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

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dc.contributor.authorBuzid, Alyah
dc.contributor.authorMuimhneacháin, Eoin Ó
dc.contributor.authorReen, F. Jerry
dc.contributor.authorHayes, Phyllis E.
dc.contributor.authorPardo, Leticia M.
dc.contributor.authorShang, Fengjun
dc.contributor.authorO'Gara, Fergal
dc.contributor.authorSperry, Jonathan
dc.contributor.authorLuong, John H. T.
dc.contributor.authorGlennon, Jeremy D.
dc.contributor.authorMcGlacken, Gerard P.
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderEnterprise Irelanden
dc.contributor.funderEuropean Commissionen
dc.contributor.funderDepartment of Agriculture, Food and the Marineen
dc.contributor.funderIrish Research Council for Science, Engineering and Technologyen
dc.contributor.funderHealth Research Boarden
dc.contributor.funderIrish Thoracic Society, Irelanden
dc.contributor.funderMarine Instituteen
dc.contributor.funderTeagascen
dc.contributor.funderUniversity College Corken
dc.date.accessioned2019-11-05T10:39:37Z
dc.date.available2019-11-05T10:39:37Z
dc.date.issued2016-09
dc.date.updated2019-11-05T10:22:13Z
dc.description.abstractPseudomonas 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.sponsorshipEuropean 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.description.statusPeer revieweden
dc.description.versionPublished Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationBuzid, 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/s00216-016-9749-8en
dc.identifier.doi10.1007/s00216-016-9749-8en
dc.identifier.endpage6367en
dc.identifier.issn1618-2650
dc.identifier.issued23en
dc.identifier.journaltitleAnalytical and Bioanalytical Chemistryen
dc.identifier.startpage6361en
dc.identifier.urihttps://hdl.handle.net/10468/8952
dc.identifier.volume408en
dc.language.isoenen
dc.publisherSpringeren
dc.relation.projectinfo: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.projectinfo:eu-repo/grantAgreement/EC/FP7::SP3::PEOPLE/607786/EU/BluePharmTrain/BLUEPHARMTRAINen
dc.relation.projectinfo:eu-repo/grantAgreement/EC/FP7::SP1::KBBE/311975/EU/Marine Microorganisms: Cultivation Methods for Improving their Biotechnological Applications/MACUMBAen
dc.relation.projectinfo:eu-repo/grantAgreement/EC/FP7::SP1::KBBE/287589/EU/Marine Microbial Biodiversity, Bioinformatics and Biotechnology/MICRO B3en
dc.relation.projectinfo:eu-repo/grantAgreement/EC/FP7::SP3::PEOPLE/256596/EU/Dissecting the role of a novel transcriptional regulator in microbial-host interactomes./MEXT REGULATIONen
dc.relation.projectinfo: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/INMAREen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.projectinfo: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.projectinfo: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.projectinfo: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.projectinfo: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.projectinfo: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.projectinfo: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.projectinfo:eu-repo/grantAgreement/SFI/SFI Investigator Programme/12/IP/1315/IE/The Direct Arylation of Pyrones, Coumarins, Pyridones and Quinolones/en
dc.relation.projectinfo: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
dc.relation.urihttps://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/s00216-016-9749-8en
dc.subjectNatural producten
dc.subjectBiomarkeren
dc.subjectPseudomonas aeruginosaen
dc.subjectElectrochemical detectionen
dc.subjectBovineen
dc.subjectCystic fibrosisen
dc.titleSynthesis and electrochemical detection of a thiazolyl-indole natural product isolated from the nosocomial pathogen Pseudomonas aeruginosaen
dc.typeArticle (non peer-reviewed)en
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