Silver(I) complex with 2-amino-4,4α-dihydro-4α,7-dimethyl-3<i>H</i>-phenoxazin-3-one (Phx-1) ligand: crystal structure, vibrational spectra and biological studies

Helios, Katarzyna; Maniak, Halina; Sowa, Michał; Zierkiewicz, Wiktor; Wasinska-Kalwa, Malgorzata; Giurg, Mirosław; Drożdżewski, Piotr; Trusek-Hołownia, A.; Malik, Magdalena; Krauze, K.

doi:10.1080/00958972.2017.1384822

Cited by 4 publications

(2 citation statements)

References 31 publications

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“…Furthermore, we aimed at discovering a new group of organic low-molecular-weight compounds which activity that weakens a pest's activity and consequently provides conditions for improving the plant defense system. The imines 1-3 were synthesized as part of a program to discover low-molecular-weight compounds that were both the inhibitors of essential enzymes overexpressed during disease development [25][26][27] and act directly against pathogenic microorganisms [28,29]. A common polypore fungus Trametes versicolor, which is an abundant tree parasite causing a white-rot of wood, was chosen as a model organism.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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A series of hydrazide-hydrazones 1–3, the imine derivatives of hydrazides and aldehydes bearing benzene rings, were screened as inhibitors of laccase from Trametes versicolor. Laccase is a copper-containing enzyme which inhibition might prevent or reduce the activity of the plant pathogens that produce it in various biochemical processes. The kinetic and molecular modeling studies were performed and for selected compounds, the docking results were discussed. Seven 4-hydroxybenzhydrazide (4-HBAH) derivatives exhibited micromolar activity Ki = 24–674 µM with the predicted and desirable competitive type of inhibition. The structure–activity relationship (SAR) analysis revealed that a slim salicylic aldehyde framework had a pivotal role in stabilization of the molecules near the substrate docking site. Furthermore, the presence of phenyl and bulky tert-butyl substituents in position 3 in salicylic aldehyde fragment favored strong interaction with the substrate-binding pocket in laccase. Both 3- and 4-HBAH derivatives containing larger 3-tert-butyl-5-methyl- or 3,5-di-tert-butyl-2-hydroxy-benzylidene unit, did not bind to the active site of laccase and, interestingly, acted as non-competitive (Ki = 32.0 µM) or uncompetitive (Ki = 17.9 µM) inhibitors, respectively. From the easily available laccase inhibitors only sodium azide, harmful to environment and non-specific, was over 6 times more active than the above compounds.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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“…We synthesized and investigated the new phenolic hydrazide-hydrazones as a part of our ongoing project to discover aromatic compounds as antifungal and antiviral agents and key enzyme inhibitors of pathogenic microorganisms and viruses [31,[85][86][87][88][89][90]. The target products were synthesized in a three-step procedure starting from carboxylic acid 1 via carboxylic acid methyl ester 2 [91] as the first intermediate product.…”

Section: Syntheses and Characterizationsmentioning

confidence: 99%

Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies

Maniak

Talma

Giurg

2021

IJMS

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Laccase from pathogenic fungi participates in both the delignification and neutralization of phytoantibiotics. Furthermore, it interferes with the hormone signaling in plants and catalyzes melanization. Infections of these pathogens contribute to loss in forestry, agriculture, and horticulture. As there is still a need to expand knowledge on efficient defense strategies against phytopathogenic fungi, the present study aimed to reveal more information on the molecular mechanisms of laccase inhibition with natural and natural-like carboxylic acid semi-synthetic derivatives. A set of hydrazide-hydrazones derived from carboxylic acids, generally including electron-rich arene units that serve as a decoy substrate, was synthesized and tested with laccase from Trametes versicolor. The classic synthesis of the title inhibitors proceeded with good to almost quantitative yield. Ninety percent of the tested molecules were active in the range of KI = 8–233 µM and showed different types of action. Such magnitude of inhibition constants qualified the hydrazide-hydrazones as strong laccase inhibitors. Molecular docking studies supporting the experimental data explained the selected derivatives’ interactions with the enzyme. The results are promising in developing new potential antifungal agents mitigating the damage scale in the plant cultivation, gardening, and horticulture sectors.

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Synthesis, crystal structure and NLO study of two new versatile Ca (II) complexes

Nadeem

Bhatti

Zierkiewicz

et al. 2018

Applied Organom Chemis

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Two new versatile supramolecular calcium complexes [Ca 2 (NPG) 4 (1,10 phen) 2 ](1) and 4 (1,10 phen) 2 ] (2) have been synthesized by the addition of 1,10-phenanthroline to the solution of already prepared corresponding calcium N-phthaloylglycinate and calcium N-phthaloyl-β-alaninate complexes, which were prepared from the reaction of calcium oxide with Nphthaloylglycine (NPG) and N-phthaloyl-β-alanine (NPß-ala), respectively.The complexes were characterized by single X-ray diffraction method. The spectroscopic and electronic properties were investigated by utilizing Fourier transform-infrared and UV-Vis spectroscopic techniques. The theoretical calculations were performed by using B3LYP-D3 method (standard hybrid density functional B3LYP method with dispersion correction D3) to find the coherent relationship between experimental and theoretical findings for structural, spectroscopic and electronic properties. The natural bond orbital analysis was performed for both complexes to study charge transfer. The solid state photoluminescence for both Ca complexes was observed experimentally. The nonlinear optical (NLO) properties of both complexes have been analyzed theoretically, and it was found that both Ca complexes showed excellent NLO prospective potential as compared with the commercial NLO active materials like para-nitrotoluene (PNA) and urea. Further, it was concluded that 2 showed much more increase in first static hyperpolarizabilty as compared with 1.

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Silver(I) complex with 2-amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazin-3-one (Phx-1) ligand: crystal structure, vibrational spectra and biological studies

Cited by 4 publications

References 31 publications

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies

Synthesis, crystal structure and NLO study of two new versatile Ca (II) complexes

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