Date published: 2025-11-1

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8-Hydroxy-5-nitroquinoline (CAS 4008-48-4)

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Alternate Names:
5-Nitro-8-quinolinol; Nitroxoline
Application:
8-Hydroxy-5-nitroquinoline is used in the synthesis of novel CO2-soluble 8-hydroxyquinoline chelating agents
CAS Number:
4008-48-4
Purity:
≥96%
Molecular Weight:
190.16
Molecular Formula:
C9H6N2O3
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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8-Hydroxy-5-nitroquinoline functions as a chelating agent in experimental applications, binding to metal ions such as copper and zinc. 8-Hydroxy-5-Nitroquinoline′s mechanism of action involves forming stable complexes with metal ions, which can be utilized in various analytical applications. 8-Hydroxy-5-nitroquinoline is employed to selectively extract and quantify metal ions from complex mixtures, aiding in the determination of metal concentrations in samples. Its ability to form metal complexes also may be useful in studying metal ion behavior and interactions in biological and environmental systems.8-Hydroxy-5-nitroquinoline′s chelating properties contribute to its role in facilitating the separation and purification of metal ions for analytical and experimental purposes. At the molecular level, 8-Hydroxy-5-nitroquinoline′s mechanism of action involves the formation of stable coordination complexes with metal ions, influencing their behavior and enabling their detection and analysis in various experimental applications.


8-Hydroxy-5-nitroquinoline (CAS 4008-48-4) References

  1. Powder diffraction study of the hydrogen bonds in nitroxoline and its hydrochloride.  |  Yatsenko, AV., et al. 2002. Acta Crystallogr C. 58: o19-21. PMID: 11781483
  2. The syntheses and structures of '3+2' and '2+2+1' oxorhenium mixed-ligand complexes employing 8-hydroxy-5-nitroquinoline as the bidentate N,O donor ligand.  |  Chen, X., et al. 2000. Inorganica Chim Acta. 308: 80-90. PMID: 20592939
  3. Schiff base chemistry of the rhenium(V)-oxo core with '3+2' ligand donor sets.  |  Chen, X., et al. 2001. Inorganica Chim Acta. 316: 33-40. PMID: 20628543
  4. Nitroxoline (8-hydroxy-5-nitroquinoline) is more a potent anti-cancer agent than clioquinol (5-chloro-7-iodo-8-quinoline).  |  Jiang, H., et al. 2011. Cancer Lett. 312: 11-7. PMID: 21899946
  5. Experimental and theoretical quantum chemical investigations of 8-hydroxy-5-nitroquinoline.  |  Arjunan, V., et al. 2012. Spectrochim Acta A Mol Biomol Spectrosc. 96: 506-16. PMID: 22728969
  6. 8-Hydroxyquinolines: a review of their metal chelating properties and medicinal applications.  |  Prachayasittikul, V., et al. 2013. Drug Des Devel Ther. 7: 1157-78. PMID: 24115839
  7. Nitroxoline induces apoptosis and slows glioma growth in vivo.  |  Lazovic, J., et al. 2015. Neuro Oncol. 17: 53-62. PMID: 25074541
  8. Nitroxoline Molecule: Planar or Not? A Story of Battle between π-π Conjugation and Interatomic Repulsion.  |  Tikhonov, DS., et al. 2018. J Phys Chem A. 122: 1691-1701. PMID: 29360361
  9. Effects of repurposed drug candidates nitroxoline and nelfinavir as single agents or in combination with erlotinib in pancreatic cancer cells.  |  Veschi, S., et al. 2018. J Exp Clin Cancer Res. 37: 236. PMID: 30241558
  10. Functional Assessment of 2,177 U.S. and International Drugs Identifies the Quinoline Nitroxoline as a Potent Amoebicidal Agent against the Pathogen Balamuthia mandrillaris.  |  Laurie, MT., et al. 2018. mBio. 9: PMID: 30377287
  11. Synthesis and evaluation of a large library of nitroxoline derivatives as pancreatic cancer antiproliferative agents.  |  Veschi, S., et al. 2020. J Enzyme Inhib Med Chem. 35: 1331-1344. PMID: 32588672
  12. [Present status of nitroxoline].  |  Bergogne-Berezin, E., et al. 1987. Pathol Biol (Paris). 35: 873-8. PMID: 3309832
  13. Excited state proton transfer in the triplet state of 8-hydroxy-5-nitroquinoline: a transient absorption and time-resolved resonance Raman spectroscopic study.  |  Wang, R., et al. 2022. Phys Chem Chem Phys. 25: 402-409. PMID: 36477748

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

8-Hydroxy-5-nitroquinoline, 5 g

sc-233708
5 g
$50.00

8-Hydroxy-5-nitroquinoline, 100 g

sc-233708A
100 g
$90.00

8-Hydroxy-5-nitroquinoline, 500 g

sc-233708B
500 g
$334.00