{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T03:02:40Z","timestamp":1789441360469,"version":"build-2803163510"},"reference-count":33,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,8,30]],"date-time":"2026-08-30T00:00:00Z","timestamp":1788048000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,8,30]],"date-time":"2026-08-30T00:00:00Z","timestamp":1788048000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["2022.02842.PTDC\u2014STAR"],"award-info":[{"award-number":["2022.02842.PTDC\u2014STAR"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["2022.08738.PTDC\u2014DRopH2O"],"award-info":[{"award-number":["2022.08738.PTDC\u2014DRopH2O"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["LSRE\u2010LCM, UID\/50020\/2025"],"award-info":[{"award-number":["LSRE\u2010LCM, UID\/50020\/2025"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["ALiCE, LA\/P\/0045\/2020"],"award-info":[{"award-number":["ALiCE, LA\/P\/0045\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/04423\/2025"],"award-info":[{"award-number":["UID\/04423\/2025"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["LA\/P\/0101\/2020"],"award-info":[{"award-number":["LA\/P\/0101\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/04378\/2025"],"award-info":[{"award-number":["UID\/04378\/2025"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["LA\/P\/0140\/2020"],"award-info":[{"award-number":["LA\/P\/0140\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["2022.00184.CEECIND\/CP1733\/CT0001"],"award-info":[{"award-number":["2022.00184.CEECIND\/CP1733\/CT0001"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Commission","doi-asserted-by":"publisher","award":["101039270"],"award-info":[{"award-number":["101039270"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Emerging contaminants are an increasing global concern, with antibiotics representing a notable case due to their continuous release and possible contribution to antimicrobial resistance. Fluoroquinolones (FQs) combine high stability, low biodegradability, and biological activity at trace levels, which result in persistence, ecotoxicity, and bioaccumulation in aquatic systems. Nadifloxacin (NAD) is a chiral FQ prescribed as a racemate for dermatological infections, but (\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010NAD is more potent than the racemate and 64 to 256 times more active than (\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010NAD against both\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    <\/jats:styled-content>\n                    and\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>Propionibacterium acnes<\/jats:italic>\n                    <\/jats:styled-content>\n                    , as well as other gram\u2010positive and gram\u2010negative pathogens. Though the stereochemistry plays a decisive role in both pharmacological activity and environmental fate, the enantioselective ecotoxicological evaluation of NAD is of high importance. Thus, this work described the enantioseparation of NAD by chiral liquid chromatography (cLC) on a Lux amylose\u20101 column (4.6\u2009mm I.D.\u2009\u00d7\u2009250\u2009mm\u2009L, particle size 5\u2009\u03bcm) under normal\u2010phase conditions. Optimized analytical conditions provided good chromatographic parameters (\n                    <jats:italic>R<\/jats:italic>\n                    s\u2009=\u20095.92,\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2009=\u20092.77, retention 6\u201310\u2009min) and were successfully scaled up to semipreparative enantioseparation on a CHIRALPAK\n                    <jats:sc>AD<\/jats:sc>\n                    \u2010H DAICEL column (10\u2009mm I.D.\u2009\u00d7\u2009250\u2009mm\u2009L, particle size 5\u2009\u03bcm), allowing the separation of both enantiomers in &gt;\u200998% enantiomeric purity. The absolute configuration and the elution order of the enantiomers were determined by the agreement between the experimental and calculated data of electronic circular dichroism. The acute ecotoxicity of the NAD racemate and its enantiomers was evaluated using\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>Daphnia magna<\/jats:italic>\n                    <\/jats:styled-content>\n                    as an aquatic model organism.\n                  <\/jats:p>","DOI":"10.1002\/chir.70143","type":"journal-article","created":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T06:48:26Z","timestamp":1788158906000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Nadifloxacin: Multimilligram Enantioresolution and Enantioselective Ecotoxicological Studies"],"prefix":"10.1002","volume":"38","author":[{"given":"Igor E.","family":"Oliveira","sequence":"first","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5711-7598","authenticated-orcid":false,"given":"Daniela","family":"Pereira","sequence":"additional","affiliation":[{"name":"LSRE\u2010LCM, ALiCE, Faculty of Engineering University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0634-603X","authenticated-orcid":false,"given":"Ana R.","family":"Carvalho","sequence":"additional","affiliation":[{"name":"LSRE\u2010LCM, ALiCE, Faculty of Engineering University of Porto  Porto Portugal"},{"name":"Associate Laboratory i4HB \u2013 Institute for Health and Bioeconomy University Institute of Health Sciences \u2010 CESPU  Gandra Portugal"},{"name":"UCIBIO\u2010Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory University Institute of Health Sciences (1H\u2010TOXRUN, IUCS\u2010CESPU)  Gandra Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-2214-7373","authenticated-orcid":false,"given":"Renata","family":"Vidal","sequence":"additional","affiliation":[{"name":"Associate