Fungicidal activity of truncated analogues of dihydrosphingosine

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 13, 2008, Pages 3728-3730

  Thevissen, Karin ^a   Hillaert, Ulrik ^b   Meert, Els M K ^a   Chow, Kuen K ^a   Cammue, Bruno P A ^a   Van Calenbergh, Serge ^b   François, Isabelle E J A ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b GHENT UNIVERSITY   (Belgium)

Author keywords

Candida albicans; Candida glabrata; Dihydrosphingosine; Fungicidal; Reactive oxygen species; Sphingoid base

Indexed keywords

ALDEHYDE; BISPHENOL A BIS(2 HYDROXYPROPYL) ETHER DIMETHACRYLATE; CARBON; FLUCONAZOLE; HEMPA; HYDROXYL GROUP; LITHIUM; PHYTOSPHINGOSINE; REACTIVE OXYGEN METABOLITE; SPHINGANINE;

ANIMAL CELL; ANTIBIOTIC RESISTANCE; ARTICLE; CANDIDA ALBICANS; CANDIDA GLABRATA; CONTROLLED STUDY; DRUG SYNTHESIS; FUNGAL STRAIN; FUNGEMIA; HUMAN; IN VITRO STUDY; INCUBATION TIME; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SPECTROFLUOROMETRY; STEREOCHEMISTRY;

ANIMALS; ANTIFUNGAL AGENTS; CANDIDA ALBICANS; CANDIDA GLABRATA; CARBON; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; OXYGEN; REACTIVE OXYGEN SPECIES; SPHINGOSINE; TECHNOLOGY, PHARMACEUTICAL;

CANDIDA ALBICANS; CANDIDA GLABRATA; SPHINGOIDEA;

EID: 44849105508     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.05.067     Document Type: Article

References (25)

1. Nenoff P., and Haustein U.F. Acta Derm. Venereol. 82 (2002) 170
2. Cheng J., Park T.S., Chio L.C., Fischl A.S., and Ye X.S. Mol. Cell. Biol. 23 (2003) 163
3. Chung N., Mao C., Heitman J., Hannun Y.A., and Obeid L.M. J. Biol. Chem. 276 (2001) 35614
4. Bibel D.J., Aly R., Shah S., and Shinefield H.R. Acta Derm. Venereol. 73 (1993) 407
5. Bibel D.J., Aly R., and Shinefield H.R. J. Invest. Dermatol. 98 (1992) 269
6. Bibel D.J., Aly R., and Shinefield H.R. Clin. Exp. Dermatol. 20 (1995) 395
7. Nicholas G.M., Li R., MacMillan J.B., and Molinski T.F. Bioorg. Med. Chem. Lett. 12 (2002) 2159
8. Fonzi W.A., and Irwin M.Y. Genetics 134 (1993) 717
9. +) was kindly provided by Dr. R. Kaur, Department of Molecular Biology and Genetics, Johns Hopkins School of Medicine, Baltimore, MD, US.
10. Marr K.A. Oncology 18 (2004) 9
11. Miyazaki H., Miyazaki Y., Geber A., Parkinson T., Hitchcock C., Falconer D.J., Ward D.J., Marsden K., and Bennett J.E. Antimicrob. Agents Chemother. 42 (1998) 1695
12. De Jonghe S., Van Overmeire I., Poulton S., Hendrix C., Busson R., Van Calenbergh S., De Keukeleire D., Spiegel S., and Herdewijn P. Bioorg. Med. Chem. Lett. 9 (1999) 3175
13. C15-DHS has earlier been mentioned in the literature, but to the best of our knowledge, no synthetic route toward this compound has been described. The synthesis of rac-C15-DHS has been reported by:. Prostenik M., and Stanavec N. J. Org. Chem. 18 (1953) 59
14. Hillaert U., Boldin-Adamsky S., Rozenski J., Busson R., Futerman A.H., and Van Calenbergh S. Bioorg. Med. Chem. Lett. 14 (2006) 5273
15. Herold P. Helv. Chim. Acta 71 (1988) 354
16. Tamotsu F., Michiharu N., Yoshihiro K., and Makoto S. J. Org. Chem. 59 (1994) 5865
17. +: 120.1019, found: 120.1029.
18. +: 176,1645, found: 176.1642.
19. +: 260,2584, found: 260,2584.
20. Overnight cultures of C. albicans and C. glabrata were 1/400 diluted in PBS and treated with the compounds or DMSO in the presence or absence of 10 mM ascorbic acid for 0 h and 5 h at 37 °C, whereafter colony forming units were counted on YPD (1% yeast extract, 2% peptone, 2% glucose; 1% agar) plates after 2 days of incubation at 30 °C. MFCs are means of at least three replicates with standard errors typically below 10%.
21. Chung N., Mao C., Heitman J., Hannun Y.A., and Obeid L.M. J. Biol. Chem. 276 (2001) 35614
22. Mormeneo D., Manresa A., Casas J., Llebaria A., and Delgado A. J. Appl. Microbiol. 104 (2008) 1075
23. Odds F.C. Rev. Iberoam. Micol. 22 (2005) 229
24. Aerts A.M., François I.E., Meert E.M., Li Q.T., Cammue B.P., and Thevissen K. J. Mol. Microbiol. Biotechnol. 13 (2007) 243
25. François I.E.J.A., Cammue B.P.A., Borgers M., Ausma J., Dispersyn G.D., and Thevissen K. Anti-Infect. Agents Med. Chem. 5 (2006) 3