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Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes

The newly synthesized Schiff's base derivative, N-allyl-2-(2-oxoacenaphthylen-1(2H)-ylidene)hydrazine-1-carbothioamide, has been characterized by different spectral techniques. Its reaction with Co(II), Ni(II), and Zn(II) acetate led to the formation of 1 : 1 (M:L) complexes. The IR and NMR spe...

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Autores principales: Abou Melha, Khlood S., Al-Hazmi, Gamil A., Althagafi, Ismail, Alharbi, Arwa, Keshk, Ali A., Shaaban, Fathy, El-Metwaly, Nashwa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Hindawi 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8012121/
https://www.ncbi.nlm.nih.gov/pubmed/33815493
http://dx.doi.org/10.1155/2021/6674394
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author Abou Melha, Khlood S.
Al-Hazmi, Gamil A.
Althagafi, Ismail
Alharbi, Arwa
Keshk, Ali A.
Shaaban, Fathy
El-Metwaly, Nashwa
author_facet Abou Melha, Khlood S.
Al-Hazmi, Gamil A.
Althagafi, Ismail
Alharbi, Arwa
Keshk, Ali A.
Shaaban, Fathy
El-Metwaly, Nashwa
author_sort Abou Melha, Khlood S.
collection PubMed
description The newly synthesized Schiff's base derivative, N-allyl-2-(2-oxoacenaphthylen-1(2H)-ylidene)hydrazine-1-carbothioamide, has been characterized by different spectral techniques. Its reaction with Co(II), Ni(II), and Zn(II) acetate led to the formation of 1 : 1 (M:L) complexes. The IR and NMR spectral data revealed keto-thione form for the free ligand. On chelation with Co(II) and Ni(II), it behaved as mononegative and neutral tridentate via O, N(1), and S donors, respectively, while it showed neutral bidentate mode via O and N(1) atoms with Zn(II). The electronic spectra indicated that all the isolated complexes have an octahedral structure. The thermal gravimetric analyses confirmed the suggested formula and the presence of coordinated water molecules. The XRD pattern of the metal complexes showed that both Co(II) and Ni(II) have amorphous nature, while Zn(II) complex has monoclinic crystallinity with an average size of 9.10 nm. DFT modeling of the ligand and complexes supported the proposed structures. The calculated HOMO-LUMO energy gap, ΔE(H-L), of the ligand complexes was 1.96–2.49 eV range where HAAT < Zn(II) < Ni(II) < Co(II). The antioxidant activity investigation showed that the ligand and Zn(II) complex have high activity than other complexes, 88.5 and 88.6%, respectively. Accordingly, the antitumor activity of isolated compounds was examined against the hepatocellular carcinoma cell line (HepG2), where both HAAT and Zn(II) complex exhibited very strong activity, IC(50) 6.45 ± 0.25 and 6.39 ± 0.18 μM, respectively.
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spelling pubmed-80121212021-04-02 Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes Abou Melha, Khlood S. Al-Hazmi, Gamil A. Althagafi, Ismail Alharbi, Arwa Keshk, Ali A. Shaaban, Fathy El-Metwaly, Nashwa Bioinorg Chem Appl Research Article The newly synthesized Schiff's base derivative, N-allyl-2-(2-oxoacenaphthylen-1(2H)-ylidene)hydrazine-1-carbothioamide, has been characterized by different spectral techniques. Its reaction with Co(II), Ni(II), and Zn(II) acetate led to the formation of 1 : 1 (M:L) complexes. The IR and NMR spectral data revealed keto-thione form for the free ligand. On chelation with Co(II) and Ni(II), it behaved as mononegative and neutral tridentate via O, N(1), and S donors, respectively, while it showed neutral bidentate mode via O and N(1) atoms with Zn(II). The electronic spectra indicated that all the isolated complexes have an octahedral structure. The thermal gravimetric analyses confirmed the suggested formula and the presence of coordinated water molecules. The XRD pattern of the metal complexes showed that both Co(II) and Ni(II) have amorphous nature, while Zn(II) complex has monoclinic crystallinity with an average size of 9.10 nm. DFT modeling of the ligand and complexes supported the proposed structures. The calculated HOMO-LUMO energy gap, ΔE(H-L), of the ligand complexes was 1.96–2.49 eV range where HAAT < Zn(II) < Ni(II) < Co(II). The antioxidant activity investigation showed that the ligand and Zn(II) complex have high activity than other complexes, 88.5 and 88.6%, respectively. Accordingly, the antitumor activity of isolated compounds was examined against the hepatocellular carcinoma cell line (HepG2), where both HAAT and Zn(II) complex exhibited very strong activity, IC(50) 6.45 ± 0.25 and 6.39 ± 0.18 μM, respectively. Hindawi 2021-03-22 /pmc/articles/PMC8012121/ /pubmed/33815493 http://dx.doi.org/10.1155/2021/6674394 Text en Copyright © 2021 Khlood S. Abou Melha et al. https://creativecommons.org/licenses/by/4.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Abou Melha, Khlood S.
Al-Hazmi, Gamil A.
Althagafi, Ismail
Alharbi, Arwa
Keshk, Ali A.
Shaaban, Fathy
El-Metwaly, Nashwa
Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes
title Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes
title_full Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes
title_fullStr Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes
title_full_unstemmed Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes
title_short Spectral, Molecular Modeling, and Biological Activity Studies on New Schiff's Base of Acenaphthaquinone Transition Metal Complexes
title_sort spectral, molecular modeling, and biological activity studies on new schiff's base of acenaphthaquinone transition metal complexes
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8012121/
https://www.ncbi.nlm.nih.gov/pubmed/33815493
http://dx.doi.org/10.1155/2021/6674394
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