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

Volumn 39, Issue 16, 1996, Pages 3132-3138

  Müller, Klaus ^a   Huang, Hsu Shan ^b   Wiegrebe, Wolfgang ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b NATIONAL DEFENSE MEDICAL CENTER   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 DIHYDROXY 10 [(4 HYDROXYPHENYL)THIO] 9(10H) ANTHRACENONE; 12 HYDROXYICOSATETRAENOIC ACID; ANTHRACENE DERIVATIVE; ANTIPSORIASIS AGENT; ARACHIDONATE 5 LIPOXYGENASE; DITHRANOL; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANIMAL TISSUE; ARTICLE; CELL PROLIFERATION; CYTOTOXICITY; DRUG SYNTHESIS; ENZYME INHIBITION; EPIDERMIS; HUMAN; HUMAN CELL; KERATINOCYTE; LIPID PEROXIDATION; NONHUMAN; OXIDATION REDUCTION REACTION; PSORIASIS; SKIN IRRITATION;

12-HYDROXY-5,8,10,14-EICOSATETRAENOIC ACID; ANIMALS; ANTHRALIN; ANTIOXIDANTS; CATTLE; CELL DIVISION; CELLS, CULTURED; EPIDERMIS; HUMANS; HYDROXYEICOSATETRAENOIC ACIDS; KERATINOCYTES; LIPOXYGENASE INHIBITORS; MICE; MOLECULAR STRUCTURE; NEUTROPHILS; PSORIASIS;

EID: 0029785089     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960259l     Document Type: Article

References (58)

1. Müller, K.; Leukel, P.; Ziereis, K.; Gawlik, I. Antipsoriatic anthrones with modulated redox properties. 2. Novel derivatives of chrysarobin and isochrysarobin-antiproliferative activity and 5-lipoxygenase inhibition. J. Med. Chem. 1994, 37, 1660-1669.
2. Kemény, L.; Ruzicka, T.; Braun-Falco, O. Dithranol: a review of the mechanism of action in the treatment of psoriasis vulgaris. Skin Pharmacol. 1990, 3, 1-20.
3. Farber, E. M.; Nall, L. Psoriasis. A review of recent advances in treatment. Drugs 1984, 28, 324-346.
4. Wiegrebe, W.; Müller, K. Treatment of psoriasis with anthrones - chemical principles, biochemical aspects, and approaches to the design of novel derivatives. Skin Pharmacol. 1995, 8, 1-24.
5. Müller, K. Antipsoriatic anthrones: aspects of oxygen radical formation, challenges and prospects. Gen. Pharmacol. 1996, 27, in press.
6. Müller, K.; Kappus, H. Hydroxyl radical formation by dithranol. Biochem. Pharmacol. 1988, 37, 4277-4280.
7. Müller, K.; Gürster, D. Hydroxyl radical damage to DNA sugar and model membranes induced by anthralin (dithranol). Biochem. Pharmacol. 1993, 46, 1695-1704.
8. Fuchs, J.; Packer, L. Investigations on anthralin free radicals in model systems and in skin of hairless mice. J. Invest. Dermatol. 1989, 92, 677-682.
9. Hayden, P. J.; Free, K. E.; Chignell, C. F. Structure-activity relationships for the formation of secondary radicals and inhibition of keratinocyte proliferation by 9-anthrones. Mol. Pharmacol. 1994, 46, 186-198.
10. Müller, K.; Wiegrebe, W.; Younes, M. Formation of active oxygen species by dithranol, III. Dithranol, active oxygen species and lipid peroxidation in vivo. Arch. Pharm. (Weinheim, Ger.) 1987, 320, 59-66.
11. Müller, K.; Gürster, D.; Piwek, S.; Wiegrebe, W. Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase. J. Med. Chem. 1993, 36, 4099-4107.
12. Sustmann, R.; Korth, H.-G. The captodative effect. Adv. Phys. Org. Chem. 1990, 26, 131-178.
13. Viehe, H. G.; Janousek, Z.; Merényi, R.; Stella, L. The captodative effect. Acc. Chem. Res. 1985, 18, 148-154.
14. nR, n = 0, 1, 2]. J. Chem. Soc., Perkin Trans. 2 1988, 2077-2085.
