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12 pages, 2230 KiB

Open AccessArticle

Dinuclear Molybdenum(VI) Complexes Based on Flexible Succinyl and Adipoyl Dihydrazones

by Edi Topić, Vladimir Damjanović, Katarina Pičuljan and Mirta Rubčić

Crystals 2024, 14(2), 135; https://doi.org/10.3390/cryst14020135 - 29 Jan 2024

Cited by 1 | Viewed by 1696

A series of molybdenum(VI) complexes with aryl-functionalized alkyl dihydrazones was prepared by the reaction of [MoO₂(acac)₂] and the appropriate dihydrazone in methanol. Their solid-state structures were elucidated via single-crystal X-ray diffraction (SC-XRD) and Fourier-transform infra-red (FTIR) spectroscopy, while the thermal stability of compounds was inspected by combined thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) experiments. The behaviour of complexes in DMSO-d₆ solution was explored by nuclear magnetic resonance (NMR). The relevant data show that all complexes are dinuclear, with dihydrazones acting as ditopic hexadentate ligands. The in vitro cytotoxic activity of the prepared molybdenum(VI) complexes was evaluated on THP-1 and HepG2 cell lines, while their antibacterial activity was tested against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Moraxella catarrhalis bacteria. The majority of compounds proved to be non-cytotoxic, while some exhibited superior antibacterial activity in comparison to dihydrazone ligands. Full article

(This article belongs to the Special Issue The Polyhedral Face of Coordination Chemistry)

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24 pages, 4960 KiB

Open AccessArticle

Bimetallic bis-Aroyldihydrazone-Isatin Complexes of High O=V(IV) and Low Cu(II) Valent Ions as Effective Biological Reagents for Antimicrobial and Anticancer Assays

by Ahmed Khalil and Mohamed Shaker S. Adam

Molecules 2024, 29(2), 414; https://doi.org/10.3390/molecules29020414 - 15 Jan 2024

Cited by 12 | Viewed by 1523

Abstract

Due to the versatile bioreactivity of aroyldihydrazone complexes as cost-effective alternatives with different transition metals, two novel bimetallic homo-complexes (VOLph and CuLph) were prepared via the coordination of a terephthalic dihydrazone diisatin ligand (H₂Lph) with VO²⁺ and Cu²⁺ ions, respectively. The structure elucidation was confirmed by alternative spectral methods. Biologically, the H₂Lph ligand and its MLph complexes (M²⁺ = VO²⁺ or Cu²⁺) were investigated as antimicrobial and anticancer agents. Their biochemical activities towards ctDNA (calf thymus DNA) were estimated using measurable titration viscometrically and spectrophotometrically, as well as the gel electrophoresis technique. The growth inhibition of both VOLph and CuLph complexes against microbial and cancer cells was measured, and the inhibition action, MIC, and IC₅₀ were compared to the inhibition action of the free H₂Lph ligand. Both VOLph and CuLph showed remarkable interactive binding with ctDNA compared to the free ligand H₂Lph, based on K_b = 16.31, 16.04 and 12.41 × 10⁷ mol⁻¹ dm³ and

Δ G_{b}^{\neq}

= 47.11, −46.89, and −44.05 kJ mol⁻¹ for VOLph, CuLph, and H₂Lph, respectively, due to the central metal ion (V^IVO and Cu^II ions). VOLph (with a higher oxidation state of the V⁴⁺ ion and oxo-ligand) exhibited enhanced interaction with the ctDNA molecule compared to CuLph, demonstrating the role and type of the central metal ion within the performed electronegative and electrophilic characters. Full article

(This article belongs to the Section Inorganic Chemistry)

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18 pages, 4243 KiB

Open AccessArticle

Synthesis, Biological Evaluation, DNA Binding, and Molecular Docking of Hybrid 4,6-Dihydrazone Pyrimidine Derivatives as Antitumor Agents

by Hairong Lan, Junying Song, Juan Yuan, Aiping Xing, Dai Zeng, Yating Hao, Zhenqiang Zhang and Shuying Feng

Molecules 2023, 28(1), 187; https://doi.org/10.3390/molecules28010187 - 26 Dec 2022

