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

Khlood S Abou Melha; Gamil A Al-Hazmi; Ismail Althagafi; Arwa Alharbi; Ali A Keshk; Fathy Shaaban; Nashwa El-Metwaly

doi:10.1155/2021/6674394

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

Bioinorg Chem Appl. 2021 Mar 22:2021:6674394. doi: 10.1155/2021/6674394. eCollection 2021.

Authors

Khlood S Abou Melha¹, Gamil A Al-Hazmi^{1

2}, Ismail Althagafi³, Arwa Alharbi³, Ali A Keshk⁴, Fathy Shaaban^{5

6}, Nashwa El-Metwaly^{3

7}

Affiliations

¹ Department of Chemistry, King Khalid University, P.O. Box 9004, Abha, Saudi Arabia.
² Department of Chemistry, Taiz University, P.O. Box 82, Taiz, Yemen.
³ Department of Chemistry, Umm-Al-Qura University, Makkah, Saudi Arabia.
⁴ Department of Chemistry, College of Science, University of Tabuk, Tabuk, Saudi Arabia.
⁵ Department of Environment and Health Research, Custodian of Two Holy Mosques Institute for Hajj and Umrah Research, Umm-Al-Qura University, Makkah, Saudi Arabia.
⁶ Department of Geomagnetic and Geoelectric, National Research Institute of Astronomy and Geophysics, Kafr Al Masallat, Egypt.
⁷ Department of Chemistry, Mansoura University, Mansoura, Egypt.

Abstract

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, N¹, and S donors, respectively, while it showed neutral bidentate mode via O and N¹ 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, IC₅₀ 6.45 ± 0.25 and 6.39 ± 0.18 μM, respectively.