Structure-Guided Development of Efficacious Antifungal Agents Targeting Candida glabrata Dihydrofolate Reductase

Chemistry and Biology

Volumn 15, Issue 9, 2008, Pages 990-996

  Liu, Jieying ^a   Bolstad, David B ^a   Smith, Adrienne E ^b   Priestley, Nigel D ^b   Wright, Dennis L ^a   Anderson, Amy C ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b Promiliad Biopharma   (United States)

Author keywords

CHEMBIO

Indexed keywords

ANTIFUNGAL AGENT; DIHYDROFOLATE REDUCTASE; FOLIC ACID ANTAGONIST; LIGAND;

ARTICLE; CANDIDA GLABRATA; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; ENZYMOLOGY; METABOLISM; MOLECULAR GENETICS; PROTEIN BINDING; SEQUENCE ALIGNMENT; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ANTIFUNGAL AGENTS; CANDIDA GLABRATA; CRYSTALLOGRAPHY, X-RAY; DRUG EVALUATION, PRECLINICAL; FOLIC ACID ANTAGONISTS; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PROTEIN BINDING; SEQUENCE ALIGNMENT; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROFOLATE DEHYDROGENASE;

CANDIDA GLABRATA;

EID: 51649118086     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2008.07.013     Document Type: Article

References (22)

1. Anderson A. Targeting DHFR in parasitic protozoa. Drug Discov. Today 10 (2005) 121-128
2. Bertino J. Karnofsky Memorial Lecture: ode to methotrexate. J. Clin. Oncol. 11 (1993) 5-14
3. Chan J., Hong J., Kuyper L., Baccanari D., Joyner S., Tansik R., Boytos C., and Rudolph S. Selective inhibitors of Candida albicans dihydrofolate reductase: activity and selectivity of 5-(arylthio)-2,4-diaminoquinazolines. J. Med. Chem. 38 (1995) 3608-3616
4. Czaplinski K.-H., Hansel W., Wiese M., and Seydel J. New benzylpyrimidines: inhibition of DHFR from various species. QSAR, CoMFA and PC analysis. Eur. J. Med. Chem. 30 (1995) 779-787
5. Davey K., Szekely A., Johnson E., and Warnock D. Comparison of a new commercial colorimetric microdilution method with a standard method for in-vitro susceptibility testing of Candida spp. and Cryptococcus neoformans. J. Antimicrob. Chemother. 42 (1998) 439-444
6. Emsley P., and Cowtan K. Coot: model-building tools for molecular graphics. Acta Crystallogr. D Biol. Crystallogr. 60 (2004) 2126-2132
7. Hajjeh R., Sofair A., Harrison L., Lyon G.M., Arthington-Skaggs B., Mirza S., Phelan M., Morgan J., Lee-Yang W., Ciblak M., et al. Incidence of bloodstream infections due to Candida species and in vitro susceptibilities of isolates collected from 1998 to 2000 in a population-based active surveillance program. J. Clin. Microbiol. 42 (2004) 1519-1527
8. Hawser S., Lociuro S., and Islam K. Dihydrofolate reductase inhibitors as antibacterial agents. Biochem. Pharmacol. 71 (2006) 941-948
9. Joska T., and Anderson A. Structure-activity relationships of Bacillus cereus and Bacillus anthracis dihydrofolate reductase: toward the identification of new potent drug leads. Antimicrob. Agents Chemother. 50 (2006) 3435-3443
10. Kuyper L., Baccanari D., Jones M., Hunter R., Tansik R., Joyner S., Boytos C., Rudolph S., Knick V., Wilson H.R., et al. High-affinity inhibitors of dihydrofolate reductase: antimicrobial and anticancer activities of 7,8-dialkyl-1,3-diaminopyrrolo[3,2-f]quinazolines with small molecular size. J. Med. Chem. 39 (1996) 892-903
11. Murshudov G., Vagin A., and Dodson E. Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr. D Biol. Crystallogr. 53 (1997) 240-255
12. Otwinowski Z., and Minor W. Processing of X-ray diffraction data collected in oscillation mode. In: Carter C.W., and Sweet R.M. (Eds). Methods in Enzymology (1997), Academic Press, New York 307-326
13. Otzen T., Wempe E., Kunz B., Bartels R., Lehwark-Yvetot G., Hansel W., Schaper K., and Seydel J. Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4′-substituted 4-aminodiphenyl sulfones. J. Med. Chem. 47 (2004) 240-253
14. Pelphrey P., Popov V., Joska T., Beierlein J., Bolstad E., Fillingham Y., Wright D., and Anderson A. Highly efficient ligands for DHFR from Cryptosporidium hominis and Toxoplasma gondii inspired by structural analysis. J. Med. Chem. 50 (2007) 940-950
15. Pfaller M., and Diekema D. Rare and emerging opportunistic fungal pathogens: concern for resistance beyond Candida albicans and Aspergillus fumigatus. J. Clin. Microbiol. 42 (2004) 4419-4431
16. Pfaller M., Messer S., Hollis R., Jones R., Doern G., Brandt M., and Hajjeh R. Trends in species distribution and susceptibility to fluconazole among blood stream isolates of Candida species in the United States. Diagn. Microbiol. Infect. Dis. 33 (1999) 217-222
17. Pfaller M., Messer S., Boyken L., Tendolkar S., Hollis R., and Diekema D. Geographic variation in the susceptibilities of invasive isolates of Candida glabrata to seven systemically active antifungal agents: a global assessment from the ARTEMIS antifungal surveillance program conducted in 2001 and 2002. J. Clin. Microbiol. 42 (2004) 3142-3146
18. Read R. Pushing the boundaries of molecular replacement with maximum likelihood. Acta Crystallogr. D Biol. Crystallogr. 57 (2001) 1373-1382
19. Rosowsky A., Forsch R., and Queener S. Inhibition of Pneumocystis carinii, Toxoplasma gondii and Mycobacterium avium dihydrofolate reductases by 2,4-diamino-5-[2-methoxy-5-(w-carboxyalkoxy)benzyl]pyramidines: marked improvement in potency relative to trimethoprim and species selectivity relative to piritrexim. J. Med. Chem. 45 (2002) 233-241
20. Trick W., Fridkin S., Edwards J., Hajjeh R., and Gaynes R. Secular trend of hospital-acquired candidemia among intensive care unit patients in the United States during 1989-1999. Clin. Infect. Dis. 35 (2002) 627-630
21. Whitlow M., Howard A., Stewart D., Hardman K., Kuyper L., Baccanari D., Fling M., and Tansik R. X-ray crystallographic studies of Candida albicans dihydrofolate reductase. J. Biol. Chem. 272 (1997) 30289-30298
22. Whitlow M., Howard A., Stewart D., Hardman K., Chan J., Baccanari D., Tansik R., Hong J., and Kuyper L. X-ray crystal structures of Candida albicans dihydrofolate reductase: high resolution ternary complexes in which the dihydronicotinamide moiety of NADPH is displaced by an inhibitor. J. Med. Chem. 44 (2001) 2928-2932