---
title: "Nadifloxacin enantioresolution and enantioselective ecotoxicity: multimilligram separation and aqu"
id: "pubmed-42670252"
canonical_url: "https://medichelpline.com/clinical-feed/pubmed-42670252"
content_type: "clinical_feed_article"
specialty: "Infectious Disease"
source_name: "PubMed / NCBI"
source_url: "https://pubmed.ncbi.nlm.nih.gov/42670252/"
doi: "10.1002/chir.70143"
published_at: "2026-09-01T00:00:00.000Z"
evidence_level: "Journal Article"
license: "CC-BY-NC-4.0 / Informational Use"
---
# Nadifloxacin enantioresolution and enantioselective ecotoxicity: multimilligram separation and aqu
## Provenance & Clinical Metadata
- **Canonical URL:** https://medichelpline.com/clinical-feed/pubmed-42670252
- **Specialty:** [Infectious Disease](https://medichelpline.com/clinical-feed/infectious-disease.md)
- **Primary Source:** PubMed / NCBI
- **Source URL:** [Original Journal Publication](https://pubmed.ncbi.nlm.nih.gov/42670252/)
- **DOI:** [10.1002/chir.70143](https://doi.org/10.1002%2Fchir.70143)
- **Published At:** 2026-09-01T00:00:00.000Z
- **Evidence Rating:** Journal Article
## Executive GIST (TL;DR)
- Emerging contaminants such as **fluoroquinolones** are persistent in aquatic environments due to high stability, low biodegradability, and biological activity at trace levels, raising ecotoxicity and antimicrobial resistance concerns. - Nadifloxacin (NAD) is a chiral fluoroquinolone prescribed as a racemate for dermatological infections; stereochemistry strongly affects potency: **(S)-NAD** is more potent than the racemate and is 64–256 times more active than (R)-NAD against Staphylococcus aureus and Propionibacterium acnes and other gram-positive and gram-negative pathogens. - The study developed an analytical enantioseparation method for NAD using chiral liquid chromatography (cLC) on a Lux amylose-1 column under normal-phase conditions, achieving good chromatographic performance (Rs = 5.92, α = 2.77, retention 6–10 min). - Analytical conditions were successfully scaled up to semipreparative enantioseparation on a CHIRALPAK AD-H DAICEL column (10 mm I.D. × 250 mm L, 5 μm), enabling multimilligram collection of both NAD enantiomers with >98% enantiomeric purity. - The absolute configuration and elution order of the enantiomers were assigned by comparing experimental and calculated electronic circular dichroism (ECD) data. - The work included an acute ecotoxicity evaluation of the NAD racemate and isolated enantiomers using **Daphnia magna** as an aquatic model organism to assess enantioselective environmental effects. - The paper emphasizes the importance of enantioselective ecotoxicological assessment for chiral antibiotics to better understand environmental fate, persistence, and potential stereoselective impacts on aquatic organisms. - Keywords highlighted in the source include: chiral antibiotic; ecotoxicity; emerging contaminants; enantioseparation; environmental fate; fluoroquinolones.
