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Synthesis, Characterization, and Low-Toxicity Study of a Magnesium(II) Complex Containing an Isovanillate Group
[Image: see text] The beneficial effect of polyphenols and magnesium(II) against oxidative stress motivated our research group to explore the antioxidant activity of phenMgIso, an aqueous soluble magnesium(II) complex containing 1,10-phenanthroline (phen) and isovanillic acid (Iso) as ligands. Combi...
Autores principales: | , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7045549/ https://www.ncbi.nlm.nih.gov/pubmed/32118165 http://dx.doi.org/10.1021/acsomega.9b03804 |
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author | Marchi, Rafael C. Silva, Eldevan S. Santos, Josenilton J. Guiloski, Izonete C. de Jesus, Hugo Cesar R. de Aguiar, Inara Kock, Flavio V. C. Venâncio, Tiago da Silva, Maria Fátima G. F. Fernandes, João Batista Vital, Maria A. B. F. Souza, Leonardo Castro Silva de Assis, Helena C. Skibsted, Leif H. Carlos, Rose M. |
author_facet | Marchi, Rafael C. Silva, Eldevan S. Santos, Josenilton J. Guiloski, Izonete C. de Jesus, Hugo Cesar R. de Aguiar, Inara Kock, Flavio V. C. Venâncio, Tiago da Silva, Maria Fátima G. F. Fernandes, João Batista Vital, Maria A. B. F. Souza, Leonardo Castro Silva de Assis, Helena C. Skibsted, Leif H. Carlos, Rose M. |
author_sort | Marchi, Rafael C. |
collection | PubMed |
description | [Image: see text] The beneficial effect of polyphenols and magnesium(II) against oxidative stress motivated our research group to explore the antioxidant activity of phenMgIso, an aqueous soluble magnesium(II) complex containing 1,10-phenanthroline (phen) and isovanillic acid (Iso) as ligands. Combined electrospray ionization–mass spectrometry and DOSY-NMR techniques identified two complexes in methanolic solution: hexacoordinated [Mg(phen)(2)(Iso)](+) and tetracoordinated [Mg(phen)(Iso)](+). The cyclic voltammogram of phenMgIso in the anodic region showed a cyclic process that interrupts the isovanillic acid degradation, probably by stabilization of the corresponding phenoxyl radical via complexation with Mg(II), which is interesting for antioxidant applications. phenMgIso competes with 2,2,6,6-tetramethylpiperidine by (1)O(2) with IC(50)((1)O(2)) = 15 μg m(–1) and with nitrotetrazolium blue chloride by superoxide ions (IC(50)(O(2)(•–)) = 3.6 μg mL(–1)). Exposure of both zebrafish (2 mg L(–1)) and wistar male rats (3 mg kg(–1) day(–1) dose for 21 days) to phenMgIso does not cause mortality or visual changes compared with the respective control groups, thus phenMgIso could be considered safe under the conditions of this study. Moreover, no significant changes in comparison to both control groups were observed in the biochemical parameters on the brain-acetylcholinesterase activity, digestive tract enzyme catalase, and glutathione-S-transferase. Conversely, the performance of superoxide dismutase activity in wistar male rats increased in the presence of a complex, resulting in enhanced capacity of rats for superoxide radical enzymatic scavenging. The synergistic action of phenMgIso may be explained by the strong electrostatic interaction between Mg(II) and the O,O(phenolate) group, which makes the Iso ligand easier to oxidize and deprotonate, generating a cyclic stable species under oxidative conditions. |
format | Online Article Text |
