Nickel(II) complexes with Schiff bases derived from 2-acetylpyrazine and tryptophan: synthesis, crystal structures and DNA interactions

Zhang, Nan; Yu, Fan; Bi, Caifeng; Zhao, Yu; Zhang, Xia; Zhang, Dongmei; Huang, Guimei

doi:10.1007/s11243-013-9712-x

Cited by 12 publications

(2 citation statements)

References 30 publications

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“…With a constant concentration of the concerned complexes (50 μM) and increasing amounts of CT‐DNA concentration (0–50 μM), considerable hyperchromisms are observed with a slight red shift. This observation attributes that all the complexes interact significantly with DNA presumably through non‐intercalative binding mode via accessing multiple hydrogen bonding sites present within both major and minor grooves and the electrostatic interaction between positively charged metal ion and the negatively charged DNA phosphate skeleton . The classical intercalation may be ruled out due to the bulky structure of 1 (non‐planer as well) and the significant non‐planarity issues (the phenyl rings containing 2,4,6‐trimethyl groups in 2 & 3 are out of the plane completely) in case of 2 & 3 .…”

Section: Resultsmentioning

confidence: 99%

Hexanuclear Zn(II) and Mononuclear Cu(II) Complexes containing imino phenol ligands: Exploitation of their Catalytic and Biological Perspectives

Mondal

Chatterjee

Tiwari

et al. 2019

Applied Organom Chemis

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A unique hexanuclear zinc(II) (1) and two mononuclear copper(II) (2 and 3) complexes anchored with imino phenol ligand HL 1 and HL 2 were synthesized with good yield and purity (where HL 1 = 4-tert-butyl-2,6-bis((mesitylimino) methylphenol and HL 2 = 5-tert-butyl-2-hydroxy-3-((mesitylimino)methyl) benzaldehyde). These complexes were characterized by utilizing various spectroscopic protocols like NMR, FTIR, UV as well as ESI-Mass spectrometry, elemental analysis and single crystal X-ray diffraction studies. Their potential to bind calf thymus DNA (CT-DNA) was tested utilizing different techniques such as UV-visible and fluorescence spectroscopy. The experiment implies that they interact with CT-DNA via non-intercalative mode with moderate capabilities (K b~1 0 4 M −1 ). On the other hand, these complexes have high capabilities to quench the fluorescence of bovine serum albumin (BSA) following the static pathway. In addition, they are active catalysts for the oxidation reaction of 3,5-di-tert-butylcatechol (3,5-DTBC) to 3,5-di-tert-butylquinone (3,5-DTBQ) under aerobic condition. From the recorded EPR signals of all complexes, it has been concluded that the oxidation reaction proceeds via ligand oriented radical pathway instead of metal based redox participation. Kinetic studies using 1-3 indicate that it follows Michaelis-Menten type of equation with moderate to high turnover number (k cat ). Apart from these aspects, complexes 1-3 were screened for their cytotoxic behavior towards HeLa cells (human cervical carcinoma) and found quite active with comparable IC 50 values to cisplatin.

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Section: Resultsmentioning

confidence: 99%

Hexanuclear Zn(II) and Mononuclear Cu(II) Complexes containing imino phenol ligands: Exploitation of their Catalytic and Biological Perspectives

Mondal

Chatterjee

Tiwari

et al. 2019

Applied Organom Chemis

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“…Furthermore, nickel is an important transition metal and its coordination compounds display interesting binding properties with proteins and nucleic acids [25]. The N -and O -containing Schiff base ligands and their nickel (II) complexes have become important due to their wide biological activity [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Schiff Base CoII, NiII and CuII Complexes Derived from 2-Hydroxy-1-naphthaldehyde and 2-Picolylamine

Kadhiravansivasamy¹,

Sivajiganesan²,

Periyathambi³

et al. 2016

Mod Chem appl

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Cu (II) and Co (II/III) complexes of N,O‐chelated Schiff base ligands: DNA interaction, protein binding, cytotoxicity, cell death mechanism and reactive oxygen species generation studies

Mondal

Jaiswal

Bera

et al. 2020

Applied Organom Chemis

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A series of copper (II) (1 and 3) and cobalt (II/III) (2, 4 and 5) complexes comprising different imino-phenolate ligands DCH, DTH and DBH 2 (where DCH = 2,4-dichloro-6-((mesitylimino)methyl)phenol, DTH = 2,4-di-tert-butyl-6-((mesitylimino)methyl) phenol and DBH 2 = 2,4-dibromo-6-((mesitylimino) methyl)phenol) have been prepared with excellent yield and high purity. By utilizing different spectroscopic tools such as UV-visible, electrospray ionization (ESI)-mass, Fourier-transform infrared (FTIR) spectrometry and elemental analysis, the prepared complexes (1-5) were thoroughly characterized. The molecular structure of the synthesized complexes was ascertained by using single-crystal X-ray diffraction studies (SCXRDs). The experiment reveals that Complexes 1-5 bind to calf thymus DNA (CT-DNA) through non-intercalative way with good interacting abilities. However, 1-5 are excellent quenchers of the fluorescence intensity of bovine serum albumin (BSA) following the static pathway. Additionally, they had shown remarkable cytotoxic potential against MCF-7 (mammary gland adenocarcinoma) and A549 (lung adenocarcinoma) cell lines. The IC 50 values associated with these complexes were much lower than the conventional drug cisplatin. Apoptosis-induced cell death was confirmed from the DNA fragmentation studies and Hoechst 33342 staining. The 2 0 ,7 0-dichlorofluorescein diacetate (DCFDA) assay indicates that the complex mediated reactive oxygen species (ROS) generation is accountable for governing the apoptosis mechanism via oxidative cell distress. Apart from these studies, by carrying out density functional theory (DFT) method, highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energy gap calculations and optimized structures of the synthesized complexes were accomplished.

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Nickel(II) complexes with Schiff bases derived from 2-acetylpyrazine and tryptophan: synthesis, crystal structures and DNA interactions

Cited by 12 publications

References 30 publications

Hexanuclear Zn(II) and Mononuclear Cu(II) Complexes containing imino phenol ligands: Exploitation of their Catalytic and Biological Perspectives

Hexanuclear Zn(II) and Mononuclear Cu(II) Complexes containing imino phenol ligands: Exploitation of their Catalytic and Biological Perspectives

Synthesis and Characterization of Schiff Base CoII, NiII and CuII Complexes Derived from 2-Hydroxy-1-naphthaldehyde and 2-Picolylamine

Cu (II) and Co (II/III) complexes of N,O‐chelated Schiff base ligands: DNA interaction, protein binding, cytotoxicity, cell death mechanism and reactive oxygen species generation studies

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