## Clinical Analysis & Structured Key Points
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Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 4 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-4 "UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences \(1H-TOXRUN, IUCS-CESPU\), Gandra, Portugal."), [Renata Vidal](https://pubmed.ncbi.nlm.nih.gov/?term=Vidal+R&cauthor_id=42670252)[ 3 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-3 "Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 4 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-4 "UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences \(1H-TOXRUN, IUCS-CESPU\), Gandra, Portugal."), [Lara da Silva Cabral](https://pubmed.ncbi.nlm.nih.gov/?term=da+Silva+Cabral+L&cauthor_id=42670252)[ 5 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-5 "Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil."), [Lucas H Martorano](https://pubmed.ncbi.nlm.nih.gov/?term=Martorano+LH&cauthor_id=42670252)[ 5 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-5 "Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil."), [Fernando M S Junior](https://pubmed.ncbi.nlm.nih.gov/?term=Junior+FMS&cauthor_id=42670252)[ 5 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-5 "Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil."), [Cláudia Ribeiro](https://pubmed.ncbi.nlm.nih.gov/?term=Ribeiro+C&cauthor_id=42670252)[ 3 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-3 "Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 4 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-4 "UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences \(1H-TOXRUN, IUCS-CESPU\), Gandra, Portugal."), [Ana R L Ribeiro](https://pubmed.ncbi.nlm.nih.gov/?term=Ribeiro+ARL&cauthor_id=42670252)[ 2 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-2 "LSRE-LCM, ALiCE, Faculty of Engineering, University of Porto, Porto, Portugal."), [Maria E Tiritan](https://pubmed.ncbi.nlm.nih.gov/?term=Tiritan+ME&cauthor_id=42670252)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-1 "Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal.")[ 3 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-3 "Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 6 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#full-view-affiliation-6 "CIIMAR/CIMAR LA, Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Matosinhos, Portugal.") Affiliations Expand ### Affiliations * 1 Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal. * 2 LSRE-LCM, ALiCE, Faculty of Engineering, University of Porto, Porto, Portugal. * 3 Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal. * 4 UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences (1H-TOXRUN, IUCS-CESPU), Gandra, Portugal. * 5 Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil. * 6 CIIMAR/CIMAR LA, Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Matosinhos, Portugal. * PMID: **42670252** * DOI: [ 10.1002/chir.70143 ](https://doi.org/10.1002/chir.70143) Item in Clipboard # Nadifloxacin: Multimilligram Enantioresolution and Enantioselective Ecotoxicological Studies Igor E Oliveira et al. Chirality. 2026 Sep. Show details Display options Display options Format Abstract PubMed PMID Chirality Actions * [ Search in PubMed ](https://pubmed.ncbi.nlm.nih.gov/?term=%22Chirality%22%5Bjour%5D&sort=date&sort_order=desc) * [ Search in NLM Catalog ](https://www.ncbi.nlm.nih.gov/nlmcatalog?term=%22Chirality%22%5BTitle+Abbreviation%5D) * [ Add to Search ](https://pubmed.ncbi.nlm.nih.gov/42670252/) . 2026 Sep;38(9):e70143. doi: 10.1002/chir.70143. ### Authors [Igor E Oliveira](https://pubmed.ncbi.nlm.nih.gov/?term=Oliveira+IE&cauthor_id=42670252)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-1 "Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal."), [Daniela Pereira](https://pubmed.ncbi.nlm.nih.gov/?term=Pereira+D&cauthor_id=42670252)[ 2 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-2 "LSRE-LCM, ALiCE, Faculty of Engineering, University of Porto, Porto, Portugal."), [Ana R Carvalho](https://pubmed.ncbi.nlm.nih.gov/?term=Carvalho+AR&cauthor_id=42670252)[ 2 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-2 "LSRE-LCM, ALiCE, Faculty of Engineering, University of Porto, Porto, Portugal.")