{"title":"S-Alkylated sulfonium betulin derivatives: Synthesis, antibacterial activities, and wound healing applications.","authors":"Yiding Deng, Ruili Wang, Zhiyuan Ma, Weiwei Zuo, Meifang Zhu","doi":"10.1016/j.bioorg.2024.108056","DOIUrl":null,"url":null,"abstract":"<p><p>Betulin, a bioactive triterpenoid derived from Betulaceae bark with antimicrobial and anti-inflammatory properties, holds great potential as a therapeutic agent. In this work, cationic sulfonium-modified betulin derivatives were synthesized to enhance their antibacterial efficacy for wound healing application. Mono- and dual S-alkylated sulfonium derivatives significantly outperformed betulin in antibacterial activity against pathogens such as S. aureus, Methicillin-resistant S. aureus (MRSA), and E. coli. S-nonylated sulfonium betulin reduced the minimum inhibitory concentration of betulin against MRSA from 24 to 0.015 mM. The sulfonium modification enhanced cationic interactions, leading to bacterial membrane disruption. The derivatives expedited the process of wound healing by mitigating inflammation and exhibited satisfactory biosafety, proposing a viable approach to the development of antibacterial agents.</p>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"154 ","pages":"108056"},"PeriodicalIF":4.5000,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1016/j.bioorg.2024.108056","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
Betulin, a bioactive triterpenoid derived from Betulaceae bark with antimicrobial and anti-inflammatory properties, holds great potential as a therapeutic agent. In this work, cationic sulfonium-modified betulin derivatives were synthesized to enhance their antibacterial efficacy for wound healing application. Mono- and dual S-alkylated sulfonium derivatives significantly outperformed betulin in antibacterial activity against pathogens such as S. aureus, Methicillin-resistant S. aureus (MRSA), and E. coli. S-nonylated sulfonium betulin reduced the minimum inhibitory concentration of betulin against MRSA from 24 to 0.015 mM. The sulfonium modification enhanced cationic interactions, leading to bacterial membrane disruption. The derivatives expedited the process of wound healing by mitigating inflammation and exhibited satisfactory biosafety, proposing a viable approach to the development of antibacterial agents.
期刊介绍：
Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry.
For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature.
The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.
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