Design and synthesis of potent "sulfur-free" transition state analogue inhibitors of 5′-methylthioadenosine nucleosidase and 5′-methylthioadenosine phosphorylase

Journal of Medicinal Chemistry

Volumn 53, Issue 18, 2010, Pages 6730-6746

  Longshaw, Alistair I ^a   Adanitsch, Florian ^a   Gutierrez, Jemy A ^b   Evans, Gary B ^a   Tyler, Peter C ^a   Schramm, Vern L ^b  

^a CALLAGHAN INNOVATION   (New Zealand)

^b ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5' METHYLTHIOADENOSINE PHOSPHORYLASE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; GLYCOSYLTRANSFERASE INHIBITOR; METHYLTHIOADENOSINE NUCLEOSIDASE; NUCLEOSIDASE; NUCLEOSIDE ANALOG; POLYAMINE; S ADENOSYLMETHIONINE; SULFUR; UNCLASSIFIED DRUG; 5'-METHYLTHIOADENOSINE NUCLEOSIDASE, E COLI; 5'-METHYLTHIOADENOSINE PHOSPHORYLASE; ESCHERICHIA COLI PROTEIN; GLYCOSIDASE; PURINE NUCLEOSIDE PHOSPHORYLASE; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; BACTERIAL VIRULENCE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SUBSTRATE; ESCHERICHIA COLI; GENE TARGETING; MICROBIAL COMMUNITY; NONHUMAN; QUORUM SENSING; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG DESIGN; HUMAN; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; DRUG DESIGN; ESCHERICHIA COLI PROTEINS; HUMANS; N-GLYCOSYL HYDROLASES; PURINE-NUCLEOSIDE PHOSPHORYLASE; PYRIMIDINES; PYRROLES; PYRROLIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956789065     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100898v     Document Type: Article

References (40)

