WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H527460
CAS#: 475-38-7
Description: Naphthazarin, also known as DHNQ, has a protective effect on the 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine-induced Parkinson's disease model. Naphthazarin enhances ionizing radiation-induced cell cycle arrest and apoptosis in human breast cancer cells.
Hodoodo Cat#: H527460
Name: Naphthazarin
CAS#: 475-38-7
Chemical Formula: C10H6O4
Exact Mass: 190.03
Molecular Weight: 190.154
Elemental Analysis: C, 63.16; H, 3.18; O, 33.65
This product is not in stock, which may be available by custom synthesis.
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Synonym: Naphthazarin; DHNQ;
IUPAC/Chemical Name: 5,8-Dihydroxy-1,4-naphthoquinone
InChi Key: RQNVIKXOOKXAJQ-UHFFFAOYSA-N
InChi Code: InChI=1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H
SMILES Code: O=C(C1=C2C(O)=CC=C1O)C=CC2=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 190.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Sharma N, Gulati A. Selective binding of Ni2+ and Cu2+ metal ions with naphthazarin esters isolated from Arnebia euchroma. Biotechnol Prog. 2020 Jul;36(4):e2985. doi: 10.1002/btpr.2985. Epub 2020 Mar 21. PMID: 32103632.
2: Bao XZ, Wang Q, Ren XR, Dai F, Zhou B. A hydrogen peroxide-activated Cu(II) pro-ionophore strategy for modifying naphthazarin as a promising anticancer agent with high selectivity for generating ROS in HepG2 cells over in L02 cells. Free Radic Biol Med. 2020 May 20;152:597-608. doi: 10.1016/j.freeradbiomed.2019.12.001. Epub 2019 Dec 2. PMID: 31805398.
3: Fan C, Lim LKP, Loh SQ, Ying Lim KY, Upton Z, Leavesley D. Application of "macromolecular crowding" in vitro to investigate the naphthoquinones shikonin, naphthazarin and related analogues for the treatment of dermal scars. Chem Biol Interact. 2019 Sep 1;310:108747. doi: 10.1016/j.cbi.2019.108747. Epub 2019 Jul 10. PMID: 31301289.
4: Rudnicka M, Ludynia M, Karcz W. Effects of Naphthazarin (DHNQ) Combined with Lawsone (NQ-2-OH) or 1,4-Naphthoquinone (NQ) on the Auxin-Induced Growth of Zea mays L. Coleoptile Segments. Int J Mol Sci. 2019 Apr 11;20(7):1788. doi: 10.3390/ijms20071788. PMID: 30978914; PMCID: PMC6479706.
5: Rudnicka M, Ludynia M, Karcz W. The Effect of Naphthazarin on the Growth, Electrogenicity, Oxidative Stress, and Microtubule Array in Z. mays Coleoptile Cells Treated With IAA. Front Plant Sci. 2019 Jan 8;9:1940. doi: 10.3389/fpls.2018.01940. PMID: 30671078; PMCID: PMC6331528.
6: Zhang J, Liu Y, Shi D, Hu G, Zhang B, Li X, Liu R, Han X, Yao X, Fang J. Synthesis of naphthazarin derivatives and identification of novel thioredoxin reductase inhibitor as potential anticancer agent. Eur J Med Chem. 2017 Nov 10;140:435-447. doi: 10.1016/j.ejmech.2017.09.027. Epub 2017 Sep 19. PMID: 28987605.
7: Dengiz C, Luppino SP, Gutierrez GD, Swager TM. Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes. J Org Chem. 2017 Jul 21;82(14):7470-7480. doi: 10.1021/acs.joc.7b01170. Epub 2017 Jul 3. PMID: 28670901.
8: Chen AD, Li H, Li YC, Zeng H. Naphthazarin suppresses cell proliferation and induces apoptosis in human colorectal cancer cells via the B-cell lymphoma 2/B-cell associated X protein signaling pathway. Oncol Lett. 2016 Dec;12(6):5211-5216. doi: 10.3892/ol.2016.5319. Epub 2016 Oct 26. PMID: 28101239; PMCID: PMC5228214.
