Ferrocenylimine-based homoleptic metal(II) complexes: Theoretical, biocompatibility, in vitro anti-proliferative, and in silico molecular docking and pharmacokinetics studies

Jayathuna, Mugamathu Ali; Ahamed, S Fayyaz; Kim, Young Guk; Gajendiran, M.; Kim, Kyobum; Rahiman, A. Kalilur

doi:10.1016/j.molstruc.2021.131905

Cited by 5 publications

(5 citation statements)

References 61 publications

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“…The nickel(II) complexes ( 1–4 ) displayed three weak d–d bands at 780–790, 820–870, and 985–1,050 nm due to 3 A 2g → 3 T 2g (F), 3 A 2g → 3 T 1g and 3 A 2g → 3 T 1g transitions, respectively, while the copper(II) complexes ( 5–8 ) displayed a broad band in the region 663–691 nm assigned to 2 Eg → 3 T 2 g transition, 27–30 which supports the octahedral geometry around nickel(II) and copper(II) ions. The zinc(II) complexes ( 9–12 ) showed only the ligand‐to‐metal charge transfer transition (LMCT) at 357–420 nm, and not displayed any d–d transition in the visible region owing to the d 10 configuration 31 . Based on the observed spectral data, octahedral geometry was assigned for all the metal(II) complexes.…”

Section: Resultsmentioning

confidence: 94%

“…The complexes 2 , 6 , and 10 exhibit high biological activity due to the presence of an electron‐donating methoxy group that might be entered into the conjugation, leading to a small energy gap and easy intramolecular charge transfer (ICT). The global reactivity descriptors such as chemical potential (μ), absolute hardness (η), absolute softness (S), and electrophilicity (ω) were calculated using the following equations, which were based on Koopman's theorem, 31 and the values are given in Table S5. The molecules with the smallest HOMO‐LUMO gap values indicate the highest reactivity.…”

Section: Resultsmentioning

confidence: 99%

“…The zinc(II) complexes (9)(10)(11)(12) showed only the ligand-to-metal charge transfer transition (LMCT) at 357-420 nm, and not displayed any d-d transition in the visible region owing to the d 10 configuration. 31 Based on the observed spectral data, octahedral geometry was assigned for all the metal(II) complexes.…”

Section: Electronic Absorption Spectramentioning

confidence: 99%

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Salicylidene‐based homoleptic metal(II) complexes: Theoretical, in silico molecular modeling and in vitro cytotoxicity studies

Jayathuna,

Sathiyaseelan,

Wang

et al. 2024

Applied Organom Chemis

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A series of 12 salicylidene‐based homoleptic nickel(II), copper(II) and zinc(II) complexes with the general formula [M(L1–4)2] (1–12) containing the tridentate ligands 2‐(((2‐(([1,1′‐biphenyl]‐3‐ylmethylene)amino)phenyl)imino)methyl)phenol (HL1), 2‐(((2‐(([1,1′‐biphenyl]‐3‐ylmethylene)amino)phenyl)imino)methyl)‐4‐methoxyphenol (HL2), 2‐(((2‐(([1,1′‐biphenyl]‐3‐ylmethylene)amino)phenyl)imino)methyl)‐4‐ethoxyphenol (HL3) and 2‐(((2‐(([1,1′‐biphenyl]‐3‐ylmethylene)amino)phenyl)imino)methyl)‐4‐nitrophenol (HL4) have been synthesized and characterized by spectroscopic analysis. The tridentate nature of the ligands form an octahedral geometry around the central metal ion through the phenolic oxygen via deprotonation and two azomethine nitrogen atoms. Further, the charge transfer transitions taking place in the complexes have been explained using HOMO‐LUMO analysis. The in vitro cytotoxicity activity screened by WST assay against human metastatic (MDA‐MB‐231), hepatoma (HepG2) and colorectal adenocarcinoma (CaCo2) cancerous, and normal mouse fibroblast (NIH3T3) cell lines showed higher activity for the complexes 2, 6 and 10 with respect to the standard drug 5‐fluorouracil. The AO/EB, PI, Rh123 and DCFH‐DA staining results indicated that the complexes induced anticancer activity through apoptosis. Furthermore, the complexes interact with FGFR and P13Kγ kinase receptors through the hydrophobic, hydrogen bonding, π–π, σ–π, van der Waals and electrostatic interaction.

