铁载体-抗生素偶联物: “特洛伊木马”策略在抗革兰氏阴性菌感染中的应用

doi:10.6023/A24070222

化学学报 ›› 2024, Vol. 82 ›› Issue (10): 1086-1108.DOI: 10.6023/A24070222 上一篇

综述

铁载体-抗生素偶联物: “特洛伊木马”策略在抗革兰氏阴性菌感染中的应用

刘畅, 王文贵, 王守锋^*()

济南大学化学化工学院山东省氟化学化工材料重点实验室济南 250022

投稿日期:2024-07-19 发布日期:2024-08-26

作者简介:

刘畅, 男, 济南大学化学化工学院博士研究生, 执业药师. 主要从事活性机制为导向的铁载体-抗生素偶联物的设计、合成及其抗革兰氏阴性菌的应用, 承担山东省中医药科技青年项目, 参与山东省中医药科技面上项目.

王文贵, 男, 济南大学化学化工学院讲师, 硕士生导师, 毕业于中国科学院上海有机化学研究所. 承担山东省自然基金面上项目、山东省重点研发项目以及企业委托研发等项目. 主要从事有机氟化学研究, 包括单电子转移、金属催化、可见光催化的含氟化合物的合成、氟利昂的转化及天然产物的修饰等.

王守锋, 男, 济南大学化学化工学院教授, 济南大学化学化工学院化学系系主任, 博士生导师, 毕业于中国科学院上海有机化学研究所, 英国曼彻斯特大学访问学者. 承担国家自然基金面上项目、国家自然基金青年基金、“973”项目子课题、山东省自然基金面上项目、山东省重点研发项目以及企业委托研发等项目. 主要研究天然产物修饰: 抗生素的半合成, 药物化学生物学: 抗生素的传输, 以及含氟精细化学品的合成. 在含氟化合物的合成、复杂天然产物的生物合成及其类似物的突变生物合成研究中取得一系列成果.

基金资助:
受国家自然科学基金(31972850); 微生物代谢国家重点实验室开放课题(MMLKF21-09)

Siderophore-Antibiotic Conjugates: Applications of the ‘Trojan horse’ Strategy in Anti-Gram-Negative Bacteria Infection

Chang Liu, Wengui Wang, Shoufeng Wang()

Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, College of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022

Received:2024-07-19 Published:2024-08-26
Contact: *E-mail: chm_wangsf@ujn.edu.cn
Supported by:
National Natural Science Foundation of China(31972850); Open Funding Project of State Key Laboratory of Microbial Metabolism(MMLKF21-09)

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摘要/Abstract

“特洛伊木马”策略的问世为细菌耐药性提供了一种有前景的解决方案. 细菌自身产生的铁载体对Fe³⁺具有很高的亲和力, 将抗生素与铁载体结合起来得到铁载体-抗生素偶联物, 利用细菌铁转运系统, 抗生素可被直接输送到细菌体内发挥药效, 这一策略在临床试验中也得到了证明. 铁载体-抗生素偶联物对具有复杂细胞壁结构和细菌外膜的革兰氏阴性病原体具有很强的抗菌活性, 偶联物可以借助细菌铁转运系统, 促进与其连接的抗生素跨膜转运, 避开与革兰氏阴性菌相关的通透性障碍和抗生素失活过程, 克服细菌耐药性. 更有趣的是, 该策略利用治疗由革兰氏阳性菌引起的感染的抗生素, 对部分革兰氏阴性菌感染同样有效. 本篇综述讨论了铁载体-抗生素偶联物治疗革兰氏阴性菌的最新进展, 还提出了“特洛伊木马”策略的未来可能的发展方向.

关键词: 铁载体-抗生素偶联物, 革兰氏阴性菌, 特洛伊木马策略, 细菌耐药

The emergence of the "Trojan horse" strategy offers a hopeful remedy for bacterial resistance. Bacterial-derived siderophores exhibit a strong attraction to ferric ion. To create siderophore-antibiotic conjugates, antibiotics are mixed with siderophores. Antibiotics can be directly introduced into bacteria through the bacterial iron transport mechanism to exert their impact and this strategy has demonstrated efficacy in clinical trials. Conjugates of siderophores and antibiotics exhibit potent antibacterial properties against Gram-negative pathogens, which are characterized by intricate cell wall configurations and bacterial external membranes. These conjugates facilitate the movement of antibiotics across membranes linked to them via the bacterial iron transport system, circumventing the permeability hurdles and antibiotic deactivation mechanisms typical of Gram-negative bacteria, and overcoming bacterial resistance. Intriguingly, this strategy also proves successful in combating certain Gram-negative infections using antibiotics targeting infections induced by Gram-positive bacteria. The review delves into recent advancements in treating Gram-negative bacteria using siderophore-antibiotic conjugates and proposes potential future directions for the "Trojan horse" strategy.

