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2-Bromo-1,4-naphthoquinone (CAS 2065-37-4)

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Alternate Names:
2-bromonaphthalene-1,4-dione; 2-bromonaphthoquinone
Application:
2-Bromo-1,4-naphthoquinone is a menadione analog used for cancer research
CAS Number:
2065-37-4
Purity:
≥97%
Molecular Weight:
237.05
Molecular Formula:
C10H5BrO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-Bromo-1,4-naphthoquinone is a naphthoquinone derivative and menadione analog. It has been used in cancer research studies to increase H2O2 production in tumor cell lines. The compound shows anticancer activity in tissue culture and has been found to effectively inhibit the growth of cancer cells by disrupting cellular metabolism. Its mechanism of action involves reactions with amines specifically at the C2 position of the naphthoquinone ring, resulting in the release of bromine radicals that readily react with DNA and various cellular components. In vitro studies have shown it has minimal toxicity and redox potentials similiar to those of water.


2-Bromo-1,4-naphthoquinone (CAS 2065-37-4) References

  1. Cytotoxicity of naphthoquinones and their capacity to generate reactive oxygen species is quenched when conjugated with gold nanoparticles.  |  Srinivas, P., et al. 2011. Int J Nanomedicine. 6: 2113-22. PMID: 22114475
  2. 2-Bromo-1,4-naphthoquinone: a potentially improved substitute of menadione in Apatone™ therapy.  |  Graciani, FS. and Ximenes, VF. 2012. Braz J Med Biol Res. 45: 701-10. PMID: 22584645
  3. Copper(II)-Mediated Synthesis of Indolequinones from Bromoquinones and Enamines.  |  Inman, M. and Moody, CJ. 2013. European J Org Chem. 2013: 2179-2187. PMID: 23704833
  4. Surface enhanced Raman spectral studies of 2-bromo-1,4-naphthoquinone.  |  Geetha, K., et al. 2015. Spectrochim Acta A Mol Biomol Spectrosc. 138: 113-9. PMID: 25481490
  5. Antimicrobial activities of active component isolated from Lawsonia inermis leaves and structure-activity relationships of its analogues against food-borne bacteria.  |  Yang, JY. and Lee, HS. 2015. J Food Sci Technol. 52: 2446-51. PMID: 25829631
  6. Time-resolved visible and infrared absorption spectroscopy data obtained using photosystem I particles with non-native quinones incorporated into the A1 binding site.  |  Makita, H. and Hastings, G. 2016. Data Brief. 7: 1463-8. PMID: 27182540
  7. Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention.  |  Freidus, LG., et al. 2020. Molecules. 25: PMID: 33003358
  8. An Alternative to Carbon Additives: The Fabrication of Conductive Layers Enabled by Soluble Conducting Polymer Precursors - A Case Study for Organic Batteries.  |  Strietzel, C., et al. 2021. ACS Appl Mater Interfaces. 13: 5349-5356. PMID: 33481558
  9. In Vivo Anti-inflammatory, Analgesic, and Sedative Studies of the Extract and Naphthoquinone Isolated from Diospyros kaki (Persimmon).  |  Bawazeer, S. and Rauf, A. 2021. ACS Omega. 6: 9852-9856. PMID: 33869965
  10. Synthesis of some NH- and NH,S- substituted 1,4-quinones.  |  Kaçmaz, A. 2021. Turk J Chem. 45: 475-484. PMID: 34104058
  11. Accessing Chemo- and Regioselective Benzylic and Aromatic Oxidations by Protein Engineering of an Unspecific Peroxygenase.  |  Knorrscheidt, A., et al. 2021. ACS Catal. 11: 7327-7338. PMID: 34631225
  12. Naphthoquinone as a New Chemical Scaffold for Leishmanicidal Inhibitors of Leishmania GSK-3.  |  Sebastián-Pérez, V., et al. 2022. Biomedicines. 10: PMID: 35625873
  13. Novel one-pot synthesis of a library of 2-aryloxy-1,4-naphthoquinone derivatives. Determination of antifungal and antibacterial activity.  |  Chaves-Carballo, K., et al. 2022. RSC Adv. 12: 18507-18523. PMID: 35799928

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Bromo-1,4-naphthoquinone, 10 g

sc-225182
10 g
$90.00