Müller, Klaus and Huang, Hsu-Shan and Wiegrebe, Wolfgang (1996) Antipsoriatic anthrones with modulated redox properties .3. 10-Thio-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of keratinocyte growth, 5-lipoxygenase, and the formation of 12(S)-HETE in mouse epidermis. JOURNAL OF MEDICINAL CHEMISTRY, 39 (16). pp. 3132-3138. ISSN 0022-2623, 1520-4804
Full text not available from this repository.Abstract
The synthesis of a series of 1,8-dihydroxy-9(10H)-anthracenones bearing sulfur-linked substituents in the 10-position is described. These compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT and the 5- and 12-lipoxygenase enzymes in bovine polymorphonuclear leukocytes and mouse epidermal homogenate, respectively. In addition, the following redox properties of the compounds were determined: reactivity against 2,2-diphenyl-1-picrylhydrazyl, generation of hydroxyl radicals as measured by deoxyribose degradation, and inhibition of lipid peroxidation in model membranes. Compounds 4e and 4h of this series compare favorably in the cellular assays with the antipsoriatic anthralin. They have the combined inhibitory action against leukotriene B-4 and 12(S)-HETE formation and are highly potent antiproliferative agents against keratinocyte growth. In contrast to anthralin, 4h, 1,8-dihydroxy-10-[(4-hydroxyphenyl)thiol]-9(10H)-anthracenone, is not cytotoxic as documented by the LDH activity released from cytoplasm of keratinocytes and does not enhance lipid peroxidation in model membranes.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ANTIOXIDANT-BASED INHIBITORS; 10-SUBSTITUTED 1,8-DIHYDROXY-9(10H)-ANTHRACENONES; 12-HYDROXYEICOSATETRAENOIC ACID; LEUKOTRIENE BIOSYNTHESIS; LIPID-PEROXIDATION; PSORIATIC SCALE; 12-LIPOXYGENASE; DERIVATIVES; ANTHRALIN; SKIN |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Jun 2023 08:28 |
| Last Modified: | 29 Jun 2023 08:28 |
| URI: | https://pred.uni-regensburg.de/id/eprint/51550 |
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