Deoxynyboquinone|NSC 165572;DNQ

Cas No.:	96748-86-6
Chemical Name:	1,4,6-Trimethylpyrido[3,2-g]quinoline-2,5,8,10(1H,9H)-tetrone
Synonyms:	NSC 165572;DNQ
SMILES:	O=C1NC2=C(C(C)=C1)C(=O)C3=C(N(C)C(=O)C=C3C)C2=O
Formula:	C₁₅H₁₂N₂O₄
M.Wt:	284.271
Purity:	>98%
Sotrage:	2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO

Description:

1 Isobutyl-deoxynyboquinone (IB-DNQ) is a selective substrate for NAD(P)H:quinone oxidoreductase (NQO1), produces ROS, and induces cytotoxicity in cancer cells in an NQO1-dependent manner; has improved solubility and biocompatibility in comparison with DNQ; a superior drug candidate for evaluating anticancer activities and tolerability in vivo.
2 Deoxynyboquinone, also known as DNQ, is a potent inducer of cancer cell death. DNQ potently induces death of cancer cells in culture, with IC(50) values between 16 and 210 nM. In addition, unlike the experimental therapeutic elesclomol, DNQ is still able to induce cancer cell death under hypoxic conditions. This mechanistic understanding of DNQ will allow for a more comprehensive evaluation of the potential of direct ROS generation as an anticancer strategy, and DNQ itself has potential as a novel anticancer agent.

References:

1: Kolossov VL, Ponnuraj N, Beaudoin JN, Leslie MT, Kenis PJ, Gaskins HR. Distinct responses of compartmentalized glutathione redox potentials to pharmacologic quinones targeting NQO1. Biochem Biophys Res Commun. 2017 Jan 29;483(1):680-686. doi: 10.1016/j.bbrc.2016.12.082. PubMed PMID: 27986568; PubMed Central PMCID: PMC5253246. 2: Lundberg AP, Francis JM, Pajak M, Parkinson EI, Wycislo KL, Rosol TJ, Brown ME, London CA, Dirikolu L, Hergenrother PJ, Fan TM. Pharmacokinetics and derivation of an anticancer dosing regimen for the novel anti-cancer agent isobutyl-deoxynyboquinone (IB-DNQ), a NQO1 bioactivatable molecule, in the domestic felid species. Invest New Drugs. 2016 Dec 14. [Epub ahead of print] PubMed PMID: 27975234. 3: Parkinson EI, Hergenrother PJ. Deoxynyboquinones as NQO1-Activated Cancer Therapeutics. Acc Chem Res. 2015 Oct 20;48(10):2715-23. doi: 10.1021/acs.accounts.5b00365. PubMed PMID: 26444384. 4: Cao L, Li LS, Spruell C, Xiao L, Chakrabarti G, Bey EA, Reinicke KE, Srougi MC, Moore Z, Dong Y, Vo P, Kabbani W, Yang CR, Wang X, Fattah F, Morales JC, Motea EA, Bornmann WG, Yordy JS, Boothman DA. Tumor-selective, futile redox cycle-induced bystander effects elicited by NQO1 bioactivatable radiosensitizing drugs in triple-negative breast cancers. Antioxid Redox Signal. 2014 Jul 10;21(2):237-50. doi: 10.1089/ars.2013.5462. PubMed PMID: 24512128; PubMed Central PMCID: PMC4060774. 5: Parkinson EI, Bair JS, Cismesia M, Hergenrother PJ. Efficient NQO1 substrates are potent and selective anticancer agents. ACS Chem Biol. 2013 Oct 18;8(10):2173-83. doi: 10.1021/cb4005832. PubMed PMID: 23937670. 6: Tian XP, Long LJ, Li SM, Zhang J, Xu Y, He J, Li J, Wang FZ, Li WJ, Zhang CS, Zhang S. Pseudonocardia antitumoralis sp. nov., a deoxynyboquinone-producing actinomycete isolated from a deep-sea sediment. Int J Syst Evol Microbiol. 2013 Mar;63(Pt 3):893-9. doi: 10.1099/ijs.0.037135-0. Erratum in: Int J Syst Evol Microbiol. 2013 May;63(Pt 5):1936. PubMed PMID: 22634702. 7: Huang X, Dong Y, Bey EA, Kilgore JA, Bair JS, Li LS, Patel M, Parkinson EI, Wang Y, Williams NS, Gao J, Hergenrother PJ, Boothman DA. An NQO1 substrate with potent antitumor activity that selectively kills by PARP1-induced programmed necrosis. Cancer Res. 2012 Jun 15;72(12):3038-47. doi: 10.1158/0008-5472.CAN-11-3135. PubMed PMID: 22532167; PubMed Central PMCID: PMC4795165. 8: Li S, Tian X, Niu S, Zhang W, Chen Y, Zhang H, Yang X, Zhang W, Li W, Zhang S, Ju J, Zhang C. Pseudonocardians A-C, new diazaanthraquinone derivatives from a deap-sea actinomycete Pseudonocardia sp. SCSIO 01299. Mar Drugs. 2011;9(8):1428-39. doi: 10.3390/md9081428. PubMed PMID: 21892356; PubMed Central PMCID: PMC3164384. 9: Bair JS, Palchaudhuri R, Hergenrother PJ. Chemistry and biology of deoxynyboquinone, a potent inducer of cancer cell death. J Am Chem Soc. 2010 Apr 21;132(15):5469-78. doi: 10.1021/ja100610m. PubMed PMID: 20345134.

MSDS

COA

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2018-0101

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