Exploring the structure-activity relationship (SAR) of Schiff bases as effective compounds in scavenging free radicals
•Two Schiff base derivatives synthesized from 2‑hydroxy-1-naphthaldehyde were synthesized.•DFT calculations show that 1 is more stable as an enol tautomer, while 2 is a keto.•The free radical scavenging potential of 1 and 2 was studied by DPPH and ABTS assay.•The SAR evaluation also included Schiff...
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| Published in: | Journal of molecular structure Vol. 1315; p. 138729 |
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| Main Authors: | , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier B.V
05-11-2024
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| Abstract | •Two Schiff base derivatives synthesized from 2‑hydroxy-1-naphthaldehyde were synthesized.•DFT calculations show that 1 is more stable as an enol tautomer, while 2 is a keto.•The free radical scavenging potential of 1 and 2 was studied by DPPH and ABTS assay.•The SAR evaluation also included Schiff base derivatives of tert‑butylphenol.•The cytotoxicity in mammalian cells was investigated.
Naphthol-imine compounds containing N-phenylethylenediamine (1) and quinoline amine (2) moieties were synthesized and characterized. Density Functional Theory (DFT) calculations were performed aiming to obtain information on the chemical properties of these molecules. In silico ADME/Tox profile analyses were performed on molecules 1 and 2 using the web tools pkCSM-pharmacokinetics, Molinspiration, and Osiris Property Explorer. Drug-likeness levels of 1 and 2 were predicted according to the Lipinski rules. The radical scavenger activity of compounds 1 and 2 was determined by in vitro assays such as 1,1-diphenyl-2-picrylhydrazyl free radicals (DPPH.) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) radicals (ABTS.+). Molecules 1 and 2 were ineffective as radical scavengers in the DPPH radical capture assay at the test doses. However, 1 showed activity in eliminating ABTS+ radical with IC50 = 17.4 ± 0.9 µM. The neutral red assay determined the cytotoxicity of 1 and 2 against the V79 cell line. Molecule 1 was more cytotoxic than 2, with IC50 values of 36.67 µM and 51.26 µM, respectively. The alkaline comet assay was used to investigate the in vitro genotoxicity of 1 and 2. After 24 h of exposure to a dose of 20 μM, 1 did not cause significant DNA damage compared to non-exposed cells. The compounds were tested for toxicity using Artemia saline assay.
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| AbstractList | •Two Schiff base derivatives synthesized from 2‑hydroxy-1-naphthaldehyde were synthesized.•DFT calculations show that 1 is more stable as an enol tautomer, while 2 is a keto.•The free radical scavenging potential of 1 and 2 was studied by DPPH and ABTS assay.•The SAR evaluation also included Schiff base derivatives of tert‑butylphenol.•The cytotoxicity in mammalian cells was investigated.
Naphthol-imine compounds containing N-phenylethylenediamine (1) and quinoline amine (2) moieties were synthesized and characterized. Density Functional Theory (DFT) calculations were performed aiming to obtain information on the chemical properties of these molecules. In silico ADME/Tox profile analyses were performed on molecules 1 and 2 using the web tools pkCSM-pharmacokinetics, Molinspiration, and Osiris Property Explorer. Drug-likeness levels of 1 and 2 were predicted according to the Lipinski rules. The radical scavenger activity of compounds 1 and 2 was determined by in vitro assays such as 1,1-diphenyl-2-picrylhydrazyl free radicals (DPPH.) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) radicals (ABTS.+). Molecules 1 and 2 were ineffective as radical scavengers in the DPPH radical capture assay at the test doses. However, 1 showed activity in eliminating ABTS+ radical with IC50 = 17.4 ± 0.9 µM. The neutral red assay determined the cytotoxicity of 1 and 2 against the V79 cell line. Molecule 1 was more cytotoxic than 2, with IC50 values of 36.67 µM and 51.26 µM, respectively. The alkaline comet assay was used to investigate the in vitro genotoxicity of 1 and 2. After 24 h of exposure to a dose of 20 μM, 1 did not cause significant DNA damage compared to non-exposed cells. The compounds were tested for toxicity using Artemia saline assay.
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| ArticleNumber | 138729 |
| Author | da Silva, Alecia F. Couto, Gabriel T. Pinheiro, Adriana C. Dias, Renieidy F.C. Ferreira, Wesley V. Bianchini, Daniela Nunes, Ianka J. Cunico, Wilson Saffi, Jenifer Casagrande, Osvaldo de L. |
| Author_xml | – sequence: 1 givenname: Ianka J. surname: Nunes fullname: Nunes, Ianka J. organization: Center of Chemical, Pharmaceutical, and Food Sciences, Group of Catalysis and Theoretical Studies, Federal University of Pelotas, Pelotas, RS, Brazil – sequence: 2 givenname: Renieidy F.C. surname: Dias fullname: Dias, Renieidy F.C. organization: Center of Chemical, Pharmaceutical, and Food Sciences, Group of Catalysis and Theoretical Studies, Federal University of Pelotas, Pelotas, RS, Brazil – sequence: 3 givenname: Alecia F. surname: da Silva fullname: da Silva, Alecia F. organization: Center of Chemical, Pharmaceutical, and Food Sciences, Group of Catalysis and Theoretical Studies, Federal University of Pelotas, Pelotas, RS, Brazil – sequence: 4 givenname: Wesley V. surname: Ferreira fullname: Ferreira, Wesley V. organization: Center of Chemical, Pharmaceutical, and Food Sciences, Group of Catalysis and Theoretical Studies, Federal University of Pelotas, Pelotas, RS, Brazil – sequence: 5 givenname: Wilson surname: Cunico fullname: Cunico, Wilson organization: Laboratory of Chemistry Applied to Bioactives, Center for Chemical, Pharmaceutical and Food Sciences, Federal University of Pelotas, Pelotas, RS, Brazil – sequence: 6 givenname: Gabriel T. surname: Couto fullname: Couto, Gabriel T. organization: Center of Chemical, Pharmaceutical, and Food Sciences, Group of Catalysis and Theoretical Studies, Federal University of Pelotas, Pelotas, RS, Brazil – sequence: 7 givenname: Daniela surname: Bianchini fullname: Bianchini, Daniela organization: Center of Chemical, Pharmaceutical, and Food Sciences, Group of Catalysis and Theoretical Studies, Federal University of Pelotas, Pelotas, RS, Brazil – sequence: 8 givenname: Osvaldo de L. orcidid: 0000-0002-9855-6159 surname: Casagrande fullname: Casagrande, Osvaldo de L. organization: Laboratory of Molecular Catalysis, Institute of Chemistry, Federal University of Rio Grande do Sul, Av. Bento Gonçalves, 9500, Porto Alegre, RS, 90501-970, Brazil – sequence: 9 givenname: Jenifer surname: Saffi fullname: Saffi, Jenifer email: jenifers@ufcspa.edu.br organization: Department of Basic Health Sciences – Laboratory of Genetic Toxicology – Federal University of Health Sciences of Porto Alegre (UFCSPA), Porto Alegre, RS, Brazil – sequence: 10 givenname: Adriana C. orcidid: 0000-0003-4092-9896 surname: Pinheiro fullname: Pinheiro, Adriana C. email: acpinheiro@ufpel.edu.br organization: Center of Chemical, Pharmaceutical, and Food Sciences, Group of Catalysis and Theoretical Studies, Federal University of Pelotas, Pelotas, RS, Brazil |
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