{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T20:49:23Z","timestamp":1767905363535,"version":"3.49.0"},"reference-count":48,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2018,7,19]],"date-time":"2018-07-19T00:00:00Z","timestamp":1531958400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002848","name":"Comisi\u00f3n Nacional de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica","doi-asserted-by":"publisher","award":["11110516"],"award-info":[{"award-number":["11110516"]}],"id":[{"id":"10.13039\/501100002848","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002848","name":"Comisi\u00f3n Nacional de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica","doi-asserted-by":"publisher","award":["79100006"],"award-info":[{"award-number":["79100006"]}],"id":[{"id":"10.13039\/501100002848","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002848","name":"Comisi\u00f3n Nacional de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica","doi-asserted-by":"publisher","award":["21130643"],"award-info":[{"award-number":["21130643"]}],"id":[{"id":"10.13039\/501100002848","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002848","name":"Comisi\u00f3n Nacional de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica","doi-asserted-by":"publisher","award":["21130628"],"award-info":[{"award-number":["21130628"]}],"id":[{"id":"10.13039\/501100002848","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A rapid emergence of resistant bacteria is occurring worldwide, endangering the efficacy of antibiotics and reducing the therapeutic arsenal available for treatment of infectious diseases. In the present study, we developed a new class of compounds with antibacterial activity obtained by a simple, two step synthesis and screened the products for in vitro antibacterial activity against ATCC\u00ae strains using the broth microdilution method. The compounds exhibited minimum inhibitory concentrations (MIC) of 1\u201332 \u03bcg\/mL against Gram-positive ATCC\u00ae strains. The structure\u2013activity relationship indicated that the thiophenol ring is essential for antibacterial activity and the substituents on the thiophenol ring module, for antibacterial activity. The most promising compounds detected by screening were tested against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF) clinical isolates. We found remarkable activity against VREF for compounds 7 and 16, were the MIC50\/90 were 2\/4 \u00b5g\/mL and 4\/4 \u00b5g\/mL, respectively, while for vancomycin the MIC50\/90 was 256\/512 \u00b5g\/mL. Neither compound affected cell viability in any of the mammalian cell lines at any of the concentrations tested. These in vitro data show that compounds 7 and 16 have an interesting potential to be developed as new antibacterial drugs against infections caused by VREF.<\/jats:p>","DOI":"10.3390\/molecules23071776","type":"journal-article","created":{"date-parts":[[2018,7,20]],"date-time":"2018-07-20T02:10:11Z","timestamp":1532052611000},"page":"1776","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["A New Kind of Quinonic-Antibiotic Useful Against Multidrug-Resistant S. aureus and E. faecium Infections"],"prefix":"10.3390","volume":"23","author":[{"given":"Javier","family":"Campanini-Salinas","sequence":"first","affiliation":[{"name":"Drug Development Laboratory, Faculty of Chemical and Pharmaceutical, Sciences, Universidad de Chile, Sergio Livingstone 1007, Santiago 8380492, Chile"},{"name":"Facultad de Medicina y Ciencia, Universidad San Sebasti\u00e1n, Lago, Panguipulli 1390, Puerto Montt 5501842, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Juan","family":"Andrades-Lagos","sequence":"additional","affiliation":[{"name":"Drug Development Laboratory, Faculty of Chemical and Pharmaceutical, Sciences, Universidad de Chile, Sergio Livingstone 1007, Santiago 8380492, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2351-1236","authenticated-orcid":false,"given":"Gerardo","family":"Gonzalez Rocha","sequence":"additional","affiliation":[{"name":"Laboratorio de Investigaci\u00f3n en Agentes Antibacterianos (LIAA), Departamento de Microbiolog\u00eda, Facultad de Ciencias Biol\u00f3gicas, Universidad de Concepci\u00f3n, Concepci\u00f3n 4070386, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7077-8972","authenticated-orcid":false,"given":"Duane","family":"Choquesillo-Lazarte","sequence":"additional","affiliation":[{"name":"Laboratorio de Estudios Cristalogr\u00e1ficos, IACT (CSIC-UGR), Av. de las Palmeras 4, 18100 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Soledad","family":"Bollo Dragnic","sequence":"additional","affiliation":[{"name":"Bioelectrochemistry Laboratory, Faculty of Chemical and Pharmaceutical, Sciences, Universidad de Chile, Santiago 8380492, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mario","family":"Fa\u00fandez","sequence":"additional","affiliation":[{"name":"Molecular Pharmacology and Toxicology Laboratory, Pharmacy Department, Faculty of Chemistry, Pontificia Universidad Cat\u00f3lica de Chile; Santiago 