>>Signaling Pathways>> Cancer Biology>> Tumor Microenvironment>>(±)-Dunnione

(±)-Dunnione (Synonyms: NSC 95403)

Catalog No.GC18787

(±)-Dunnione is a naturally occurring naphthoquinone with diverse biological activities.

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(±)-Dunnione Chemical Structure

Cas No.: 521-49-3

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

(±)-Dunnione is a naturally occurring naphthoquinone with diverse biological activities.[1][2][3][4]  It exhibits fungicidal activity against ten agriculturally relevant plant fungi in vitro (MICs = 5-20 mg/L) and in infected wheat and barley plants (EC50s = 2-20 mg/L)[1]. (±)-Dunnione also reduces the growth of T. cruzi epimastigotes (IC50 = 4.01 μM)[2]. It is a substrate for NAD(P)H:quinone oxidoreductase 1 (NQO1) that increases production of reactive oxygen species (ROS) and induces cell death of A549 lung carcinoma cells (IC50 = 6.1 μM).[3] (±)-Dunnione (20 mg/kg per day for 4 days) increases intracellular NAD+ and prevents inflammatory cytokine production and small intestinal damage induced by cisplatin in mice.[4]

Reference:

[1]. Khambay, B.P.S., Batty, D., Jewess, P.J., et al. Mode of action and pesticidal activity of the natural product dunnione and of some analogues Pest. Manag. Sci. 59(2), 174-182 (2003).
[2]. Salas, C.O., Faúndez, M., Morello, A., et al. Natural and synthetic naphthoquinones active against Trypanosoma cruzi: An initial step towards new drugs for Chagas disease Curr. Med. Chem. 18(1), 144-161 (2011).
[3]. Bian, J., Xu, L., Deng, B., et al. Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1) Bioorg. Med. Chem. Lett. 25(6), 1244-1248 (2015).
[4]. Pandit, A., Kim, H.-J., Oh, G.-S., et al. Dunnione ameliorates cisplatin-induced small intestinal damage by modulating NAD(+) metabolism Biochem. Bioph. Res. Commun. 467(4), 697-703 (2015).

Chemical Properties

Cas No. 521-49-3 SDF
Synonyms NSC 95403
Chemical Name 2,3-dihydro-2,3,3-trimethyl-naphtho[1,2-b]furan-4,5-dione
Canonical SMILES O=C(C1=CC=CC=C1C2=C3C(C)(C)C(C)O2)C3=O
Formula C15H14O3 M.Wt 242.3
Solubility DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 4.1271 mL 20.6356 mL 41.2712 mL
5 mM 0.8254 mL 4.1271 mL 8.2542 mL
10 mM 0.4127 mL 2.0636 mL 4.1271 mL
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Review for (±)-Dunnione

Average Rating: 5 ★★★★★ (Based on Reviews and 30 reference(s) in Google Scholar.)

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