Open AccessSynthesis, characterization, quantum chemical calculations and anticancer activity of a Schiff base NNOO chelate ligand and Pd(II) complex
Author(s) -
Shahrul Nizam Ahmad,
El Hassane Anouar,
Amalina Mohd Tajuddin,
Kalavathy Ramasamy,
Bohari Mohd. Yamin,
Hadariah Bahron
Publication year - 2020
Publication title -
plos one
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.99
H-Index - 332
ISSN - 1932-6203
DOI - 10.1371/journal.pone.0231147
Subject(s) - bathochromic shift , density functional theory , schiff base , chemistry , ligand (biochemistry) , crystallography , absorption spectroscopy , basis set , chemical shift , quantum chemical , proton nmr , infrared spectroscopy , molecule , computational chemistry , stereochemistry , organic chemistry , physics , biochemistry , receptor , quantum mechanics , fluorescence
This paper reports the synthesis, characterization, anticancer screening and quantum chemical calculation of a tetradentate Schiff base 2,2'-((1 E ,1' E )-((2,2-dimethylpropane-1,3-diyl)bis- (azanylylidene))bis(methanylylidene))bis(4-fluorophenol) ( L2F ) and its Pd (II) complex ( PdL2F ). The compounds were characterized via UV-Visible, NMR, IR spectroscopy and single crystal x-ray diffraction. Density Functional Theory (DFT) and time-dependent DFT calculations in gas and solvent phases were carried out using B3LYP, B3P86, CAM-B3LYP and PBE0 hybrid functionals combined with LanL2DZ basis set. Complexation of L2F to form PdL2F was observed to cause a bathochromic shift of the maximum absorption bands of n–π* from 327 to 410 nm; an upfield shift for δ (HC = N) from 8.30 to 7.96 ppm and a decreased wavenumber for ν(C = N) from 1637 to 1616 cm -1 . Overall, the UV-Vis, NMR and IR spectral data are relatively well reproduced through DFT and TD-DFT methods. L2F and PdL2F showed IC 50 of 90.00 and 4.10 μg/mL, respectively, against human colorectal carcinoma (HCT116) cell lines, signifying increased anticancer activity upon complexation with Pd (II).