{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,11]],"date-time":"2025-11-11T13:41:03Z","timestamp":1762868463838,"version":"build-2065373602"},"reference-count":32,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T00:00:00Z","timestamp":1619827200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100001518","name":"Maurice and Phyllis Paykel Trust","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001518","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003524","name":"New Zealand Ministry of Business Innovation and Employment","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003524","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic & Medicinal Chemistry"],"published-print":{"date-parts":[[2021,5]]},"DOI":"10.1016\/j.bmc.2021.116110","type":"journal-article","created":{"date-parts":[[2021,3,13]],"date-time":"2021-03-13T23:05:35Z","timestamp":1615676735000},"page":"116110","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":9,"special_numbering":"C","title":["Repurposing primaquine as a polyamine conjugate to become an antibiotic adjuvant"],"prefix":"10.1016","volume":"38","author":[{"given":"A. Norrie","family":"Pearce","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dan","family":"Chen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Liam R.","family":"Edmeades","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Melissa M.","family":"Cadelis","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Azza","family":"Troudi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jean Michel","family":"Brunel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marie-Lise","family":"Bourguet-Kondracki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brent R.","family":"Copp","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmc.2021.116110_b0005","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1038\/nbt.2786","article-title":"Clinical Development Success Rates for Investigational Drugs","volume":"32","author":"Hay","year":"2014","journal-title":"Nat Biotechnol"},{"key":"10.1016\/j.bmc.2021.116110_b0010","doi-asserted-by":"crossref","first-page":"3683","DOI":"10.1016\/j.bmcl.2014.06.053","article-title":"Confronting the Challenges of Discovery of Novel Antibacterial Agents","volume":"24","author":"Singh","year":"2014","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmc.2021.116110_b0015","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1128\/CMR.00030-10","article-title":"Challenges of Antibacterial Discovery","volume":"24","author":"Silver","year":"2011","journal-title":"Clin Microbiol Rev"},{"key":"10.1016\/j.bmc.2021.116110_b0020","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1038\/nrd2201","article-title":"Drugs for Bad Bugs: Confronting the Challenges of Antibacterial Discovery","volume":"6","author":"Payne","year":"2007","journal-title":"Nat Rev Drug Discov"},{"key":"10.1016\/j.bmc.2021.116110_b0025","doi-asserted-by":"crossref","first-page":"1037","DOI":"10.1016\/j.cell.2007.03.004","article-title":"Molecular Mechanisms of Antibacterial Multidrug Resistance","volume":"128","author":"Alekshun","year":"2007","journal-title":"Cell"},{"key":"10.1016\/j.bmc.2021.116110_b0030","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1021\/acsinfecdis.7b00071","article-title":"The Challenge of Overcoming Antibiotic Resistance: An Adjuvant Approach?","volume":"3","author":"Melander","year":"2017","journal-title":"ACS Infect Dis"},{"key":"10.1016\/j.bmc.2021.116110_b0035","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1038\/nchembio.559","article-title":"Combinations of Antibiotics and Nonantibiotic Drugs Enhance Antimicrobial Efficacy","volume":"7","author":"Ejim","year":"2011","journal-title":"Nat Chem Biol"},{"key":"10.1016\/j.bmc.2021.116110_b0040","doi-asserted-by":"crossref","first-page":"4221","DOI":"10.1016\/j.bmcl.2017.08.027","article-title":"Antibiotic adjuvants \u2013 A strategy to Unlock Bacterial Resistance to Antibiotics","volume":"27","author":"Gonz\u00e1lez-Bello","year":"2017","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmc.2021.116110_b0045","doi-asserted-by":"crossref","first-page":"111743","DOI":"10.1016\/j.ejmech.2019.111743","article-title":"Recent