15. Pečar, S.; Schara, M.; Müller, K.; Wiegrebe, W. Reduction of nitroxides by anthralin and some of its derivatives. Free Radical Biol. Med. 1995, 78, 459-465.
16. Schultz, O. E.; Schultze-Mosgau, H. H. Die Substitution des 1,8-Dihydroxyanthrons-9 in meso-(10)-Stellung. X. Mitt. über Laxantien (Substitution of 1,8-dihydroxyanthrone-9 in meso-(10)-position). Arch. Pharm. (Weinheim, Ger.) 1965, 298, 273-281.
17. d'Ischia, M.; Privitera, A.; Prota, G. Interaction of anthralin with cysteine: a new entry into the chemistry of biologically active anthrones. Tetrahedron Lett. 1984, 25, 4837-4840.
18. d'Ischia, M.; Prota, G. Synthesis of 10-alkylthio- and arylthio-1,8-dihydroxy-9-anthrones, a new class of anthracene derivatives of potential pharmacological interest. Synthesis 1986, 430-431.
19. Fry, L. Psoriasis. Br. J. Dermatol. 1988, 119, 445-461.
20. Klem, E. B. Effects of antipsoriasis drugs and metabolic inhibitors on the growth of epidermal cells in culture. J. Invest. Dermatol. 1978, 70, 27-32.
21. Müller, K. 5-Lipoxygenase and 12-lipoxygenase: attractive targets for the development of novel antipsoriatic drugs. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 3-19.
22. Müller, K.; Gawlik, I. Novel 10-substituted antipsoriatic anthrones as inhibitors of epidermal 12-lipoxygenase and lipid peroxidation in membranes. Biochem. Pharmacol. 1995, 50, 2077-2083.
23. Bonnekoh, B.; Farkas, B.; Geisel, J.; Mahrle, G. Lactate dehydrogenase release as an indicator of dithranol-induced membrane injury in cultured human keratinocytes. Arch. Dermatol. Res. 1990, 282, 325-329.
24. Greaves, M. W. Neutrophil polymorphonuclears, mediators, and the pathogenesis of psoriasis. Br. J. Dermatol. 1983, 109, 115-118.
25. Janssen-Timmen, U.; Vickers, P. J.; Wittig, U.; Lehmann, W. D.; Stark, H.-J.; Fusening, N. E.; Rosenbach, T.; Rådmark, O.; Samuelsson, B.; Habenicht, A. J. R. Expression of 5-lipoxygenase in differentiating human skin keratinocytes. Proc. Natl. Acad. Sci. USA 1995, 92, 6966-6970.
26. Jones, G. H.; Venuti, M. C.; Young, J. M.; Krishna Murthy, D. V.; Loe, B. E.; Simpson, R. A.; Berks, A. H.; Spires, D. A.; Maloney, P. J.; Kruseman, M.; Rouhafza, S.; Kappas, K. C.; Beard, C. C.; Unger, S. H.; Cheung, P. S. Topical nonsteroidal antipsoriatic agents: 1. 1,2,3,4-Tetraoxygenated naphthalene derivatives. J. Med. Chem. 1986, 29, 1504-1511.
27. Venuti, M. C.; Loe, B. E.; Jones, G. H.; Young, J. M. Topical nonsteroidal antipsoriatic drugs. 2. 2,3-(Alkylidenedioxy)naphthalene analogues of lonapalene. J. Med. Chem. 1988, 31, 2132-2136.
28. Batt, D. G.; Maynard, G. D.; Petraitis, J. J.; Shaw, J. E.; Galbraith, W.; Harris, R. R. 2-Substituted-1-naphthols as potent 5-lipoxygenase inhibitors with topical antiinflammatory activity. J. Med. Chem. 1990, 33, 360-370.
29. Hamer, R. R. L.; Tegeler, J. J.; Kurtz, E. S.; Allen, R. C.; Bailey, S. C.; Elliot, M. E.; Hellyer, L.; Helsley, G. C.; Przekop, P.; Freed, B. S.; White, J.; Martin, L. L. Dibenzoxepinone hydroxylamines and hydroxamic acids: dual inhibitors of cyclooxygenase and 5-lipoxygenase with potent topical antiinflammatory activity. J. Med. Chem. 1996, 39, 246-252.
