Synthesis and evaluation of hydroquinone derivatives as inhibitors of isocitrate lyase

Archives of Pharmacal Research

Volumn 30, Issue 8, 2007, Pages 955-961

  Yang, Hyeong Cheol ^a   Yu, Jisu ^a   Oh, Ki Bong ^a,b   Shin, Dong Sun ^a   Cho, Won Jea ^c   Shin, Jongheon ^a   Kim, Sanghee ^a  

^a Seoul National University   (South Korea)

^b Seoul National University   (South Korea)

^c Chonnam National University   (South Korea)

Author keywords

C. albicans; Halisulfate; Hydroquinone; Inhibitor; Isocitrate lyase

Indexed keywords

ANTIFUNGAL AGENT; ENZYME INHIBITOR; HYDROQUINONE; HYDROQUINONE DERIVATIVE; ISOCITRATE LYASE;

ARTICLE; CANDIDA ALBICANS; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; IC 50; SYNTHESIS;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; ENZYME INHIBITORS; HYDROQUINONES; INHIBITORY CONCENTRATION 50; ISOCITRATE LYASE;

EID: 34548747571     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02993963     Document Type: Article

References (26)

1. Abdul Lattif, A., Prasad, R., Banerjee, U., Gupta, N., Mohammad, S., and Baquer, N. Z., The glyoxylate cycle enzyme activities in the pathogenic isolates of Candida albicans obtained from HIV/AIDS, diabetic and burn patients. Mycoses, 49, 85-90 (2006).
2. Berman, J. and Sudbery, P. E., Candida albicans: A molecular revolution built on lessons from budding yeast. Nat. Rev. Genet., 3, 918-932 (2002).
3. Britton, K. L., Langridge, S. J., Baker, P. J., Weeradechapon, K., Sedelnikova, S. E., De Lucas, J. R., Rice, D. W., and Turner, G., The crystal structure and active site location of isocitrate lyase from the fungus Aspergillus nidulans. Structure, 8, 349-362 (2000).
4. Calderone, R. A. and Fonzi, W. A., Virulence factors of Candida albicans. Trends Microbiol., 9, 327-335 (2001).
5. Chatterjee, A. K., Choi, T.-L., Sanders, D. P., and Grubbs, R. H., A general model for selectivity in olefin cross metathesis. J. Am. Chem. Soc., 125, 11360-11370 (2003).
6. Chatterjee, A. K., Toste, F. D., Choi, T.-L., and Grubbs, R. H., Ruthenium-catalyzed olefin cross metathesis of styrenes as an alternative to the Heck and cross-coupling reactions. Adv. Synth. Catal., 344, 634-637 (2002).
7. Connon, S. J. and Blechert, S., Recent developments in olefin cross-metathesis. Angew. Chem., Int. Ed., 42, 1900-1923 (2003).
8. Ebel, F., Schwienbacher, M., Beyer, J., Heesemann, J., Brakhage, A. A., and Brock, M., Analysis of the regulation, expression, and localisation of the isocitrate lyase from Aspergillus fumigatus, a potential target for antifungal drug development. Fungal Genet. Biol., 43, 476-489 (2006).
9. Goldstein, A. L. and McCusker, J. H., Development of Saccharomyces cerevisiae as a model pathogen: a system for the genetic identification of gene products required for survival in the mammalian host environment. Genetics, 159, 499-513 (2001).
10. Hautzel, R., Anke, H., and Sheldrick, W. S., Mycenon, a new metabolite from a Mycena species TA 87202 (basidiomycetes) as an inhibitor of isocitrate lyase. J. Antibiot., 43, 1240-1244 (1990).
11. Howard, B. M., Clarkson, K., and Bernstein, R. L., Simple prenylated hydroquinone derivatives from the marine urochordate Aplidium califomicum. Natural anticancer and antimutagenic agents. Tetrahedron Lett., 46, 4449-4452 (1979).
12. Kaposzta, R., Marodi, L., Hollinshead, M., Gordon, S., and Da Silva, R. P., Rapid recruitment of late endosomes and lysosomes in mouse macrophages ingesting Candida albicans. J. Cell. Sci., 112, 3237-3248 (1999).
13. Kawagishi, H., Hamajima, K., and Inoue, Y., Novel hydroquinone as a matrix metallo-proteinase inhibitor from the mushroom, Piptoporus betulinus. Biosci. Biotechnol. Biochem., 66, 2748-2750 (2002).
14. Kim, S.-Y., Park, J.-S., and Oh, K.-B., Effects of isocitrate lyase inhibitors on spore germination and appressorium development in Magnaporthe grisea. J. Microbiol. Biotechnol., 16, 1158-1162 (2006).
15. Ko, Y. H. and McFadden, B. A., Alkylation of isocitrate lyase from Escherichia coli by 3-bromopyruvate. Arch. Biochem. Biophys., 278, 373-380 (1990).
16. Ko, Y. H., Vanni, P., and McFadden, B. A., The interaction of 3-phosphoglycerate and other substrate analogs with the glyoxylate- and succinate-binding sites of isocitrate lyase. Arch. Biochem. Biophys., 274, 155-160 (1989).
17. Lee, H.-S., Lee, T.-H., Yang, S. H., Shin, H. J., Shin, J., and Oh, K.-B., Sesterterpene sulfates as isocitrate lyase inhibitors from tropical sponge Hippospongia sp. Bioorg. Med. Chem. Lett., 17, 2483-2486 (2007).
18. Lee, K. C., Moon, B. S., Lee, J. H., Chung, K.-H., Katzenellenbogen, J. A., and Chi, D. Y., Synthesis and binding affinities of fluoroalkylated raloxifenes. Bioorg. Med. Chem., 11, 3649-3658 (2003).
19. Lorenz, M. C., Bender, J. A., and Fink, G. R., Transcriptional response of Candida albicans upon internalization by macrophages. Eukaryotic Cell, 3, 1076-1087 (2004).
20. Lorenz, M. C. and Fink, G. R., Life and death in a macrophage: role of the glyoxylate cycle in virulence. Eukaryotic Cell, 1, 657-662 (2002).
21. Lorenz, M. C. and Fink, G. R., The glyoxylate cycle is required for fungal virulence. Nature, 412, 83-86 (2001).
22. McFadden, B. A. and Purohit, S., Itaconate, an isocitrate lyase-directed inhibitor in Pseudomonas indigofera. J. Bacteriol., 131, 136-144 (1977).
23. Schloss, J. V. and Cleland, W. W., Inhibition of isocitrate lyase by 3-nitropropionate, a reaction-intermediate analog. Biochemistry, 21, 4420-4427 (1982).
24. Shin, D.-S., Kim, S., Yang, H.-C., and Oh, K.-B., Cloning and expression of isocitrate lyase, a key enzyme of the glyoxylate cycle, of Candida albicans for development of antifungal drugs. J. Microbiol. Biotechnol., 15, 652-655 (2005).
25. Snider, B. B. and Lu, Q., Total Synthesis of (+/-)-Leporin A. J. Org. Chem., 61, 2839-2844 (1996).
26. Tadahiro, K., Shin-Ichi, E., Tohru, F., Hirota, T., and Masahiro, H., Synthesis of (1S, 2R, 12S)-2-hydroxy-11-dihydroneocembrene. Tetrahedron Asymmetry, 10, 3691-3700 (1999).