新氨基糖苷类化合物的化学合成策略及其生物活性的综合评述。
Comprehensive review of chemical strategies for the preparation of new aminoglycosides and their biological activities.
机构信息
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536-0596, USA.
出版信息
Chem Soc Rev. 2018 Feb 19;47(4):1189-1249. doi: 10.1039/c7cs00407a.
Abstract
A systematic analysis of all synthetic and chemoenzymatic methodologies for the preparation of aminoglycosides for a variety of applications (therapeutic and agricultural) reported in the scientific literature up to 2017 is presented. This comprehensive analysis of derivatization/generation of novel aminoglycosides and their conjugates is divided based on the types of modifications used to make the new derivatives. Both the chemical strategies utilized and the biological results observed are covered. Structure-activity relationships based on different synthetic modifications along with their implications for activity and ability to avoid resistance against different microorganisms are also presented.
摘要
本文对截至 2017 年在科学文献中报道的各种应用（治疗和农业）的氨基糖苷类药物的合成和化学酶法制备方法进行了系统分析。根据用于制备新衍生物的修饰类型，对新型氨基糖苷类药物及其缀合物的衍生/生成进行了全面分析。涵盖了所使用的化学策略和观察到的生物学结果。还基于不同的合成修饰提出了基于结构-活性关系及其对活性和避免对不同微生物产生抗性的能力的影响。
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本文引用的文献
1
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Chem Sci. 2015 Oct 1;6(10):5837-5846. doi: 10.1039/c5sc01969a. Epub 2015 Jul 9.
2
Combating Enhanced Intracellular Survival (Eis)-Mediated Kanamycin Resistance of Mycobacterium tuberculosis by Novel Pyrrolo[1,5-a]pyrazine-Based Eis Inhibitors.新型基于吡咯并[1,5-a]吡嗪的Eis抑制剂对抗结核分枝杆菌增强的细胞内存活（Eis）介导的卡那霉素耐药性
ACS Infect Dis. 2017 Apr 14;3(4):302-309. doi: 10.1021/acsinfecdis.6b00193. Epub 2017 Feb 17.
3
Antimicrobial Activity, AME Resistance, and A-Site Binding Studies of Anthraquinone-Neomycin Conjugates.蒽醌-新霉素缀合物的抗菌活性、AME耐药性及A位点结合研究
ACS Infect Dis. 2017 Mar 10;3(3):206-215. doi: 10.1021/acsinfecdis.6b00176. Epub 2017 Feb 17.
4
Discovery and Optimization of Two Eis Inhibitor Families as Kanamycin Adjuvants against Drug-Resistant .发现并优化两个作为卡那霉素佐剂对抗耐药性的Eis抑制剂家族。
ACS Med Chem Lett. 2016 Sep 15;7(12):1219-1221. doi: 10.1021/acsmedchemlett.6b00261. eCollection 2016 Dec 8.
5
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J Med Chem. 2016 Dec 8;59(23):10619-10628. doi: 10.1021/acs.jmedchem.6b01161. Epub 2016 Nov 22.
6
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J Org Chem. 2016 Nov 18;81(22):10651-10663. doi: 10.1021/acs.joc.6b01189. Epub 2016 Oct 18.
7
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Biochim Biophys Acta Gen Subj. 2017 Jan;1861(1 Pt A):3464-3473. doi: 10.1016/j.bbagen.2016.09.012. Epub 2016 Sep 14.
8
Synthesis and Antiribosomal Activities of 4'-O-, 6'-O-, 4″-O-, 4',6'-O- and 4″,6″-O-Derivatives in the Kanamycin Series Indicate Differing Target Selectivity Patterns between the 4,5- and 4,6-Series of Disubstituted 2-Deoxystreptamine Aminoglycoside Antibiotics.卡那霉素系列中4'-O-、6'-O-、4″-O-、4',6'-O-和4″,6″-O-衍生物的合成及抗核糖体活性表明，4,5-和4,6-系列二取代2-脱氧链霉胺氨基糖苷类抗生素之间存在不同的靶点选择性模式。
ACS Infect Dis. 2015 Oct 9;1(10):479-86. doi: 10.1021/acsinfecdis.5b00069. Epub 2015 Aug 6.
9
Comparative Study of Eis-like Enzymes from Pathogenic and Nonpathogenic Bacteria.致病细菌与非致病细菌中类Eis酶的比较研究
ACS Infect Dis. 2015 Jun 12;1(6):272-83. doi: 10.1021/acsinfecdis.5b00036. Epub 2015 May 4.
10
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