Protein Information

Name menadione reductase
Synonyms Diaphorase; DHQU; DIA 4; DIA4; DT diaphorase; DTD; Diaphorase (NADH/NADPH); Diaphorase (NADH/NADPH) (cytochrome b 5 reductase)…

Compound Information

Name 1-naphthol
CAS 1-naphthalenol

Reference List

PubMed Abstract RScore(About this table)
6200119 Doherty MD, Cohen GM, Smith MT: Mechanisms of toxic injury to isolated hepatocytes by 1-naphthol. . Biochem Pharmacol. 1984 Feb 15;33(4):543-9.

The toxicity of 1-naphthol and the naphthoquinones was potentiated by dicoumarol, an inhibitor of DT-diaphorase (NAD (P) H:quinone oxidoreductase).
81(1,1,1,1) Details
12719939 Blumel S, Stolz A: Cloning and characterization of the gene coding for the aerobic azoreductase from Pigmentiphaga kullae K24. Appl Microbiol Biotechnol. 2003 Aug;62(2-3):186-90. Epub 2003 Apr 26.

The azoreductase was heterologously expressed in Escherichia coli and shown to convert the sulfonated azo dye Orange I and furthermore Magneson II [4-(4-nitrophenylazo)-1-naphthol].
33(0,1,1,3) Details
1567468 Wortelboer HM, de Kruif CA, van Iersel AA, Falke HE, Noordhoek J, Blaauboer BJ: Acid reaction products of indole-3-carbinol and their effects on cytochrome P450 and phase II enzymes in rat and monkey hepatocytes. Biochem Pharmacol. 1992 Apr 1;43(7):1439-47.

In rat hepatocytes DIM, CTI and BII enhanced DT-diaphorase (DTD) (= NAD (P) H-quinone reductase) activity, and DIM and BII the glucuronidation of 1-naphthol.
31(0,1,1,1) Details
16906435 Elovaara E, Mikkola J, Stockmann-Juvala H, Luukkanen L, Keski-Hynnila H, Kostiainen R, Pasanen M, Pelkonen O, Vainio H: Polycyclic aromatic hydrocarbon (PAH) metabolizing enzyme activities in human lung, and their inducibility by exposure to naphthalene, phenanthrene, pyrene, chrysene, and benzo (a) pyrene as shown in the rat lung and liver. Arch Toxicol. 2007 Mar;81(3):169-82. Epub 2006 Aug 12.

PAH treatment increased the CYP1A-catalyzed activity of pyrene 1-hydroxylation and 7-ethoxyresorufin O-deethylation in rat liver by up to 28- and 279-fold, and in rat lung by up to 22- and 51-fold, respectively. 1-Naphthol (hUGT1A6), 1-hydroxypyrene (hUGT1A6/1A9), and entacapone (hUGT1A9) are markers of PAH-glucuronidating human uridine diphosphate-glucuronosyltransferases (UGT).
NADPH:quinone oxidoreductase 1 (NQO1) and glutathione S-transferase activities increased up to 5.3- and 1.6-fold (liver), and up to 4.4- and 1.4-fold (lung), respectively.
3(0,0,0,3) Details
9849642 Carr BA, Franklin MR: Drug-metabolizing enzyme induction by 2,2'-dipyridyl, 1,7-phenanthroline, 7,8-benzoquinoline and oltipraz in mouse. Xenobiotica. 1998 Oct;28(10):949-56.

UDP-glucuronosyltransferase (UGT) activities showed only limited changes, UGT activity towards 4-nitrophenol and 1-naphthol was induced by the 75 mg/kg dose of 2,2'-dipyridyl and UGT activity towards morphine was induced by 150 mg/kg doses of 7,8-benzoquinoline and oltipraz.
In contrast with the limited effect on UGT activities, glutathione S-transferase and NAD (P) H:quinone oxidoreductase activities were significantly elevated by most compounds.
2(0,0,0,2) Details
11719866 Martucciello G, Favre A, Torre M, Pini Prato A, Jasonni V: A new rapid acetylcholinesterase histochemical method for the intraoperative diagnosis of Hirschsprung's disease and intestinal neuronal dysplasia. Eur J Pediatr Surg. 2001 Oct;11(5):300-4.

We propose the following diagnostic protocols: a) for preoperative histochemical study: conventional AChE plus LDH and NADPH-diaphorase; b) for intraoperative study: rapid AChE plus ANE.
To avoid these limitations, in 1994 Kobayashi et al first proposed an accelerated modified method in two different versions, the first using diaminobenzydine (DAB) reagent, the second using 4-chloro-1-naphthol as final reagent.
1(0,0,0,1) Details
6506770 Fujita S, Suzuki M, Suzuki T: Structure-activity relationships in the induction of hepatic drug metabolism by azo compounds. Xenobiotica. 1984 Jul;14(7):565-8.

Lipophilic azo compounds possessing 1-phenylazo-2-naphthol or 1-phenylazo-2-naphthylamine moieties induced cytochrome P-448 and related mono-oxygenase activities, UDP-glucuronyltransferase activity towards p-nitrophenol, glutathione-S-transferase activity towards 1-chloro-2,4-dinitrobenzene, aldehyde dehydrogenase, and menadione reductase activities.
None of the hydrophilic azo compounds tested and none of the other lipophilic azo compounds tested including 4-phenylazo-1-naphthol induced these activities.
1(0,0,0,1) Details
3143406 Haniu M, Yuan H, Chen SA, Iyanagi T, Lee TD, Shively JE: Structure-function relationship of NAD (P) H:quinone reductase: characterization of NH2-terminal blocking group and essential tyrosine and lysine residues. Biochemistry. 1988 Sep 6;27(18):6877-83.


The amino terminal blocked peptide of rat liver NAD (P) H:quinone reductase (DT-diaphorase) was determined by amino acid sequence analysis and by mass spectrometry.
1(0,0,0,1) Details