Synthesis, characterization and antibacterial applications of pyrazolyl-sulfonamides and their palladium complexes

Amoah, Cephas; Obuah, Collins; Ainooson, Michael K.; Adokoh, Christian K.; Muller, Alfred

doi:10.1039/d0nj05143h

Cited by 7 publications

(5 citation statements)

References 30 publications

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“…Complex one demonstrated notable antibacterial activity against B. subtilis and S. aureus, consistent with Amoah et al [ 138 ]. These authors suggested that metal complexes penetrate and disrupt bacterial cell walls [ 139 ].…”

Section: Resultssupporting

confidence: 88%

Study of novel bidentate heterocyclic amine-based metal complexes and their biological activities: cytotoxicity and antimicrobial activity evaluation

et al. 2023

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Metallic antitumor drugs with heterocyclic ligands, such as novel AMI (amino methyl imidazole) complexes [Pd(AMI)Cl2](1), [Cu(AMI)L1](2), and [Cu(AMI)L2·2H2O](3) where L1 = oxalate and L2 = malonate, were synthesized and characterized. Assessments included elemental analyses, mass spectrometry, Fourier transform-infrared spectroscopy, ultraviolet–visible spectroscopy, and thermal analysis. The cytotoxicity of AMI complexes compared to cisplatin was assessed using MTT (3-[4,5-dimethylthiazol-2-yl] 2,5diphenyl tetrazolium bromide) assay with breast (MCF-7) and cervical (HeLa) cancer cell lines. After treating these cells with the AMI complexes' IC50 values for 48 h, malondialdehyde levels and catalase activity were used to assess oxidative stress, antioxidant activity was evaluated with DPPH radical scavenging method, comet assays assessed DNA damage, and DNA fragmentation was evaluated using the gel electrophoresis. In vitro, antimicrobial activity was assessed using a disc diffusion method. The anticancer activity results showed that IC50 (half-maximal inhibitory concentration) values of complex one, two, and three against MCF-7 and HeLa cancer cells are 0.156 ± 0.0006, 0.125 ± 0.001, 0.277 ± 0.002 μM respectively for MCF-7 cells and 0.222 ± 0.0005, 0.126 ± 0.0009, 0.152 ± 0.001 μM respectively for HeLa cells. Complex two demonstrated strong anticancer activity against MCF-7 and Hela cells. The study of oxidative stress parameters revealed that Malondialdehyde levels increased in cancer cell lines treated with complexes compared to untreated cells. Catalase activity decreased in cells treated with palladium chelate. The DPPH radical scavenging assay results identified that complex one was a more potent antioxidant in MCF-7 and Hela cells than other complexes with SC50 values of 227.5 ± 0.28 and 361 ± 1.2 μL/mL, respectively. The comet assay results showed that complex two caused significant DNA damage in MCF-7 and HeLa cancer cells treated. Antimicrobial assays identified complex three as the most effective. Copper complexes give better antifungal activity against A. flavus than the palladium complex. We conclude that complex two is the most active in both cell types and might be assessed as a clinically useful drug for breast cancer treatment. The significance of the current study is the synthesis of antitumor drugs containing heterocyclic ligands, such as novel AMI complexes, and the study of their biological activities.

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Section: Resultssupporting

confidence: 88%

Study of novel bidentate heterocyclic amine-based metal complexes and their biological activities: cytotoxicity and antimicrobial activity evaluation

et al. 2023

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“…Another problem is that the ink cannot be erased permanently. There are some methods in which water is used for writing and erasing, [41,[48][49][50][51] however the use of azo dyes for inkless writing and erasing has emerged recently. [52,53] Consequently, we aimed to develop rewritable paper strip or erasable inks using HDBS because of the added advantages of reducing paper waste and chemical pollution.…”

Section: Real-world Applications Of Hdbsmentioning

confidence: 99%

Unraveling Halochromism of Azo‐Based Sulphonamide and Its Real‐World Applications: A Combined Experimental and Theoretical Approach

