Protein Information

Name NADPH cytochrome P450 reductase
Synonyms CPR; CYPOR; Cytochrome P 450 reductase; Cytochrome P450 reductase; NADPH cytochrome P450 reductase; NADPH cytochrome P450 reductase; P450 (cytochrome) oxidoreductase; P450R…

Compound Information

Name anthraquinone
CAS 9,10-anthracenedione

Reference List

PubMed Abstract RScore(About this table)
9488113 Chat M, Bayol-Denizot C, Suleman G, Roux F, Minn A: Drug metabolizing enzyme activities and superoxide formation in primary and immortalized rat brain endothelial cells. Life Sci. 1998;62(2):151-63.

The superoxide production observed during NADPH-cytochrome P450 reductase-dependent monoelectronic reduction of four xenobiotics, menadione, anthraquinone, nitrofurazone and diquat, was also investigated in these cultured cells at confluence.
82(1,1,1,2) Details
2826236 Sushkov DG, Gritsan NP, Weiner LM: Generation of OH radical during enzymatic reduction of 9,10-anthraquinone-2-sulphonate. FEBS Lett. 1987 Dec 10;225(1-2):139-44.

Spin-trapping experiments have shown that 9,10-anthraquinone-2-sulphonate (AQS) can be reduced enzymatically with NADPH-cytochrome P-450 reductase (FP) producing OH radicals.
81(1,1,1,1) Details
11697035 Ohkuma Y, Hiraku Y, Kawanishi S: Sequence-specific DNA damage induced by carcinogenic danthron and anthraquinone in the presence of Cu (II), cytochrome P450 reductase and NADPH. Free Radic Res. 2001 Jun;34(6):595-604.
7(0,0,1,2) Details
12688675 Pawlowska J, Tarasiuk J, Wolf CR, Paine MJ, Borowski E: Differential ability of cytostatics from anthraquinone group to generate free radicals in three enzymatic systems: NADH dehydrogenase, NADPH cytochrome P450 reductase, and xanthine oxidase. Oncol Res. 2003;13(5):245-52.
7(0,0,1,2) Details
2823819 Graham MA, Newell DR, Butler J, Hoey B, Patterson LH: The effect of the anthrapyrazole antitumour agent CI941 on rat liver microsome and cytochrome P-450 reductase mediated free radical processes. Biochem Pharmacol. 1987 Oct 15;36(20):3345-51.

In view of the proposed role of drug free radical formation, superoxide generation and lipid peroxidation in anthracycline and anthraquinone induced toxicities, the redox biochemistry of CI941 has been investigated.
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10838165 Bayol-Denizot C, Daval JL, Netter P, Minn A: Xenobiotic-mediated production of superoxide by primary cultures of rat cerebral endothelial cells, astrocytes, and neurones. Biochim Biophys Acta. 2000 Jun 2;1497(1):115-26.

In order to characterise the risk of oxidative stress to both the central nervous system and the blood-brain barrier, we measured in the present work the release of superoxide in the culture medium of rat cerebrovascular endothelial cells during the metabolism of menadione, anthraquinone, diquat or nitrofurazone.
Superoxide formation by microsomes prepared from the cultured cells was decreased by immunoinhibition of NADPH-cytochrome P450 reductase or by its irreversible inhibition by diphenyliodonium chloride, suggesting the involvement of this flavoprotein in radical production.
1(0,0,0,1) Details
10521685 Marczylo TH, Hayatsu T, Arimoto-Kobayashi S, Tada M, Fujita K, Kamataki T, Nakayama K, Hayatsu H: Protection against the bacterial mutagenicity of heterocyclic amines by purpurin, a natural anthraquinone pigment. Mutat Res. 1999 Aug 18;444(2):451-61.

Finally, purpurin was responsible for the inhibition of human CYP1A2 and human NADPH-cytochrome P450 reductase and a decrease in the bioactivation of Trp-P-2 by these enzymes when they were expressed in Salmonella typhimurium TA1538ARO.
1(0,0,0,1) Details
9625728 Kumagai Y, Nakajima H, Midorikawa K, Homma-Takeda S, Shimojo N: Inhibition of nitric oxide formation by neuronal nitric oxide synthase by quinones: nitric oxide synthase as a quinone reductase. Chem Res Toxicol. 1998 Jun;11(6):608-13.


Reductase activity of PQ by purified nNOS required CaCl2/calmodulin and was markedly suppressed by the flavoprotein inhibitor diphenyleneiodonium but not by l-nitroarginine which is a specific inhibitor for NO formation. nNOS effectively reduced the quinones as well as PQ causing a marked decrease in the production of NO from l-arginine, while 1, 4-benzoquinone, 9,10-anthraquinone, mitomycin C, and lapachol, which show negligible inhibitory action on nNOS activity, were poor substrates for the enzyme on reduction.
0(0,0,0,0) Details
12744663 Marczylo T, Sugiyama C, Hayatsu H: Protection against Trp-P-2 DNA adduct formation in C57bl6 mice by purpurin is accompanied by induction of cytochrome P450. J Agric Food Chem. 2003 May 21;51(11):3334-7.

Purpurin, an anthraquinone constituent from madder root, has previously been reported as antimutagenic in the Ames Salmonella bacterial mutagenicity assay and as antigenotoxic in Drosophila melanogaster, against a range of environmental carcinogens.
The decrease in adduct formation was accompanied by significant, dose-dependent inductions of hepatic cytochrome P450-dependent dealkylations of methoxy- (CYP1A2), ethoxy- (CYP1A1), and pentoxy- (CYP2B) resorufins, total cytochrome P450, and NADPH cytochrome P450 reductase.
1(0,0,0,1) Details
12379470 Takahashi E, Fujita K, Kamataki T, Arimoto-Kobayashi S, Okamoto K, Negishi T: Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. Mutat Res. 2002 Oct 31;508(1-2):147-56.

We also examined the effects of these pigments on the mutagenicities of MeIQx and B [a] P in the Ames test, using Salmonella typhimurium TA1538 co-expressing each form of human CYP and NADPH-cytochrome P450 reductase (OR).
Recently we have shown that anthraquinone food pigments such as purpurin and alizarin suppress the genotoxic activities of several mutagens including heterocyclic amines and polycyclic aromatic hydrocarbons in the Drosophila DNA repair test and in the Ames test.
1(0,0,0,1) Details
1324674 Cummings J, Graham MA, Hoey BM, Butler J, Fry AM, Hickson ID, Leonard G, French R, Smyth JF: Studies on the molecular pharmacology of GR63178A. Biochem Pharmacol. 1992 Aug 4;44(3):433-9.

In conclusion, GR63178A is unlikely to mediate its antitumour activity by DNA binding, topoisomerase II inhibition or free radical formation in direct contrast to similar anthracycline- and anthraquinone-based anticancer drugs.
Free radical chemistry was studied by both pulse radiolysis and ESR spectroscopy as well as by in vitro drug incubations with NADPH-fortified rat liver microsomes and purified cytochrome P450 reductase.
1(0,0,0,1) Details
2850767 Vile GF, Winterbourn CC: Microsomal reduction of low-molecular-weight Fe3+ chelates and ferritin: enhancement by adriamycin, paraquat, menadione, and anthraquinone 2-sulfonate and inhibition by oxygen. Arch Biochem Biophys. 1988 Dec;267(2):606-13.

0(0,0,0,0) Details
1963615 Fisher GR, Brown JR, Patterson LH: Involvement of hydroxyl radical formation and DNA strand breakage in the cytotoxicity of anthraquinone antitumour agents. Free Radic Res Commun. 1990;11(1-3):117-25.

0(0,0,0,0) Details