基于碘康唑发现具有广谱抗真菌活性的强效三唑衍生物

IF 6 2区 医学 Q1 CHEMISTRY, MEDICINAL European Journal of Medicinal Chemistry Pub Date : 2024-10-09 DOI:10.1016/j.ejmech.2024.116949
{"title":"基于碘康唑发现具有广谱抗真菌活性的强效三唑衍生物","authors":"","doi":"10.1016/j.ejmech.2024.116949","DOIUrl":null,"url":null,"abstract":"<div><div>The widespread use of broad-spectrum antibiotics, the growing number of immunocompromised individuals, and the emergence of drug-resistant strains have resulted in the increasing incidence and mortality of invasive fungal infections. Azole drugs are the primary treatment for invasive fungal infections, and Iodiconazole is a potent azole drug with strong antifungal activity, but its stability is poor. In order to improve stability, a series of triazole compounds containing ethynyl group were designed and synthesized. Most of the compounds showed strong inhibitory activity against pathogenic fungi, among which compound <strong>20l</strong> showed excellent inhibitory activity against pathogenic fungi and drug-resistant fungi. Importantly, and the stability of <strong>20l</strong> (T<sub>1/2</sub> = 30.2 min) was obviously improved compared with Iodiconazole (T<sub>1/2</sub> = 4.39 min<strong>)</strong>. In addition, the preferred compound <strong>20l</strong> can prevent fungal phase transition and the formation of fungal biofilm, and show satisfactory fungicidal activity. In addition, the compound <strong>20l</strong> was almost non-toxic to mammalian HUVEC cell and 293T cell. <em>In vivo</em> pharmacokinetic studies showed that <strong>20l</strong> had acceptable pharmacokinetic properties. These results strongly demonstrate that compound <strong>20l</strong> was worth further investigation as a potential antifungal inhibitor.</div></div>","PeriodicalId":314,"journal":{"name":"European Journal of Medicinal Chemistry","volume":null,"pages":null},"PeriodicalIF":6.0000,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Discovery of highly potent triazole derivatives with broad-spectrum antifungal activity based on Iodiconazole\",\"authors\":\"\",\"doi\":\"10.1016/j.ejmech.2024.116949\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The widespread use of broad-spectrum antibiotics, the growing number of immunocompromised individuals, and the emergence of drug-resistant strains have resulted in the increasing incidence and mortality of invasive fungal infections. Azole drugs are the primary treatment for invasive fungal infections, and Iodiconazole is a potent azole drug with strong antifungal activity, but its stability is poor. In order to improve stability, a series of triazole compounds containing ethynyl group were designed and synthesized. Most of the compounds showed strong inhibitory activity against pathogenic fungi, among which compound <strong>20l</strong> showed excellent inhibitory activity against pathogenic fungi and drug-resistant fungi. Importantly, and the stability of <strong>20l</strong> (T<sub>1/2</sub> = 30.2 min) was obviously improved compared with Iodiconazole (T<sub>1/2</sub> = 4.39 min<strong>)</strong>. In addition, the preferred compound <strong>20l</strong> can prevent fungal phase transition and the formation of fungal biofilm, and show satisfactory fungicidal activity. In addition, the compound <strong>20l</strong> was almost non-toxic to mammalian HUVEC cell and 293T cell. <em>In vivo</em> pharmacokinetic studies showed that <strong>20l</strong> had acceptable pharmacokinetic properties. These results strongly demonstrate that compound <strong>20l</strong> was worth further investigation as a potential antifungal inhibitor.</div></div>\",\"PeriodicalId\":314,\"journal\":{\"name\":\"European Journal of Medicinal Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":6.0000,\"publicationDate\":\"2024-10-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"European Journal of Medicinal Chemistry\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0223523424008304\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Medicinal Chemistry","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0223523424008304","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

摘要

广谱抗生素的广泛使用、免疫力低下人群的不断增加以及耐药菌株的出现,导致侵袭性真菌感染的发病率和死亡率不断上升。唑类药物是治疗侵袭性真菌感染的主要药物,碘康唑是一种强效唑类药物,具有很强的抗真菌活性,但其稳定性较差。为了提高稳定性,我们设计并合成了一系列含有乙炔基的三唑化合物。大部分化合物对病原真菌有很强的抑制活性,其中化合物 20l 对病原真菌和耐药真菌有很好的抑制活性。重要的是,与碘环唑(T1/2 = 4.39 分钟)相比,20l 的稳定性(T1/2 = 30.2 分钟)明显提高。此外,优选化合物 20l 还能阻止真菌相变和真菌生物膜的形成,并显示出令人满意的杀真菌活性。此外,化合物 20l 对哺乳动物 HUVEC 细胞和 293T 细胞几乎无毒。体内药代动力学研究表明,20l 具有可接受的药代动力学特性。这些结果有力地证明了化合物 20l 作为一种潜在的抗真菌抑制剂值得进一步研究。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Discovery of highly potent triazole derivatives with broad-spectrum antifungal activity based on Iodiconazole
The widespread use of broad-spectrum antibiotics, the growing number of immunocompromised individuals, and the emergence of drug-resistant strains have resulted in the increasing incidence and mortality of invasive fungal infections. Azole drugs are the primary treatment for invasive fungal infections, and Iodiconazole is a potent azole drug with strong antifungal activity, but its stability is poor. In order to improve stability, a series of triazole compounds containing ethynyl group were designed and synthesized. Most of the compounds showed strong inhibitory activity against pathogenic fungi, among which compound 20l showed excellent inhibitory activity against pathogenic fungi and drug-resistant fungi. Importantly, and the stability of 20l (T1/2 = 30.2 min) was obviously improved compared with Iodiconazole (T1/2 = 4.39 min). In addition, the preferred compound 20l can prevent fungal phase transition and the formation of fungal biofilm, and show satisfactory fungicidal activity. In addition, the compound 20l was almost non-toxic to mammalian HUVEC cell and 293T cell. In vivo pharmacokinetic studies showed that 20l had acceptable pharmacokinetic properties. These results strongly demonstrate that compound 20l was worth further investigation as a potential antifungal inhibitor.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
11.70
自引率
9.00%
发文量
863
审稿时长
29 days
期刊介绍: The European Journal of Medicinal Chemistry is a global journal that publishes studies on all aspects of medicinal chemistry. It provides a medium for publication of original papers and also welcomes critical review papers. A typical paper would report on the organic synthesis, characterization and pharmacological evaluation of compounds. Other topics of interest are drug design, QSAR, molecular modeling, drug-receptor interactions, molecular aspects of drug metabolism, prodrug synthesis and drug targeting. The journal expects manuscripts to present the rational for a study, provide insight into the design of compounds or understanding of mechanism, or clarify the targets.
期刊最新文献
Development of selective sigma-1 receptor ligands with antiallodynic activity: a focus on piperidine and piperazine scaffolds Advances in the synthesis and engineering of conotoxins Synthesis and preclinical evaluation of diarylamine derivative as Tau-PET radiotracer for Alzheimer’s Disease Next-generation cancer therapeutics: PROTACs and the role of heterocyclic warheads in targeting resistance Multicomponent Syntheses Enable the Discovery of Novel Quisinostat-Derived Chemotypes as Histone Deacetylase Inhibitors
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1