[ 3 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-3 "Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 4 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-4 "UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences \(1H-TOXRUN, IUCS-CESPU\), Gandra, Portugal."), [Renata Vidal](https://pubmed.ncbi.nlm.nih.gov/?term=Vidal+R&cauthor_id=42670252)[ 3 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-3 "Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 4 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-4 "UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences \(1H-TOXRUN, IUCS-CESPU\), Gandra, Portugal."), [Lara da Silva Cabral](https://pubmed.ncbi.nlm.nih.gov/?term=da+Silva+Cabral+L&cauthor_id=42670252)[ 5 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-5 "Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil."), [Lucas H Martorano](https://pubmed.ncbi.nlm.nih.gov/?term=Martorano+LH&cauthor_id=42670252)[ 5 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-5 "Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil."), [Fernando M S Junior](https://pubmed.ncbi.nlm.nih.gov/?term=Junior+FMS&cauthor_id=42670252)[ 5 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-5 "Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil."), [Cláudia Ribeiro](https://pubmed.ncbi.nlm.nih.gov/?term=Ribeiro+C&cauthor_id=42670252)[ 3 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-3 "Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 4 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-4 "UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences \(1H-TOXRUN, IUCS-CESPU\), Gandra, Portugal."), [Ana R L Ribeiro](https://pubmed.ncbi.nlm.nih.gov/?term=Ribeiro+ARL&cauthor_id=42670252)[ 2 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-2 "LSRE-LCM, ALiCE, Faculty of Engineering, University of Porto, Porto, Portugal."), [Maria E Tiritan](https://pubmed.ncbi.nlm.nih.gov/?term=Tiritan+ME&cauthor_id=42670252)[ 1 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-1 "Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal.")[ 3 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-3 "Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal.")[ 6 ](https://pubmed.ncbi.nlm.nih.gov/42670252/#short-view-affiliation-6 "CIIMAR/CIMAR LA, Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Matosinhos, Portugal.") ### Affiliations * 1 Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal. * 2 LSRE-LCM, ALiCE, Faculty of Engineering, University of Porto, Porto, Portugal. * 3 Associate Laboratory i4HB - Institute for Health and Bioeconomy, University Institute of Health Sciences - CESPU, Gandra, Portugal. * 4 UCIBIO-Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences (1H-TOXRUN, IUCS-CESPU), Gandra, Portugal. * 5 Universidade Federal Fluminense, Institute of Chemistry, Niteroi, RJ, Brazil. * 6 CIIMAR/CIMAR LA, Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Matosinhos, Portugal. * PMID: **42670252** * DOI: [ 10.1002/chir.70143 ](https://doi.org/10.1002/chir.70143) Item in Clipboard Cite Display options Display options Format Abstract PubMed PMID ## Abstract 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 (S)-NAD is more potent than the racemate and 64 to 256 times more active than (R)-NAD against both Staphylococcus aureus and Propionibacterium acnes, as well as other gram-positive and gram-negative 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-1 column (4.6 mm I.D. × 250 mm L, particle size 5 μm) under normal-phase conditions. Optimized analytical conditions provided good chromatographic parameters (Rs = 5.92, α = 2.77, retention 6-10 min) and were successfully scaled up to semipreparative enantioseparation on a CHIRALPAK AD-H DAICEL column (10 mm I.D. × 250 mm L, particle size 5 μm), allowing the separation of both enantiomers in > 98% 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 Daphnia magna as an aquatic model organism. **Keywords:** chiral antibiotic; ecotoxicity; emerging contaminants; enantioseparation; environmental fate; fluoroquinolones. © 2026 Wiley Periodicals LLC. [PubMed Disclaimer](https://pubmed.ncbi.nlm.nih.gov/disclaimer/) ## Similar articles * [ Enantioselective evaluation of the chiral pesticide cyclaniliprole: Bioactivity, toxicity, and effects on strawberries flavor quality. ](https://pubmed.ncbi.nlm.nih.gov/41162083/) Liu Y, Zhang N, Song D, Liu R, Nie Y, Zhang Y, Guan W, Zhu W, Zhou Z, Diao J.Liu Y, et al.Pestic Biochem Physiol. 2025 Dec;215:106700. doi: 10.1016/j.pestbp.2025.106700. Epub 2025 Sep 18.Pestic Biochem Physiol. 2025.PMID: 41162083 * [ Toxicity of the 3,4-Methylenedioxymethamphetamine and Its Enantiomers to _Daphnia magna_ after Isolation by Semipreparative Chromatography. ](https://pubmed.ncbi.nlm.nih.gov/36771119/) Costa AR, Gonçalves VMF, Castro BB, Carrola JS, Langa I, Pereira A, Carvalho AR, Tiritan ME, Ribeiro C.Costa AR, et al.Molecules. 2023 Feb 2;28(3):1457. doi: 10.3390/molecules28031457.Molecules. 2023.PMID: 36771119Free PMC article. * [ Separation and aquatic toxicity of enantiomers of 1-(substituted phenoxyacetoxy)alkylphosphonate herbicides. ](https://pubmed.ncbi.nlm.nih.gov/18092302/) Li L, Zhou S, Zhao M, Zhang A, Peng H, Tan X, Lin C, He H.Li L, et al.Chirality. 2008 Feb;20(2):130-8. doi: 10.1002/chir.20511.Chirality. 2008.PMID: 18092302 * [ Chiral fungicide penconazole: Absolute configuration, bioactivity, toxicity, and stereoselective degradation in apples. ](https://pubmed.ncbi.nlm.nih.gov/34861299/) Li Y, Nie J, Zhang J, Xu G, Zhang H,
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