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

Bhattacharjee T., Adhikari S., Sheikh A. H., Mahmoudi G., Mlowe S., Akerman M. P., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1269, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1269
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.molstruc.2022.133717
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Schiff base, Hydrogen bond, Supramolecular architecture, Hirshfeld surface, DFT, Anticancer, ION-PAIR RECEPTOR, COORDINATION-COMPOUNDS, INTERMOLECULAR INTERACTIONS, CO(II) COMPLEXES, ACID, NICKEL(II), BINDING, TAUTOMERISM, DERIVATIVES, HYDRAZONE
  • Çukurova Üniversitesi Adresli: Evet

Özet

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-k3N <^> N <^> O] nickel(II) ( 2 ) have been reported and characterized by spectral techniques (IR, 1 H NMR, Mass). Solid state structures and non-covalent interactions persisting in 1 and 2 are studied by Density Functional The-ory (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 middotmiddotmiddotO1i [(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 middotmiddotmiddot pi, pi middotmiddotmiddot pi stacking, van der Waals interactions, and C - H middotmiddotmiddotO type intermolecular hydrogen bonds. The HS study and 2D Finger Print (FP) plots corroborate well with XRD data and show prominent O middotmiddotmiddotH/H middotmiddotmiddotO spikes (2.2 A < de +di < 2.3 A) and C middotmiddotmiddotH/H middotmiddotmiddotC (2.5 A < de +di < 2.6 A) spikes that arise from C-H middotmiddotmiddotO type H-bonds and C - H middotmiddotmiddot pi interactions respectively, along with significant C middotmiddotmiddotC interactions (de +di & SIM;3.3 A) due to pi middotmiddotmiddot pi 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 com-plex demonstrates dose-dependent cytotoxicity in vitro , killing A549 lung cancer cells via an apoptotic pathway.(c) 2022 Elsevier B.V. All rights reserved.