Development of Membrane-active Molecules as Antibacterial Agents","volume":"184","author":"Zhang","year":"2019","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0050","doi-asserted-by":"crossref","first-page":"2070","DOI":"10.1128\/AAC.01472-06","article-title":"Polyamine Effects on Antibiotic Susceptibility in Bacteria","volume":"51","author":"Kwon","year":"2007","journal-title":"Antimicrob Agents Ch"},{"key":"10.1016\/j.bmc.2021.116110_b0055","doi-asserted-by":"crossref","first-page":"963","DOI":"10.4155\/fmc-2016-0011","article-title":"Polyamine Derivatives: a Revival of an Old Neglected Scaffold to Fight Resistant Gram-negative Bacteria?","volume":"8","author":"Blanchet","year":"2016","journal-title":"Future Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0060","doi-asserted-by":"crossref","first-page":"2927","DOI":"10.1021\/ja3120955","article-title":"Synthesis and Activity of Biomimetic Biofilm Disruptors","volume":"135","author":"B\u04e7ttcher","year":"2013","journal-title":"JACS"},{"key":"10.1016\/j.bmc.2021.116110_b0065","doi-asserted-by":"crossref","first-page":"4263","DOI":"10.1021\/jm500194e","article-title":"New Ianthelliformisamine Derivatives as Antibiotic Enhancers against Resistant Gram-Negative Bacteria","volume":"57","author":"Pieri","year":"2014","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0070","doi-asserted-by":"crossref","first-page":"3140","DOI":"10.1021\/acs.jmedchem.5b01912","article-title":"Antibacterial Diamines Targeting Bacterial Membranes","volume":"59","author":"Wang","year":"2016","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0075","doi-asserted-by":"crossref","first-page":"852","DOI":"10.1128\/AAC.50.3.852-861.2006","article-title":"Structural Correlates of Antibacterial and Membrane-Permeabilizing Activities in Acylpolyamines","volume":"50","author":"Balakrishna","year":"2006","journal-title":"Antimicrob Agents Ch"},{"key":"10.1016\/j.bmc.2021.116110_b0080","doi-asserted-by":"crossref","first-page":"10750","DOI":"10.1021\/acs.jmedchem.6b01435","article-title":"Antibacterial and Antibiofilm Activity of Cationic Small Molecules with Spatial Positioning of Hydrophobicity: An in Vitro and in Vivo Evaluation","volume":"59","author":"Hoque","year":"2016","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0085","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1021\/np1008619","article-title":"Didemnidines A and B, Indole Spermidine Alkaloids from the New Zealand Ascidian Didemnum sp","volume":"74","author":"Finlayson","year":"2011","journal-title":"J Nat Prod"},{"key":"10.1016\/j.bmc.2021.116110_b0090","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1016\/j.ejmech.2013.07.055","article-title":"Synthesis and In Vitro and In Vivo Evaluation of Antimalarial Polyamines","volume":"69","author":"Liew","year":"2013","journal-title":"Euro J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0095","doi-asserted-by":"crossref","first-page":"3138","DOI":"10.3390\/md12063138","article-title":"Investigation of Indolglyoxamide and Indolacetamide Analogues of Polyamines as Antimalarial and Antitrypanosomal Agents","volume":"12","author":"Wang","year":"2014","journal-title":"Mar Drugs"},{"key":"10.1016\/j.bmc.2021.116110_b0100","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1016\/j.ejmech.2017.09.040","article-title":"Synthesis and Antimalarial Evaluation of Artesunate-polyamine and Trioxolane-polyamine Conjugates","volume":"140","author":"Pearce","year":"2017","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0105","doi-asserted-by":"crossref","first-page":"2090","DOI":"10.1016\/j.bmc.2019.04.004","article-title":"6-Bromoindolglyoxylamido Derivatives as Antimicrobial Agents and Antibiotic Enhancers","volume":"27","author":"Li","year":"2019","journal-title":"Bioorg Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0110","doi-asserted-by":"crossref","first-page":"3440","DOI":"10.1021\/jm010854+","article-title":"Synthesis and Biological Evaluation of S-Triazine Substituted Polyamines as Potential new Anti-Trypanosomal drugs","volume":"44","author":"Klenke","year":"2001","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0115","doi-asserted-by":"crossref","first-page":"2480","DOI":"10.1021\/jo005637f","article-title":"Nitrile Reduction in the Presence of Boc-protected Amino Groups by Catalytic Hydrogenation over Palladium-activated Raney-Nickel","volume":"66","author":"Klenke","year":"2001","journal-title":"J Org Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0120","doi-asserted-by":"crossref","first-page":"710","DOI":"10.1021\/jm00336a006","article-title":"Analogs of Spermine and Spermidine. 