9: Aljanadi O, Alzoubi K, Bissinger R, Lang F. Stimulation of Suicidal Erythrocyte Death by Naphthazarin. Basic Clin Pharmacol Toxicol. 2015 Dec;117(6):369-74. doi: 10.1111/bcpt.12420. Epub 2015 Jun 16. PMID: 26013059.
10: Kim MY, Park SJ, Shim JW, Yang K, Kang HS, Heo K. Naphthazarin enhances ionizing radiation-induced cell cycle arrest and apoptosis in human breast cancer cells. Int J Oncol. 2015 Apr;46(4):1659-66. doi: 10.3892/ijo.2015.2857. Epub 2015 Jan 28. PMID: 25633658.
11: Dragana SV, Pushilin MA, Glazunov VP, Denisenko VA, Anufriev VP. Total synthesis of hybocarpone, a cytotoxic naphthazarin derivative from the lichen Lecanora hybocarpa, and related compounds. Nat Prod Commun. 2014 Dec;9(12):1765-8. PMID: 25632480.
12: Son TG, Kawamoto EM, Yu QS, Greig NH, Mattson MP, Camandola S. Naphthazarin protects against glutamate-induced neuronal death via activation of the Nrf2/ARE pathway. Biochem Biophys Res Commun. 2013 Apr 19;433(4):602-6. doi: 10.1016/j.bbrc.2013.03.041. Epub 2013 Mar 26. PMID: 23537652; PMCID: PMC3652233.
13: Utkina NK, Pokhilo ND. Free radical scavenging activities of naturally occurring and synthetic analogues of sea urchin naphthazarin pigments. Nat Prod Commun. 2012 Jul;7(7):901-4. PMID: 22908577.
14: Choi SY, Son TG, Park HR, Jang YJ, Oh SB, Jin B, Lee J. Naphthazarin has a protective effect on the 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine-induced Parkinson's disease model. J Neurosci Res. 2012 Sep;90(9):1842-9. doi: 10.1002/jnr.23061. Epub 2012 Apr 19. PMID: 22513651.
15: Kim JA, Lee EK, Park SJ, Kim ND, Hyun DH, Lee CG, Lee JH, Yang KM, Heo K, Son TG. Novel anti-cancer role of naphthazarin in human gastric cancer cells. Int J Oncol. 2012 Jan;40(1):157-62. doi: 10.3892/ijo.2011.1195. Epub 2011 Sep 8. PMID: 21904775.
16: Acharya BR, Bhattacharyya S, Choudhury D, Chakrabarti G. The microtubule depolymerizing agent naphthazarin induces both apoptosis and autophagy in A549 lung cancer cells. Apoptosis. 2011 Sep;16(9):924-39. doi: 10.1007/s10495-011-0613-1. PMID: 21667044.
17: Chaisuksant R, Palkawong-Na-Ayuthaya W, Grudpan K. Spectrophotometric determination of copper in alloys using naphthazarin. Talanta. 2000 Dec 4;53(3):579-85. doi: 10.1016/s0039-9140(00)00534-8. PMID: 18968145.
18: Kim DW, Hong GH, Lee HH, Choi SH, Chun BG, Won CK, Hwang IK, Won MH. Effect of colloidal silver against the cytotoxicity of hydrogen peroxide and naphthazarin on primary cultured cortical astrocytes. Int J Neurosci. 2007 Mar;117(3):387-400. doi: 10.1080/00207450600592016. PMID: 17365122.
19: Pekin G, Ganzera M, Senol S, Bedir E, Korkmaz KS, Stuppner H. Determination of naphthazarin derivatives in endemic Turkish Alkanna species by reversed phase high performance liquid chromatography. Planta Med. 2007 Mar;73(3):267-72. doi: 10.1055/s-2007-967110. Epub 2007 Feb 22. PMID: 17318780.
20: Kundaković T, Stanojković T, Juranić Z, Kovacević N. Cytotoxicity in vitro of naphthazarin derivatives from Onosma arenaria. Phytother Res. 2006 Jul;20(7):602-4. doi: 10.1002/ptr.1899. PMID: 16718737.
