Cargando…

The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains

This work presents the successful synthesis of a library of novel peptidomimetics via Ugi multicomponent reaction. Most of these peptidomimetics contain differently substituted aminocoumarin; 7-amino-4-methylcoumarin and 7-amino-4-(trifluoromethyl) coumarin. Inspired by the biological properties of...

Descripción completa

Detalles Bibliográficos
Autores principales: Kowalczyk, Paweł, Wilk, Monika, Parul, Parul, Szymczak, Mateusz, Kramkowski, Karol, Raj, Stanisława, Skiba, Grzegorz, Sulejczak, Dorota, Kleczkowska, Patrycja, Ostaszewski, Ryszard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8510199/
https://www.ncbi.nlm.nih.gov/pubmed/34640121
http://dx.doi.org/10.3390/ma14195725
_version_ 1784582518674030592
author Kowalczyk, Paweł
Wilk, Monika
Parul, Parul
Szymczak, Mateusz
Kramkowski, Karol
Raj, Stanisława
Skiba, Grzegorz
Sulejczak, Dorota
Kleczkowska, Patrycja
Ostaszewski, Ryszard
author_facet Kowalczyk, Paweł
Wilk, Monika
Parul, Parul
Szymczak, Mateusz
Kramkowski, Karol
Raj, Stanisława
Skiba, Grzegorz
Sulejczak, Dorota
Kleczkowska, Patrycja
Ostaszewski, Ryszard
author_sort Kowalczyk, Paweł
collection PubMed
description This work presents the successful synthesis of a library of novel peptidomimetics via Ugi multicomponent reaction. Most of these peptidomimetics contain differently substituted aminocoumarin; 7-amino-4-methylcoumarin and 7-amino-4-(trifluoromethyl) coumarin. Inspired by the biological properties of coumarin derivatives and peptidomimetics, we proposed the synthesis of coumarin incorporated peptidomimetics. We studied the potential of synthesized compounds as antimicrobial drugs on model E. coli bacterial strains (k12 and R2–R4). To highlight the importance of coumarin in antimicrobial resistance, we also synthesized the structurally similar peptidomimetics, using benzylamine. Preliminary cellular studies suggest that the compounds with coumarin derivatives have more potential as antimicrobial agents compared to the compounds without coumarin. We also analyzed the effect of aldehyde, free acid group and ester group on the course of their antimicrobial properties.
format Online
Article
Text
id pubmed-8510199
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-85101992021-10-13 The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains Kowalczyk, Paweł Wilk, Monika Parul, Parul Szymczak, Mateusz Kramkowski, Karol Raj, Stanisława Skiba, Grzegorz Sulejczak, Dorota Kleczkowska, Patrycja Ostaszewski, Ryszard Materials (Basel) Article This work presents the successful synthesis of a library of novel peptidomimetics via Ugi multicomponent reaction. Most of these peptidomimetics contain differently substituted aminocoumarin; 7-amino-4-methylcoumarin and 7-amino-4-(trifluoromethyl) coumarin. Inspired by the biological properties of coumarin derivatives and peptidomimetics, we proposed the synthesis of coumarin incorporated peptidomimetics. We studied the potential of synthesized compounds as antimicrobial drugs on model E. coli bacterial strains (k12 and R2–R4). To highlight the importance of coumarin in antimicrobial resistance, we also synthesized the structurally similar peptidomimetics, using benzylamine. Preliminary cellular studies suggest that the compounds with coumarin derivatives have more potential as antimicrobial agents compared to the compounds without coumarin. We also analyzed the effect of aldehyde, free acid group and ester group on the course of their antimicrobial properties. MDPI 2021-09-30 /pmc/articles/PMC8510199/ /pubmed/34640121 http://dx.doi.org/10.3390/ma14195725 Text en © 2021 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
Kowalczyk, Paweł
Wilk, Monika
Parul, Parul
Szymczak, Mateusz
Kramkowski, Karol
Raj, Stanisława
Skiba, Grzegorz
Sulejczak, Dorota
Kleczkowska, Patrycja
Ostaszewski, Ryszard
The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains
title The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains
title_full The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains
title_fullStr The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains
title_full_unstemmed The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains
title_short The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains
title_sort synthesis and evaluation of aminocoumarin peptidomimetics as cytotoxic agents on model bacterial e. coli strains
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8510199/
https://www.ncbi.nlm.nih.gov/pubmed/34640121
http://dx.doi.org/10.3390/ma14195725
work_keys_str_mv AT kowalczykpaweł thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT wilkmonika thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT parulparul thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT szymczakmateusz thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT kramkowskikarol thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT rajstanisława thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT skibagrzegorz thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT sulejczakdorota thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT kleczkowskapatrycja thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT ostaszewskiryszard thesynthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT kowalczykpaweł synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT wilkmonika synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT parulparul synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT szymczakmateusz synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT kramkowskikarol synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT rajstanisława synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT skibagrzegorz synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT sulejczakdorota synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT kleczkowskapatrycja synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains
AT ostaszewskiryszard synthesisandevaluationofaminocoumarinpeptidomimeticsascytotoxicagentsonmodelbacterialecolistrains