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Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy

Facial amphiphilicity is an extraordinary chemical structure feature of a variety of antimicrobial peptides and polymers. Vast efforts have been dedicated to small molecular, macromolecular and dendrimer-like systems to mimic this highly preferred structure or conformation, including local facial am...

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Autores principales: Buzoglu Kurnaz, Leman, Luo, Yuanyuan, Yang, Xiaoming, Alabresm, Amjed, Leighton, Ryan, Kumar, Rani, Hwang, JiHyeon, Decho, Alan W., Nagarkatti, Prakash, Nagarkatti, Mitzi, Tang, Chuanbing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: KeAi Publishing 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9253162/
https://www.ncbi.nlm.nih.gov/pubmed/35846842
http://dx.doi.org/10.1016/j.bioactmat.2022.06.009
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author Buzoglu Kurnaz, Leman
Luo, Yuanyuan
Yang, Xiaoming
Alabresm, Amjed
Leighton, Ryan
Kumar, Rani
Hwang, JiHyeon
Decho, Alan W.
Nagarkatti, Prakash
Nagarkatti, Mitzi
Tang, Chuanbing
author_facet Buzoglu Kurnaz, Leman
Luo, Yuanyuan
Yang, Xiaoming
Alabresm, Amjed
Leighton, Ryan
Kumar, Rani
Hwang, JiHyeon
Decho, Alan W.
Nagarkatti, Prakash
Nagarkatti, Mitzi
Tang, Chuanbing
author_sort Buzoglu Kurnaz, Leman
collection PubMed
description Facial amphiphilicity is an extraordinary chemical structure feature of a variety of antimicrobial peptides and polymers. Vast efforts have been dedicated to small molecular, macromolecular and dendrimer-like systems to mimic this highly preferred structure or conformation, including local facial amphiphilicity and global amphiphilicity. This work conceptualizes Facial Amphiphilicity Index (FAI) as a numerical value to quantitatively characterize the measure of chemical compositions and structural features in dictating antimicrobial efficacy. FAI is a ratio of numbers of charges to rings, representing both compositions of hydrophilicity and hydrophobicity. Cationic derivatives of multicyclic compounds were evaluated as model systems for testing antimicrobial selectivity against Gram-negative and Gram-positive bacteria. Both monocyclic and bicyclic compounds are non-antimicrobial regardless of FAIs. Antimicrobial efficacy was observed with systems having larger cross-sectional areas including tricyclic abietic acid and tetracyclic bile acid. While low and high FAIs respectively lead to higher and lower antimicrobial efficacy, in consideration of cytotoxicity, the sweet spot is typically suited with intermediate FAIs for each specific system. This can be well explained by the synergistic hydrophobic-hydrophobic and electrostatic interactions with bacterial cell membranes and the difference between bacterial and mammalian cell membranes. The adoption of FAI would pave a new avenue toward the design of next-generation antimicrobial macromolecules and peptides.
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spelling pubmed-92531622022-07-15 Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy Buzoglu Kurnaz, Leman Luo, Yuanyuan Yang, Xiaoming Alabresm, Amjed Leighton, Ryan Kumar, Rani Hwang, JiHyeon Decho, Alan W. Nagarkatti, Prakash Nagarkatti, Mitzi Tang, Chuanbing Bioact Mater Article Facial amphiphilicity is an extraordinary chemical structure feature of a variety of antimicrobial peptides and polymers. Vast efforts have been dedicated to small molecular, macromolecular and dendrimer-like systems to mimic this highly preferred structure or conformation, including local facial amphiphilicity and global amphiphilicity. This work conceptualizes Facial Amphiphilicity Index (FAI) as a numerical value to quantitatively characterize the measure of chemical compositions and structural features in dictating antimicrobial efficacy. FAI is a ratio of numbers of charges to rings, representing both compositions of hydrophilicity and hydrophobicity. Cationic derivatives of multicyclic compounds were evaluated as model systems for testing antimicrobial selectivity against Gram-negative and Gram-positive bacteria. Both monocyclic and bicyclic compounds are non-antimicrobial regardless of FAIs. Antimicrobial efficacy was observed with systems having larger cross-sectional areas including tricyclic abietic acid and tetracyclic bile acid. While low and high FAIs respectively lead to higher and lower antimicrobial efficacy, in consideration of cytotoxicity, the sweet spot is typically suited with intermediate FAIs for each specific system. This can be well explained by the synergistic hydrophobic-hydrophobic and electrostatic interactions with bacterial cell membranes and the difference between bacterial and mammalian cell membranes. The adoption of FAI would pave a new avenue toward the design of next-generation antimicrobial macromolecules and peptides. KeAi Publishing 2022-06-27 /pmc/articles/PMC9253162/ /pubmed/35846842 http://dx.doi.org/10.1016/j.bioactmat.2022.06.009 Text en © 2022 The Authors https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Buzoglu Kurnaz, Leman
Luo, Yuanyuan
Yang, Xiaoming
Alabresm, Amjed
Leighton, Ryan
Kumar, Rani
Hwang, JiHyeon
Decho, Alan W.
Nagarkatti, Prakash
Nagarkatti, Mitzi
Tang, Chuanbing
Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy
title Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy
title_full Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy
title_fullStr Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy
title_full_unstemmed Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy
title_short Facial amphiphilicity index correlating chemical structures with antimicrobial efficacy
title_sort facial amphiphilicity index correlating chemical structures with antimicrobial efficacy
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9253162/
https://www.ncbi.nlm.nih.gov/pubmed/35846842
http://dx.doi.org/10.1016/j.bioactmat.2022.06.009
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