The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Modane     1,8-dihydroxyanthracene-9,10- dione

Synonyms: Dantrona, Dantrone, Diaquone, Dorbanex, Istizine, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Modane

  • Based on these findings, we conclude that DHAQ produces a long-term (greater than 200 days) toxicity in rats that is not detectable by short-duration toxicity screening [1].
  • A condition closely resembling human melanosis coli was induced in the guinea pig large intestine by daily oral administration of the anthraquinone danthron [2].
  • The binding isotherms for the interaction of DHAQ with Clostridium perfringens DNA and poly(dA-dT).poly(dA-dT) exhibit a small positive slope at low r values, suggestive of cooperative binding [3].
  • 1,4-Dihydroxy-5,8-bis[[2-(hydroxyethyl)amino]ethyl]amino-9,10-anthracenedione (DHAQ) was found to possess potent inhibitory activity against both the P-388 leukemia system (T/C of 299 at 0.5 mg/kg with 4/6 cures) and the B-16 melanoma system (T/C of 503 at 1 mg/kg with 7/10 cures) [4].
  • At low r (bound drug/DNA base pair) values, r less than 0.03, DHAQ binds, in a highly cooperative manner, to calf thymus and Micrococcus lysodeikticus DNAs [3].

High impact information on Modane


Chemical compound and disease context of Modane


Biological context of Modane


Anatomical context of Modane

  • Continued danthron administration caused progressive accumulation of pigmented macrophages in the bowel wall, whereas ongoing migration of pigmented macrophages to regional lymph nodes resulted, after danthron was ceased, in sequential loss of the pigmented cells from the superficial and deep lamina propria [2].
  • PGE2 levels in the colorectal mucosa were significantly (P < 0.05 and 0.001) elevated after DHAQ treatment and showed some evidence of a dependence of DHAQ dose, consistent with the plasma PGE2 levels [16].
  • The effects of 1,8-dihydroxyanthraquinone (DHAQ), a stimulant laxative named danthron, on cell kinetics and prostaglandin (PG) biosynthesis in the gastrointestinal tract were investigated in male 8-week-old F344 rats divided into three groups, each consisting of 10 animals [16].
  • At autopsy performed 5 h after dosing, the highest percentage of the administered DHAQ was in the liver (49.7% +/- 2.7%), followed by the small intestine (7.1% +/- 0.7%), kidneys (2.7% +/- 0.1%), lung (1.9% +/- 0.3%), spleen (1.6% +/- 0.3%), and stomach (1.3% +/- 0.1%) [17].
  • All of the effective mice (17) which were given 0.2% chrysazin diet and which survived more than 500 days developed adenomatous hyperplasia with cystic glands of the cecum [18].

Associations of Modane with other chemical compounds


Gene context of Modane


Analytical, diagnostic and therapeutic context of Modane

  • Electron microscopy of L1210 cells exposed a short time (90 min) to 0.21-21 microM DHAQ reveals segregation of nucleoli; the segregated granular portion shows increased electron opacity [24].
  • A single injection of DHAQ (3 mg/kg i.p.) was equally uneffective up to 200 days after treatment (survival, greater than 90%) [1].
  • Circular dichroism imaging microscopy: application to enantiomorphous twinning in biaxial crystals of 1,8-dihydroxyanthraquinone [25].
  • The direct viral inactivation study demonstrated that HAQ, DHAQ, poly r(A-U) and the HAQ (or DHAQ)/poly r(A-U) combinations did not inactivate the VSV at concentrations near the viral 50% inhibitory dose [26].
  • Studies on laxatives: biliary and urinary excretion in rats given danthron by intravenous infusion or gastric intubation [27].


