合成,物理化学表征和三种新型阿米诺酸衍生的 Schiff 基体的生物杀伤性评估,其中包括具有分子内结合的基体
Alexander Carreño1,2, Vania Artigas2, Belén Gómez-Arteaga2
1Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Av. República 275, Santiago 8370146, Chile.
International journal of molecular sciences
|November 13, 2025
概括
希夫基的化增强了它们的抗微生物特性,有的化合物显示出对格拉姆阳性细菌的选择性强度和降低了毒性. 这项研究确定了开发新抗菌剂的有希望的支架.
科学领域:
- 药用化学 医学化学
- 有机合成 有机合成
- 抗菌研究 抗菌研究
背景情况:
- 来自氨基酸的希夫基是由于可调节的电子性质而有前途的抗微生物导体.
- 化被探索为调节氧化还原行为和增强抗菌功能的策略.
研究的目的:
- 调查化对氨基酸衍生希夫基的氧化还原特性和抗菌活性的影响.
- 假设更重的素将有利地调整物理化学和电子描述器以增强抗菌作用.
主要方法:
- 三种基希夫基衍生物 (SB-3/Cl,SB-4/Br,SB-5/I) 的合成.
- 使用FTIR,NMR,UV-Vis,HRMS和X射线衍射进行结构确认.
- 通过循环电压测量和计算研究 (DFT) 进行电化学分析.
- 对各种细菌和真菌进行抗微生物敏感性测试,以及对哺乳动物细胞的细胞毒性评估.
主要成果:
- 化调节了氧化还原行为,在化衍生品中观察到可逆的 imine 减少.
- SB-5 (含) 显示出对格拉姆阳性细菌 (低至中微分子范围的MIC) 的选择性强度.
- 对厌氧生物具有显著的活性,包括*Clostridioides difficile* (MIC 0.1 μM) 和*Blautia coccoides* (MIC 0.01 μM).
- 没有针对格拉姆阴性细菌的活性或对*Botrytis cinerea*显著的杀菌作用.
- 哺乳动物细胞测试显示度依赖的行为,表明潜在的治疗窗口.
结论:
- 化,特别是化,有效调整氧化还原特性,增强选择性格拉姆阳性抗菌活性.
- 作为一个发展新型抗菌剂的支架,SB-5显示出有前途的前景,具有有利的安全性.
- 这项研究突出了通过化对抗微生物药物发现的氧化还原调节的潜力.
相关概念视频
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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
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To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates higher...
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates higher...
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In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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