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

doi:10.6023/A24070222

Acta Chimica Sinica ›› 2024, Vol. 82 ›› Issue (10): 1086-1108.DOI: 10.6023/A24070222 Previous Articles

Review

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)

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

Cite this article

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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Fig. & Tab. 25

Figure 1. Siderophore structural and functional units

Figure 2. Transportational mechanism of siderophore-Fe3+

Figure 3. The strategy of “Trojan Horse”

Figure 4. Natural sideromycins albomycin and salmycin

Figure 5. First synthetic siderophore-antibiotic conjugate

Figure 6. Previous reported linkers of siderophore-antibiotic conjugates

Figure 7. Structure of cefiderocol and its analog

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

Figure 9. Structure of fimsbactins (A~F)

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

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

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

Figure 13. Structures of enterobactin, MECAM and DOTAM

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

Figure 15. Structures of SACs against E. coli

Figure 16. Ent-antibiotic conjugates with hydrolysable linker

Figure 17. Hydrolysis of Ent-cipro by IroD

Figure 18. Structures of synthetic SACs against E. coli

Figure 19. Natural siderophores of P. aeruginosa

Figure 20. Structures of PCH-antibiotic conjugates

Figure 21. Structures of PVD-antibiotic conjugates

Figure 22. Structures of synthetic SACs against P. aeruginosa

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

Figure 24. GT-1 and GT-055

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

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