S-Alkylated sulfonium betulin derivatives: Synthesis, antibacterial activities, and wound healing applications

IF 4.7 2区医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioorganic Chemistry Pub Date : 2025-01-01 Epub Date: 2024-12-11 DOI:10.1016/j.bioorg.2024.108056

Yiding Deng, Ruili Wang, Zhiyuan Ma, Weiwei Zuo, Meifang Zhu

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.

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S-烷基化锍白桦脂衍生物：合成、抗菌活性和伤口愈合应用。

桦木素是一种从桦木科树皮中提取的生物活性三萜，具有抗菌和抗炎的特性，作为一种治疗剂具有很大的潜力。本文合成了阳离子磺化改性白桦素衍生物，以提高其抗菌效果，应用于伤口愈合。单和双s -烷基化磺酸衍生物对金黄色葡萄球菌、耐甲氧西林金黄色葡萄球菌（MRSA）和大肠杆菌等病原体的抗菌活性明显优于白桦林。s -壬基化白桦素磺酸将白桦素对MRSA的最低抑制浓度从24 mM降低到0.015 mM。磺化改性增强了阳离子相互作用，导致细菌膜破坏。该衍生物具有减轻炎症、加速伤口愈合的作用，并具有良好的生物安全性，为抗菌药物的开发提供了一条可行的途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

9.70

自引率

3.90%

发文量

679

审稿时长

31 days

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.