Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Dec 16;25(24):5973.
doi: 10.3390/molecules25245973.

Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3 H)-Quinazolinone-Derived Schiff Base

Ubale Panchsheela Ashok  1   2 , Shiva Prasad Kollur  3 , Nishad Anil  4 , Bansode Prakash Arun  5 , Sanjay Namdev Jadhav  6 , Sanjay Sarsamkar  7 , Vasant Baburao Helavi  1 , Asha Srinivasan  8 , Sandeep Kaulage  9 , Ravindra Veerapur  10 , Sarah Al-Rashed  11 , Asad Syed  11 , Joaquín Ortega-Castro  12 , Juan Frau  12 , Norma Flores-Holguín  13 , Daniel Glossman-Mitnik  12   13
Affiliations

Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3 H)-Quinazolinone-Derived Schiff Base

Ubale Panchsheela Ashok et al. Molecules. .

Abstract

Herein, we report the synthesis and characterization of a new Schiff base ligand 3-[[(E)-(3-hydroxyphenyl)-methylidene]amino]-2-methyl-quinazolin-4(3H)-one (HAMQ) and its Cd(II), Ni(II), Zn(II), and Cu(II) complexes (C1-C4). The ligand HAMQ was synthesized by reacting 3-hydroxybenzaldehyde and 3-amino-2-methyl-4(3H)-quinazolinone in a 1:1 molar ratio. The structure of the ligand and its complexes (C1-C4) were evaluated using ultraviolet (UV)-visible (Vis) light spectroscopy, 1H-NMR, Fourier-transform infrared (FT-IR) spectroscopy, MS, elemental analysis, conductance data, and thermogravimetric analysis (TGA). The characterization results suggested that the bidentate ligand, HAMQ, coordinated to the metal center through the lactum oxygen and the azomethine nitrogen. Moreover, all the metal complexes were analyzed using powder X-ray diffraction studies, which revealed that all of them belong to a triclinic crystal system. The research was supplemented by density functional theory (DFT) studies on the IR and UV-Vis spectra, as well as the chemical reactivity of the HAMQ and its four metallic derivatives making use of conceptual density functional theory (CDFT) by means of KID (Koopmans in DFT) methodology. The synthesized complexes displayed significant in vitro anticancer activity against human cancer cell lines (HeLa and HCT-115).

Keywords: 3-quinolin-4(3H)-one; chemical reactivity properties; conceptual DFT; metal complexes; spectral studies.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Sulforhodamine B colorimetric assay in colorectal cancer cell culture (HCT115) to analyze the percentage inhibition for all complexes. Doxorubicin was used as a positive control, while dimethyl sulfoxide (DMSO) was used as a vehicle control.
Figure 2
Figure 2
Sulforhodamine B (SRB) colorimetric assay in HeLa cell line (cervical cancer) culture to analyze percentage inhibition for all complexes. Doxorubicin was used as a positive control, while DMSO was used as a vehicle control.
Figure 3
Figure 3
Optimized structures of (a) HMAQ, as well as (b) C1 (c) C2, (d) C3, and (e) C4 complexes.
Scheme 1
Scheme 1
General route for the synthesis of 3-[[(E)-(3-hydroxyphenyl)-methylidene]amino]-2-methyl-quinazolin-4(3H)-one (HMAQ) ligand.
See this image and copyright information in PMC

References

    1. Misra R., Acharya S., Sahoo S.K. Cancer nanotechnology: Application of nanotechnology in cancer therapy. Drug Discov. Today. 2010;15:842–850. doi: 10.1016/j.drudis.2010.08.006. - DOI - PubMed
    1. Masoud V., Pagès G. Targeted therapies in breast cancer: New challenges to fight against resistance. World J. Clin. Oncol. 2017;8:120–134. doi: 10.5306/wjco.v8.i2.120. - DOI - PMC - PubMed
    1. Shaili E. Platinum anticancer drugs and photochemotherapeutic agents: Recent advances and future developments. Sci. Prog. 2014;97:20–40. doi: 10.3184/003685014X13904811808460. - DOI - PMC - PubMed
    1. King A.P., Gellineau H.A., Ahn J.E., MacMillan S.N., Wilson J.J. Bis(thiosemicarbazone) Complexes of Cobalt(III). Synthesis, Characterization, and Anticancer Potential. Inorg. Chem. 2017;56:6609–6623. doi: 10.1021/acs.inorgchem.7b00710. - DOI - PMC - PubMed
    1. Ambika S., Manojkumar Y., Arunachalam S., Gowdhami B., Sundaram K.K.M., Solomon R.V., Venuvanalingam P., Akbarsha M.A., Sundararaman M. Biomolecular Interaction, Anti-Cancer and Anti-Angiogenic Properties of Cobalt(III) Schiff Base Complexes. Sci Rep. 2019;9:2721. doi: 10.1038/s41598-019-39179-1. - DOI - PMC - PubMed

LinkOut - more resources