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Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

Due to the lack of new antimicrobial drug discovery in recent years and an ever-growing prevalence of multidrug-resistant “superbugs”, there is a pressing need to explore alternative ways to combat pathogenic bacterial and fungal infections. Building upon our previous work in the field of medicinal...

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Autores principales: Villegas, Jessica, Ball, Bryce C, Shouse, Katelyn M, VanArragon, Caleb W, Wasserman, Ashley N, Bhakta, Hannah E, Oliver, Allen G, Orozco-Nunnelly, Danielle A, Pruet, Jeffrey M
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10548253/
https://www.ncbi.nlm.nih.gov/pubmed/37799174
http://dx.doi.org/10.3762/bjoc.19.108
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author Villegas, Jessica
Ball, Bryce C
Shouse, Katelyn M
VanArragon, Caleb W
Wasserman, Ashley N
Bhakta, Hannah E
Oliver, Allen G
Orozco-Nunnelly, Danielle A
Pruet, Jeffrey M
author_facet Villegas, Jessica
Ball, Bryce C
Shouse, Katelyn M
VanArragon, Caleb W
Wasserman, Ashley N
Bhakta, Hannah E
Oliver, Allen G
Orozco-Nunnelly, Danielle A
Pruet, Jeffrey M
author_sort Villegas, Jessica
collection PubMed
description Due to the lack of new antimicrobial drug discovery in recent years and an ever-growing prevalence of multidrug-resistant “superbugs”, there is a pressing need to explore alternative ways to combat pathogenic bacterial and fungal infections. Building upon our previous work in the field of medicinal phytochemistry, the present study is focused on designing, synthesizing, and testing the altered bioactivity of new variants of two original bioactive molecules found in the Argemone mexicana plant. Herein, we report upon 14 variants of berberine and four variants of chelerythrine that have been screened against a pool of 12 microorganisms (five Gram-positive and four Gram-negative bacteria, and three fungi). Additionally, the crystal structures of two berberine variants are described. Several berberine variants show enhanced antibacterial activity compared to the unaltered plant-derived molecule. We also report promising preliminary tumor cytotoxicity effects for a number of the berberine derivatives.
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spelling pubmed-105482532023-10-05 Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials Villegas, Jessica Ball, Bryce C Shouse, Katelyn M VanArragon, Caleb W Wasserman, Ashley N Bhakta, Hannah E Oliver, Allen G Orozco-Nunnelly, Danielle A Pruet, Jeffrey M Beilstein J Org Chem Full Research Paper Due to the lack of new antimicrobial drug discovery in recent years and an ever-growing prevalence of multidrug-resistant “superbugs”, there is a pressing need to explore alternative ways to combat pathogenic bacterial and fungal infections. Building upon our previous work in the field of medicinal phytochemistry, the present study is focused on designing, synthesizing, and testing the altered bioactivity of new variants of two original bioactive molecules found in the Argemone mexicana plant. Herein, we report upon 14 variants of berberine and four variants of chelerythrine that have been screened against a pool of 12 microorganisms (five Gram-positive and four Gram-negative bacteria, and three fungi). Additionally, the crystal structures of two berberine variants are described. Several berberine variants show enhanced antibacterial activity compared to the unaltered plant-derived molecule. We also report promising preliminary tumor cytotoxicity effects for a number of the berberine derivatives. Beilstein-Institut 2023-09-29 /pmc/articles/PMC10548253/ /pubmed/37799174 http://dx.doi.org/10.3762/bjoc.19.108 Text en Copyright © 2023, Villegas et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Villegas, Jessica
Ball, Bryce C
Shouse, Katelyn M
VanArragon, Caleb W
Wasserman, Ashley N
Bhakta, Hannah E
Oliver, Allen G
Orozco-Nunnelly, Danielle A
Pruet, Jeffrey M
Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
title Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
title_full Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
title_fullStr Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
title_full_unstemmed Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
title_short Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
title_sort synthesis and biological evaluation of argemone mexicana-inspired antimicrobials
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10548253/
https://www.ncbi.nlm.nih.gov/pubmed/37799174
http://dx.doi.org/10.3762/bjoc.19.108
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