Synthesis of <scp>l</scp> -β-(6-azulenyl)alanine and the fluorescent actin disruptor (6-azuleno)chalasin H
l-β-(6-Azulenyl)alanine was synthesised for the first time. Supplementation of this compound to <i>Pyricularia grisea</i> Δ<i>pyiA</i> led to the biosynthesis of the unnatural (6-azuleno)chalasin H and its 1'-bromo congener that have unprecedented natural product skeletons and that are both fluorescent and highly cytotoxic, with IC<sub>50</sub> of 0.18 μg mL<sup>-1</sup> <i>vs.</i> L929 cells <i>in vitro</i>. Actin staining showed that both compounds are potent, but partially reversible, actin disruptors.
Authors
- Jennifer Gerke (ORCID: https://orcid.org/0000-0001-7301-2676)
- Markus Kalesse (ORCID: https://orcid.org/0000-0003-4858-3957)
- Maurice Hauser (ORCID: https://orcid.org/0009-0003-0758-8521)
- Russell J. Cox (ORCID: https://orcid.org/0000-0002-1844-0157)
- Theresia E. B. Stradal (ORCID: https://orcid.org/0000-0002-0352-9474)
- K. Gerdes (ORCID: https://orcid.org/0009-0006-1252-0283)
- Katharina Schmidt (ORCID: https://orcid.org/0000-0003-1512-1748)
- Cheng Yi (ORCID: https://orcid.org/0009-0008-4217-585X)
- Leonard Beiderwieden
Institutions
- Leibniz University Hannover (DE)
- Helmholtz Centre for Infection Research (DE)
Publication Details
- Journal
- RSC Advances
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ra04702a
- Citations
- 2
- Primary Topic
- Photochromic and Fluorescence Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.04
Funders
- Deutsche Forschungsgemeinschaft