在偶氮还原酶存在下释放异硫氰酸酯的假硫代葡萄糖苷（psGSLs）的合成及评价。

IF 2.6 4区生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

ChemBioChem Pub Date : 2025-05-09 DOI:10.1002/cbic.202500152

Aishi Chakrabarti, Charity S G Ganskow, Mervic D Kagho, Claire C Jimidar, Lorenz Wiese, Neslihan Beyazit, Ulrike Beutling, Magarita Seeger, Silvana Smits, Stella Nyström, Anett Schallmey, Anne Farewell, Mark Brönstrup, Philipp Klahn

{"title":"在偶氮还原酶存在下释放异硫氰酸酯的假硫代葡萄糖苷（psGSLs）的合成及评价。","authors":"Aishi Chakrabarti, Charity S G Ganskow, Mervic D Kagho, Claire C Jimidar, Lorenz Wiese, Neslihan Beyazit, Ulrike Beutling, Magarita Seeger, Silvana Smits, Stella Nyström, Anett Schallmey, Anne Farewell, Mark Brönstrup, Philipp Klahn","doi":"10.1002/cbic.202500152","DOIUrl":null,"url":null,"abstract":"Naturally occurring isothiocyanates (ITCs) display multiple interesting bioactivities, but their medicinal exploitation is very limited as ITCs are non-druglike compounds with problematic pharmacokinetic properties. The concept of pseudoglucosinolates (psGSLs) provides a novel prodrug approach for the release of ITCs which can be adjusted to different triggers such as enzymatic and chemical microenvironments. Here, we report the first adaptation of this concept towards the release of ITCs in the presence of azoreductases within a turn-on fluorescence probe and underline its applicability in covalent protein labelling.","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":" ","pages":"e202500152"},"PeriodicalIF":2.6000,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and evaluation of pseudoglucosinolates (psGSLs) releasing isothiocyanates (ITCs) in the presence of azoreductases.\",\"authors\":\"Aishi Chakrabarti, Charity S G Ganskow, Mervic D Kagho, Claire C Jimidar, Lorenz Wiese, Neslihan Beyazit, Ulrike Beutling, Magarita Seeger, Silvana Smits, Stella Nyström, Anett Schallmey, Anne Farewell, Mark Brönstrup, Philipp Klahn\",\"doi\":\"10.1002/cbic.202500152\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Naturally occurring isothiocyanates (ITCs) display multiple interesting bioactivities, but their medicinal exploitation is very limited as ITCs are non-druglike compounds with problematic pharmacokinetic properties. The concept of pseudoglucosinolates (psGSLs) provides a novel prodrug approach for the release of ITCs which can be adjusted to different triggers such as enzymatic and chemical microenvironments. Here, we report the first adaptation of this concept towards the release of ITCs in the presence of azoreductases within a turn-on fluorescence probe and underline its applicability in covalent protein labelling.\",\"PeriodicalId\":140,\"journal\":{\"name\":\"ChemBioChem\",\"volume\":\" \",\"pages\":\"e202500152\"},\"PeriodicalIF\":2.6000,\"publicationDate\":\"2025-05-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ChemBioChem\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1002/cbic.202500152\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemBioChem","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1002/cbic.202500152","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 0

摘要

天然异硫氰酸酯（ITCs）具有多种有趣的生物活性，但由于ITCs是非药物样化合物，其药代动力学性质存在问题，因此其药用开发非常有限。假硫代葡萄糖苷（psGSLs）的概念为ITCs的释放提供了一种新的药前途径，ITCs可以根据不同的触发因素（如酶和化学微环境）进行调节。在这里，我们报告了首次将这一概念应用于在开启荧光探针中偶氮还原酶存在的情况下ITCs的释放，并强调了其在共价蛋白标记中的适用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Synthesis and evaluation of pseudoglucosinolates (psGSLs) releasing isothiocyanates (ITCs) in the presence of azoreductases.

Naturally occurring isothiocyanates (ITCs) display multiple interesting bioactivities, but their medicinal exploitation is very limited as ITCs are non-druglike compounds with problematic pharmacokinetic properties. The concept of pseudoglucosinolates (psGSLs) provides a novel prodrug approach for the release of ITCs which can be adjusted to different triggers such as enzymatic and chemical microenvironments. Here, we report the first adaptation of this concept towards the release of ITCs in the presence of azoreductases within a turn-on fluorescence probe and underline its applicability in covalent protein labelling.

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

ChemBioChem 生物-生化与分子生物学

CiteScore

6.10

自引率

3.10%

发文量

407

审稿时长

1 months

期刊介绍： ChemBioChem (Impact Factor 2018: 2.641) publishes important breakthroughs across all areas at the interface of chemistry and biology, including the fields of chemical biology, bioorganic chemistry, bioinorganic chemistry, synthetic biology, biocatalysis, bionanotechnology, and biomaterials. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and supported by the Asian Chemical Editorial Society (ACES).