{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,11]],"date-time":"2025-12-11T20:58:19Z","timestamp":1765486699783,"version":"build-2065373602"},"reference-count":36,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2021,12,22]],"date-time":"2021-12-22T00:00:00Z","timestamp":1640131200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"DICYT USACH","award":["022041MC_POSTDOC"],"award-info":[{"award-number":["022041MC_POSTDOC"]}]},{"DOI":"10.13039\/501100010751","name":"FONDECYT","doi-asserted-by":"publisher","award":["1180265 and 1191902"],"award-info":[{"award-number":["1180265 and 1191902"]}],"id":[{"id":"10.13039\/501100010751","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The aquatic infectious pancreatic necrosis virus (IPNV) causes a severe disease in farmed salmonid fish that generates great economic losses in the aquaculture industry. In the search for new tools to control the disease, in this paper we show the results obtained from the evaluation of the antiviral effect of [Cu(NN1)2](ClO4) Cu(I) complex, synthesized in our laboratory, where the NN1 ligand is a synthetic derivate of the natural compound coumarin. This complex demonstrated antiviral activity against IPNV at 5.0 and 15.0 \u00b5g\/mL causing a decrease viral load 99.0% and 99.5%, respectively. The Molecular Docking studies carried out showed that the copper complex would interact with the VP2 protein, specifically in the S domain, altering the process of entry of the virus into the host cell.<\/jats:p>","DOI":"10.3390\/molecules27010032","type":"journal-article","created":{"date-parts":[[2021,12,23]],"date-time":"2021-12-23T02:01:19Z","timestamp":1640224879000},"page":"32","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Evaluation of the Antiviral Activity against Infectious Pancreatic Necrosis Virus (IPNV) of a Copper (I) Homoleptic Complex with a Coumarin as Ligand"],"prefix":"10.3390","volume":"27","author":[{"given":"Daniela","family":"Guti\u00e9rrez","sequence":"first","affiliation":[{"name":"Laboratory of Natural Product Chemistry, Center of Aquatic Biotechnology, Department of Environmental Sciences, Faculty of Chemistry and Biology, University of Santiago de Chile, Santiago 3363, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Almendra","family":"Benavides","sequence":"additional","affiliation":[{"name":"Laboratory of Natural Product Chemistry, Center of Aquatic Biotechnology, Department of Environmental Sciences, Faculty of Chemistry and Biology, University of Santiago de Chile, Santiago 3363, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Beatriz","family":"Valenzuela","sequence":"additional","affiliation":[{"name":"Laboratory of Natural Product Chemistry, Center of Aquatic Biotechnology, Department of Environmental Sciences, Faculty of Chemistry and Biology, University of Santiago de Chile, Santiago 3363, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Carolina","family":"Mascayano","sequence":"additional","affiliation":[{"name":"Laboratory of Computational Simulations and Rational Drug Design, Department of Environmental Sciences, Faculty of Chemistry and Biology, University of Santiago de Chile, Santiago 3363, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maialen","family":"Aldabaldetrecu","sequence":"additional","affiliation":[{"name":"Laboratory of Coordination Compounds and Supramolecularity, Faculty of Chemistry and Biology, University of Santiago of Chile, Santiago 9170002, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Angel","family":"Olgu\u00edn","sequence":"additional","affiliation":[{"name":"Laboratory of Natural Product Chemistry, Center of Aquatic Biotechnology, Department of Environmental Sciences, Faculty of Chemistry and Biology, University of Santiago de Chile, Santiago 3363, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9827-5162","authenticated-orcid":false,"given":"Juan","family":"Guerrero","sequence":"additional","affiliation":[{"name":"Laboratory of Coordination Compounds and Supramolecularity, Faculty of Chemistry and Biology, University of Santiago of Chile, Santiago 9170002, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5292-0480","authenticated-orcid":false,"given":"Brenda","family":"Modak","sequence":"additional","affiliation":[{"name":"Laboratory of Natural Product Chemistry, Center of Aquatic Biotechnology, Department of Environmental Sciences, Faculty of Chemistry and Biology, University of Santiago de Chile, Santiago 3363, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,12,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Tapia, D., Eissler, Y., Reyes-Lopez, F., Kuznar, J., and Y\u00e1\u00f1ez, J. (2021). Infectious pancreatic necrosis virus in salmonids: Molecular epidemiology and host response to infection. Rev. Aquac., 1\u201319.","DOI":"10.1111\/raq.12623"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1393","DOI":"10.3389\/fmicb.2016.01393","article-title":"Infectious Pancreatic Necrosis Virus Causing Clinical and Subclinical Infections in Atlantic Salmon Have Different Genetic Fingerprints","volume":"7","author":"Mutoloki","year":"2016","journal-title":"Front. Microbiol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1111\/jfd.13113","article-title":"Comparison of mortality and viral load in rainbow trout (Oncorhynchus mykiss) infected with infectious pancreatic necrosis virus (IPNV) genogroups 1 and 5","volume":"43","author":"Tapia","year":"2020","journal-title":"J. Fish Dis."