7820436, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pedro","family":"Alarc\u00f3n","sequence":"additional","affiliation":[{"name":"Agents of bacterial meningitis laboratory, Instituto de Salud P\u00fablica de Chile, Santiago 7780050, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Francisco","family":"Silva","sequence":"additional","affiliation":[{"name":"Microbiology Unit, Clinical Laboratory, Clinical Hospital University of Chile; Santiago 8380456, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4223-1985","authenticated-orcid":false,"given":"Roberto","family":"Vidal","sequence":"additional","affiliation":[{"name":"Antibiotics Laboratory, Microbiology Program, Biomedical Sciences Institute, Faculty of Medicine, Universidad de Chile, Santiago 8380453, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Edison","family":"Salas-Huenuleo","sequence":"additional","affiliation":[{"name":"Nanobiotechnology and Nanotoxicology Laboratory, Faculty of Chemical and Pharmaceutical Sciences, Universidad de Chile, Santiago 8380494, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marcelo","family":"Kogan","sequence":"additional","affiliation":[{"name":"Nanobiotechnology and Nanotoxicology Laboratory, Faculty of Chemical and Pharmaceutical Sciences, Universidad de Chile, Santiago 8380494, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2434-8461","authenticated-orcid":false,"given":"Jaime","family":"Mella","sequence":"additional","affiliation":[{"name":"Institute of Chemistry and Biochemistry, Faculty of Sciences, Universidad de Valpara\u00edso, Playa Ancha, Valpara\u00edso 2360102, Chile"},{"name":"Escuela de Quimica y Farmacia, Facultad de Medicina, Universidad Andres Bello, Quillota 980, Vi\u00f1a del Mar 2531015, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7763-7830","authenticated-orcid":false,"given":"Gonzalo","family":"Recabarren Gajardo","sequence":"additional","affiliation":[{"name":"Laboratory of Synthesis of Bioactive Heterocycles, Pharmacy Department, Faculty of Chemistry, Pontificia Universidad Cat\u00f3lica de Chile; Santiago 7820436, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0635-4857","authenticated-orcid":false,"given":"David","family":"V\u00e1squez-Vel\u00e1squez","sequence":"additional","affiliation":[{"name":"Drug Development Laboratory, Faculty of Chemical and Pharmaceutical, Sciences, Universidad de Chile, Sergio Livingstone 1007, Santiago 8380492, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2018,7,19]]},"reference":[{"key":"ref_1","unstructured":"Review on Antimicrobial Resistance (2014). Antimicrobial Resistance: Tackling a Crisis for the Health and Wealth of Nations, Review on Antimicrobial Resistance."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1086\/595011","article-title":"Bad bugs, no drugs: No eskape! An update from the infectious diseases society of america","volume":"48","author":"Boucher","year":"2009","journal-title":"Clin. Infect. Dis."},{"key":"ref_3","unstructured":"World Health Organization (2017). Global Priority List of Antibiotic-Resistant Bacteria to Guide Research, Discovery, and Development of New Antibiotics, WHO."},{"key":"ref_4","unstructured":"CDC-Centers for Disease Control and Prevention (2018, July 10). Antibiotic Resistance Threats in the United States, Available online: http:\/\/www.cdc.gov\/drugresistance\/threat-report-2013\/index.html."},{"key":"ref_5","unstructured":"World Health Organization (2014). Antimicrobial Resistance: Global Report on Surveillance, WHO."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5437","DOI":"10.2807\/ese.13.47.19046-en","article-title":"Emergence and spread of vancomycin resistance among enterococci in europe","volume":"13","author":"Werner","year":"2008","journal-title":"Euro Surveill."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1086\/421946","article-title":"Nosocomial bloodstream infections in us hospitals: Analysis of 24,179 cases from a prospective nationwide surveillance study","volume":"39","author":"Wisplinghoff","year":"2004","journal-title":"Clin. Infect. Dis."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1016\/j.coph.2012.07.004","article-title":"New classes of antibiotics","volume":"12","author":"Moir","year":"2012","journal-title":"Curr. Opin. Pharmacol."},{"key":"ref_9","first-page":"1140","article-title":"Looking for new targets: Simple coumarins as antibacterial agents","volume":"8","author":"Matos","year":"2012","journal-title":"Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"201","DOI":"10.2165\/00126839-200708040-00001","article-title":"Novel genetic techniques and approaches in the microbial genomics era: Identification and\/or validation of targets for the discovery of new antibacterial agents","volume":"8","author":"Pucci","year":"2007","journal-title":"Drugs R D"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"358","DOI":"10.3390\/md10020358","article-title":"Synthetic strategies to terpene quinones\/hydroquinones","volume":"10","author":"Gordaliza","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1007\/BF00229240","article-title":"The mechanism of action of quinone antibiotics","volume":"55","author":"Lown","year":"1983","journal-title":"Mol. Cell. Biochem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1014","DOI":"10.1002\/ptr.5090","article-title":"Antitubercular and antibacterial activity of quinonoid natural products against multi-drug resistant clinical isolates","volume":"28","author":"Dey","year":"2014","journal-title":"Phytother. Res."