  1. Effect of dihydroxyanthraquinone (NSC 279836) and thoracic irradiation on long-term survival of rats. Kimler, B.F., Henderson, S.D., Mansfield, C.M., Svoboda, D.J., Cheng, C.C. Cancer Res. (1982) [Pubmed]
  2. Melanosis coli. A consequence of anthraquinone-induced apoptosis of colonic epithelial cells. Walker, N.I., Bennett, R.E., Axelsen, R.A. Am. J. Pathol. (1988) [Pubmed]
  3. The antitumor agent mitoxantrone binds cooperatively to DNA: evidence for heterogeneity in DNA conformation. Rosenberg, L.S., Carvlin, M.J., Krugh, T.R. Biochemistry (1986) [Pubmed]
  4. Antineoplastic agents. Structure-activity relationship study of bis(substituted aminoalkylamino)anthraquinones. Zee-Cheng, R.K., Cheng, C.C. J. Med. Chem. (1978) [Pubmed]
  5. Mutagenicity of quinones: pathways of metabolic activation and detoxification. Chesis, P.L., Levin, D.E., Smith, M.T., Ernster, L., Ames, B.N. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  6. Hydroxyanthraquinones as tumor promoters: enhancement of malignant transformation of C3H mouse fibroblasts and growth stimulation of primary rat hepatocytes. Wölfle, D., Schmutte, C., Westendorf, J., Marquardt, H. Cancer Res. (1990) [Pubmed]
  7. Genotoxicity of a variety of mycotoxins in the hepatocyte primary culture/DNA repair test using rat and mouse hepatocytes. Mori, H., Kawai, K., Ohbayashi, F., Kuniyasu, T., Yamazaki, M., Hamasaki, T., Williams, G.M. Cancer Res. (1984) [Pubmed]
  8. Comparison of the effects of dihydroxyanthraquinone and adriamycin on the survival of cultured Chinese hamster cells. Kimler, B.F., Cheng, C.C. Cancer Res. (1982) [Pubmed]
  9. Ultrastructural evidence of cardiac damage resulting from thoracic irradiation and anthracyclines in the rat. Kimler, B.F., Mansfield, C.M., Svoboda, D.J., Cox, G.G. Int. J. Radiat. Oncol. Biol. Phys. (1984) [Pubmed]
  10. Factors affecting the genotoxic potency ranking of natural anthraquinones in mammalian cell culture systems. Müeller, S.O., Lutz, W.K., Stopper, H. Mutat. Res. (1998) [Pubmed]
  11. Influence of mitoxantrone on nucleolar function in MDA-MB-231 human breast tumor cell line. Chegini, N., Safa, A.R. Cancer Lett. (1987) [Pubmed]
  12. Acute mouse and chronic dog toxicity studies of danthron, dioctyl sodium sulfosuccinate, poloxalkol and combinations. Case, M.T., Smith, J.K., Nelson, R.A. Drug and chemical toxicology. (1977) [Pubmed]
  13. Comparative structure-genotoxicity study of three aminoanthraquinone drugs and doxorubicin. Au, W.W., Butler, M.A., Matney, T.S., Loo, T.L. Cancer Res. (1981) [Pubmed]
  14. Effect of dihydroxyanthraquinone and radiation on G2 progression. Kimler, B.F. Cancer Res. (1980) [Pubmed]
  15. Action of dihydroxyanthraquinone on cell cycle progression and survival of a variety of cultured mammalian cells. Traganos, F., Evenson, D.P., Staiano-Coico, L., Darzynkiewicz, Z., Melamed, M.R. Cancer Res. (1980) [Pubmed]
  16. Enhancement of cell proliferation and prostaglandin biosynthesis by 1,8-dihydroxyanthraquinone in the rat large intestine. Nishikawa, A., Kase, Y., Hayakawa, T., Yanagisawa, T., Kanno, J., Hayashi, Y. Carcinogenesis (1997) [Pubmed]
  17. Pharmacological disposition of 1,4-dihydroxy-5-8-bis[[2 [(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione dihydrochloride in the dog. Lu, K., Savaraj, N., Loo, T.L. Cancer Chemother. Pharmacol. (1984) [Pubmed]
  18. Carcinogenicity of chrysazin in large intestine and liver of mice. Mori, H., Sugie, S., Niwa, K., Yoshimi, N., Tanaka, T., Hirono, I. Jpn. J. Cancer Res. (1986) [Pubmed]
  19. Clinical kinetics of 1, 4-dihydroxy-5,8-bis [(2-[(2-hydroxyethyl) amino] ethyl] amino ]-9, 10-anthracenedione. Savaraj, N., Lu, K., Valdivieso, M., Burgess, M., Umsawasdi, T., Benjamin, R.S., Loo, T.L. Clin. Pharmacol. Ther. (1982) [Pubmed]
  20. Inhibition of DNA replication and repair by anthralin or danthron in cultured human cells. Clark, J.M., Hanawalt, P.C. J. Invest. Dermatol. (1982) [Pubmed]
  21. Promoting and synergistic effects of chrysazin on 1,2-dimethylhydrazine-induced carcinogenesis in male ICR/CD-1 mice. Sugie, S., Mori, Y., Okumura, A., Yoshimi, N., Okamoto, K., Sato, S., Tanaka, T., Mori, H. Carcinogenesis (1994) [Pubmed]
  22. Inactivation of mouse epidermal 12-lipoxygenase by anthralin--implications for the role of oxygen radicals. Müller, K., Gawlik, I. Biochem. Pharmacol. (1996) [Pubmed]
  23. Sequence-specific DNA damage induced by carcinogenic danthron and anthraquinone in the presence of Cu(II), cytochrome P450 reductase and NADPH. Ohkuma, Y., Hiraku, Y., Kawanishi, S. Free Radic. Res. (2001) [Pubmed]
  24. Relationship between the pharmacological activity of antitumor drugs Ametantrone and mitoxantrone (Novatrone) and their ability to condense nucleic acids. Kapuscinski, J., Darzynkiewicz, Z. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  25. Circular dichroism imaging microscopy: application to enantiomorphous twinning in biaxial crystals of 1,8-dihydroxyanthraquinone. Claborn, K., Puklin-Faucher, E., Kurimoto, M., Kaminsky, W., Kahr, B. J. Am. Chem. Soc. (2003) [Pubmed]
  26. Enhancement of the antiviral activity of poly r(A-U) by ametantrone and mitoxantrone. Jamison, J.M., Krabill, K., Flowers, D.G., Tsai, C. Life Sci. (1990) [Pubmed]
  27. Studies on laxatives: biliary and urinary excretion in rats given danthron by intravenous infusion or gastric intubation. Sund, R.B. Pharmacol. Toxicol. (1987) [Pubmed]
WikiGenes - Universities