Synonym
DMNQ; NSC 69355; NSC-69355; NSC69355;
IUPAC/Chemical Name
2,3-Dimethoxynaphthalene-1,4-dione
InChi Key
ZEGDFCCYTFPECB-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H10O4/c1-15-11-9(13)7-5-3-4-6-8(7)10(14)12(11)16-2/h3-6H,1-2H3
SMILES Code
O=C1C(OC)=C(OC)C(C2=C1C=CC=C2)=O
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
>3 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
2934.99.03.00
Biological target:
DMNQ is a redox cycling agent that generates both superoxide and hydrogen peroxide.
In vitro activity:
DMNQ decreased monocyte ATP-linked respiration, maximal respiration, and reserve capacity and caused an increase in proton leak and non-mitochondrial respiration compared to monocytes not treated with DMNQ. These data suggest that monocytes are susceptible to oxidative stress mediated by DMNQ and this can be accurately assessed by the BHI (Bioenergetic Health Index).
Reference: Redox Biol. 2016 Aug;8:43-50. https://pubmed.ncbi.nlm.nih.gov/26748041/
In vivo activity:
Furthermore, i.p. administration of DMNQ S-52 at 5 mg/kg resulted in a potent inhibition of the growth of LLC cells implanted on the right flank of C57BL/6 mice compared to untreated control. Immunohistochemical analysis revealed the decreased tumor cell proliferation and increased tumor cell apoptosis in DMNQ S-52 treated tumor sections using terminal deoxynucleotidyl transferase-mediated deoxyuridine triphosphate nick-end labeling (TUNEL) and proliferation cell nuclear antigen (PCNA). Taken together, these findings demonstrate that DMNQ S-52 may exhibit anti-tumor activity by inducing apoptosis via caspases and mitogen activated protein (MAP) kinase-dependent pathways.
Reference: Cancer Lett. 2006 Feb 20;233(1):57-67. https://pubmed.ncbi.nlm.nih.gov/15893420/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
50.0 |
0.09 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
218.21
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:
1. Chacko BK, Zhi D, Darley-Usmar VM, Mitchell T. The Bioenergetic Health Index is a sensitive measure of oxidative stress in human monocytes. Redox Biol. 2016 Aug;8:43-50. doi: 10.1016/j.redox.2015.12.008. Epub 2015 Dec 24. PMID: 26748041; PMCID: PMC4712317.
2. Shi MM, Kugelman A, Iwamoto T, Tian L, Forman HJ. Quinone-induced oxidative stress elevates glutathione and induces gamma-glutamylcysteine synthetase activity in rat lung epithelial L2 cells. J Biol Chem. 1994 Oct 21;269(42):26512-7. PMID: 7929374.
3. Lee SJ, Sakurai H, Koizumi K, Song GY, Bae YS, Kim HM, Kang KS, Surh YJ, Saiki I, Kim SH. MAPK regulation and caspase activation are required in DMNQ S-52 induced apoptosis in Lewis lung carcinoma cells. Cancer Lett. 2006 Feb 20;233(1):57-67. doi: 10.1016/j.canlet.2005.02.042. PMID: 15893420.
4. Kim SH, Kang IC, Yoon TJ, Park YM, Kang KS, Song GY, Ahn BZ. Antitumor activities of a newly synthesized shikonin derivative, 2-hyim-DMNQ-S-33. Cancer Lett. 2001 Oct 30;172(2):171-5. doi: 10.1016/s0304-3835(01)00665-6. PMID: 11566493.
In vitro protocol:
1. Chacko BK, Zhi D, Darley-Usmar VM, Mitchell T. The Bioenergetic Health Index is a sensitive measure of oxidative stress in human monocytes. Redox Biol. 2016 Aug;8:43-50. doi: 10.1016/j.redox.2015.12.008. Epub 2015 Dec 24. PMID: 26748041; PMCID: PMC4712317.
2. Shi MM, Kugelman A, Iwamoto T, Tian L, Forman HJ. Quinone-induced oxidative stress elevates glutathione and induces gamma-glutamylcysteine synthetase activity in rat lung epithelial L2 cells. J Biol Chem. 1994 Oct 21;269(42):26512-7. PMID: 7929374.
In vivo protocol:
1. Lee SJ, Sakurai H, Koizumi K, Song GY, Bae YS, Kim HM, Kang KS, Surh YJ, Saiki I, Kim SH. MAPK regulation and caspase activation are required in DMNQ S-52 induced apoptosis in Lewis lung carcinoma cells. Cancer Lett. 2006 Feb 20;233(1):57-67. doi: 10.1016/j.canlet.2005.02.042. PMID: 15893420.
2. Kim SH, Kang IC, Yoon TJ, Park YM, Kang KS, Song GY, Ahn BZ. Antitumor activities of a newly synthesized shikonin derivative, 2-hyim-DMNQ-S-33. Cancer Lett. 2001 Oct 30;172(2):171-5. doi: 10.1016/s0304-3835(01)00665-6. PMID: 11566493.
1: Horvathova E, Eckl PM, Bresgen N, Slamenova D. Evaluation of genotoxic and cytotoxic effects of H2O2 and DMNQ on freshly isolated rat hepatocytes; protective effects of carboxymethyl chitin-glucan. Neuro Endocrinol Lett. 2008 Oct;29(5):644-8. PubMed PMID: 18987600.
2: Park MJ, Kwon HY, Lee EO, Lee HJ, Ahn KS, Kim MO, Kim CH, Ahn KS, Kim SH. DMNQ-S17 inhibits constitutive NF-kappaB activation leading to induction of apoptosis through the activation of caspase-3 in human myeloid leukemia U937 cells. Life Sci. 2008 Sep 26;83(13-14):460-7. doi: 10.1016/j.lfs.2008.07.010. Epub 2008 Jul 30. PubMed PMID: 18718843.
3: Lim ES, Rhee YH, Park MK, Shim BS, Ahn KS, Kang H, Yoo HS, Kim SH. DMNQ S-64 induces apoptosis via caspase activation and cyclooxygenase-2 inhibition in human nonsmall lung cancer cells. Ann N Y Acad Sci. 2007 Jan;1095:7-18. PubMed PMID: 17404012.
4: Ishihara Y, Shiba D, Shimamoto N. Enhancement of DMNQ-induced hepatocyte toxicity by cytochrome P450 inhibition. Toxicol Appl Pharmacol. 2006 Jul 15;214(2):109-17. Epub 2006 Jan 20. PubMed PMID: 16430935.
5: Lee SJ, Sakurai H, Koizumi K, Song GY, Bae YS, Kim HM, Kang KS, Surh YJ, Saiki I, Kim SH. MAPK regulation and caspase activation are required in DMNQ S-52 induced apoptosis in Lewis lung carcinoma cells. Cancer Lett. 2006 Feb 20;233(1):57-67. PubMed PMID: 15893420.
6: Watanabe N, Forman HJ. Autoxidation of extracellular hydroquinones is a causative event for the cytotoxicity of menadione and DMNQ in A549-S cells. Arch Biochem Biophys. 2003 Mar 1;411(1):145-57. PubMed PMID: 12590933; PubMed Central PMCID: PMC2795776.
7: Gao F, Yi J, Shi G, Li H, Shi X, Wang Z, Tang X. [Ascorbic acid enhances the apoptosis of U937 cells induced by arsenic trioxide in combination with DMNQ and its mechanism]. Zhonghua Xue Ye Xue Za Zhi. 2002 Jan;23(1):9-11. Chinese. PubMed PMID: 12015080.
