Syntheses, crystal structures, theoretical studies, and anticancer properties of an unsymmetrical Schiff base ligand N-2-(6- methylpyridyl)-2-hydroxy-1-naphthaldimine and its Ni(II) complex

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Bhattacharjee, Tirtha and Adhikari, Suman and Sheikh, Afzal H. and Mahmoudi, Ghodrat and Mlowe, Sixberth and Akerman, Matthew P. and Choudhury, Nurul A. and Chakraborty, Surajit and Butcher, Raymond J. and Kennedy, Alan and Demir, Burcu S. and Ors, Aylin and Saygideger, Yasemin (2022) Syntheses, crystal structures, theoretical studies, and anticancer properties of an unsymmetrical Schiff base ligand N-2-(6- methylpyridyl)-2-hydroxy-1-naphthaldimine and its Ni(II) complex. Journal of Molecular Structure, 1269. 133717. ISSN 0022-2860 (https://doi.org/10.1016/j.molstruc.2022.133717)

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Abstract

In this work, syntheses of Schiff-base ligand, N-2-(6-methylpyridyl)-2-hydroxy-1-naphthaldimine (1) and its hitherto unknown chelate with a Ni(II) salt, bis[N-2-(6-methylpyridyl)-2-oxo-1-naphthaldimnato-k 3N^N^O] nickel(II) (2) have been reported and characterized by spectral techniques (IR, 1H NMR, Mass). Solid state structures and non-covalent interactions persisting in 1 and 2 are studied by Density Functional Theory (DFT) optimizations and Hirshfeld Surface (HS) analysis. X-ray diffraction (XRD) study shows zwitter ionic keto-amine tautomer form of planar Schiff base 1 that exists as dimer formed by C13 ̶ H13A···O1 i [(i) -x+1, -y, -z+1] hydrogen bonds and distorted octahedral geometry around Ni +2 center in chelate 2, where overall crystal structure stability may be attributed to weak C ̶ H···π, π···π stacking, van der Waals interactions, and C ̶ H···O type intermolecular hydrogen bonds. The HS study and 2D Finger Print (FP) plots corroborate well with XRD data and show prominent O···H/H···O spikes (2.2 Å < d e+d i < 2.3 Å) and C···H/H···C (2.5 Å < d e+d i < 2.6 Å) spikes that arise from C ̶ H···O type H-bonds and C ̶ H···π interactions respectively, along with significant C···C interactions (d e+d i ∼ 3.3 Å) due to π···π stacking (2). The anticancer activity has been investigated by using cytotoxicity measure (MTT assay), apoptosis assay, quantitative polymerase chain reaction (qPCR), and colony formation assays. The Ni(II) metal complex demonstrates dose-dependent cytotoxicity in vitro, killing A549 lung cancer cells via an apoptotic pathway.

ORCID iDs

Bhattacharjee, Tirtha, Adhikari, Suman, Sheikh, Afzal H., Mahmoudi, Ghodrat, Mlowe, Sixberth, Akerman, Matthew P., Choudhury, Nurul A., Chakraborty, Surajit, Butcher, Raymond J., Kennedy, Alan ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Demir, Burcu S., Ors, Aylin and Saygideger, Yasemin;
  • Item type:Article
    ID code:81510
    Dates:
    Date
    Event
    5 December 2022
    Published
    14 July 2022
    Published Online
    12 July 2022
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:21 Jul 2022 10:08
    Last modified:14 Dec 2024 01:32
    URI:https://strathprints.strath.ac.uk/id/eprint/81510
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