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Efficient Synthesis for a Wide Variety of Patellamide Derivatives and Phosphatase Activity of Copper-Patellamide Complexes.

ABSTRACT: Copper complexes of patellamides have shown catalytic activity in a variety of reactions but their biological function remains unknown. There are significant differences between the natural macrocycles and synthetic analogues in the various catalytic activities. It therefore is essential to be able to perform in vivo and ex vivo reference measurements with the natural patellamide macrocycles, very similar derivatives and a large range of synthetic analogues. The preparative method described allows for a highly adaptable synthetic process producing building blocks for a large range of patellamide derivatives: apart from natural compounds, a new synthetic patellamide was prepared that does not have any substituents at any of the four heterocycles. Together with the variation of substituents at the aliphatic backbone, this allowed to elucidate the catalytic activity for phosphoester hydrolysis as a function of the structure and dynamics of the dicopper(II)-patellamide complexes, both by experiment and DFT-based mechanistic studies.

SUBMITTER: Baur P

PROVIDER: S-EPMC9311697 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Efficient Synthesis for a Wide Variety of Patellamide Derivatives and Phosphatase Activity of Copper-Patellamide Complexes.

Baur Philipp P Comba Peter P Velmurugan Gunasekaran G

Chemistry (Weinheim an der Bergstrasse, Germany) 20220318 23

Copper complexes of patellamides have shown catalytic activity in a variety of reactions but their biological function remains unknown. There are significant differences between the natural macrocycles and synthetic analogues in the various catalytic activities. It therefore is essential to be able to perform in vivo and ex vivo reference measurements with the natural patellamide macrocycles, very similar derivatives and a large range of synthetic analogues. The preparative method described allo ...[more]

PMID: 35179261

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Project description:Five new copper(II) acrylate complexes (acr is the acrylate anion: C₃H₃O₂) with imidazole derivatives (2-methylimidazole/2-MeIm, 5-methylimidazole/5-MeIm, 2-ethylimidazole/2-EtIm) of type: cis-[Cu(2-RIm)₂(acr)₂]·xH₂O ((1): R = ⁻CH₃, x = 2; (4): R = ⁻CH₂⁻CH₃, x = 0), trans-[Cu(2-RIm)₂(acr)₂] ((2): R = ⁻CH₃; (5): R = ⁻CH₂⁻CH₃) and trans-[Cu(5-RIm)₂(acr)₂] ((3): R = ⁻CH₃) have been prepared and characterized by elemental analysis, Fourier Transform Infrared spectrometry (FTIR), Electron Paramagnetic Resonance (EPR), electronic reflectance spectroscopy, scanning electron microscopy, and mass spectrometry. The single crystal X-ray diffraction study of complexes (2) and (5) reveals that the copper(II) ion is located on an inversion center and show elongated octahedral geometry completed by two coplanar bidentate acrylates and two unidentate imidazole derivatives displayed in trans positions. For complex (4) the single crystal X-ray diffraction shows that the copper(II) ion is in a distorted octahedral environment which can be easily confused with a trigonal prism completed by two bidentate acrylates and two unidentate imidazole derivatives displayed in cis positions. These results indicate the fact that complexes (4) and (5) are the geometric isomers of the same compound bis(acrylate)-bis(2-ethylimidazole)-copper(II). Complexes (1) and (2), as well as (4) and (5), were produced simultaneously in the reaction of the corresponding copper(II) acrylate with imidazole derivatives in methanol solution. Furthermore, in order to be able to formulate potential applications of the obtained compounds, our next goal was to investigate the in vitro antimicrobial activity of the synthesized complexes against Gram-positive and Gram-negative bacteria, as well as fungal strains, of both clinical and ecological importance (biodeterioration of historical buildings). The trans isomers (2) and (5), followed by (4) have shown the broadest range of antimicrobial activity. In case of (1) and (2) isomers, the trans isomer (2) was significantly more active than cis (1), while the cis isomer (4) proved to be more active than trans (5). Taken together, the biological evaluation results indicate that the trans (2) was the most active complex, demonstrating its potential for the development of novel antimicrobial agents, with potential applications in the biomedical and restoration of architectural monuments fields.

Dataset Information

Efficient Synthesis for a Wide Variety of Patellamide Derivatives and Phosphatase Activity of Copper-Patellamide Complexes.

Publications

Efficient Synthesis for a Wide Variety of Patellamide Derivatives and Phosphatase Activity of Copper-Patellamide Complexes.

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