Azulene hydrazide-hydrazones for selective targeting of pancreatic cancer cells

Brogyányi, Tereza; Kaplánek, Robert; Kejík, Zdeněk; Hosnedlová, Božena; Antonyová, Veronika; Abramenko, Nikita; Veselá, Kateřina; Martásek, Pavel; Vokurka, Martin; Richardson, Des R.; Jakubek, Milan

doi:10.1016/j.biopha.2022.113736

Cited by 9 publications

(3 citation statements)

References 51 publications

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“…The charge is at (29069 cm), which indicates that the cobalt complex has a tetrahedral structure (44.45.36) . As for the Ni(II) complex Fig (12), the electronic spectrum showed that it has an absorption band at (12476 cm -1 ) returns to electronic transition 1 A 1 g 1 A 2 g(υ 1 ) and a second band at (22551cm -1 ) attributed to electronic transition 1 A 1 g 1 B 1 g( υ 2) ,and charge transfer at (30303 cm -1 ) and the appearance of these bands indicating that this complex has a square planar structure around the nickel (II) ion. (6,37,(46)(47)(48) Cu(II) complex Fig ( 13) showed a wide absorption band in the region (12576 cm -1 ) this band belongs to the 2 T 2 (D) 2 E(D) electronic transition and the charge transfer band at (30721 cm -1 ) , it is in agreement with the magnetic measurements of the complex and with the published research that indicates that it is a tetrahedral structure.…”

Section: Resultsmentioning

confidence: 99%

“…Because of the ability of hydrazones to react with electrophilic and nucleophilic groups, this led to their use in the preparation of many organic compounds, especially heterocyclic compounds (5) ,which have proven effective in many pharmaceutical applications. (6) ,agricultural (7) ,and biological (8,9) as it is included in the treatment of tuberculosis (10,11) ,the treatment of cancerous tumors, and the expansion of constricted blood vessels (12) .Hydrazones are prepared from the condensation reaction between hydrazide and aldehyde or ketones. where the oxygen atom in the carbonyl group in the carbonyl compound is replaced by the functional group (HN-NH 2 -) linked to the hydrazide .…”

Section: Introductionmentioning

confidence: 99%

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New Metal(II) Complexes of 2-Hydroxy-N-(2-Hydroxynaph Thalene-1-yl) Methylene Benzohydrazide: Synthesis and Spectroscopic Studies

Tawfik¹,

Altayy²

2023

CBERJ

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The study includes the preparation of complexes Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II) with Schiff base ligand (HNMBH2) which is derived from the condensation reaction of 2hydroxybenzohydrazide with 2-Hydroxy-1-naphthalene carboxaldehyde. The properties of which were characterized by infrared, magnetic measurements, molar conductivity measurements, electronic spectra, nuclear magnetic resonance spectra of 1 H and 13 C, and gas chromatographymass spectrometry. It is found that the ligand acts as neutral tridentate to give high-stability mononuclear complexes that have a tetrahedral or square planar structure.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Metal(II) Complexes of 2-Hydroxy-N-(2-Hydroxynaph Thalene-1-yl) Methylene Benzohydrazide: Synthesis and Spectroscopic Studies

Tawfik¹,

Altayy²

2023

CBERJ

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“…Conditional constants (K values) were calculated from the absorbance changes (∆A) of tryptanthrin derivates and their complexes with Cu(II), Fe(II) and Fe(III) ions at their spectral maximum by regression analysis (Letagrop Spefo 2005 software). The details of computational model have been described and discussed by Silen et al [28], and the same method was used to analyse the binding affinity of the organic receptors for metal ions in aqueous media [29][30][31][32][33][34][35][36]. Solutions were mixed in the cuvette during the whole titration and after each addition of metal guests.…”

