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Chemical Compound Review

Cygnoline     anthracene-1,8,9-triol

Synonyms: Batidrol, Cygnolin, Dermaline, Derobin, Psoriacide, ...
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Disease relevance of Cignolin

  • Dithranol for psoriasis [1].
  • These retinoids also inhibited the appearance of papillomas in mouse epidermis in the two-stage tumorigenesis model using 7,12-dimethylbenz(a)anthracene (200 nmol) as the initiator and anthralin (444 nmol) as the promoter during the 32-week period of promotion [2].
  • No parallel effect was observed for epidermal Langerhans (Ia+) cells, the second major epidermal immunofunctional cell type, except in the case of anthralin, a finding which is consistent with the reported toxicity of this agent [3].
  • In the cyanobacterium Synechococcus PCC 6311 anthralin increases the pH gradient and decreases ATP levels [4].
  • Finally, we have shown that hyperthermia and anthralin treatments are toxic for LC whereas they have little or no effect on keratinocyte viability [5].

Psychiatry related information on Cignolin


High impact information on Cignolin

  • It is concluded that dithranol inflammation is initiated by formation of free radicals; these may act through lipid peroxidation and production of inflammatory endoperoxides or by a more direct mechanism [7].
  • However, despite its superiority in terms of cost and patient acceptability, P.U.V.A. cannot be recommended as the first line of treatment for patients with uncomplicated, dithranol-responsive plaque psoriasis until there is more information on relapse-rate and toxicity [8].
  • Inhibition by retinoids of anthralin-induced mouse epidermal ornithine decarboxylase activity and anthralin-promoted skin tumor formation [2].
  • The skin tumor-promoting ability of 1,8-dihydroxy-3-methyl-9-anthrone (chrysarobin) was compared with that of 12-O-tetradecanoylphorbol-13-acetate (TPA) and 1,8-dihydroxy-9-anthrone (anthralin) in SENCAR mice [9].
  • Maximal papilloma responses were achieved by 15 weeks of promotion with TPA whereas at least 25 weeks of promotion were necessary to achieve maximal papilloma responses with chrysarobin or anthralin indicating marked differences in tumor latency between the two classes of compounds [9].

Chemical compound and disease context of Cignolin


Biological context of Cignolin


Anatomical context of Cignolin


Associations of Cignolin with other chemical compounds


Gene context of Cignolin


Analytical, diagnostic and therapeutic context of Cignolin

  • Dithranol or photochemotherapy for psoriasis [27]?
  • MALDI spectra of medium molar mass PET, representative of the entire molar mass distribution, were obtained only when a good solvent for PET was used, such as 1,1,1,3,3,3-hexafluoro-2-propanol (commonly referred to as HFIP), as the sample preparation solvent and dithranol as the matrix [28].
  • Oral administration of 30 mg/kg TMK688, a dose which markedly inhibits tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated LTB4 formation in mouse skin, markedly inhibited both TPA-promoted and a non-TPA-type tumor promoter anthralin-promoted skin tumor formation in 7,12-dimethylbenz[a]anthracene (DMBA)-initiated CD-1 mice [29].
  • Treatment of human skin in organ culture produced similar levels of adducts, while treatment with dithranol, a non-mutagenic therapeutic agent, resulted in chromatograms indistinguishable from those from untreated controls [30].
  • These results are correlated with those obtained with intact whole human epidermis and suction blister fluid showing that, in the former case, anthralin binds to protein as suggested by absorption and fluorescence spectroscopies [31].


