Header

UZH-Logo

Maintenance Infos

Syntheses and biological investigations of kirkamide and oseltamivir hybrid derivatives


Sieber, Simon; Hsiao, Chien-Chi; Emmanouilidou, Despina; Debowski, Aleksandra W; Stubbs, Keith A; Gademann, Karl (2020). Syntheses and biological investigations of kirkamide and oseltamivir hybrid derivatives. Tetrahedron, 76(51):131386.

Abstract

The C7N-aminocyclitol kirkamide was recently isolated from the plant obligate symbiont Candidatus Burkholderia kirkii and was hypothesized to be beneficial to the plant host due to its cytotoxic activity against insects and arthropods. To study its mechanism of action and inspired by its structural similarity with N-acetylglucosamine (GlcNAc) and oseltamivir, kirkamide-oseltamivir hybrid derivatives were synthesized and investigated for their biological activity. Interestingly, kirkamide analogues were reasonably potent against a known bacterial neuraminidase.

Abstract

The C7N-aminocyclitol kirkamide was recently isolated from the plant obligate symbiont Candidatus Burkholderia kirkii and was hypothesized to be beneficial to the plant host due to its cytotoxic activity against insects and arthropods. To study its mechanism of action and inspired by its structural similarity with N-acetylglucosamine (GlcNAc) and oseltamivir, kirkamide-oseltamivir hybrid derivatives were synthesized and investigated for their biological activity. Interestingly, kirkamide analogues were reasonably potent against a known bacterial neuraminidase.

Statistics

Citations

Altmetrics

Downloads

3 downloads since deposited on 20 Jan 2021
3 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
Scopus Subject Areas:Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry, Biochemistry, Drug Discovery
Language:English
Date:1 December 2020
Deposited On:20 Jan 2021 06:10
Last Modified:21 Jan 2021 21:04
Publisher:Elsevier
ISSN:0040-4020
OA Status:Hybrid
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1016/j.tet.2020.131386
Project Information:
  • : FunderSNSF
  • : Grant IDCRSII5_186410
  • : Project TitleA New Class of Signal Molecules in Bacteria: Data-Driven Discovery, Mechanism, and Biological Function (Signalinâ��Bac)
  • : FunderSNSF
  • : Grant ID200021_182043
  • : Project TitleMechanism-Based Design, Synthesis, Biological Evaluation, and Delivery of Next-Generation Antibiotics
  • : FunderSNSF
  • : Grant IDCRSII3_154430
  • : Project TitleInvestigations on the obligate leave nodule symbiosis

Download

Hybrid Open Access

Download PDF  'Syntheses and biological investigations of kirkamide and oseltamivir hybrid derivatives'.
Preview
Content: Published Version
Filetype: PDF
Size: 473kB
View at publisher
Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)