Synthesis, Chiral Separation, Absolute Configuration Assignment, and Biological Activity of Enantiomers of Retro-1 as Potent Inhibitors of Shiga Toxin

ChemMedChem

Volumn 10, Issue 7, 2015, Pages 1153-1156

  Abdelkafi, Hajer ^a   Michau, Aurélien ^a   Clerget, Alexandra ^a   Buisson, David Alexandre ^a   Johannes, Ludger ^b   Gillet, Daniel ^a   Barbier, Julien ^a   Cintrat, Jean Christophe ^a  

^a CEA SACLAY   (France)

^b CNRS UMR3666   (France)

Author keywords

benzodiazepines; Retro 1; retrograde transport; Shiga toxin

Indexed keywords

ANTITOXIN; RETRO 1; SHIGA TOXIN; SHIGA TOXIN INHIBITOR; UNCLASSIFIED DRUG; 7-BROMO-5-PHENYL-4-PROPIONYL-1,3,4,5-TETRAHYDRO-2H-1,4-BENZODIAZEPIN-2-ONE; BENZODIAZEPINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PRIORITY JOURNAL; X RAY DIFFRACTION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; ESCHERICHIA COLI; ISOLATION AND PURIFICATION; METABOLISM; SHIGELLA DYSENTERIAE; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZODIAZEPINONES; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; ESCHERICHIA COLI; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SHIGA TOXIN; SHIGELLA DYSENTERIAE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84933514040     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201500139     Document Type: Article

References (21)

1. D. W. K. Acheson, G. T. Keusch, in The Comprehensive Sourcebook of Bacterial Protein Toxins, 2nd ed. (Eds.:, J. E. Alouf, J. H. Freer,), Elsevier, Paris, 1999, pp. 229-242.
2. A. D. O'Brien, R. K. Holmes, Microbiol. Rev. 1987, 51, 206-220.
3. P. I. Tarr, C. A. Gordon, W. L. Chandler, Lancet 2005, 365, 1073-1086.
4. C. Frank, D. Werber, J. P. Cramer, M. Askar, M. Faber, M. an der Heiden, H. Bernard, A. Fruth, R. Prager, A. Spode, M. Wadl, A. Zoufaly, S. Jordan, M. J. Kemper, P. Follin, L. Muller, L. A. King, B. Rosner, U. Buchholz, K. Stark, G. Krause, N. Engl. J. Med. 2011, 365, 1771-1780.
5. H. Karch, E. Denamur, U. Dobrindt, B. B. Finlay, R. Hengge, L. Johannes, E. Z. Ron, T. Tønjum, P. J. Sansonetti, M. Vicente, EMBO Mol. Med. 2012, 4, 841-848.
6. P. I. Tarr, J. E. Sadler, W. L. Chandler, J. N. George, H. M. Tsai, Lancet 2012, 379, 516-517.
7. F. Proulx, J. P. Turgeon, G. Delage, L. Lafleur, L. Chicoine, J. Pediatr. 1992, 121, 299-303.
8. H. Trachtman, A. Cnaan, E. Christen, K. Gibbs, S. Zhao, D. W. Acheson, R. Weiss, F. J. Kaskel, A. Spitzer, G. H. Hirschman, JAMA J. Am. Med. Assoc. 2003, 290, 1337-1344.
9. A. L. Lapeyraque, M. Malina, V. Fremeaux-Bacchi, T. Boppel, M. Kirschfink, M. Oualha, F. Proulx, M. J. Clermont, F. Le Deist, P. Niaudet, F. Schaefer, N. Engl. J. Med. 2011, 364, 2561-2563.
10. J. Menne, M. Nitschke, R. Stingele, M. Abu-Tair, J. Beneke, J. Bramstedt, J. P. Bremer, R. Brunkhorst, V. Busch, R. Dengler, G. Deuschl, K. Fellermann, H. Fickenscher, C. Gerigk, A. Goettsche, J. Greeve, C. Hafer, F. Hagenmuller, H. Haller, S. Herget-Rosenthal, B. Hertenstein, C. Hofmann, M. Lang, J. T. Kielstein, U. C. Klostermeier, J. Knobloch, M. Kuehbacher, U. Kunzendorf, H. Lehnert, M. P. Manns, T. F. Menne, T. N. Meyer, C. Michael, T. Munte, C. Neumann-Grutzeck, J. Nuernberger, H. Pavenstaedt, L. Ramazan, L. Renders, J. Repenthin, W. Ries, A. Rohr, L. C. Rump, O. Samuelsson, F. Sayk, B. M. Schmidt, S. Schnatter, H. Schocklmann, S. Schreiber, C. U. von Seydewitz, J. Steinhoff, S. Stracke, S. Suerbaum, A. van de Loo, M. Vischedyk, K. Weissenborn, P. Wellhoner, M. Wiesner, S. Zeissig, J. Buning, M. Schiffer, T. Kuehbacher, BMJ 2012, 345, e 4565.
11. L. Johannes, V. Popoff, Cell 2008, 135, 1175-1187.
12. P. Watson, R. A. Spooner, Adv. Drug Delivery Rev. 2006, 58, 1581-1596.
13. K. Sandvig, B. Spilsberg, S. U. Lauvrak, M. L. Torgersen, T. G. Iversen, B. van Deurs, Int. J. Med. Microbiol. 2004, 293, 483-490.
14. J. M. Lord, L. M. Roberts, W. I. Lencer, Curr. Top. Microbiol. Immunol. 2005, 300, 149-168.
15. J. Barbier, C. Bouclier, L. Johannes, D. Gillet, Toxins 2012, 4, 15-27.
16. B. Stechmann, S. K. Bai, E. Gobbo, R. Lopez, G. Merer, S. Pinchard, L. Panigai, D. Tenza, G. Raposo, B. Beaumelle, D. Sauvaire, D. Gillet, L. Johannes, J. Barbier, Cell 2010, 141, 231-242.
17. X. Ming, K. Carver, M. Fisher, R. Noel, J. C. Cintrat, D. Gillet, J. Barbier, C. Cao, J. Bauman, R. L. Juliano, Nucleic Acids Res. 2013, 41, 3673-3687.
18. N. Gupta, V. Pons, R. Noel, D. A. Buisson, A. Michau, L. Johannes, D. Gillet, J. Barbier, J. C. Cintrat, ACS Med. Chem. Lett. 2014, 5, 94-97.
19. L. H. Easson, E. Stedman, Biochem. J. 1933, 27, 1257-1266.
20. M. Czugler, A. Kálmán, J. Röhricht, M. Low, L. Ürögdi, L. Kisfaludy, Tetrahedron Lett. 1977, 18, 917-920.
21. C. Bertucci, A. Demuro, G. Giannaccini, J. Pharm. Biomed. Anal. 1997, 15, 803-809.