Synthesis and electrochemical detection of a thiazolyl-indole natural product isolated from the nosocomial pathogen Pseudomonas aeruginosa

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dc.contributor.author Buzid, Alyah
dc.contributor.author Muimhneacháin, Eoin Ó
dc.contributor.author Reen, F. Jerry
dc.contributor.author Hayes, Phyllis E.
dc.contributor.author Pardo, Leticia M.
dc.contributor.author Shang, Fengjun
dc.contributor.author O'Gara, Fergal
dc.contributor.author Sperry, Jonathan
dc.contributor.author Luong, John H. T.
dc.contributor.author Glennon, Jeremy D.
dc.contributor.author McGlacken, Gerard P.
dc.date.accessioned 2019-11-05T10:39:37Z
dc.date.available 2019-11-05T10:39:37Z
dc.date.issued 2016-09
dc.identifier.citation Buzid, A., Muimhneacháin, E. Ó., Reen, F. J., Hayes, P. E., Pardo, L. M., Shang, F., O’Gara, F., Sperry, J., Luong, J. H. T., Glennon, J. D. and McGlacken, G. P. (2016) 'Synthesis and electrochemical detection of a thiazolyl-indole natural product isolated from the nosocomial pathogen Pseudomonas aeruginosa', Analytical and Bioanalytical Chemistry, 408(23), pp. 6361-6367. DOI: 10.1007/s00216-016-9749-8 en
dc.identifier.volume 408 en
dc.identifier.issued 23 en
dc.identifier.startpage 6361 en
dc.identifier.endpage 6367 en
dc.identifier.issn 1618-2650
dc.identifier.uri http://hdl.handle.net/10468/8952
dc.identifier.doi 10.1007/s00216-016-9749-8 en
dc.description.abstract Pseudomonas aeruginosa is a Gram-negative opportunistic pathogen, capable of surviving in a broad range of natural environments and quickly acquiring resistance. It is associated with hospital-acquired infections, particularly in patients with compromised immunity, and is the primary cause of morbidity and mortality in cystic fibrosis (CF) patients. P. aeruginosa is also of nosocomial importance on dairy farms and veterinary hospitals, where it is a key morbidity factor in bovine mastitis. P. aeruginosa uses a cell-cell communication system consisting of signalling molecules to coordinate bacterial secondary metabolites, biofilm formation, and virulence. Simple and sensitive methods for the detection of biomolecules as indicators of P. aeruginosa infection would be of great clinical importance. Here, we report the synthesis of the P. aeruginosa natural product, barakacin, which was recently isolated from the bovine ruminal strain ZIO. A simple and sensitive electrochemical method was used for barakacin detection using a boron-doped diamond (BDD) and glassy carbon (GC) electrodes, based on cyclic voltammetry (CV) and differential pulse voltammetry (DPV). The influence of electrolyte pH on the peak potential and peak currents was also investigated. At pH 2.0, the peak current was linearly dependent on barakacin concentration (in the range used, 1-10 mu M), with correlation coefficients greater than 0.98 on both electrodes. The detection limit (S/N = 3) on the BDD electrode was 100-fold lower than that obtained on the GC electrode. The optimized method using the BDD electrode was extended to bovine (cow feces) and human (sputum of a CF patient) samples. Spiked barakacin was easily detected in these matrices at a limit of 0.5 and 0.05 mu M, respectively. en
dc.description.sponsorship European Commission (FP7-KBBE-2012-6, CP-TP-312184); Science Foundation Ireland (SSPC-2); Department of Agriculture, Food and the Marine (FIRM/RSF/CoFoRD; FIRM 08/RDC/629; FIRM 1/F009/MabS; FIRM 13/F/516); Irish Research Council for Science, Engineering and Technology (PD/2011/2414; GOIPG/2014/647); Health Research Board/Irish Thoracic Society (MRCG-2014-6);Marine Institute (Beaufort award C2CRA 2007/082); Teagasc (Walsh Fellowship 2013); Irish Research Council for Science, Engineering and Technology (GOIPG/2013/336); University College Cork (Strategic Research Fund Ph.D. Studentship) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Springer en
dc.relation.uri https://link.springer.com/article/10.1007%2Fs00216-016-9749-8
dc.rights © Springer-Verlag Berlin Heidelberg 2016. This is a pre-print of an article published in Analytical and Bioanalytical Chemistry. The final authenticated version is available online at: https://doi.org/10.1007/s00216-016-9749-8 en