},{"key":"ref_14","first-page":"420","article-title":"Synthesis, characterization and antibacterial and antifungal evaluation of some para-quinone derivatives","volume":"64","author":"Amani","year":"2014","journal-title":"Drug Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"270","DOI":"10.1002\/(SICI)1521-3773(19990201)38:3<270::AID-ANIE270>3.0.CO;2-0","article-title":"The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products","volume":"38","author":"Papageorgiou","year":"1999","journal-title":"Angewandte Chem. Int. Ed."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4056","DOI":"10.1248\/cpb.34.4056","article-title":"Synthesis of renierone, 7-methoxy-1,6-dimethyl-5,8-dihydroisoquinoline-5,8-dione and N-formyl-1,2-dihydrorenierone, antimicrobial metabolites from a marine sponge, reniera sp.","volume":"34","author":"Kubo","year":"1986","journal-title":"Chem. Pharm. Bull."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1016\/j.ejmech.2016.03.042","article-title":"Design, synthesis and biological evaluation of diaziridinyl quinone isoxazole hybrids","volume":"117","author":"Swapnaja","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1488","DOI":"10.1080\/14786419.2012.722086","article-title":"Three bioactive sesquiterpene quinones from the fijian marine sponge of the genus hippospongia","volume":"27","author":"Kumar","year":"2013","journal-title":"Nat. Prod. Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5324","DOI":"10.1016\/j.bmcl.2005.08.032","article-title":"Synthesis and biological evaluation of novel (l)-alpha-amino acid methyl ester, heteroalkyl, and aryl substituted 1,4-naphthoquinone derivatives as antifungal and antibacterial agents","volume":"15","author":"Tandon","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3463","DOI":"10.1016\/j.bmcl.2005.04.075","article-title":"Synthesis and biological evaluation of novel 1,4-naphthoquinone derivatives as antibacterial and antiviral agents","volume":"15","author":"Tandon","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"395","DOI":"10.1128\/mr.56.3.395-411.1992","article-title":"Agents that increase the permeability of the outer membrane","volume":"56","author":"Vaara","year":"1992","journal-title":"Microbiol. Rev."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"26723","DOI":"10.1074\/jbc.270.45.26723","article-title":"Siderophores: Structure and function of microbial iron transport compounds","volume":"270","author":"Neilands","year":"1995","journal-title":"J. Biol. Chem."},{"key":"ref_23","first-page":"M100-S25","article-title":"Performance standards for antimicrobial susceptibility testing; twenty-fifth informational supplement","volume":"35","author":"Patel","year":"2015","journal-title":"Clin. Lab. Stand. Inst."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"213","DOI":"10.2174\/187152011795255902","article-title":"Redox-active quinones and ascorbate: An innovative cancer therapy that exploits the vulnerability of cancer cells to oxidative stress","volume":"11","author":"Verrax","year":"2011","journal-title":"Anti-Cancer Agents Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1016\/0891-5849(89)90126-3","article-title":"Redox and addition chemistry of quinoid compounds and its biological implications","volume":"7","author":"Brunmark","year":"1989","journal-title":"Free Radic. Biol. Med."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1021\/cr60056a010","article-title":"Some relations between reaction rates and equilibrium constants","volume":"17","author":"Hammett","year":"1935","journal-title":"Chem. Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1016\/j.ijantimicag.2014.05.007","article-title":"In vitro antimicrobial activity of the novel oxazolidinone tedizolid and comparator agents against staphylococcus aureus and linezolid-resistant Gram-positive pathogens: A multicentre study in china","volume":"44","author":"Chen","year":"2014","journal-title":"Int. J. Antimicrob. Agents"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4608","DOI":"10.1128\/AAC.00458-12","article-title":"In vitro activity and microbiological efficacy of tedizolid (TR-700) against Gram-positive clinical isolates from a phase 2 study of oral tedizolid phosphate (TR-701) in patients with complicated skin and skin structure infections","volume":"56","author":"Prokocimer","year":"2012","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.diagmicrobio.2014.08.011","article-title":"Results of the surveillance of tedizolid activity and resistance program: In vitro susceptibility of Gram-positive pathogens collected in 2011 and 2012 from the united states and europe","volume":"81","author":"Sahm","year":"2015","journal-title":"Diagn. Microbiol. Infect. Dis."