The antipsoriatic anthrones anthralin and butantrone caused degradation of the DNA sugar deoxyribose in the presence of ferric salt. The degradation was substantially inhibited by iron-binding hydroxyl radical scavengers, iron chelators, superoxide dismutase (SOD) and catalase, suggesting a mechanism in which antipsoriatic anthrones generate hydroxyl radicals via the Fenton reaction or an iron-catalysed Haber-Weiss reaction. Butantrone was markedly less efficient at generating hydroxyl radicals than anthralin. Using bovine brain phospholipid liposomes as model membranes to study the effects of antipsoriatic anthrones on lipid peroxidation, the peroxidation of liposomal membranes in the presence of ferric salt was maximally enhanced by anthralin and butantrone at 12.5 and 5 microM, respectively. Higher concentrations of the drugs resulted in less peroxidation. Chain-breaking antioxidants and iron chelators strongly decreased anthralin-enhanced lipid peroxidation, suggesting the involvement of hydroxyl, peroxyl or alkoxyl radicals. In contrast to their stimulatory effects on liposomal membrane peroxidation, both anthralin and butantrone diminished Fe3+/ascorbate-induced lipid peroxidation in liposomes. Butantrone was more effective as an inhibitor of lipid peroxidation than was anthralin. The antioxidant properties of antipsoriatic anthrones were determined in terms of their reactivities with the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). Antioxidant activity of antipsoriatic anthrones requires the presence of free hydroxyl groups at C-1 and C-8 and at least one hydrogen atom at C-10 of the anthrone nucleus. The role of active oxygen species produced by antipsoriatic anthrones and the biological effects on cellular targets are discussed with respect to the mode of action and manifestation of side effects of these drugs.

01 Aug 1990·Contact DermatitisQ2 · MEDICINE

Studies on the contact sensitizing activity of dithranol (anthralin) and 10‐butyryl dithranol (butantrone)

Q2 · MEDICINE

Article

Author: Matti Viluksela ; Kristiina Haasio ; Pekka T. Männistö

The contact sensitizing activity of dithranol and butantrone (10‐butyryl dithranol) was studied in 3 animal models: the guinea pig maximization test (GPMT). the closed patch test (CPT), and the mouse ear swelling lest (MUST) in 2 different mouse strains. In the GPMT. both dithranol and, to a greater extent, butantrone showed sensitizing potential. Because butaintrone was less irritant, the concentrations used were 10 x higher than those of dithranol. In the CPT, only butantrone was slightly positive. In the MEST. with both CF‐1 and Balb/c mice, dithranol caused less swelling of the test ear after challenge than butantrone. According to the evalution criteria of the MEST, only butantrone caused sensitization in 50% of the CF‐1 mice and in 40% of the Balb/c mice. Thus, the GPMT was the only test which indicated the minor contact sensitizing potential of dithranol. On the other hand, the 10‐butyryl analogue of dithranol showed undoubtedly stronger contact sensitizing potential than the parent compound in all tests. Therefore, as compared to dithranol, an increased risk of sensitization should be considered.

01 Apr 1989·British Journal of DermatologyQ1 · MEDICINE

Inhibition of proliferation of HeLa cells by dithranol (anthralin) and 10-butyryl dithranol (butantrone)

Q1 · MEDICINE

Article

Author: Arja‐Leena Kariniemi ; Stig Nordling ; Anita Remitz ; Eero Lehtonen

The effects were studied of two antipsoriatic drugs, dithranol (anthralin) and butantrone on the proliferation of HeLa cells. Non-confluent monolayers of HeLa cells were treated with various concentrations (10(-5)-10(-8) M) of dithranol or butantrone for 45 min. The cells were then cultivated for up to 48 h and treated with 10 microM bromodeoxyuridine (BrdU) and 10 microM fluorodeoxyuridine for 30 min before harvesting. Both drugs at concentrations of 10(-6) and 10(-5) M inhibited the BrdU uptake of HeLa cells, but did not cause any significant change in the proportion of cells in S-phase. The inhibitory effect of dithranol on cell number was linear with concentration 24 h after incubation. The highest (10(-5) M) concentration of butantrone caused an abrupt decrease in cell number.

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Indication	Highest Phase	Country/Location	Organization	Date
Psoriasis	Phase 1	-	-	01 Jan 1987

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