  1. Dithranol for psoriasis. Whitefield, M. Lancet (1979) [Pubmed]
  2. Inhibition by retinoids of anthralin-induced mouse epidermal ornithine decarboxylase activity and anthralin-promoted skin tumor formation. Dawson, M.I., Chao, W.R., Helmes, C.T. Cancer Res. (1987) [Pubmed]
  3. Effect of tumor-promoting agents on density and morphometric parameters of mouse epidermal Langerhans and Thy-1+ cells. Baxter, C.S., Andringa, A., Chalfin, K., Miller, M.L. Carcinogenesis (1991) [Pubmed]
  4. The antipsoriatic compound anthralin influences bioenergetic parameters and redox properties of energy transducing membranes. Fuchs, J., Nitschmann, W.H., Packer, L. J. Invest. Dermatol. (1990) [Pubmed]
  5. Inhibition of a Langerhans cell-mediated immune response by treatment modalities useful in psoriasis. Morhenn, V.B., Orenberg, E.K., Kaplan, J., Pfendt, E., Terrell, C., Engleman, E.G. J. Invest. Dermatol. (1983) [Pubmed]
  6. Clinical studies with a novel dithranol formulation (Micanol) in combination with UVB at day-care centres. Christensen, O.B., Brolund, L. Acta dermato-venereologica. Supplementum. (1992) [Pubmed]
  7. Inhibition of dithranol inflammation by free-radical scavengers. Finnen, M.J., Lawrence, C.M., Shuster, S. Lancet (1984) [Pubmed]
  8. Comparison of photochemotherapy and dithranol in the treatment of chronic plaque psoriasis. Rogers, S., Marks, J., Shuster, S., Briffa, D.V., Warin, A., Greaves, M. Lancet (1979) [Pubmed]
  9. Mechanism of mouse skin tumor promotion by chrysarobin. DiGiovanni, J., Decina, P.C., Prichett, W.P., Cantor, J., Aalfs, K.K., Coombs, M.M. Cancer Res. (1985) [Pubmed]
  10. Tumor-producing and skin-irritating activity of dithranol (anthralin) and its 10-acyl analogues in SENCAR mice. Viluksela, M., Puotunen, E., Newman, A.J., Männistö, P.T. Carcinogenesis (1986) [Pubmed]
  11. Dithranol modulates the leukotriene B4-induced intraepidermal accumulation of polymorphonuclear leukocytes. Chang, A., Alkemade, H., van de Kerkhof, P.C. J. Invest. Dermatol. (1989) [Pubmed]
  12. Psoriasis: utilising the treatment options. Marks, J.M. Drugs (1980) [Pubmed]
  13. Epidermal activity of NAD-dependent isocitrate dehydrogenase in psoriasis during treatment with dithranol. Hammar, H. J. Invest. Dermatol. (1975) [Pubmed]
  14. Nonspecific inhibition of DNA repair synthesis by tumor promoters in human diploid fibroblasts damaged with N-acetoxy-2-acetylaminofluorene. Poirier, M.C., De Cicco, B.T., Lieberman, M.W. Cancer Res. (1975) [Pubmed]
  15. Effect of tumor promoters on ultraviolet light-induced mutation and mitotic recombination in Saccharomyces cerevisiae. Kunz, B.A., Hannan, M.A., Haynes, R.H. Cancer Res. (1980) [Pubmed]
  16. Anti-psoriatic drug anthralin activates transcription factor NF-kappa B in murine keratinocytes. Schmidt, K.N., Podda, M., Packer, L., Baeuerle, P.A. J. Immunol. (1996) [Pubmed]
  17. The effect of anthralin and its derivatives on epidermal cell kinetics. Fisher, L.B., Maibach, H.I. J. Invest. Dermatol. (1975) [Pubmed]
  18. Anthralin (1,8-dihydroxyanthrone) is a potent inhibitor of leukotriene production and LTB4-omega oxidation by human neutrophils. Schröder, J.M. J. Invest. Dermatol. (1986) [Pubmed]
  19. Anthralin decreases keratinocyte TGF-alpha expression and EGF-receptor binding in vitro. Gottlieb, A.B., Khandke, L., Krane, J.F., Staiano-Coico, L., Ashinoff, R., Krueger, J.G. J. Invest. Dermatol. (1992) [Pubmed]
  20. Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase. Müller, K., Gürster, D., Piwek, S., Wiegrebe, W. J. Med. Chem. (1993) [Pubmed]
  21. Induction of plasminogen activator in cultured cells by macrocyclic plant diterpene esters and other agents related to tumor promotion. Wigler, M., DeFeo, D., Weinstein, I.B. Cancer Res. (1978) [Pubmed]
  22. Differential effects of structurally unrelated chemical irritants on the density and morphology of epidermal CD1+ cells. Willis, C.M., Stephens, C.J., Wilkinson, J.D. J. Invest. Dermatol. (1990) [Pubmed]
  23. Anthralin inhibition of mouse epidermal arachidonic acid lipoxygenase in vitro. Bedord, C.J., Young, J.M., Wagner, B.M. J. Invest. Dermatol. (1983) [Pubmed]
  24. Comparison of tumour promoter-induced prostaglandin E2 release in human and rat keratinocytes. Lawrence, J.N., Benford, D.J. Carcinogenesis (1995) [Pubmed]
  25. Anthralin (dithranol) in vitro inhibits human monocytes to secrete IL-6, IL-8 and TNF-alpha, but not IL-1. Mrowietz, U., Jessat, H., Schwarz, A., Schwarz, T. Br. J. Dermatol. (1997) [Pubmed]
  26. Dithranol upregulates IL-10 receptors on the cultured human keratinocyte cell line HaCaT. Farkas, A., Kemény, L., Szöny, B.J., Bata-Csörgö, Z., Pivarcsi, A., Kiss, M., Széll, M., Koreck, A., Dobozy, A. Inflamm. Res. (2001) [Pubmed]
  27. Dithranol or photochemotherapy for psoriasis? Howell, D.R. Lancet (1979) [Pubmed]
  28. Importance of solubility in the sample preparation of poly(ethylene terephthalate) for MALDI TOFMS. Hoteling, A.J., Mourey, T.H., Owens, K.G. Anal. Chem. (2005) [Pubmed]
  29. Inhibition of two-stage skin carcinogenesis as well as complete skin carcinogenesis by oral administration of TMK688, a potent lipoxygenase inhibitor. Jiang, H., Yamamoto, S., Kato, R. Carcinogenesis (1994) [Pubmed]
  30. Formation of DNA adducts in the skin of psoriasis patients, in human skin in organ culture, and in mouse skin and lung following topical application of coal-tar and juniper tar. Schoket, B., Horkay, I., Kósa, A., Páldeák, L., Hewer, A., Grover, P.L., Phillips, D.H. J. Invest. Dermatol. (1990) [Pubmed]
  31. Physicochemical properties and stability of anthralin in model systems and human skin. Melo, T.S., Dubertret, L., Prognon, P., Gond, A., Mahuzier, G., Santus, R. J. Invest. Dermatol. (1983) [Pubmed]
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