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3236","DOI":"10.1128\/AAC.00228-09","article-title":"In vitro activity of TR-700, the active ingredient of the antibacterial prodrug TR-701, a novel oxazolidinone antibacterial agent","volume":"53","author":"Schaadt","year":"2009","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2892","DOI":"10.1128\/AAC.00274-13","article-title":"Activity of tedizolid (TR-700) against well-characterized methicillin-resistant staphylococcus aureus strains of diverse epidemiological origins","volume":"57","author":"Thomson","year":"2013","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1111\/1469-0691.12463","article-title":"European perspective and update on the management of complicated skin and soft tissue infections due to methicillin-resistant staphylococcus aureus after more than 10 years of experience with linezolid","volume":"20","author":"Bassetti","year":"2014","journal-title":"Clin. Microbiol. Infect."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4442","DOI":"10.1128\/AAC.00859-08","article-title":"In vitro activity of TR-700, the antibacterial moiety of the prodrug TR-701, against linezolid-resistant strains","volume":"52","author":"Shaw","year":"2008","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_34","unstructured":"Victor, L. (1996). Post antibiotic effect. Antibiotics in Laboratory Medicine, Williams and Wilkins. [2nd ed.]."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Valderrama, J.A., Gonzalez, M.F., Colonelli, P., and Vasquez, D. (2006). Design and synthesis of angucyclinone 5-aza analogues. Synlett, 2777\u20132780.","DOI":"10.1055\/s-2006-950254"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"10172","DOI":"10.1016\/j.bmc.2008.10.064","article-title":"Studies on quinones. Part 44: Novel angucyclinone n-heterocyclic analogues endowed with antitumoral activity","volume":"16","author":"Valderrama","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_37","unstructured":"Vasquez-Velasquez, D.R. (2009). Dise\u00f1o, S\u00edntesis y Evaluaci\u00f3n Antitumoral de Aza-An\u00e1logos de Anguciclinonas y Derivados de Aminopirimidoisoquinolinquinonas. [Ph.D Thesis, Pontificia Universidad Cat\u00f3lica de Chile]."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"5234","DOI":"10.1016\/j.ejmech.2010.08.040","article-title":"Studies on quinones. Part 46. Synthesis and in vitro antitumor evaluation of aminopyrimidoisoquinolinequinones","volume":"45","author":"Vasquez","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3398","DOI":"10.1016\/j.ejmech.2011.05.003","article-title":"Studies on quinones. Part 47. Synthesis of novel phenylaminophenanthridinequinones as potential antitumor agents","volume":"46","author":"Valderrama","year":"2011","journal-title":"Eur. J. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1016\/j.jneumeth.2008.04.020","article-title":"Apex 3: A multi-purpose test platform for auditory psychophysical experiments","volume":"172","author":"Francart","year":"2008","journal-title":"J. Neurosci. Methods"},{"key":"ref_41","unstructured":"Sheldrick, G.M. (2012). SADABS-2012\/1. Bruker\/Siemens Area Detector Absorption Correction Program, Bruker AXS Inc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of shelx","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1811","DOI":"10.1128\/AAC.04616-14","article-title":"Telavancin in vitro activity against a collection of methicillin-resistant staphylococcus aureus isolates, including resistant subsets, from the united states","volume":"59","author":"Mendes","year":"2015","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_44","first-page":"M07-A9","article-title":"Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard\u2014ninth edition","volume":"32","author":"Cockerill","year":"2012","journal-title":"Clin. Lab. Stand. Inst."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1128\/AAC.18.5.699","article-title":"Method of reliable determination of minimal lethal antibiotic concentrations","volume":"18","author":"Pearson","year":"1980","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_46","unstructured":"Lorian, V. (1996). Antibiotics in Laboratory Medicine, The Williams & Wilkins Co.. [4th ed.]."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"142","DOI":"10.1128\/AAC.23.1.142","article-title":"Determination of minimum bactericidal concentrations of oxacillin for staphylococcus aureus: Influence and significance of technical factors","volume":"23","author":"Taylor","year":"1983","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Methods"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/7\/1776\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:13:05Z","timestamp":1760195585000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/7\/1776"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,7,19]]},"references-count":48,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2018,7]]}},"alternative-id":["molecules23071776"],"URL":"https:\/\/doi.org\/10.3390\/molecules23071776","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,7,19]]}}}