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Dopazo, C.P. (2020). The Infectious Pancreatic Necrosis Virus (IPNV) and its Virulence Determinants: What is Known and What Should be Known. Pathogens, 9.","DOI":"10.3390\/pathogens9020094"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5110","DOI":"10.1016\/j.vaccine.2012.05.062","article-title":"Evaluation of the immune response against immature viral particles of infectious pan-creatic necrosis virus (IPNV): A new model to develop an attenuated vaccine","volume":"30","author":"Martin","year":"2012","journal-title":"Vaccine"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1903","DOI":"10.1093\/nar\/3.8.1903","article-title":"Size and structure of the genome of infectious pancreatic necrosis virus","volume":"3","author":"Dobos","year":"1976","journal-title":"Nucleic Acids Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3655","DOI":"10.1128\/jvi.61.12.3655-3664.1987","article-title":"Synthesis of the infectious pancreatic necrosis vi-rus polyprotein, detection of a virus-encoded protease, and fine structure mapping of genome segment A coding regions","volume":"61","author":"Duncan","year":"1987","journal-title":"J. Virol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2231","DOI":"10.1099\/vir.0.80012-0","article-title":"Peptides resulting from the pVP2 C-terminal processing are present in infectious pancreatic necrosis virus particles","volume":"85","author":"Galloux","year":"2004","journal-title":"J. Gen. Virol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1016\/0959-8030(93)90037-C","article-title":"Use of monoclonal antibodies in identification and of fish viruses","volume":"3","author":"Nicholson","year":"1993","journal-title":"Annu. Rev. Fish Dis."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3484","DOI":"10.1128\/JVI.73.4.3484-3490.1999","article-title":"Infectious pancreatic necrosis virus: Identification of a VP3-containing ribonucleoprotein core structure and evidence for Olinked glycosylation of the capsid protein","volume":"73","author":"Hjalmarsson","year":"1999","journal-title":"J. Virol."},{"key":"ref_11","first-page":"7","article-title":"Factores asociados a la infecci\u00f3n celular por el virus de la necrosis pancre\u00e1tica infecciosa (IPNV)","volume":"39","author":"Ortega","year":"2007","journal-title":"Arch. Med. Veter."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"9206","DOI":"10.1128\/JVI.79.14.9206-9216.2005","article-title":"Infectious Pancreatic Necrosis Virus VP5 Is Dispensable for Virulence and Persistence Infectious Pancreatic Necrosis Virus VP5 Is Dispensable for Virulence and Persistence","volume":"79","author":"Santi","year":"2005","journal-title":"J. Virol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/0959-8030(95)00003-8","article-title":"The molecular biology of infectious pancreatic necrosis virus (IPNV)","volume":"5","author":"Dobos","year":"1995","journal-title":"Annu. Rev. Fish Dis."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1016\/0042-6822(91)90887-H","article-title":"Sequence analysis of infectious pancreatic necrosis virus genome segment B and its encoded VP1 protein: A putative RNA-dependent RNA polymerase lacking the Gly-Asp-Asp motif","volume":"181","author":"Duncan","year":"1991","journal-title":"Virology"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1089\/vim.2007.0043","article-title":"Immunogenicity properties of authentic and heterologously synthesized structural protein VP2 of infectious pancreatic necrosis virus","volume":"20","author":"Fridholm","year":"2007","journal-title":"Viral Immunol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"401","DOI":"10.15547\/tjs.2019.04.018","article-title":"Infectious pancreatic necrosis of salmonid fish\u2014Distribution and laboratory methods for diagnosis","volume":"17","author":"Mileva","year":"2019","journal-title":"Trakia J. Sci."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1005","DOI":"10.1111\/jfd.12317","article-title":"Persistent infections with infectious pancreatic necrosis virus (IPNV) of different virulence in Atlantic salmon, Salmo salar L.","volume":"38","author":"Julin","year":"2014","journal-title":"J. Fish Dis."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2446","DOI":"10.1128\/AEM.07358-11","article-title":"Thermal Inactivation of Infectious Pancreatic Necrosis Virus in a Peptone-Salt Medium Mimicking the Water-Soluble Phase of Hydrolyzed Fish By-Products","volume":"78","author":"Nygaard","year":"2012","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1","DOI":"10.4061\/2011\/594529","article-title":"Copper and Its Complexes in Medicine: A Biochemical Approach","volume":"2011","author":"Iakovidis","year":"2011","journal-title":"Mol. Biol. Int."