Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

HPLC/DAD-based chemical investigation of a coral-associated gliding bacterium of the genus Tenacibaculum yielded three desferrioxamine-class siderophores, designated tenacibactins K (1), L (2), and M (3). Their chemical structures, comprising repeated cadaverine–succinic acid motifs terminated by a...

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Autores principales: Igarashi, Yasuhiro, Ge, Yiwei, Zhou, Tao, Sharma, Amit Raj, Harunari, Enjuro, Oku, Naoya, Trianto, Agus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767563/
https://www.ncbi.nlm.nih.gov/pubmed/35096180
http://dx.doi.org/10.3762/bjoc.18.12
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author Igarashi, Yasuhiro
Ge, Yiwei
Zhou, Tao
Sharma, Amit Raj
Harunari, Enjuro
Oku, Naoya
Trianto, Agus
author_facet Igarashi, Yasuhiro
Ge, Yiwei
Zhou, Tao
Sharma, Amit Raj
Harunari, Enjuro
Oku, Naoya
Trianto, Agus
author_sort Igarashi, Yasuhiro
collection PubMed
description HPLC/DAD-based chemical investigation of a coral-associated gliding bacterium of the genus Tenacibaculum yielded three desferrioxamine-class siderophores, designated tenacibactins K (1), L (2), and M (3). Their chemical structures, comprising repeated cadaverine–succinic acid motifs terminated by a hydroxamic acid functionality, were elucidated by NMR and negative MS/MS experiments. Compounds 1–3 were inactive against bacteria and a yeast but displayed cytotoxicity against 3Y1 rat embryonic fibroblasts and P388 murine leukemia cells at GI(50) in submicromolar to micromolar ranges. Their iron-chelating activity was comparable to deferoxamine mesylate.
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spelling pubmed-87675632022-01-27 Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum Igarashi, Yasuhiro Ge, Yiwei Zhou, Tao Sharma, Amit Raj Harunari, Enjuro Oku, Naoya Trianto, Agus Beilstein J Org Chem Full Research Paper HPLC/DAD-based chemical investigation of a coral-associated gliding bacterium of the genus Tenacibaculum yielded three desferrioxamine-class siderophores, designated tenacibactins K (1), L (2), and M (3). Their chemical structures, comprising repeated cadaverine–succinic acid motifs terminated by a hydroxamic acid functionality, were elucidated by NMR and negative MS/MS experiments. Compounds 1–3 were inactive against bacteria and a yeast but displayed cytotoxicity against 3Y1 rat embryonic fibroblasts and P388 murine leukemia cells at GI(50) in submicromolar to micromolar ranges. Their iron-chelating activity was comparable to deferoxamine mesylate. Beilstein-Institut 2022-01-13 /pmc/articles/PMC8767563/ /pubmed/35096180 http://dx.doi.org/10.3762/bjoc.18.12 Text en Copyright © 2022, Igarashi et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Igarashi, Yasuhiro
Ge, Yiwei
Zhou, Tao
Sharma, Amit Raj
Harunari, Enjuro
Oku, Naoya
Trianto, Agus
Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum
title Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum
title_full Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum
title_fullStr Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum
title_full_unstemmed Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum
title_short Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum
title_sort tenacibactins k–m, cytotoxic siderophores from a coral-associated gliding bacterium of the genus tenacibaculum
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767563/
https://www.ncbi.nlm.nih.gov/pubmed/35096180
http://dx.doi.org/10.3762/bjoc.18.12
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