id | pubmed-7045549 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-70455492020-02-28 Synthesis, Characterization, and Low-Toxicity Study of a Magnesium(II) Complex Containing an Isovanillate Group Marchi, Rafael C. Silva, Eldevan S. Santos, Josenilton J. Guiloski, Izonete C. de Jesus, Hugo Cesar R. de Aguiar, Inara Kock, Flavio V. C. Venâncio, Tiago da Silva, Maria Fátima G. F. Fernandes, João Batista Vital, Maria A. B. F. Souza, Leonardo Castro Silva de Assis, Helena C. Skibsted, Leif H. Carlos, Rose M. ACS Omega [Image: see text] The beneficial effect of polyphenols and magnesium(II) against oxidative stress motivated our research group to explore the antioxidant activity of phenMgIso, an aqueous soluble magnesium(II) complex containing 1,10-phenanthroline (phen) and isovanillic acid (Iso) as ligands. Combined electrospray ionization–mass spectrometry and DOSY-NMR techniques identified two complexes in methanolic solution: hexacoordinated [Mg(phen)(2)(Iso)](+) and tetracoordinated [Mg(phen)(Iso)](+). The cyclic voltammogram of phenMgIso in the anodic region showed a cyclic process that interrupts the isovanillic acid degradation, probably by stabilization of the corresponding phenoxyl radical via complexation with Mg(II), which is interesting for antioxidant applications. phenMgIso competes with 2,2,6,6-tetramethylpiperidine by (1)O(2) with IC(50)((1)O(2)) = 15 μg m(–1) and with nitrotetrazolium blue chloride by superoxide ions (IC(50)(O(2)(•–)) = 3.6 μg mL(–1)). Exposure of both zebrafish (2 mg L(–1)) and wistar male rats (3 mg kg(–1) day(–1) dose for 21 days) to phenMgIso does not cause mortality or visual changes compared with the respective control groups, thus phenMgIso could be considered safe under the conditions of this study. Moreover, no significant changes in comparison to both control groups were observed in the biochemical parameters on the brain-acetylcholinesterase activity, digestive tract enzyme catalase, and glutathione-S-transferase. Conversely, the performance of superoxide dismutase activity in wistar male rats increased in the presence of a complex, resulting in enhanced capacity of rats for superoxide radical enzymatic scavenging. The synergistic action of phenMgIso may be explained by the strong electrostatic interaction between Mg(II) and the O,O(phenolate) group, which makes the Iso ligand easier to oxidize and deprotonate, generating a cyclic stable species under oxidative conditions. American Chemical Society 2020-02-13 /pmc/articles/PMC7045549/ /pubmed/32118165 http://dx.doi.org/10.1021/acsomega.9b03804 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Marchi, Rafael C. Silva, Eldevan S. Santos, Josenilton J. Guiloski, Izonete C. de Jesus, Hugo Cesar R. de Aguiar, Inara Kock, Flavio V. C. Venâncio, Tiago da Silva, Maria Fátima G. F. Fernandes, João Batista Vital, Maria A. B. F. Souza, Leonardo Castro Silva de Assis, Helena C. Skibsted, Leif H. Carlos, Rose M. Synthesis, Characterization, and Low-Toxicity Study of a Magnesium(II) Complex Containing an Isovanillate Group |
title | Synthesis, Characterization, and Low-Toxicity Study
of a Magnesium(II) Complex Containing an Isovanillate Group |
title_full | Synthesis, Characterization, and Low-Toxicity Study
of a Magnesium(II) Complex Containing an Isovanillate Group |
title_fullStr | Synthesis, Characterization, and Low-Toxicity Study
of a Magnesium(II) Complex Containing an Isovanillate Group |
title_full_unstemmed | Synthesis, Characterization, and Low-Toxicity Study
of a Magnesium(II) Complex Containing an Isovanillate Group |
title_short | Synthesis, Characterization, and Low-Toxicity Study
of a Magnesium(II) Complex Containing an Isovanillate Group |
title_sort | synthesis, characterization, and low-toxicity study
of a magnesium(ii) complex containing an isovanillate group |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7045549/ https://www.ncbi.nlm.nih.gov/pubmed/32118165 http://dx.doi.org/10.1021/acsomega.9b03804 |
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