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Aldabaldetrecu, M., Parra, M., Soto, S., Arce, P., Tello, M., Guerrero, J., and Modak, B. (2020). New Copper (I) Complex with a Coumarin as Ligand with Antibacterial Activity against Flavobacterium psychrophilum. Molecules, 25.","DOI":"10.3390\/molecules25143183"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Soto-Aguilera, S., Modak, B., Aldabaldetrecu, M., Lozano, C.P., Guerrero, J., Lefimil, C., and Parra, M. (2021). In Vitro Effect of Copper (I) Complex [Cu(NN1)2](ClO4) on Vibrio harveyi BB170 Bio-film Formation. Microorganisms, 9.","DOI":"10.3390\/microorganisms9112273"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3477","DOI":"10.1016\/j.bmc.2019.06.033","article-title":"Rational approaches, design strategies, structure activity relationship and mechanistic insights for therapeutic coumarin hybrids","volume":"27","author":"Singh","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"ref_23","first-page":"53","article-title":"Homeostasis and Toxicology of Essential Metals","volume":"Volume 31","author":"Chris","year":"2012","journal-title":"Fish Physiology"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"849","DOI":"10.3390\/chemistry2040056","article-title":"New Antimicrobial Strategies Based on Metal Complexes","volume":"2","author":"Claudel","year":"2020","journal-title":"Chemistry"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1016\/j.saa.2013.11.089","article-title":"Spectroscopic (FT-IR, FT-Raman, 1H, 13C NMR, UV\/VIS), thermogravimetric and antimicrobial studies of Ca(II), Mn(II), Cu(II), Zn(II) and Cd(II) complexes of ferulic acid","volume":"122","author":"Kalinowska","year":"2014","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_26","unstructured":"Mahy, B.W.J., and Van Regenmortel, M.H.V. (2008). Viral Membranes. Encyclopedia of Virology, Academic Press. [3rd ed.]."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1223","DOI":"10.1111\/raq.12521","article-title":"Compilation of antiviral treatments and strategies to fight fish viruses","volume":"13","author":"Pereiro","year":"2021","journal-title":"Rev. Aquac."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"10289","DOI":"10.1128\/JVI.79.16.10289-10299.2005","article-title":"Molecular determinants of Infectious Pancreatic Necrosis Virus virulence and cell culture adaptation","volume":"79","author":"Song","year":"2005","journal-title":"J. Virol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1833","DOI":"10.1007\/BF01384345","article-title":"Attachment and entry of infectious pancreatic necrosis virus (IPNV) into CHSE-214 cells","volume":"140","author":"Kuznar","year":"1995","journal-title":"Arch. Virol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/j.vetmic.2009.09.005","article-title":"Inhibitory effect of aromatic geranyl derivatives isolated from Heliotropium filifolium on infectious pancreatic necrosis virus replication","volume":"141","author":"Modak","year":"2010","journal-title":"Veter. Microbiol."},{"key":"ref_31","unstructured":"Dennington, R., Keith, T., and May, J.M. (2009). GaussView, Semichem Inc.. Version 5."},{"key":"ref_32","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2009). Gaussian 09, Gaussian, Inc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1792","DOI":"10.1128\/JVI.01536-09","article-title":"Crystal Structure of an Aquabirnavirus Particle: Insights into Antigenic Diversity and Virulence Determinism","volume":"84","author":"Coulibaly","year":"2010","journal-title":"J. Virol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1639","DOI":"10.1002\/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B","article-title":"Automated Docking Using a Lamarckian Genetic Algorithm and an Empirical Binding Free Energy Function","volume":"19","author":"Morris","year":"1998","journal-title":"J. Comput. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1781","DOI":"10.1002\/jcc.20289","article-title":"Scalable molecular dynamics with NAMD","volume":"26","author":"Phillips","year":"2005","journal-title":"J. Comput. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3684","DOI":"10.1063\/1.448118","article-title":"Molecular dynamics with coupling to an external bath","volume":"81","author":"Berendsen","year":"1984","journal-title":"J. Chem. Phys."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/1\/32\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:51:03Z","timestamp":1760169063000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/1\/32"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,12,22]]},"references-count":36,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2022,1]]}},"alternative-id":["molecules27010032"],"URL":"https:\/\/doi.org\/10.3390\/molecules27010032","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2021,12,22]]}}}