bipyridine (bipy), 1,10-phenanthroline (phen), 4,4′-methylbipyridine (Me-bipy) and 4,4′-methoxybipyridine (MeO-bipy)/phosphine/ruthenium(II) complexes containing lapachol (Lap, 2-hydroxy-3- The Ru(III) complex, [RuCl 2 (Lap)(dppb)], was also characterized by the EPR technique. The structure of the complexes [Ru(Lap)(PPh 3 ) 2 (bipy)]PF 6 and [RuCl 2 (Lap)(dppb)] was elucidated by X-ray diffraction. The evaluation of the antiparasitic activities of the complexes against Leishmania amazonensis and Plasmodium falciparum demonstrated that lapachol-ruthenium complexes are more potent than the free lapachol. The [RuCl 2 (Lap)(dppb)] complex is the most potent and selective antiparasitic compound among the five new ruthenium complexes studied in this work, exhibiting an activity comparable to the reference drugs.

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“…Cells were incubated in the presence of different concentrations of α-hispanolol for 24, 48 or 72 h, before they reacted with MTT (2 mg/ml) (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide) at 37°C for 3 h. The reaction product, formazan, was extracted with dimethyl sulfoxide (DMSO) and the absorbance was read at 540 nm as previously described (Oramas-Royo et al, 2013). Assays were performed in triplicate, and results are expressed as the percent reduction in cell viability compared to untreated control cultures for at least three independent experiments.…”

Section: Methodsmentioning

confidence: 99%