Key words: siderophore-antibiotic conjugates, gram-negative bacteria, trojan horse strategy, antimicrobial resistance

引用此文

刘畅, 王文贵, 王守锋. 铁载体-抗生素偶联物: “特洛伊木马”策略在抗革兰氏阴性菌感染中的应用[J]. 化学学报, 2024, 82(10): 1086-1108.

Chang Liu, Wengui Wang, Shoufeng Wang. Siderophore-Antibiotic Conjugates: Applications of the ‘Trojan horse’ Strategy in Anti-Gram-Negative Bacteria Infection[J]. Acta Chimica Sinica, 2024, 82(10): 1086-1108.

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图/表 25

图1. 铁载体结构功能单元

Figure 1. Siderophore structural and functional units

图2. 铁载体-Fe3+转运机制

Figure 2. Transportational mechanism of siderophore-Fe3+

图3. “特洛伊木马”策略

Figure 3. The strategy of “Trojan Horse”

图4. 天然铁载体阿波霉素和沙利霉素

Figure 4. Natural sideromycins albomycin and salmycin

图5. 首个合成铁载体-抗生素偶联物

Figure 5. First synthetic siderophore-antibiotic conjugate

图6. 先前报道的铁载体-抗生素偶联物的连接基团

Figure 6. Previous reported linkers of siderophore-antibiotic conjugates

图7. 头孢地尔及其类似物结构

Figure 7. Structure of cefiderocol and its analog

图8. pre-acinetobactin, acinetobactin和baumannoferrins (A/B)的结构

Figure 8. Structure of pre-acinetobactin, acinetobactin and baumannoferrins (A/B)

图9. Fimsbactins (A~F)的结构

Figure 9. Structure of fimsbactins (A~F)

图10. 抗鲍曼不动杆菌的β-内酰胺类SACs结构

Figure 10. Structures of the β-lactam SACs against A. baumannii

图11. anguibactin的结构和pre-acinetobactin的非酶异构化

Figure 11. Structures of the anguibactin and pre-acinetobactin non-enzymatic isomerization

图12. 抗鲍曼不动杆菌的多肽类SACs结构

Figure 12. Structures of the polypeptide SACs against A. baumannii

图13. Ent, MECAM和DOTAM的结构

Figure 13. Structures of enterobactin, MECAM and DOTAM

图14. Fe3+-肠杆菌素和肠杆菌素-cargo偶联物的结构

Figure 14. Structures of Fe3+-enterobactin and enterobactin-cargo conjugates

图15. 抗大肠杆菌的SACs结构

Figure 15. Structures of SACs against E. coli

图16. 含有可水解连接基团的肠杆菌素-抗生素偶联物

Figure 16. Ent-antibiotic conjugates with hydrolysable linker

图17. 肠杆菌素-环丙沙星被IroD水解

Figure 17. Hydrolysis of Ent-cipro by IroD

图18. 抗大肠杆菌的合成SACs结构

Figure 18. Structures of synthetic SACs against E. coli

图19. 铜绿假单胞菌天然铁载体

Figure 19. Natural siderophores of P. aeruginosa

图20. PCH-抗生素偶联物的结构

Figure 20. Structures of PCH-antibiotic conjugates

图21. PVD-抗生素偶联物的结构

Figure 21. Structures of PVD-antibiotic conjugates

图22. 抗铜绿假单胞菌的合成SACs结构

Figure 22. Structures of synthetic SACs against P. aeruginosa

图23. 抗铜绿假单胞菌的MECAM和DOTAM-抗生素偶联物

Figure 23. MECAM and DOTAM-based-antibiotic conjugates in P. aeruginosa

图24. GT-1和GT-055

Figure 24. GT-1 and GT-055

图25. 铁载体-PNA偶联物结构

Figure 25. Schematic representation of the siderophore-PNA conjugate structure

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