Laboratory i4HB \u2013 Institute for Health and Bioeconomy University Institute of Health Sciences \u2010 CESPU  Gandra Portugal"},{"name":"UCIBIO\u2010Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory University Institute of Health Sciences (1H\u2010TOXRUN, IUCS\u2010CESPU)  Gandra Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-2027-9918","authenticated-orcid":false,"given":"Lara","family":"da Silva Cabral","sequence":"additional","affiliation":[{"name":"Universidade Federal Fluminense Institute of Chemistry  Niteroi RJ Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucas H.","family":"Martorano","sequence":"additional","affiliation":[{"name":"Universidade Federal Fluminense Institute of Chemistry  Niteroi RJ Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3711-6659","authenticated-orcid":false,"given":"Fernando M. S.","family":"Junior","sequence":"additional","affiliation":[{"name":"Universidade Federal Fluminense Institute of Chemistry  Niteroi RJ Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cl\u00e1udia","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"Associate Laboratory i4HB \u2013 Institute for Health and Bioeconomy University Institute of Health Sciences \u2010 CESPU  Gandra Portugal"},{"name":"UCIBIO\u2010Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory University Institute of Health Sciences (1H\u2010TOXRUN, IUCS\u2010CESPU)  Gandra Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana R. L.","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"LSRE\u2010LCM, ALiCE, Faculty of Engineering University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3320-730X","authenticated-orcid":false,"given":"Maria E.","family":"Tiritan","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"},{"name":"Associate Laboratory i4HB \u2013 Institute for Health and Bioeconomy University Institute of Health Sciences \u2010 CESPU  Gandra Portugal"},{"name":"CIIMAR\/CIMAR LA, Interdisciplinary Centre of Marine and Environmental Research University of Porto  Matosinhos Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,30]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/toxics13080616"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s42452-025-07716-5"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.5004\/dwt.2023.29789"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.3390\/jox14040076"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.envpol.2024.123894"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1289\/ehp.5947"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.hazl.2024.100105"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.3390\/ph16081105"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2024.171944"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21040268"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.3390\/toxics11120966"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ecoenv.2018.02.067"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1517\/14656566.7.14.1957"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.2147\/tcrm.2007.3.2.309"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030101q"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijmmb.2025.100788"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.3390\/antibiotics12061058"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jclepro.2023.137762"},{"issue":"4","key":"e_1_2_7_20_1","first-page":"25","article-title":"Enantioseparation of Nadifloxacin by High Performance Liquid Chromatography","volume":"2","author":"Sharma S. D.","year":"2012","journal-title":"Advances in Analytical Chemistry of Scientific and Academic Publishing"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.22861"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.70050"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemosphere.2018.05.005"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.aquatox.2024.106906"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/etc.5646"},{"key":"e_1_2_7_26_1","volume-title":"Spartan'14","author":"Wavefunction, Inc","year":"2014"},{"key":"e_1_2_7_27_1","volume-title":"OriginPro8","author":"OriginLab Corporation","year":"2007"},{"key":"e_1_2_7_28_1","unstructured":"M. J.Frisch H. B.Schlegel G. E.Scuseria et\u00a0al. \u201cGaussian 16 Revision C.01 \u201d Wallingford CT USA: Gaussian Inc.; 2016."},{"key":"e_1_2_7_29_1","unstructured":"Test No. 202:Daphniasp. Acute Immobilisation Test. Sect. Section\u00a02(2004)."},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2022.463555"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781119802280.ch5"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2023.169573"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24050865"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/wer.1631"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.70143","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chir.70143","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.70143","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T02:17:09Z","timestamp":1789438629000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.70143"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,30]]},"references-count":33,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2026,9]]}},"alternative-id":["10.1002\/chir.70143"],"URL":"https:\/\/doi.org\/10.1002\/chir.70143","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,30]]},"assertion":[{"value":"2026-04-11","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-08-14","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-08-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70143"}}