Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid Derivatives

Two new Ag(I) complexes with coumaric carboxylic acid derivatives have been synthesized. Structural studies of these noncrystalline complexes have been performed using a methodology that combines laboratory and synchrotron techniques, supported by density functional theory calculations. The arrangem...

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Main Authors: Anna Wolska, Aleksandra Drzewiecka-Antonik, Cristina Aparecida Barboza, Marta Struga, Joanna Stefanska, Pawel Rejmak, Marcin Klepka
Format: Article
Language:English
Published: MDPI AG 2024-10-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/29/21/4993
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author Anna Wolska
Aleksandra Drzewiecka-Antonik
Cristina Aparecida Barboza
Marta Struga
Joanna Stefanska
Pawel Rejmak
Marcin Klepka
author_facet Anna Wolska
Aleksandra Drzewiecka-Antonik
Cristina Aparecida Barboza
Marta Struga
Joanna Stefanska
Pawel Rejmak
Marcin Klepka
author_sort Anna Wolska
collection DOAJ
description Two new Ag(I) complexes with coumaric carboxylic acid derivatives have been synthesized. Structural studies of these noncrystalline complexes have been performed using a methodology that combines laboratory and synchrotron techniques, supported by density functional theory calculations. The arrangement of ligands around the Ag(I) cation has been refined using infrared, extended X-ray absorption fine structure, and X-ray absorption near edge structure spectroscopies. Different coordination modes of carboxylate ligands are observed for the studied compounds. Carboxylate bridges are characteristic for the Ag(I) complex with 4-oxo-4<i>H</i>-1-benzopyran-2-carboxylic acid (<b>1</b>), while a bidentate chelating motif was found for the complex with 2-oxo-2<i>H</i>-1-benzopyran-3-carboxylic acid (<b>2</b>). Additionally, the carbonyl oxygen atom of the coumarin ring coordinates to the silver cation in complex <b>2</b>, while it is inactive in complex <b>1</b>. Antimicrobial evaluation has been performed for both compounds. The complexes show activity against selected bacteria as well as <i>Candida</i> yeast. This activity is slightly lower for bacteria and the same or higher for <i>Candida</i> in relation to the reference substances: ciprofloxacin or fluconazole.
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spelling doaj-art-0537bdb78f2444898d29502fd865138c2024-11-08T14:37:59ZengMDPI AGMolecules1420-30492024-10-012921499310.3390/molecules29214993Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid DerivativesAnna Wolska0Aleksandra Drzewiecka-Antonik1Cristina Aparecida Barboza2Marta Struga3Joanna Stefanska4Pawel Rejmak5Marcin Klepka6Institute of Physics, Polish Academy of Sciences, Aleja Lotnikow 32/46, PL-02668 Warsaw, PolandInstitute of Physics, Polish Academy of Sciences, Aleja Lotnikow 32/46, PL-02668 Warsaw, PolandInstitute of Physics, Polish Academy of Sciences, Aleja Lotnikow 32/46, PL-02668 Warsaw, PolandChair and Department of Biochemistry, Medical University of Warsaw, Banacha 1, PL-02097 Warsaw, PolandDepartment of Pharmaceutical Microbiology and Bioanalysis, Centre for Preclinical Research, Medical University of Warsaw, Banacha 1B, PL-02097 Warsaw, PolandInstitute of Physics, Polish Academy of Sciences, Aleja Lotnikow 32/46, PL-02668 Warsaw, PolandInstitute of Physics, Polish Academy of Sciences, Aleja Lotnikow 32/46, PL-02668 Warsaw, PolandTwo new Ag(I) complexes with coumaric carboxylic acid derivatives have been synthesized. Structural studies of these noncrystalline complexes have been performed using a methodology that combines laboratory and synchrotron techniques, supported by density functional theory calculations. The arrangement of ligands around the Ag(I) cation has been refined using infrared, extended X-ray absorption fine structure, and X-ray absorption near edge structure spectroscopies. Different coordination modes of carboxylate ligands are observed for the studied compounds. Carboxylate bridges are characteristic for the Ag(I) complex with 4-oxo-4<i>H</i>-1-benzopyran-2-carboxylic acid (<b>1</b>), while a bidentate chelating motif was found for the complex with 2-oxo-2<i>H</i>-1-benzopyran-3-carboxylic acid (<b>2</b>). Additionally, the carbonyl oxygen atom of the coumarin ring coordinates to the silver cation in complex <b>2</b>, while it is inactive in complex <b>1</b>. Antimicrobial evaluation has been performed for both compounds. The complexes show activity against selected bacteria as well as <i>Candida</i> yeast. This activity is slightly lower for bacteria and the same or higher for <i>Candida</i> in relation to the reference substances: ciprofloxacin or fluconazole.https://www.mdpi.com/1420-3049/29/21/4993metal-organic ligand complexesXAFSATR-IR spectroscopystructural analysisantimicrobial activity
spellingShingle Anna Wolska
Aleksandra Drzewiecka-Antonik
Cristina Aparecida Barboza
Marta Struga
Joanna Stefanska
Pawel Rejmak
Marcin Klepka
Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid Derivatives
Molecules
metal-organic ligand complexes
XAFS
ATR-IR spectroscopy
structural analysis
antimicrobial activity
title Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid Derivatives
title_full Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid Derivatives
title_fullStr Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid Derivatives
title_full_unstemmed Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid Derivatives
title_short Structural and Biological Studies of Bioactive Silver(I) Complexes with Coumarin Acid Derivatives
title_sort structural and biological studies of bioactive silver i complexes with coumarin acid derivatives
topic metal-organic ligand complexes
XAFS
ATR-IR spectroscopy
structural analysis
antimicrobial activity
url https://www.mdpi.com/1420-3049/29/21/4993
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