Investigation of cobalt(<scp>iii</scp>)-triazole systems as prototypes for hypoxia-activated drug delivery

Souza, Isabela Cristina Aguiar de; Faro, Letícia V.; Pinheiro, Carlos B.; Gonzaga, Daniel T. G.; Silva, Fernando de Carvalho da; Ferreira, Vı́tor F.; Miranda, Fabio da Silva; Scarpellini, Marciela; Lanznaster, Maurício

doi:10.1039/c6dt02456d

Cited by 36 publications

(23 citation statements)

References 27 publications

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“…Complex 2 has the two TCC 2– oxygen atoms trans to the two nitrogen atoms of the ethylenediamine backbone in the equatorial plane. The average Co–O and Co–N bond lengths is 1.9 Å, which is within the expected range for low spin cobalt(III) complexes with N 4 , O 2 ‐donor ligands , …”

Section: Resultssupporting

confidence: 73%

“…The average Co-O and Co-N bond lengths is 1.9 Å, which is within the expected range for low spin cobalt(III) complexes with N 4 ,O 2 -donor ligands. [31,32] ESI-MS spectra of 1 in methanol and 2 in DMSO/methanol (Figs. S5-S6) revealed a prominent peak at m/z + = 592.56 for 1 (Figure 3), confirming the identity of the species in solution.…”

Section: Resultsmentioning

confidence: 99%

“…This interpretation corroborates with the more negative potential for Co 3+ /Co 2+ reduction in complex 2. [32,42,43] To evaluate the energies involved in the hypothetical Co 3+ /Co 2+ reduction associated with ligand dissociation, calculations were also performed for the reduced complexes [Co II (TPA)(TCC)] and [Co II (py 2 en)(TCC)] and the corresponding species generated after dissociation of the TCC ligand. Since two distinct spin multiplicities are expected for Co 2+ , S = 3/2 for t 2 g 5 eg 2 (HS) and S = 1 / 2 for t 2 g 6 eg 1 (LS), the spin density was calculated for both high and low-spin configurations.…”

Section: Resultsmentioning

confidence: 99%

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Investigation of Cobalt(III)‐Tetrachlorocatechol Complexes as Models for Catechol‐Based Anticancer Prodrugs

et al. 2019

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Two novel cobalt(III) complexes, [Co(TPA)(TCC)]ClO4·H2O (1) and [Co(py2en)(TCC)]ClO4·2H2O (2), were synthesized and fully characterized by IR, UV/Vis and 1H NMR spectroscopy, ESI mass spectrometry, and X‐ray diffraction. Cyclic voltammetry experiments revealed an irreversible reduction of the Co3+ center for both complexes. The Co3+/Co2+ redox potential, –0.91 V for 1 and –1.15 V for 2 (vs. Fc/Fc+), was obtained by square wave voltammetry in DMSO. Reactions of 1 and 2 with ascorbic acid and sodium dithionite at pH 7.4 and 6.2 were carried out in argon and open‐air atmospheres, to simulate biological redox activation under hypoxia and normoxia. Neither the Co3+/Co2+ reduction nor the dissociation of TCC2– was observed. Thermodynamic parameters calculated for the Co3+/Co2+ reduction and substitution of the TCC2– ligand by water indicate an endothermic non‐spontaneous reaction.

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Section: Resultssupporting

confidence: 73%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Investigation of Cobalt(III)‐Tetrachlorocatechol Complexes as Models for Catechol‐Based Anticancer Prodrugs

et al. 2019

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“…The ν(C=O) from the lactone was maintained around 1714 cm –1 . The presence of the auxiliary ligands (TPA and Py 2 en) in complexes 1 and 2 , respectively, was endorsed by their characteristic stretchings (Table S1) , , , . Absorptions at 1074 and 621 cm –1 confirmed the presence of ClO 4 – as the counterion, , for compounds 1 and 2 .…”

Section: Resultsmentioning

confidence: 82%

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

et al. 2019

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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]

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“…В последнее десятилетие стало известно о высокой антигипоксической активности металлокомплексных соединений, включающих в себя в качестве лигандов различные эндогенные биологически активные вещества (витамины, антиоксиданты, аминокислоты и др.) [4,17].…”

Section: Keywtrbunclassified

Comparative analysis of metal-complex and aminothiol antihypoxants efficiencies in the experiment

Евсеев

Викторович²,

Surmenev

et al. 2018

Rev Clin Pharm Drug Ther

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Aim. Comparative analysis of the efficiency of metal-complex (πQ1983, πQ2721) and aminothiol (Amtizole, Sunazole) antihypoxants in experiments on rats exposed to acute hypoxia with hypercapnia. Methods. Experiments performed on 182 male rats of Wistar line weighing 150-170 g. The study of antihypoxic activity of substances was carried out on the model the AH+Hc. The condition of acute hypoxia in rats was formed by placing them in glass airtight containers with a free volume of 1.0 L. Antihypoxic effect was evaluated by the life expectancy of animals in the described conditions. Substances πQ2721, πQ1983, Amtizole and Sunazole was administered once intraperitoneally at doses of 25, 50 and 100 mg/kg. Previously each substance was dissolved in 0.9% NaCl (1.0 ml). Testing the effectiveness of the substances on AH+Hc model was carried out after 1 h after administration of the substances and after 24 h. Animals of control groups were injected with 1.0 ml of 0.9% NaCl. In animals exposed to test AH+Hc in 1 h after administration were performed measurements of the rectal temperature before the experiment and through 1 h after administration, i.e. before AH+Hc. In animals selected for 24-hour observation, rectal temperature was measured before the experiment, and then after 1, 3, 6, 12, 18 and 24 h of observation, after which they were exposed to AH+Hc. Results. The antihypoxic effect of a selenium-containing substance πQ2721 based on Zn2+ was confirmed in experiments on rats. In a number of substances for comparison the πQ2721 proved himself not only as equally effective. It is found that after 1 h after administration at a dose of 50 mg/kg πQ2721 superior to all studied compounds, including antihypoxant with succinate Sunazole. An important advantage of the new promising antihypoxic agent was the preservation of its action for 24 hours after injection. (For citation: Evseev AV, Surmenev DV, Evseeva MA, et al. Comparative analysis of metal-complex and aminothiol antihypoxants efficiencies in the experiment. Reviews on Clinical Pharmacology and Drug Therapy. 2018;16(2):18-24. doi: 10.17816/RCF16218-24).

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Investigation of cobalt(iii)-triazole systems as prototypes for hypoxia-activated drug delivery

Cited by 36 publications

References 27 publications

Investigation of Cobalt(III)‐Tetrachlorocatechol Complexes as Models for Catechol‐Based Anticancer Prodrugs

Investigation of Cobalt(III)‐Tetrachlorocatechol Complexes as Models for Catechol‐Based Anticancer Prodrugs

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

Comparative analysis of metal-complex and aminothiol antihypoxants efficiencies in the experiment

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