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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...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
KeAi Publishing
2022
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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. |
format | Online Article Text |
id | pubmed-9253162 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | KeAi Publishing |
record_format | MEDLINE/PubMed |
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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