30. Musser, J. H.; Kreft, A. F. 5-Lipoxygenase: properties, pharmacology, and the quinolinyl(bridged)aryl class of inhibitors. J. Med. Chem. 1992, 35, 2501-2524.
31. Ikuta, H.; Shirota, H.; Kobayashi, S.; Yamagishi, Y.; Yamada, K.; Yamatsu, I.; Katayama, K. Synthesis and antiinflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones. J. Med. Chem. 1987, 30, 1995-1998.
32. Hammond, M. L.; Kopka, I. E.; Zambias, R. A.; Caldwell, C. G.; Boger, J.; Baker, F.; Bach, T.; Luell, S.; MacIntyre, D. E. 2,3-Dihydro-5-benzofuranols as antioxidant-based inhibitors of leukotriene biosynthesis. J. Med. Chem. 1989, 32, 1006-1020.
33. Hammond, M. L.; Zambias, R. A.; Chang, M. N.; Jensen, N. P.; McDonald, J.; Thompson, K.; Boulton, D. A.; Kopka, I. E.; Hand, K. M.; Opas, E. E.; Luell, S.; Bach, T.; Davies, P.; MacIntyre, D. E.; Bonney, R. J.; Humes, J. L. Antioxidant-based inhibitors of leukotriene biosynthesis. The discovery of 6-[1-[2-(hydroxymethyl)phenyl]-1-propen-3-yl]-2,3-dihydro-5-benzofuranol, a potent topical antiinflammatory agent. J. Med. Chem. 1990, 33, 908-918.
34. Lazer, E. S.; Wong, H.-C.; Possanza, G. J.; Graham, A. G.; Farina, P. R. Antiinflammatory 2,6-di-tert-butyl-4-(2-arylethenyl)phenols. J. Med. Chem. 1989, 32, 100-104.
35. Lazer, E. S.; Wong, H.-C.; Wegner, C. D.; Graham, A. G.; Farina, P. R. Effect of structure on potency and selectivity in 2,6-disubstituted 4-(2-arylethenyl)phenol lipoxygenase inhibitors. J. Med. Chem. 1990, 33, 1892-1898.
36. Ruzicka, T.; Vitto, A.; Printz, M. P. Epidermal arachidonate lipoxygenase. Biochim. Biophys. Acta 1983, 757, 359-374.
37. Duell, E. A.; Ellis, C. N.; Voorhees, J. J. Determination of 5,12, and 15-lipoxygenase products in keratomed biopsies of normal and psoriatic skin. J. Invest. Dermatol. 1988, 91, 446-450.
38. Hussain, H.; Shornick, L. P.; Shannon, V. R.; Wilson, J. D.; Funk, C. D.; Pentland, A. P.; Holtzman, M. J. Epidermis contains platelet-type 12-lipoxygenase that is overexpressed in germinal layer keratinocytes in psoriasis. Am. J. Physiol. 1994, 266, C243-C253.
39. 4 and 12-hydroxyeicosatetraenoic acid stimulate epidermal proliferation in vivo in the guinea pig. J. Invest. Dermatol. 1985, 85, 333-334.
40. Fallon, J. D.; Kragballe, K. Increased platelet metabolism of arachidonic acid in psoriasis associated with stimulation of platelet aggregation and epidermal keratinocyte proliferation. J. Invest. Dermatol. 1984, 82, 400.
41. Dowd, P. M.; Kobza Black, A.; Woollard, P. M.; Camp, R. D. R.; Greaves, M. W. Cutaneous responses to 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE), J. Invest. Dermatol. 1986, 84, 537-541.
42. Huang, F.-C.; Shoupe, T. S.; Lin, C. J.; Lee, T. D. Y.; Chan, W.-K.; Tan, J.; Schnapper, M.; Suh, J. T.; Gordon, R. J.; Sonnino, P. A.; Sutherland, C. A.; Van Inwegen, R. G.; Coutts, S. M. Differential effects of a series of hydroxamic acid derivatives on 5-lipoxygenase and cyclooxygenase from neutrophils and 12-lipoxygenase from platelets and their in vivo effects on inflammation and anaphylaxis. J. Med. Chem. 1989, 32, 1836-1842.
