Oxolinic acid
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| Category | Antibiotics |
| Catalog number | BBF-05909 |
| CAS | 14698-29-4 |
| Molecular Weight | 261.23 |
| Molecular Formula | C13H11NO5 |
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Description
Oxolinic acid is an inhibitor of the enzyme DNA gyrase and DNA synthesis.
Specification
| Synonyms | Urinox; NSC 110364; Nidantin; Dioxacin; Emyrenil |
| IUPAC Name | 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid |
| Canonical SMILES | CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O |
| InChI | InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17) |
| InChI Key | KYGZCKSPAKDVKC-UHFFFAOYSA-N |
Properties
| Boiling Point | 473.2±45.0 °C at 760 mmHg |
| Melting Point | 314-316°C (dec.) |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Photodegradation of oxolinic acid in aquaculture effluents under solar irradiation: is it possible to enhance efficiency by the use of TiO2/carbon quantum dots composites?
Valentina Silva, Inês Invêncio, Carla Patrícia Silva, Marta Otero, Diana L D Lima Chemosphere. 2022 Dec;308(Pt 3):136522. doi: 10.1016/j.chemosphere.2022.136522. Epub 2022 Sep 20.
Antibiotics, such as oxolinic acid (OXA), in aquaculture effluents contribute to the dissemination of antimicrobial resistance, which makes it urgent to develop efficient and sustainable processes for their removal. Aiming a photocatalytic degradation under solar radiation, different carbon quantum dots (CQDs) were produced in this work through a bottom-up hydrothermal methodology and incorporated into TiO2 by a simple calcination method. A total of thirteen materials were synthesized and tested for OXA photocatalytic removal from synthetic and real matrices. Among them, CQDs produced with citric acid and incorporated into TiO2 at 4% (w/w) (TiO2/CQDs-CA 4% (w/w)) were the most efficient photocatalysts, providing an OXA half-life time (t1/2) decrease of 91%, 79% and 85% in phosphate buffer solution (PBS), synthetic sea salts (SSS) and brackish aquaculture effluent (BAE), respectively. Therefore, the herein synthesized TiO2/CQDs-CA 4% (w/w) composites have shown to be promising materials for a sustainable solar-driven removal of antibiotics from aquaculture effluents.
2. Survey of Oxolinic Acid-Resistant Erwinia amylovora in Korean Apple and Pear Orchards, and the Fitness Impact of Constructed Mutants
Hyeonheui Ham, Ga-Ram Oh, Dong Suk Park, Yong Hoon Lee Plant Pathol J. 2022 Oct;38(5):482-489. doi: 10.5423/PPJ.OA.04.2022.0059. Epub 2022 Oct 1.
Fire blight caused by Erwinia amylovora (Ea) is a devastating disease in apple and pear trees. Oxolinic acid (OA), a quinolone family antibiotic that inhibits DNA gyrase, has been employed to control fire blight in South Korea since 2015. The continuous use of this bactericide has resulted in the emergence of OA-resistant strains in bacterial pathogens in other countries. To investigate the occurrence of OA-resistant Ea strains in South Korea, we collected a total of 516 Ea isolates from diseased apple and pear trees in 2020-2021 and assessed their sensitivities to OA. We found that all isolates were susceptible to OA. To explore the possibility of emerging OA-resistant Ea by continuous application of OA, we exposed Ea stains to a range of OA concentrations and constructed OA-resistant mutant strains. Resistance was associated with mutations in the GyrA at codons 81 and 83, which result in glycine to cysteine and serine to arginine amino acid substitutions, respectively. The in vitro growth of the mutants in nutrient media and their virulence in immature apple fruits were lower than those of wild-type. Our results suggest that OA-resistance decreases the fitness of Ea. Future work should clarify the mechanisms by which OA-resistance decreases virulence of this plant pathogen. Continuous monitoring of OA-resistance in Ea is required to maintain the efficacy of this potent bactericide.
3. Synergistic effects of dietary oxolinic acid combined with oxytetracycline on nonspecific immune responses and resistance against Vibrio parahaemolyticus infection of white shrimp (Penaeus vannamei)
Huai-Ting Huang, Jui-Jen Chang, Yu-Ru Lin, Yin-Yu Chen, Yung-Han Wu Chang, Bo-Ying Chen, Fan-Hua Nan Fish Shellfish Immunol. 2022 Aug;127:740-747. doi: 10.1016/j.fsi.2022.06.066. Epub 2022 Jul 2.
This study investigated the synergistic effects of oxolinic acid (OA) combined with oxytetracycline (OTC) on white shrimp (Penaeus vannamei). Disk diffusion susceptibility testing was performed to analyze the sensitivity of Vibrio alginolyticus and Vibrio parahaemolyticus to different concentrations of OA and OTC. The results revealed that 50 mg OA/L combined with 50 mg OTC/L exhibited stronger antibacterial effects on V. alginolyticus and V. parahaemolyticus. The results of in vitro tests indicated that cotreatment with OA and OTC significantly reduced superoxide anion production and phenoloxidase activity, but not phagocytic activity. Subsequently, feeding trials were performed to investigate the immunomodulatory effects and bioaccumulation of dietary OA combined with OTC on shrimp. The healthy shrimp (15.13 ± 1.02 g) were divided into four groups: control, 100 mg OA/kg combined with 50 mg OTC/kg, 50 mg OA/kg combined with 100 mg OTC/kg, and 50 mg OA/kg combined with 50 mg OTC/kg. The shrimp were sampled to determine innate immunity parameters and residual OA and OTC levels in the muscle during a 28-day feeding regimen; the shrimp were fed the experimental diet from day 1 to day 5 and a commercial diet from day 6 to day 28. Residual OA levels were considerably higher in the group fed 100 mg OA/kg combined with 50 mg OTC/kg compared with the other groups and peaked on day 4. The residual OA levels of all the groups were below the detection limit after without providing OA. The residual OTC levels of the group fed 50 mg OA/kg combined with 100 mg OTC/kg were considerably higher from day 1 to day 4. The residual OTC levels in all the groups decreased rapidly and could not be detected on day 28. The administration of 50 mg OA/kg combined with 100 mg OTC/kg exerted the least effect on the white shrimp. Moreover, the survival rates of the treatment groups after the V. parahaemolyticus challenge were higher than those of the control group, especially the group fed 50 mg OA/kg combined with 100 mg OTC/kg. This result indicated that the synergistic effects of dietary OA and OTC are safe and effective. Combination therapy is a new method of antibiotic use in aquaculture.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