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

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Salicylidene‐based homoleptic metal(II) complexes: Theoretical, in silico molecular modeling and in vitro cytotoxicity studies

Jayathuna,

Sathiyaseelan,

Wang

et al. 2024

Applied Organom Chemis

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“…Importantly, universal descriptors such as absolute softness (S), electrophilicity (ω), electronegativity (χ) and absolute hardness (η) were calculated using the following equations, based on Koopman's theorem (Table S5). The molecules with the lowest HOMO‐LUMO gap values indicate higher reactivity [40] …”

Section: Resultsmentioning

confidence: 99%

“…The molecules with the lowest HOMO-LUMO gap values indicate higher reactivity. [40] 2.5. Biological studies…”

Section: Frontier Molecular Orbitals (Fmos)mentioning

confidence: 99%

Theoretical, DNA/BSA Binding, Molecular Docking and In Vitro Cytotoxicity Studies of Homoleptic Metal(II) Complexes Derived from 2‐Formylpyridine‐Based Ligands

Jayathuna,

Rajagopal,

Anand

et al. 2024

ChemistrySelect

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A new class of homoleptic metal(II) complexes of general formula [M(L1–4)2]2Cl in which L1=1‐([1,1′‐biphenyl]‐4‐yl)‐N‐(2‐((‐pyridin‐2‐ylmethylene)amino)ethyl)methanimine, L2=1‐([1,1′‐biphenyl]‐4‐yl)‐N‐(2‐((‐pyridin‐2‐ylmethylene)amino)phenyl)methanimine, L3=1‐([1,1′‐biphenyl]‐4‐yl)‐N‐(2‐((‐pyridin‐2‐ylmethylene)amino)‐4‐nitrophenyl)methanimine and L4=4‐(([1,1′‐biphenyl]‐4‐ylmethylene)amino)‐3‐((−pyridin‐2‐ylmethylene)amino)benzophenone, and M=Ni(II) (1–4), Cu(II) (5–8) and Zn(II) (9–12) have been synthesized and characterized. The IR spectra reveal the involvement of azomethine and 2‐formylpyridine ring nitrogen atoms in chelation. The UV‐Vis and EPR spectral studies envisage distorted octahedral geometry around metal(II) ion. All the complexes were stable for 72 h in biologically relevant solutions, and copper(II) complexes were reduced to Cu+ center in the presence of ascorbic acid solution. The binding studies of complexes with calf thymus DNA (CT‐DNA) indicate groove mode of binding, and the complexes 3, 7 and 11 containing the 4‐nitrophenyl substituent exhibit the highest binding affinity than the other complexes. Furthermore, the spectral studies also revealed the interaction of complexes with BSA through static mechanism. In vitro cytotoxicity activity of the complexes was screened against human lung adenocarcinoma (A549) and breast adenocarcinoma (MCF‐7) cancerous, and normal murine fibrosarcoma (L929) cell lines. The molecular docking studies of the homoleptic metal(II) complexes show hydrophobic, π–π, σ–π and hydrogen bonding interactions with EGFR/VEGFR2 kinase receptors.

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Investigation of antimicrobial potential of nanocomposites based on functionalization of graphene oxide with zinc porphyrin complexes

Yasmeen,

Ahmed,

Bhat

et al. 2024

Inorganica Chimica Acta

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Ferrocenylimine-based homoleptic metal(II) complexes: Theoretical, biocompatibility, in vitro anti-proliferative, and in silico molecular docking and pharmacokinetics studies

Cited by 5 publications

References 61 publications

Salicylidene‐based homoleptic metal(II) complexes: Theoretical, in silico molecular modeling and in vitro cytotoxicity studies

Salicylidene‐based homoleptic metal(II) complexes: Theoretical, in silico molecular modeling and in vitro cytotoxicity studies

Theoretical, DNA/BSA Binding, Molecular Docking and In Vitro Cytotoxicity Studies of Homoleptic Metal(II) Complexes Derived from 2‐Formylpyridine‐Based Ligands

Investigation of antimicrobial potential of nanocomposites based on functionalization of graphene oxide with zinc porphyrin complexes

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