Header

UZH-Logo

Maintenance Infos

Preparation of fluorescent microcystin derivatives by direct arginine labelling and their biological evaluation


Grundler, Verena; Faltermann, Susanne; Fent, Karl; Gademann, Karl (2015). Preparation of fluorescent microcystin derivatives by direct arginine labelling and their biological evaluation. Chembiochem, 16(11):1657-1662.

Abstract

Microcystin is the most prevalent toxin produced by cyanobacteria and poses a severe threat to livestock, humans and entire ecosystems. We report the preparation of a series of fluorescent microcystin derivatives by direct arginine labelling of the unprotected peptides at the guanidinium side chain. This new method allows a simple late-stage diversification strategy for native peptides devoid of protecting groups under mild conditions. A series of fluorophores were conjugated to microcystin-LR in good to very good yield. The fluorescent probes displayed biological activity comparable to that of unlabelled microcystin, in both phosphatase inhibition assays and toxicity tests on the crustacean Thamnocephalus platyurus. In addition, we demonstrate that the fluorescent probes penetrated Huh7 cells. Whole-animal imaging was performed on T. platyurus: labelled compound was mainly observed in the digestive tract.

Abstract

Microcystin is the most prevalent toxin produced by cyanobacteria and poses a severe threat to livestock, humans and entire ecosystems. We report the preparation of a series of fluorescent microcystin derivatives by direct arginine labelling of the unprotected peptides at the guanidinium side chain. This new method allows a simple late-stage diversification strategy for native peptides devoid of protecting groups under mild conditions. A series of fluorophores were conjugated to microcystin-LR in good to very good yield. The fluorescent probes displayed biological activity comparable to that of unlabelled microcystin, in both phosphatase inhibition assays and toxicity tests on the crustacean Thamnocephalus platyurus. In addition, we demonstrate that the fluorescent probes penetrated Huh7 cells. Whole-animal imaging was performed on T. platyurus: labelled compound was mainly observed in the digestive tract.

Statistics

Citations

Dimensions.ai Metrics
3 citations in Web of Science®
3 citations in Scopus®
3 citations in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

20 downloads since deposited on 22 Aug 2017
11 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:chemical biology, cyanobacteria, fluorescent probes, microbiology, toxicology
Language:English
Date:12 June 2015
Deposited On:22 Aug 2017 16:12
Last Modified:19 Aug 2018 09:55
Publisher:Wiley-VCH Verlag
ISSN:1439-4227
OA Status:Green
Publisher DOI:https://doi.org/10.1002/cbic.201500181
PubMed ID:26010357
Project Information:
  • : FunderSNSF
  • : Grant ID206021_150760
  • : Project TitleStudies in the Molecular Sciences Enabled by High Sensitivity NMR
  • : FunderSNSF
  • : Grant IDPDFMP3_132466
  • : Project TitleCyanobacterial toxins: characterization and toxicity to aquatic organisms

Download

Download PDF  'Preparation of fluorescent microcystin derivatives by direct arginine labelling and their biological evaluation'.
Preview
Content: Accepted Version
Language: English
Filetype: PDF
Size: 2MB
View at publisher