1. Synthesis of Polymethylenepolyamines by Reduction of Cyanoethylated \u03b1, \u03c9-Alkylenediamines","volume":"7","author":"Israel","year":"1964","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0125","first-page":"1301","article-title":"Building a Better Quaternary Ammonium Compound (QAC): Branched Tetracationic Antiseptic Amphiphiles","volume":"11","author":"Forman","year":"2016","journal-title":"ChemMedChem"},{"key":"10.1016\/j.bmc.2021.116110_b0130","doi-asserted-by":"crossref","unstructured":"Yang T, Moreira W, Nyantakyi A, Chen H, binte Aziz D, Go M-L, Dick T. Amphiphilic Indole Derivatives as Antimycobacterial Agents: Structure-Activity Relationships and Membrane Targeting Properties. J Med Chem. 2017;60:2745-2763. doi: 10.1021\/acs\/jmedchem.6b01530.","DOI":"10.1021\/acs.jmedchem.6b01530"},{"key":"10.1016\/j.bmc.2021.116110_b0135","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1002\/jhet.5570200203","article-title":"Assignments of Dissociation Constants of Primaquine by 13C-NMR Spectroscopy","volume":"20","author":"Hufford","year":"1983","journal-title":"J Heterocyclic Chem"},{"key":"10.1016\/j.bmc.2021.116110_b0140","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.bbamem.2010.08.009","article-title":"Effects of the Antimalarial Drug Primaquine on the Dynamic Structure of Lipid Model Membranes","volume":"1808","author":"Basso","year":"2011","journal-title":"Biochim Biophys Acta"},{"key":"10.1016\/j.bmc.2021.116110_b0145","doi-asserted-by":"crossref","first-page":"5103","DOI":"10.1016\/j.electacta.2006.03.085","article-title":"Molecular Modelling of the Votammetric Oxidation at a Glassy Carbon Electrode of the Antimalarial drug Primaquine and its Prodrugs Succinylprimaquine and Maleylprimaquine","volume":"51","author":"La-Scalea","year":"2006","journal-title":"Electrochim Acta"},{"key":"10.1016\/j.bmc.2021.116110_b0150","article-title":"Rapid Aromatic Hydrogen Exchange in the Antimalarial Primaquine","volume":"184\u2013186","author":"McChesney","year":"1984","journal-title":"Pharm Res"},{"key":"10.1016\/j.bmc.2021.116110_b0155","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1021\/acsinfecdis.5b00044","article-title":"Helping Chemists Discover New Antibiotics","volume":"1","author":"Blaskovich","year":"2015","journal-title":"ACS Infect Dis"},{"key":"10.1016\/j.bmc.2021.116110_b0160","doi-asserted-by":"crossref","first-page":"47","DOI":"10.3390\/md8010047","article-title":"Inhibitory Activity of Marine Sponge-Derived Natural Products against Parasitic Protozoa","volume":"8","author":"Orhan","year":"2010","journal-title":"Mar Drugs"}],"container-title":["Bioorganic & Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0968089621001188?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0968089621001188?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T01:11:34Z","timestamp":1760836294000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0968089621001188"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5]]},"references-count":32,"alternative-id":["S0968089621001188"],"URL":"https:\/\/doi.org\/10.1016\/j.bmc.2021.116110","relation":{},"ISSN":["0968-0896"],"issn-type":[{"type":"print","value":"0968-0896"}],"subject":[],"published":{"date-parts":[[2021,5]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Repurposing primaquine as a polyamine conjugate to become an antibiotic adjuvant","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmc.2021.116110","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2021 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"116110"}}