Cited by 4 | Viewed by 2858

Abstract

In the present paper, on the basis of molecular hybridization, a series of 4,6-dihydrazone pyrimidine derivatives containing the pyridine moiety were synthesized, structurally characterized, and evaluated in vitro for their antitumor activity. According to the results, all the tested compounds demonstrated broad-spectrum antitumor activity against selected tumor cell lines (MCF-7, BGC-823, A549, and BEL-7402) and no obvious toxicity toward normal cells HL-7702. In particular, compounds 10a and 10f were found to be the most promising antitumor agents among the tested compounds against BGC-823 cells (IC₅₀ = 9.00 μM and 7.89 μM) and BEL-7402 cells (IC₅₀ = 6.70 μM and 7.66 μM), respectively. Compounds 10a and 10f exhibited higher potency against BGC-823 and BEL-7402 than the positive control 5-FU (IC₅₀ = 15.18 μM and 15.81 μM). Further mechanism investigations demonstrated that compounds 10a and 10f could significantly increase the level of cellular ROS and induce early apoptosis of BGC-823 cells in a dose-dependent manner. Moreover, the DNA binding results from UV/Vis, CD spectroscopy, and molecular docking studies indicated that 10a and 10f bind with DNA via groove binding and partial intercalation. These results demonstrated that 10a and 10f may serve as novel lead compounds for the discovery of more dihydrazone pyrimidine derivatives with improved antitumor potency and selectivity. Full article

(This article belongs to the Special Issue Novel Anti-cancer Lead Compounds)

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13 pages, 1807 KiB

Open AccessArticle

Succinyl and Adipoyl Dihydrazones: A Solid-State, Solution and Antibacterial Study

by Edi Topić, Vladimir Damjanović, Katarina Pičuljan, Višnja Vrdoljak and Mirta Rubčić

Crystals 2022, 12(8), 1175; https://doi.org/10.3390/cryst12081175 - 21 Aug 2022

Cited by 3 | Viewed by 2400

Abstract

A series of aryl-functionalized alkyl dihydrazones was prepared by condensation of succinyl or adipoyl dihydrazide and selected ortho-hydroxybenzaldehydes (2-hydroxybenzaldehyde, 2-hydroxy-1-naphthaldehyde, 2,3-dihydroxybenzaldehyde, and 2,4-dihydroxybenzaldehyde) in solution. The obtained products were structurally characterized in the solid state by single-crystal X-ray diffraction (SC-XRD), thermal analysis (TGA-DSC), and Fourier transform infrared (FTIR) spectroscopy and in DMSO-d₆ solution by nuclear magnetic resonance (NMR) techniques. Combined FTIR and crystal structure data point to a N–NH–C=O tautomeric form of the hydrazone parts as well as the enol-imino tautomeric form of the aldehyde residues and a robust trans-syn conformation for the structurally investigated ones. While the molecules retain the same tautomeric form in the DMSO-d₆ solution, they adopt several conformations, due to rotations around C_ar–C, C–N, and N–N bonds. The compounds show exceptional thermal stability, with a complex degradation pattern. Slight differences in thermal behavior correlate to alkyl chain length and aryl substituents. The in vitro cytotoxic activity of prepared dihydrazones was evaluated on THP-1 and HepG2 cell lines, while their antibacterial activity was tested against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Moraxella catarrhalis bacteria. All compounds proved to be non-cytotoxic, and some exhibited moderate antibacterial activity. Full article

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23 pages, 900 KiB

Open AccessArticle

Synthesis and Antibacterial Activity of New Azole, Diazole and Triazole Derivatives Based on p-Aminobenzoic Acid

by Birutė Sapijanskaitė-Banevič, Vykintas Palskys, Rita Vaickelionienė, Jūratė Šiugždaitė, Povilas Kavaliauskas, Birutė Grybaitė and Vytautas Mickevičius

Molecules 2021, 26(9), 2597; https://doi.org/10.3390/molecules26092597 - 29 Apr 2021

Cited by 21 | Viewed by 4780

Abstract

The p-aminobenzoic acid was applied for the synthesis of substituted 1-phenyl-5-oxopyrrolidine derivatives containing benzimidazole, azole, oxadiazole, triazole, dihydrazone, and dithiosemicarbazide moieties in the structure. All the obtained compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Salmonella enteritidis, Escherichia coli, and Pseudomonas aeruginosa by using MIC and MBC assays. This study showed a good bactericidal activity of γ-amino acid and benzimidazoles derivatives. The antimicrobial activity of the most promising compounds was higher than ampicillin. Furthermore, two benzimidazoles demonstrated good antimicrobial activity against L. monocytogenes (MIC 15.62 µg/mL) that was four times more potent than ampicillin (MIC 65 µg/mL). Further studies are needed to better understand the mechanism of the antimicrobial activity as well as to generate antimicrobial compounds based on the 1-phenyl-5-oxopyrrolidine scaffold. Full article

(This article belongs to the Special Issue Heterocycles in Organic Synthesis: A Theme Issue in Honor of Prof. Dr. Albert Padwa)

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