Section: Determining the Conditional Binding Constants And The Comple...mentioning

confidence: 99%

Preparation of Tryptanthrin Derivates Bearing a Thiosemicarbazone Moiety to Inhibit SARS-CoV-2 Replication

et al. 2023

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SARS-CoV-2 is a serious viral pathogen, and agents that inhibit its replication are in high demand. In the present work, we prepared two novel tryptanthrin derivates bearing a thiosemicarbazone moiety as potential antiviral agents. Both compounds displayed potent chelation activity against Fe(III/II) ion-associated COVID-19. The molecular docking results suggest that the compounds can display significant affinity towards SARS-CoV-2 papain-like proteases and SARS-CoV-2 main proteases. In addition, administering T8H-TSC can repress viral replication in the used model (Vero cells). Moreover, the therapeutic potential of the prepared compounds was predicted and analysed in terms of Lipinski’s rules, drug-likeness and drug score.

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Synthesis, Structural Determination, DFT Calculation and Biological Evaluation Supported by Molecular Docking Approach of Some New Complexes Incorporating (E)‐N'‐(3,5‐di‐Tert‐Butyl‐2‐Hydroxybenzylidene) Isonicotino Hydrazide Ligand

Al‐Farraj,

Qasem,

Aouad

et al. 2024

Applied Organom Chemis

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The synthesis and structural analysis of complexes derived from (E)‐N′‐(3,5‐di‐tert‐butyl‐2‐hydroxybenzylidene) isonicotino hydrazide (ITB ligand) were examined using multiple analytical techniques. These techniques included TGA, decomposition point determination, elemental analysis (CHN), spectroscopic (IR, NMR, mass spectrometry) analysis, magnetic susceptibility, conductivity, as well UV–Vis spectrum analysis, along with theoretical studies. Molar conductance values indicated that the Cd (II), Co (II), Cu (II), Ni (II), and Zn (II) complexes are non‐electrolytes in fresh DMSO solutions, with conductance values ranging from 8.5 to 14.35 Ω−1 cm2 mol−1. IR spectra suggested which the ligand coordinates through the metal ions in a tridentate fashion, utilizing the (N & O) donor sites from the (CN & CO & CO) groups in the hydroxybenzylidene moiety. Analytical data from solution complexation, job's method suggested a 1:1 (metal:ligand) molar ratio. The stability order of the complexes was determined as ITBCo > ITBCu > ITBNi > ITBZn > ITBCd, consistent with the stability constant (Kf) values. The pH profile indicated that the studied complexes exhibit stability upon a wide pH scale, typically between (pH = 4:10). Magnetic and electronic spectral analyses helped deduce the ligand coordination abilities and the geometric structures of the complexes. In vitro (antimicrobial & anticancer) performances of the studied complexes were tested versus various (microbial strains & cancer cell lines), revealing higher activity in the chelates assessed to the free (ITB) ligand. The antioxidant potential was also assessed using the DPPH assay. Finally, molecular docking was performed toward estimate the binding efficiency between various protein receptors and the compounds, with results aligning with the biological investigations.

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Azulene hydrazide-hydrazones for selective targeting of pancreatic cancer cells

Cited by 9 publications

References 51 publications

New Metal(II) Complexes of 2-Hydroxy-N-(2-Hydroxynaph Thalene-1-yl) Methylene Benzohydrazide: Synthesis and Spectroscopic Studies

New Metal(II) Complexes of 2-Hydroxy-N-(2-Hydroxynaph Thalene-1-yl) Methylene Benzohydrazide: Synthesis and Spectroscopic Studies

Preparation of Tryptanthrin Derivates Bearing a Thiosemicarbazone Moiety to Inhibit SARS-CoV-2 Replication

Synthesis, Structural Determination, DFT Calculation and Biological Evaluation Supported by Molecular Docking Approach of Some New Complexes Incorporating (E)‐N'‐(3,5‐di‐Tert‐Butyl‐2‐Hydroxybenzylidene) Isonicotino Hydrazide Ligand

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