Desketoneoenactin-siderophore conjugates for Candida: Evidence of iron transport-dependent species selectivity

Antimicrobial Agents and Chemotherapy

Volumn 49, Issue 1, 2005, Pages 241-248

  Bernier, Geneviève ^a   Girijavallabhan, Vinay ^b   Murray, Aaron ^b   Niyaz, Noormohamed ^b   Ding, Pingyu ^b   Miller, Marvin J ^b   Malouin, François ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' BIPYRIDINE; ANTIFUNGAL AGENT; CARBON 13; CASIT1 PROTEIN; DESKETONEOENACTIN; ENACTIN DERIVATIVE; FERRICHROME; FERRIOXAMINE; FUNGAL PROTEIN; HYDROXAMIC ACID DERIVATIVE; IRON 55; ORNITHINE; RHODOTORULIC ACID; SIDEROPHORE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA; CANDIDA ALBICANS; CANDIDA PSEUDOTROPICALIS; CANDIDA STELLATOIDEA; CONTROLLED STUDY; DRUG ACTIVITY; FUNGUS GROWTH; IRON RESTRICTION; IRON TRANSPORT; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CANDIDA; CANDIDA ALBICANS; CULTURE MEDIA; HYDROXAMIC ACIDS; IRON; MICROBIAL SENSITIVITY TESTS; SIDEROPHORES; SPECIES SPECIFICITY;

EID: 11244258728     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.49.1.241-248.2005     Document Type: Article

References (18)

1. Ardon, O., H. Bussey, C. Philpott, D. M. Ward, S. Davis-Kaplan, S. Verraneau, B. Jiang, and J. Kaplan. 2001. Identification of a Candida albicans ferrichrome transporter and its characterization by expression in Saccharomyces cerevisiae. J. Biol. Chem. 276:43049-43055.
2. Ding, P., N. M. Niyaz, C. E. Schous, A. Sheinkman, and M. J. Miller. Design and synthesis of a novel siderophore analog for applications in iron transport-mediated drug delivery and syntheses of potent antifungal drug conjugates. Manuscript in preparation.
3. 5-hydroxy-L-ornithine. J. Med. Chem. 34:956-968.
4. Fonzi, W. A., and M. Y. Irwin. 1993. Isogenic strain construction and gene mapping in Candida albicans. Genetics 134:717-728.
5. Heymann, P., M. Gerads, M. Schaller, F. Dromer, G. Winkelmann, and J. F. Ernst. 2002. The siderophore iron transporter of Candida albicans (Sit1p/Arn1p) mediates uptake of ferrichrome-type siderophores and is required for epithelial invasion. Infect. Immun. 70:5246-5255.
6. Hu, C. J., C. Bai, X. D. Zheng, Y. M. Wang, and Y. Wang. 2002. Characterization and functional analysis of the siderophore-iron transporter CaArn1p in Candida albicans. J. Biol. Chem. 277:30598-30605.
7. Ismail, A., G. W. Bedell, and D. M. Lupan. 1985. Siderophore production by the pathogenic yeast, Candida albicans. Biochem. Biophys. Res. Commun. 130:885-891.
8. Lee, B. H., M. J. Miller, C. A. Prody, and J. B. Neilands. 1985. Artificial siderophores. 2. Syntheses of trihydroxamate analogues of rhodotorulic acid and their biological iron transport capabilities in Escherichia coli. J. Med. Chem. 28:323-327.
9. Miller, M. J., and F. Malouin. 1994. Siderophore-mediated drug delivery: the design, synthesis, and study of siderophore-antibiotic and antifungal conjugates, p. 275-306. In R. Bergeron (ed.), Microbial iron chelates. CRC Press, Boca Raton, Fla.
10. Murray, A. P., and M. J. Miller. 2003. The Preparation of a fully differentiated "multiwarhead" siderophore precursor. J. Org. Chem. 68:191-194.
11. Neilands, J. B. 1995. Siderophores: structure and function of microbial iron transport compounds. J. Biol. Chem. 270:26723-26726.
12. Nikaido, H. 1994. Porins and specific diffusion channels in bacterial outer membranes. J. Biol. Chem. 269:3905-3908.
13. Ramanan, N., and Y. Wang. 2000. A high-affinity iron permease essential for Candida albicans virulence. Science 288:1062-1064.
14. Roosenberg, J. M., Y. M. Lin, Y. Lu, and M. J. Miller. 2000. Studies and syntheses of siderophores, microbial iron chelators, and analogs as potential drug delivery agents. Curr. Med. Chem. 7:159-197.
15. Stearman, R., D. S. Yuan, Y. Yamaguchi-Iwai, R. D. Klausner, and A. Dancis. 1996. A permease-oxidase complex involved in high-affinity iron uptake in yeast. Science 271:1552-1557.
16. Sweet, S. P., and L. J. Douglas. 1991. Effect of iron concentration on siderophore synthesis and pigment production by Candida albicans. FEMS Microbiol. Lett. 64:87-91.
17. Ward, P. P., and O. M. Conneely. 2004. Lactoferrin: Role in iron homeostasis and host defense against microbial infection. BioMetals 17:203-208.
18. Weissman, Z., R. Shemer, and D. Kornitzer. 2002. Deletion of the copper transporter CaCCC2 reveals two distinct pathways for iron acquisition in Candida albicans. Mol. Microbiol. 44:1551-1560.