Joshi,

Ganorkar

et al. 2023

ChemistrySelect

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Halochromic azo dyes have versatile applications, including sensing and anti‐counterfeiting, due to their reversible color‐changing properties. In this work we investigated the structure‐dependent halochromism of azo compound (E)‐4‐((2‐hydroxynaphthalen‐1‐yl)diazenyl)benzenesulfonamide (HDBS) and explore its potential applications using experimental and theoretical approaches. Different spectroscopic techniques confirm the structural change in the dye as a consequence of tautomerism reaction upon changing pH (7 to 13). The stable form of hydrazone is isolated and characterized. Based on the spectroscopic characterization, it is concluded that the azo form exists at pH ≤ 9, whereas the hydrazone form at highly alkaline pH. To understand the origin of the absorption peaks, the stability, and tautomerism in water, DFT and TD‐DFT calculations are performed. A reasonable agreement between the theoretical and experimental observations enabled us to unravel the structure‐dependent halochromism. Further, we have shown that HDBS‐coated paper can be a real‐time visual sensor to monitor fish freshness and for anti‐counterfeiting ink. It changes colors with pH shifts, alerts consumers about the status of food. Additionally, erasable paper strip reduces paper waste and chemical pollution. The findings presented in this work provide a promising avenue for the development of halochromic azo compounds with potential applications in sensing and anti‐counterfeiting.

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“…In this respect, transition metal complexes are promising sources for new antimicrobials as they offer augmented electronic properties and a rich variety of three-dimensional structures if compared to their organic counterparts. − According to the literature, a number of complexes of transition metals (including Mn, Cu, Zn, Ru, Rh, Pd, Ag, Ir, Pt, Au, etc .) were shown to possess antibacterial properties, − with few of them that reached the clinical use. − However, many opportunities offered by the application of inorganic chemistry to this field of research remain unexplored.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium(II) Polypyridyl Complexes and Metronidazole Derivatives: A Powerful Combination in the Design of Photoresponsive Antibacterial Agents Effective under Hypoxic Conditions

et al. 2023

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Ruthenium(II) polypyridyl complexes (RPCs) are gaining momentum in photoactivated chemotherapy (PACT), thanks to the possibility of overcoming the classical reliance on molecular oxygen of photodynamic therapy while preserving the selective drug activation by using light. However, notwithstanding the intriguing perspectives, the translation of such an approach in the development of new antimicrobials has been only barely considered. Herein, MTZH-1 and MTZH-2, two novel analogues of metronidazole (MTZ), a mainstay drug in the treatment of anaerobic bacterial infections, were designed and inserted in the strained ruthenium complexes [Ru(tpy)(dmp)(MTZ-1)]PF6 (Ru2) and [Ru(tpy)(dmp)(MTZ-2)]PF6 (Ru3) (tpy = terpyridine, dmp = 2,9-dimethyl-1,10-phenanthroline) (Chart 1). Analogously to the parental compound [Ru(tpy)(dmp)(5NIM)]PF6 (Ru1) (5-nitroimidazolate), the Ru(II)-imidazolate coordination of MTZ derivatives resulted in promising Ru(II) photocages, capable to easily unleash the bioactive ligands upon light irradiation and increase the antibacterial activity against Bacillus subtilis, which was chosen as a model of Gram-positive bacteria. The photoreleased 5-nitroimidazole-based ligands led to remarkable phototoxicities under hypoxic conditions (<1% O2), with the lead compound Ru3 that exhibited the highest potency across the series, being comparable to the one of the clinical drug MTZ. Besides, the chemical architectures of MTZ derivatives made their interaction with NimAunfavorable, being NimA a model of reductases responsible for bacterial resistance against 5-nitroimidazole-based antibiotics, thus hinting at their possible use to combat antimicrobial resistance. This work may therefore provide fundamental knowledge in the design of novel photoresponsive tools to be used in the fight against infectious diseases. For the first time, the effectiveness of the “photorelease antimicrobial therapy” under therapeutically relevant hypoxic conditions was demonstrated.

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Synthesis, characterization and antibacterial applications of pyrazolyl-sulfonamides and their palladium complexes

Abstract: A series of pyrazolyl sulfonamide compounds were prepared by a multi-step procedure involving preparation of phenyl pyrazolyl compounds (C1, C2) and their chlorosulfonated derivatives (C3-C5), which were then converted to...

Cited by 7 publications

References 30 publications

Study of novel bidentate heterocyclic amine-based metal complexes and their biological activities: cytotoxicity and antimicrobial activity evaluation

Study of novel bidentate heterocyclic amine-based metal complexes and their biological activities: cytotoxicity and antimicrobial activity evaluation

Unraveling Halochromism of Azo‐Based Sulphonamide and Its Real‐World Applications: A Combined Experimental and Theoretical Approach

Ruthenium(II) Polypyridyl Complexes and Metronidazole Derivatives: A Powerful Combination in the Design of Photoresponsive Antibacterial Agents Effective under Hypoxic Conditions

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