43. Cho, H.; Ueda, M.; Tamaoka, M.; Hamaguchi, M.; Aisaka, K.; Kiso, Y.; Inoue, T.; Ogino, R.; Tatsuoka, T.; Ishihara, T.; Noguchi, T.; Morita, I.; Murota, S.-I. Novel caffeic acid derivatives: extremely potent inhibitors of 12-lipoxygenase. J. Med. Chem. 1991, 34, 1503-1505.
44. Nakadate, T.; Yamamoto, S.; Aizu, E.; Kato, R. Inhibition of mouse epidermal 12-lipoxygenase by 2,3,4-trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone (AA861). J. Pharm. Pharmacol. 1985, 37, 71-73.
45. Opas, E. E.; Argenbright, L. W.; Humes, J. L. An enzymatic method for distinguishing the stereoisomers of 12-hydroxyeicosatetraenoic acid in human epidermis and psoriatic scale. Br. J. Dermatol. 1989, 120, 49-58.
46. Schopf, R. E.; Altmeyer, P.; Lemmel, E. M. Increased respiratory burst activity of monocytes and polymorphonuclear leukocytes in psoriasis. Br. J. Dermatol. 1982, 107, 505-510.
47. Kato, T.; Terui, T.; Takematsu, H.; Tagami, H. Effects of psoriatic scale extracts on oxidative metabolic responses in granulocytes assessed by chemiluminescence. Inflammation 1989, 13, 59-66.
48. Dixit, R.; H. Mukhtar; Bickers, D. R. Studies on the role of reactive oxygen species in mediating lipid peroxide formation in epidermal microsomes of rat skin. J. Invest. Dermatol. 1983, 81, 369-375.
49. Trenam, C. W.; Blake, D. R.; Morris, C. J. Skin inflammation: reactive oxygen species and the role of iron. J. Invest. Dermatol. 1992, 99, 675-682.
50. Popov, I.; Lewin, G. A deficient function of the antioxidative system of the organism as an aetiopathogenetic factor in psoriasis. Med. Hypotheses 1991, 35, 229-236.
51. Laughton, M. J.; Halliwell, B.; Evans, P. J.; Hoult, J. R. S. Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Effects on lipid peroxidation, hydroxyl radical generation and bleomycin-dependent damage to DNA. Biochem. Pharmacol. 1989, 38, 2859-2865.
52. Aruoma, O. I.; Evans, P. J.; Kaur, H.; Sutcliffe, L.; Halliwell, B. An evaluation of the antioxidant and potential pro-oxidant properties of food additives and of trolox C, vitamin E and probucol. Free Radical Res. Commun. 1990, 10, 143-157.
53. Müller, K.; Leukel, P.; Mayer, K. K.; Wiegrebe, W. Modification of DNA bases by anthralin and related compounds. Biochem. Pharmacol. 1995, 49, 1607-1613.
54. Winyard, P. G.; Morris, C. J.; Winrow, V. R.; Zaidi, M.; Blake, D. R. Free radical pathways in the inflammatory response. New Compr. Biochem. 1994, 28, 361-383.
55. Müller, K.; Kanner, R. C.; Foote, C. S. Kinetic studies on anthralin photooxidation. Photochem. Photobiol. 1990, 52, 445-450.
56. Boukamp, P.; Petrussevska, R. T.; Breitkreutz, D.; Hornung, J.; Markham, A.; Fusening, N. E. Normal keratinization in a spontaneously immortalized aneuploid human keratinocyte cell line. J. Cell Biol. 1988, 761, 761-771.
57. Müller, K.; Gawlik, I.; Wiegrebe, W. Acidity and stability of 10-substituted 1,8-dihydroxy-9(10H)-anthracenones. Arch. Pharm. (Weinheim, Ger.) 1995, 328, 359-362.
58. Bruce, J. M. Thio-containing anthralin analogs for the treatment of psoriasis, and their preparation, pharmaceutical compositions, and use. Eur. Pat. Appl. EP 314,405. Chem. Abstr. 1989, 111, 173808h.