dc.subject Natural product en
dc.subject Biomarker en
dc.subject Pseudomonas aeruginosa en
dc.subject Electrochemical detection en
dc.subject Bovine en
dc.subject Cystic fibrosis en
dc.title Synthesis and electrochemical detection of a thiazolyl-indole natural product isolated from the nosocomial pathogen Pseudomonas aeruginosa en
dc.type Article (non peer-reviewed) en
dc.internal.authorcontactother Gerard P. Mcglacken, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: g.mcglacken@ucc.ie en
dc.internal.availability Full text available en
dc.date.updated 2019-11-05T10:22:13Z
dc.description.version Published Version en
dc.internal.rssid 372345143
dc.internal.wokid 000382681900013
dc.contributor.funder Science Foundation Ireland en
dc.contributor.funder Enterprise Ireland en
dc.contributor.funder European Commission en
dc.contributor.funder Department of Agriculture, Food and the Marine en
dc.contributor.funder Irish Research Council for Science, Engineering and Technology en
dc.contributor.funder Health Research Board en
dc.contributor.funder Irish Thoracic Society, Ireland en
dc.contributor.funder Marine Institute en
dc.contributor.funder Teagasc en
dc.contributor.funder University College Cork en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Analytical and Bioanalytical Chemistry en
dc.internal.copyrightchecked No
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress g.mcglacken@ucc.ie en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/12/TIDA/B2405/IE/Optimised detection of key biomarkers of Pseudomonas aeruginosa towards a clinical application/ en
dc.relation.project info:eu-repo/grantAgreement/EC/FP7::SP3::PEOPLE/607786/EU/BluePharmTrain/BLUEPHARMTRAIN en
dc.relation.project info:eu-repo/grantAgreement/EC/FP7::SP1::KBBE/311975/EU/Marine Microorganisms: Cultivation Methods for Improving their Biotechnological Applications/MACUMBA en
dc.relation.project info:eu-repo/grantAgreement/EC/FP7::SP1::KBBE/287589/EU/Marine Microbial Biodiversity, Bioinformatics and Biotechnology/MICRO B3 en
dc.relation.project info:eu-repo/grantAgreement/EC/FP7::SP3::PEOPLE/256596/EU/Dissecting the role of a novel transcriptional regulator in microbial-host interactomes./MEXT REGULATION en
dc.relation.project info:eu-repo/grantAgreement/EC/H2020::IA/634486/EU/Industrial Applications of Marine Enzymes: Innovative screening and expression platforms to discover and use the functional protein diversity from the sea/INMARE en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA) - Training Award/13/TIDA/B2625 TIDA Training 2014/IE/Small molecule inhibitors of HIF-1: a new class of anti-cancer therapeutics./ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/13/TIDA/B2625/IE/Small molecule inhibitors of HIF-1: a new class of anti-cancer therapeutics./ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/12/TIDA/B2411/IE/Development of small molecule therapeutics for medical intervention: anti-biofilm inhibitors for the medical device sector./ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/12/TIDA/B2405/IE/Optimised detection of key biomarkers of Pseudomonas aeruginosa towards a clinical application/ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/14/TIDA/2438/IE/Next Generation Antibiotics: anti-biofilm, anti-pathogenic natural bioactives from marine microorganisms./ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Strategic Research Cluster/08/SRC/B1412/IE/SRC ISSC: Irish Separation Science Cluster-Comprehensive multi-dimensional and multi-modal separation science for complex biological systems/ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Investigator Programme/12/IP/1315/IE/The Direct Arylation of Pyrones, Coumarins, Pyridones and Quinolones/ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Frontiers Programme (RFP)/09/RFP/CHS2353/IE/The asymmetric synthesis of 13-hydroxyketones using hydrazones with (-)-sparteine as chiral ligand and 13-aminoalcohols using an aldol-Tishchenko type reaction with sulfinylimines./ en


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