确定达托霉素的构效关系。
Establishing the Structure-Activity Relationship of Daptomycin.
作者信息
Chow Hoi Yee, Po Kathy Hiu Laam, Jin Kang, Qiao Guanlin, Sun Zhenquan, Ma Wenjie, Ye Xiyun, Zhou Ning, Chen Sheng, Li Xuechen
机构信息
Department of Chemistry, State Key Lab of Synthetic Chemistry, The University of Hong Kong, Pok Fu Lam, Hong Kong.
Department of Infectious Diseases and Public Health, Jockey Club College of Veterinary Medicine and Life Sciences, City University of Hong Kong, Kowloon, Hong Kong.
出版信息
ACS Med Chem Lett. 2020 Jun 3;11(7):1442-1449. doi: 10.1021/acsmedchemlett.0c00175. eCollection 2020 Jul 9.
Abstract
Daptomycin is effective in treating infections caused by antibiotic-resistant Gram-positive pathogens, including methicillin-resistant (MRSA), vancomycin-resistant (VRE), and vancomycin-resistant (VRSA). Due to its distinct mechanism of action toward multidrug-resistant bacteria, daptomycin provides an attractive structural motif to generate new daptomycin-based antibiotics to combat the problem of bacterial resistance. In this study, we used the total synthesis method to produce daptomycin analogues with a variety in terms of types and sites of modifications. Five classes of daptomycin analogues were synthesized, and the antimicrobial activities of the analogues were analyzed by several biological assays. From this study, we established a comprehensive structure-activity relationship of daptomycin which will lay the foundation for the further development of daptomycin-based antibiotics.
摘要
达托霉素对治疗由耐抗生素革兰氏阳性病原体引起的感染有效，这些病原体包括耐甲氧西林金黄色葡萄球菌（MRSA）、耐万古霉素肠球菌（VRE）和耐万古霉素金黄色葡萄球菌（VRSA）。由于其对多重耐药菌独特的作用机制，达托霉素提供了一个有吸引力的结构基序，以产生新的基于达托霉素的抗生素来对抗细菌耐药性问题。在本研究中，我们使用全合成方法制备了在修饰类型和位点方面具有多样性的达托霉素类似物。合成了五类达托霉素类似物，并通过多种生物学测定分析了这些类似物的抗菌活性。通过本研究，我们建立了达托霉素全面的构效关系，这将为基于达托霉素的抗生素的进一步开发奠定基础。
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2
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3
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4
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5
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6
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7
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