1. Schramm, V. L. Enzymatic transition state theory and transition state analogue design J. Biol. Chem. 2007, 282, 28297-28300
2. Lewandowicz, A.; Schramm, V. L. Transition state analysis for human and Plasmodium falciparum purine nucleoside phosphorylases Biochemistry 2004, 43, 1458-1468
3. Singh, V.; Schramm, V. L. Transition state structure of human 5′-methylthioadenosine phosphorylase J. Am. Chem. Soc. 2006, 128, 14691-14696
4. Singh, V.; Lee, J. E.; Nunez, S.; Howell, P. L.; Schramm, V. L. Transition state structure of 5′-methylthioadenosine/ S- adenosylhomocysteine nucleosidase from Escherichia coli and its similarity to transition state analogues Biochemistry 2005, 44, 11647-11659 (Pubitemid 41262698)
5. Singh, V.; Luo, M.; Brown, R. L; Norris, G. E; Schramm, V. L. Transition state structure of Neisseria meningitides 5′-methylthioadenosine/ S-adenosylhomocysteine nucleosidase J. Am. Chem. 2007, 129, 13831-13833
6. Singh, V.; Schramm, V. L. Transition state analysis of S. pneumoniae 5′-methylthioadenosine/ S-adenosylhomocysteine nucleosidase J. Am. Chem. Soc. 2007, 129, 2783-2795
7. Evans, G. B. The synthesis of N-ribosyl transferase inhibitors based on a transition state blueprint Aust. J. Chem. 2004, 57, 837-854
8. Basu, I.; Cordovano, G.; Das, I.l; Belbin, T. J.; Guha, C.; Schramm, V. L. A transition state analogue of 5′-methylthioadenosine phosphorylase induces apoptosis in head and neck cancers J. Biol. Chem. 2007, 282, 21477-21486
9. Gutierrez, J. A.; Luo, M.; Singh, V.; Li, L.; Brown, R. L.; Norris, G. E.; Evans, G. B.; Furneaux, R. H.; Tyler, P. C.; Painter, G. F.; Lenz, D. H.; Schramm, V. L. Picomolar inhibitors as transition-state probes of 5′-methylthioadenosine nucleosidases ACS Chem. Biol. 2007, 2, 725-734
10. Stroeher, U. H.; Paton, A. W.; Ogunniyi, A. D.; Paton, J. C. Mutation of luxS of Streptococcus pneumoniae affects virulence in a mouse model Infect. Immun. 2003, 71, 3206-3212
11. Winzer, K.; Sun, Y. H.; Green, A.; Delory, M.; Blackley, D.; Hardie, K. R.; Baldwin, T. J.; Tang, C. M. Role of Neisseria meningitidis luxS in cell-to-cell signaling and bacteremic infection Infect. Immun. 2002, 70, 2245-2248
12. Parsek, M. R.; Val, D. L.; Hanzelka, B. L.; Cronan, J. E., Jr; Greenberg, E. P. Acyl homoserine-lactone quorum-sensing signal generation Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4360-4365
13. Schauder, S.; Shokat, K.; Surette, M. G.; Bassler, B. L. The LuxS family of bacterial autoinducers: biosynthesis of a novel quorum-sensing signal molecule Mol. Microbiol. 2001, 41, 463-476
14. Thomas, T.; Thomas, T. J. Polyamines in cell growth and cell death: molecular mechanisms and therapeutic applications Cell. Mol. Life Sci. 2001, 58, 244-258
15. Marton, L. J; Pegg, A. E. Polyamines as targets for therapeutic intervention Annu. Rev. Pharmacol. Toxicol. 1995, 35, 55-91
16. Seiler, N.; Atanassov, C. L.; Raul, F. Polyamine metabolism as target for cancer chemoprevention (review) Int. J. Oncol. 1998, 13, 993-1006
17. Chattopadhyay, S.; Zhao, R.; Tsai, E.; Schramm, V. L.; Goldman, I. D. The effect of a novel transition state inhibitor of methylthioadenosine phosphorylase on pemetrexed activity Mol. Cancer Ther. 2006, 5, 2549-2555
18. Singh, V.; Evans, G. B.; Lenz, D. H.; Mason, J. M.; Clinch, K.; Mee, S.; Painter, G. F.; Tyler, P. C.; Furneaux, R. H.; Lee, J. E.; Howell, P. L.; Schramm, V. L. Femtomolar transition analogue inhibitors of 5′- methylthioadenosine/ S-adenosylhomocysteine nucleosidase from Escherichia coli J. Biol. Chem. 2005, 280, 18265-18273
19. Evans, G. B.; Furneaux, R. H.; Lenz, D. H.; Painter, G. F.; Schramm, V. L.; Singh, V.; Tyler, P. C. Second generation transition state analogue inhibitors of human 5′-methylthioadenosine phosphorylase J. Med. Chem. 2005, 48, 4679-4689
20. Gutierrez, J. A.; Crowder, T.; Rinaldo-Matthis, A.; Ho, M.-C.; Almo, S. C.; Schramm, V. L. Transition state analogs of 5′-methylthioadenosine nucleosidase disrupt quorum sensing Nat. Chem. Biol. 2009, 5, 251-257
21. Gutierrez, J. A.; Schramm, V. L. Unpublished results.
22. Evans, G. B.; Furneaux, R. H.; Tyler, P. C.; Schramm, V. L. Synthesis of a transition state analogue inhibitor of purine nucleoside phosphorylase via the mannich reaction Org. Lett. 2003, 5, 3639-3640
23. Hansen, S. U.; Bols, M. 1-Azaribofuranoside analogues as designed inhibitors of purine nucleoside phosphorylase. Synthesis and biological evaluation Acta Chem. Scand. 1998, 52, 1214-1222
24. Rives, A.; Génisson, Y.; Faugeroux, V.; Zedde, C.; Lepetit, C.; Chauvin, R.; Andrieu-Abadie, N.; Colié, S.; Levade, T.; Baltas, M. Highly regioselective oxirane ring-opening of a versatile epoxypyrrolidine precursor of new imino-sugar-based sphingolid mimics Eur. J. Org. Chem. 2009, 2474-2489
25. Cren, S.; Gurcha, S. S.; Blake, A. J.; Besra, G. S.; Thomas, N. R. Synthesis and biological evaluation of new inhibitors of UDP-Gal f transferase-a key enzyme in M. tuberculosis cell wall biosynthesis Org. Biomol. Chem. 2004, 2, 2418-2420
26. Kamal, A.; Shaik, A. A.; Sandbhor, M.; Malik, M. S.; Azeeza, S. Chemoenzymatic synthesis of (3 R,4 S)-and (3 S,4 R)-3-methoxy-4- methylaminopyrrolidine Tetrahedron: Asymmetry 2006, 17, 2876-2883
27. Yamaguchi, M.; Hirao, I. An efficient method for the alkynylation of oxiranes using alkynyl boranes Tetrahedron Lett. 1983, 24, 391-394
28. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddtion between azides and alkynes Med. Res. Rev. 2008, 28, 278-308
29. Tsuzuki, Y.; Chiba, K.; Mizuno, K.; Tomita, K.; Suzuki, K. Practical synthesis of (3 S,4 S)-3-methoxy-4-methylpyrolidine Tetrahedron: Asymmetry 2002, 12, 2989-2997
30. Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057-3064
31. Rostovtsev, V. V; Green, L. G; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
32. Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Efficient synthesis of 2-substituted-1,2,3-triazoles Org. Lett. 2008, 10, 3171-3174
33. Loren, J. C.; Krasiński, Fokin, V. V; Sharpless, K. B. N H-1,2,3-Triazoles from azidomethyl pivalate and carbamates: base-labile N-protecting groups Synlett 2005, 2847-2850
34. Becer, C. R.; Hoogenboom, R.; Schubert, U. S. Click chemistry beyond metal-catalyzed cycloaddition Angew. Chem., Int. Ed. 2009, 48, 4900-4908
35. Heidecke, C. D.; Lindhorst, T. K. Iterative synthesis of spacered glycodendrons as oligomannoside mimetics and evaluation of their antiadhesive properties Chem.-Eur. J. 2007, 13, 9056-9067
36. Henin, F.; Muzart, J. Cis-and trans-opening of oxirane by vinyl Grignard Reagents Synth. Commun. 1984, 1355-1358
37. Clinch, K; Evans, G. B.; Furneaux, R. H.; Lenz, D.; Mason, J. M.; Mee, S. P.; Tyler, P. C.; Wilcox, S. J. A Practical synthesis of (3 R,4 R)-N-tert-butoxycarbonyl-4-hydroxymethylpyrrolidin-3-ol Org. Biomol. Chem. 2007, 5, 2800-2802
38. Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products Synthesis 1981, 1-28
39. Clinch, K; Evans, G. B.; Fleet, G. W.; Furneaux, R. H.; Johnson, S. W.; Lenz, D.; Mee, S. P.; Rands, P. R.; Schramm, V. L.; Taylor Ringia, E. A; Tyler, P. C. Syntheses and bio-activities of the l-enantiomers of two potent transition state analogue inhibitors of purine nucleoside phosphorylases Org. Biomol. Chem. 2006, 4, 1131-1139
40. Murkin, A. S.; Tyler, P. C.; Schramm, V. L. Transition state interactions revealed in purine nucleoside phosphorylase by binding isotope effects J. Am. Chem. Soc. 2008, 130, 2166-2167