Adenosine analogues as selective inhibitors of glyceraldehyde-3-phosphate dehydrogenase of trypanosomatidae via structure-based drug design

Journal of Medicinal Chemistry

Volumn 44, Issue 13, 2001, Pages 2080-2093

  Bressi, J C ^a   Verlinde, C L M J ^a   Aronov, A M ^b   Shaw, M L ^c   Shin, S S ^a   Nguyen, L N ^a   Suresh, S ^a,d   Buckner, F S ^a   van Voorhis, W C ^a   Kuntz, I D ^b   Hol, W G J ^a,c,d   Gelb, M H ^a,c  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

^d HOWARD HUGHES MEDICAL INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DERIVATIVE; ANTITRYPANOSOMAL AGENT; ENZYME INHIBITOR; GLYCERALDEHYDE 3 PHOSPHATE DEHYDROGENASE; N 6 (1 NAPHTHALENEMETHYL) 2' DEOXY 2' (3 METHOXYBENZAMIDO)ADENOSINE; N 6 (1 NAPHTHALENEMETHYL) 2' DEOXY 2' (3,5 DIMETHOXYBENZAMIDO)ADENOSINE; N 6 (2 NAPHTHALENEMETHYL) 2' DEOXY 2' (3 METHOXYBENZAMIDO)ADENOSINE; N 6 (2 NAPHTHALENEMETHYL) 2' DEOXY 2' (3,5 DIMETHOXYBENZAMIDO)ADENOSINE; N 6 (NAPHTHALENEMETHYL) 2' DEOXY 2' (BENZAMIDO)ADENOSINE; N 6 [1 (3 HYDROXYNAPHTHALENE)METHYL] 2' DEOXY 2' (3,5 DIMETHOXYBENZAMIDO)ADENOSINE; N 6 [1 (3 METHOXYNAPHTHALENE)METHYL] 2' DEOXY 2' (3,5 DIMETHOXYBENZAMIDO)ADENOSINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50; LEISHMANIA MEXICANA; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI;

3T3 CELLS; ADENOSINE; ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; ENZYME INHIBITORS; GLYCERALDEHYDE-3-PHOSPHATE DEHYDROGENASES; LEISHMANIA MEXICANA; MICE; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMA CRUZI; TRYPANOSOMATINA;

EID: 0035927424     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000472o     Document Type: Article

References (50)

1. Human African trypanosomiasis: An emerging public health crisis
2. The current status of antiparasite chemotherapy
3. Chemotherapy of Chagas' disease: The how and the why
4. The treatment of human African trypanosomiasis
5. Biochemical peculiarities of trypanosomes, African and South American
6. Compartmentation of carbohydrate metabolism in trypanosomes
7. Protein trafficking in kinetoplastid protozoa
8. Trypanosomiasis: An approach to chemotherapy by the inhibition of carbohydrate catabolism
9. Glycolysis in bloodstream form trypanosoma brucei can be understood in terms of the kinetics of the glycolytic enzymes
10. What controls glycolysis in bloodstream form Trypanosoma brucei?
11. From the cover: Compartmentation protects Trypanosomes from the dangerous design of glycolysis
12. Aerobic glucose fermentation by Trypanosoma cruzi axenic culture amastigote-like forms during growth and differentiation to epimastigotes
13. Structure of glycosomal glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma brucei determined from laue data
14. Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase: Structure, catalytic mechanism and targeted inhibitor design
15. Crystal structure of glycosomal glyceraldehyde-3-phosphate dehydrogenase from leishmania Mexicana: Implications for structure-based drug design and a new position for the inorganic phosphate binding site
16. Twinning in crystals of human skeletal muscle D-glyceraldehyde-3 -phosphate dehydrogenase
17. Synthesis and conformational analysis of 2′-deoxy-2′-(3-methoxybenzamido)adenosine. A rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH)
18. Selective inhibition of trypanosomal glyceraldehyde-3-phosphate dehydrogenase by protein structure-based design: Toward new drugs for the treatment of sleeping sickness
19. Synthesis and structure - Activity relationships of analogues of 2′-deoxy-2′ -(3-methoxybenzamido)adenosine. A selective inhibitor of trypanosomal glycosomal glyceraldehyde-3-phosphate dehydrogenase
20. Selective tight binding inhibitors of trypanosomal glyceraldehyde-3-phosphate dehydrogenase via structure-based drug design
21. Structure-based design of submicromolar, biologically active inhibitors of trypanosomatid glyceraldehyde-3-phosphate dehydrogenase
22. Nucleic acid related compounds. 42. A general procedure for the efficient deoxygenation of secondary alcohols. Regiospecific and stereoselective conversion of ribonucleosides to 2′-deoxynucleosides
23. Nucleic acid related compounds. 6. Sugar-modified N6-(3-Methyl-2-butenyl)adenosine derivatives, N6-benzyl analogues, and cytokinin-related nucleosides containing sulfur or formycin
24. 2′-Amino-2′-deoxyN6-(1-naphthylmethyl)adenosine as novel scaffold for a polymerassisted amidation protocol
25. Safety catch principle in solid phase peptide synthesis
26. Activation method to prepare a highly reactive acylsulfonamide "Safety-Catch" linker for solid-phase synthesis
27. Synthesis, biotransformation, and pharmacokinetic studies of 9-β-D-arabinofuranosyl)-6-azidopurine: A prodrug for Ara-A designed to utilize the azide reduction pathway
28. Nucleosides and nucleotides. 103. 2-Alkynyladenosines: A novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects
29. Practical method for the parallel synthesis of 2′-amido-2′-deoxyadenosines
30. +-binding sites of parasite enzymes
31. Efficient one-pot preparation of nitriles from aldehydes using N-methyl-pyrrolidone
32. Photochemistry of substituted 1-naphthylmethyl esters of phenylacetic and 3-phenylpropanoic acid: Radical pairs, ion pairs, and Marcus electron transfer
33. 2-(Aminomethyl)phenols, a new class of saluretic agents. 1. Effects of nuclear substitution
34. 2-(Aminomethyl)phenols, a new class of saluretic agents. 5. Fused-ring analogues
35. QXP: Powerful, rapid computer algorithms for structure-based drug design
36. Three-dimensional models of ACE and NEP inhibitors and their use in the design of potent dual ACE/NEP inhibitors
37. Conformational properties of o-alkoxybenzamides in different solvents
38. 3D search and research using the cambridge structural database
39. Rational design of selective submicromolar inhibitors of tritrichomonas foetus hypoxanthineguanine-xanthine phosphoribosyltransferase
40. Critical evaluation of search algorithms for automated molecular docking and database screening
41. Inclusion of solvation in ligand binding free energy calculations using the generalized born model
42. Continuous cultivation of trypanosoma brucei blood stream forms in a medium containing a low concentration of serum protein without feeder cell layers
43. The alamar blue assay to determine drug sensitivity of african trypanosomes (T.b. rhodesiense and T.b. gambiense) In vitro
44. Efficient technique for screening drugs for activity against trypanosoma cruzi using parasites expressing beta-galactosidase