Issue 7, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis and biological activity of analogues of vanchrobactin, a siderophore from Vibrio anguillarum serotype O2

Raquel G. Soengas,a   Marta Larrosa,a   Miguel Balado,b   Jaime Rodríguez,*a   Manuel L. Lemosb  and  Carlos Jiménez*a  

* Corresponding authors

a Departamento de Química Fundamental, Facultade de Ciencias, Universidade da Coruña, Campus da Zapateira, A Coruña, Spain
E-mail: carlosjg@udc.es, jaimer@ udc.es
Fax: +34 9811 67065
Tel: +34 9811 67065

b Departamento de Microbiologia y Parasitologia, Instituto de Acuicultura, Universidade de Santiago de Compostela, Santiago de Compostela, Spain
E-mail: mlemos@usc.es
Fax: +34 9815 47165
Tel: +34 9815 63100

Abstract

Several analogues of vanchrobactin, a catechol siderophore isolated from the bacterial fish pathogen Vibrio anguillarum serotype O2 strain RV22, have been synthesized. The biological evaluation of these novel compounds showed that most of them are active as siderophores, as determined by growth promotion assays using the producer strain, as well as V. anguillarum serotype O1, Salmonella enterica, and Erwinia chrysanthemi. These compounds also gave a positive chrome azurol-S (CAS) test. On the basis of these results, we were able to deduce some structure–activity relationships. Furthermore, we found an analogue with siderophore activity that has appropriate functionality (an amino group) for use as an antibiotic vector to be employed in a “Trojan horse strategy”.

Graphical abstract: Synthesis and biological activity of analogues of vanchrobactin, a siderophore from Vibrio anguillarum serotype O2

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Article information

DOI
https://doi.org/10.1039/B719713F
Article type
Paper
Submitted
21 Dec 2007
Accepted
11 Feb 2008
First published
29 Feb 2008

Org. Biomol. Chem., 2008,6, 1278-1287

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Synthesis and biological activity of analogues of vanchrobactin, a siderophore from Vibrio anguillarum serotype O2

R. G. Soengas, M. Larrosa, M. Balado, J. Rodríguez, M. L. Lemos and C. Jiménez, Org. Biomol. Chem., 2008, 6, 1278 DOI: 10.1039/B719713F

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