Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate

Journal of Medicinal Chemistry

Volumn 51, Issue 6, 2008, Pages 1747-1754

  Boëdec, Angélique ^a   Sicard, Hélène ^a   Dessolin, Jean ^b   Herbette, Gaëtan ^c   Ingoure, Sophie ^a   Raymond, Cédric ^a   Belmant, Christian ^a   Kraus, Jean Louis ^d  

^a INNATE PHARMA   (France)

^b CNRS   (France)

^c AIX MARSEILLE UNIVERSITY   (France)

^d AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 2 METHYLBUT 2 ENYL 4 DIPHOSPHATE; 1 HYDROXY 2 METHYLPENT 2 ENYLPHOSPHONATE; 1 HYDROXY 2 METHYLPENT 2 ENYLPYROPHOSPHONATE; 1 HYDROXY 3 METHYLBUT 2 ENYLDIPHOSPHATE; 1 HYDROXY 3 METHYLPENT 2 ENYLPHOSPHONATE; 1 HYDROXY 3 METHYLPENT 2 ENYLPYROPHOSPHONATE; PHOSPHONIC ACID DERIVATIVE; PYROPHOSPHORIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STABILITY; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; FEMALE; HUMAN; HUMAN EXPERIMENT; MALE; NONHUMAN; NORMAL HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; T LYMPHOCYTE;

ANIMALS; DIPHOSPHATES; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HUMANS; INJECTIONS, INTRAVENOUS; MACACA FASCICULARIS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, ANIMAL; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; RATS; STEREOISOMERISM; T-LYMPHOCYTES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 41149131299     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701101g     Document Type: Article

References (23)

1. Constant, P.; Davodeau, F.; Peyrat, M. A.; Poquet, Y.; Puzo, G.; BonnevilleM.; Fournie, J. J. Stimulation of human gamma delta T cells by nonpeptidic mycobacterial ligands. Science 1994, 264, 267-270.
2. Allison, T. J.; Winter, C. C.; Fournie, J. J; Bonneville, M.; Garboczi, D. N. Structure of a human gamma delta T-cell antigen receptor. Nature 2001, 411, 820-824.
3. Bonneville, M.; Scotet, E. Human Vγ9Vδ2 T cells: Promising new leads for immunotherapy of infections and tumors. Curr. Opin. Immunol. 2006, 18, 1-8.
4. Sicard, H.; Fournie, J. J. Metabolic routes as targets for immunological discrimination of host and parasite. Infect. Immun. 2000, 68, 4375-4377.
5. Espinosa, E.; Belmant, C.; Pont, F.; Luciani, B.; Poupot, R.; Romagné, F.; Brailly, H.; Bonneville, M.; Fournié, J. J. Chemical synthesis and biological activity of bromohydrin pyrophosphate, a potent stimulator of human γδ T cells. J. Biol. Chem. 2001, 276, 18337-18344.
6. Amslinger, S.; Kis, K.; Hecht, S.; Adam, P.; Rohdich, F.; Arigoni, D.; Bacher, A.; Eisenreich, W. Biosynthesis of terpenes. Preparation of (E-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate, an intermediate of the deoxyxylulose phosphate pathway. J. Org. Chem. 2002, 67, 4590-4594.
7. Hecht, S.; Amslinger, S.; Jauch, J.; Kis, K.; Trentinaglia, V.; Adam, P.; Eisenreich, W.; Bacher, A.; Rohdich, F. Studies on the non-mevalonate isoprenoid biosynthetic pathway. Simple methods for preparation of isotope-labeled (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate. Tetrahedron Lett. 2002, 43, 8929-8933.
8. Amslinger, S.; Hecht, S.; Rohdich, F.; Eisenreich, W.; Adam, P.; Bacher, A.; Bauer, S. Stimulation of Vγ9/Vδ2 T-lymphocyte proliferation by the isoprenoid precursor, (E)-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate. Immunobiology 2007, 212, 47-55.
9. Patani, G. A.; LaVoie, E. J. Bioisosterism: A rational approach in drug design. Chem. Rev. 1996, 96, 3147-3176.
10. Thornber, C. W. Isosterism and molecular modification in drug design. Chem. Soc. Rev. 1979, 8, 563-580.
11. Sicard, H.; Ingoure, S.; Luciani, B.; Serraz, C.; Fournie, J. J.; Bonneville, M.; Tiollier, J.; Romagne, F. In vivo immunomanipulation of V gamma 9V delta 2 T cells with a synthetic phosphoantigen in a preclinical nonhuman primate model. J. Immunol. 2005, 175, 5471-5480.
12. Cooper, J.; Knight, D. W.; Gallagher, P. T. Total synthesis of (-)-α-kainic acid. J. Chem. Soc., Perkin Trans. 1 1992, 5, 553-559.
13. Kondo, K.; Matsui, K.; Negishi, A. Polyprenyl sulfides. Jpn. Kokai Tokkyo Koho, JP 49042627, 1974.
14. Valentijn, A. R. P. M.; van der Marel, G. A.; Cohen, L. H.; van Boom, J. H. An expeditious synthesis of pyrophosphate analogues of farnesyl pyrophosphate using the phosphonylating agent methyl methylphosphonomorpholidate. Synlett 1991, 9, 663-664.
15. Pont, F.; Luciani, B.; Belmant, C.; Fournie, J. J. Characterization of phosphoantigens by high-performance anion-exchange chromatography-electrospray ionization ion trap mass spectrometry and nanoelectrospray ionization ion trap mass spectrometry. Anal. Chem. 2001, 73, 35623569..
16. Poquet, Y.; Constant, P.; Peyrat, M. A.; Poupot, R.; Halary, F.; Bonneville, M.; Fournie, J. J. High-pH anion-exchange chromatographic analysis of phosphorylated compounds: Application to isolation and characterization of nonpeptide mycobacterial antigens. Anal. Biochem. 1996, 243, 119-126.
17. Belmant, C.; Espinosa, E.; Halary, F.; Tang, Y.; Peyrat, M. A.; Sicard, H.; Kozikowski, A.; Buelow, R.; Poupot, R.; Bonneville, M.; Fournie, J. J. A chemical basis for selective recognition of nonpeptide antigens by human delta T cells. FASEB J. 2000, 14, 16691670..
18. Bennouna, J.; Medioni, J.; Rolland, F.; Misset, J. L.; Campone, M.; Sicard, H.; Tiollier, J.; Romagné, F.; Douillard, J. Y.; Calvo, F. Phase I clinical trial of bromohydrine pyrophosphate, BrHPP (phosphostim), a Vg9Vd2 T lymphocytes agonist in combination with low dose interleukin-2 in patients with solid tumors. J. Clin. Oncol. 2005, 23, 174.
19. Coquerel, G.; Aubin, E. Preparation of phosphoantigens salts of organic bases and methods for their crystallization. PCT Int. Appl. WO 2007039635, 2007.
20. Halgren, T. A. Merck molecular force field. I. Basis form, scope parameterization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519.
21. Chang, G.; Guida, W. C.; Still, W. C. An internal-coordinate Monte Carlo method for searching conformational space. J. Am. Chem. Soc. 1989, 111, 4379-4386.
22. Saunders, M.; Houk, K. N.; Wu, Y. D.; Still, W. C.; Lipton, M.; Chang, G.; Guida, W. C. Conformations of cycloheptadecane. A comparison of methods for conformational searching. J. Am. Chem. Soc. 1990, 112, 1419-1427.
23. Shenkin, P. S.; McDonald, D. Q. Cluster analysis of molecular conformations. J. Comput. Chem. 1994, 15, 899-916.