Malassezin - A novel agonist of the Arylhydrocarbon receptor from the yeast Malassezia furfur

Bioorganic and Medicinal Chemistry

Volumn 9, Issue 4, 2001, Pages 955-960

  Wille, Gregor ^a   Mayser, Peter ^b   Thoma, Wiebke ^b   Monsees, Thomas ^b   Baumgart, Annette ^c   Schmitz, Hans Joachim ^c   Schrenk, Dieter ^c   Polborn, Kurt ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

^c Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; ARYLHYDROCARBON RECEPTOR; CYTOCHROME A; FUNGAL PROTEIN; MALASSEZIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL GROWTH; DRUG DETERMINATION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER CELL; MALASSEZIA FURFUR; MALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT;

ANIMALS; CHROMATOGRAPHY, THIN LAYER; CYTOCHROME P-450 CYP1A1; ENZYME INHIBITORS; HEPATOCYTES; INDICATORS AND REAGENTS; INDOLES; MALASSEZIA; MALE; MODELS, MOLECULAR; MONOPHENOL MONOOXYGENASE; RATS; RATS, WISTAR; RECEPTORS, ARYL HYDROCARBON;

EID: 0035030912     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00319-9     Document Type: Article

References (32)

1. Guého E., Midgley G., Guillot J. Antonie Van Leeuwenhoek. 69:1996;337.
2. Yarrow, D.; Ahearn, D. C. In The Yeasts: A Taxonomic Study; Rij, N. J. W. K.-v., Ed.; North Holland Publishing Company: Amsterdam, 1984, pp 882.
3. Borelli D., Jacobs P.H., Nall L. J. Am. Acad. Dermatol. 25:1991;300.
4. Hay, R. J.; Roberts, S. O. B.; Mackenzie, D. W. R. In Textbook of Dermatology; Champion, R. H., Burton, J. L., Ebling, F. J. G., Ed.; Blackwell Scientific Publications: Oxford, 1992, Vol. 2, pp 1176.
5. Further information about the disease and pictures from patients are available on the web, http://www.dermis.net/bilddb/diagnose/englisch/i111000.htm.
6. Solomon E.I., Sundaram U.M., Machonkin T.E. Chem. Rev. 96:1996;2563.
7. Cai D., Klinman J.P. Biochemistry. 33:1994;7647.
8. Klinman J.P. Chem. Rev. 96:1996;2541.
9. Mayser P., Wille G., Imkampe A., Thoma W., Arnold N., Monsees T. Mycoses. 1:1998;265.
10. Mayser P., Pape B. Antonie van Leeuwenhoek. 73:1998;315.
11. Mayser, P. Habilitation Thesis. University of Gießen, Germany, 1999.
12. Sundberg R.J., Russell H.F. J. Org. Chem. 38:1973;3324.
13. Saulnier M.G., Gribble G.W. J. Org. Chem. 47:1982;757.
14. An alternative method for the conversion of carbinol 4 into 2,3′-methylenebisindole (6) has been described by Tholander and Bergman (ref 20).
15. Jackson, A. H.; Prasitpan, N.; Shannon, P. V. R.; Tinker, A. C. J. Chem. Soc. Perkin Trans. I 1987, 2543.
16. Gribble G.W., Pelcman B. J. Org. Chem. 57:1992;3636.
17. 3.
18. X-ray crystal structures were calculated with SHELXS86 (Sheldrick, G.M. University of Göttingen, Germany, 1986) and refined with SHELXL93 (Sheldrick, G. M. University of Göttingen, Germany, 1993).
19. Pindur U., Müller J. Arch. Pharm. 320:1987;280.
20. Tholander J., Bergman J. Tetrahedron Lett. 39:1998;1619.
21. Kistenmacher A., Müllen K. J. Heterocyclic Chem. 29:1992;1237.
22. Gillner M., Bergman J., Cambillau C., Fernström B., Gustafsson J.-Ä. Mol. Pharm. 28:1985;357.
23. Burke M.D., Murray G.I., Lees G.M. Biochem. J. 212:1983;15.
24. Janosik T., Bergman J. Tetrahedron. 55:1999;2371.
25. Kwon C.-S., Grose K.R., Riby J., Chen Y.-H., Bjeldanes L.F. J. Agric. Food. Chem. 42:1994;2536.
26. Bjeldanes L.F., Kim J.-Y., Grose K.R., Bartholomew J.C., Bradfield C.A. Proc. Natl. Acad. Sci. U.S.A. 88:1991;9543.
27. Rannug U., Rannug A., Sjöberg U., Li H., Westerholm R., Bergman J. Chem. Biol. 2:1995;841.
28. Schrenk D., Riebniger D., Till M., Vetter S., Fiedler H.-P. Biochem. Pharm. 54:1997;165.
29. Illi, V. O. Synthesis 1979, 136. We prepared compound 2 in 85% yield following the procedure of ref 13.
30. Schmitz H.-J., Hagenmaier A., Hagenmeier H., Bock K.W., Schrenk D. Toxicology. 99:1995;47.
31. Burke M.D., Mayer R.T. Drug Metab. Dispos. 2:1974;583.
32. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. J. Biol. Chem. 193:1951;265.