Cargando…
Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones
In this paper we describe the synthesis of new N-heterocyclic carbene (NHC) gold(I) derivatives with flavone-derived ligands with a propargyl ether group. The compounds were screened for their antimicrobial and anticancer activities, showing greater activity against bacteria than against colon cance...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9612383/ https://www.ncbi.nlm.nih.gov/pubmed/36297498 http://dx.doi.org/10.3390/pharmaceutics14102064 |
_version_ | 1784819761900683264 |
---|---|
author | Mármol, Inés Quero, Javier Azcárate, Paula Atrián-Blasco, Elena Ramos, Carla Santos, Joana Gimeno, María Concepción Rodríguez-Yoldi, María Jesús Cerrada, Elena |
author_facet | Mármol, Inés Quero, Javier Azcárate, Paula Atrián-Blasco, Elena Ramos, Carla Santos, Joana Gimeno, María Concepción Rodríguez-Yoldi, María Jesús Cerrada, Elena |
author_sort | Mármol, Inés |
collection | PubMed |
description | In this paper we describe the synthesis of new N-heterocyclic carbene (NHC) gold(I) derivatives with flavone-derived ligands with a propargyl ether group. The compounds were screened for their antimicrobial and anticancer activities, showing greater activity against bacteria than against colon cancer cells (Caco-2). Complexes [Au(L2b)(IMe)] (1b) and [Au(L2b)(IPr)] (2b) were found to be active against both Gram-positive and Gram-negative strains. The mechanism of action of 1b was evaluated by measurement of thioredoxin reductase (TrxR) and dihydrofolate reductase (DHFR) activity, besides scanning electron microscopy (SEM). Inhibition of the enzyme thioredoxin reductase is not observed in either Escherichia Coli or Caco-2 cells; however, DHFR activity is compromised after incubation of E. coli cells with complex 1b. Moreover, loss of structural integrity and change in bacterial shape is observed in the images obtained from scanning electron microscopy (SEM) after treatment E. coli cells with complex 1b. |
format | Online Article Text |
id | pubmed-9612383 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-96123832022-10-28 Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones Mármol, Inés Quero, Javier Azcárate, Paula Atrián-Blasco, Elena Ramos, Carla Santos, Joana Gimeno, María Concepción Rodríguez-Yoldi, María Jesús Cerrada, Elena Pharmaceutics Article In this paper we describe the synthesis of new N-heterocyclic carbene (NHC) gold(I) derivatives with flavone-derived ligands with a propargyl ether group. The compounds were screened for their antimicrobial and anticancer activities, showing greater activity against bacteria than against colon cancer cells (Caco-2). Complexes [Au(L2b)(IMe)] (1b) and [Au(L2b)(IPr)] (2b) were found to be active against both Gram-positive and Gram-negative strains. The mechanism of action of 1b was evaluated by measurement of thioredoxin reductase (TrxR) and dihydrofolate reductase (DHFR) activity, besides scanning electron microscopy (SEM). Inhibition of the enzyme thioredoxin reductase is not observed in either Escherichia Coli or Caco-2 cells; however, DHFR activity is compromised after incubation of E. coli cells with complex 1b. Moreover, loss of structural integrity and change in bacterial shape is observed in the images obtained from scanning electron microscopy (SEM) after treatment E. coli cells with complex 1b. MDPI 2022-09-27 /pmc/articles/PMC9612383/ /pubmed/36297498 http://dx.doi.org/10.3390/pharmaceutics14102064 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Mármol, Inés Quero, Javier Azcárate, Paula Atrián-Blasco, Elena Ramos, Carla Santos, Joana Gimeno, María Concepción Rodríguez-Yoldi, María Jesús Cerrada, Elena Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones |
title | Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones |
title_full | Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones |
title_fullStr | Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones |
title_full_unstemmed | Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones |
title_short | Biological Activity of NHC-Gold-Alkynyl Complexes Derived from 3-Hydroxyflavones |
title_sort | biological activity of nhc-gold-alkynyl complexes derived from 3-hydroxyflavones |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9612383/ https://www.ncbi.nlm.nih.gov/pubmed/36297498 http://dx.doi.org/10.3390/pharmaceutics14102064 |
work_keys_str_mv | AT marmolines biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT querojavier biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT azcaratepaula biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT atrianblascoelena biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT ramoscarla biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT santosjoana biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT gimenomariaconcepcion biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT rodriguezyoldimariajesus biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones AT cerradaelena biologicalactivityofnhcgoldalkynylcomplexesderivedfrom3hydroxyflavones |