Metallopeptidase inhibitors of tetanus toxin: A combinatorial approach

Journal of Medicinal Chemistry

Volumn 42, Issue 3, 1999, Pages 515-525

  Martin, Loïc ^a   Cornille, Fabrice ^a   Turcaud, Serge ^a   Meudal, Hervé ^a   Roques, Bernard P ^a   Fournié Zaluski, Marie Claude ^a  

^a Laboratoire de Pharmacochimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 (BUTYLOXYCARBONYLAMINO) 2 [(4 METHOXYBENZYL)SULFANYL] 6 OXO(TRITYLAMINO)HEXANOIC ACID; 3 (BUTYLOXYCARBONYLAMINO) 3 [3 (TERT BUTYLSULFAMOYL)PHENYL] 2 [(4 METHOXYBENZYL)SULFANYL]PROPANOIC ACID; 4 (TERT BUTYLSULFAMOYL) 2 (CARBAMAZEPINEAMINO)BUTANOIC ACID; METALLOPROTEINASE INHIBITOR; SYNAPTOBREVIN; TETANUS TOXIN; UNCLASSIFIED DRUG;

ARTICLE; CLOSTRIDIUM TETANI; ENZYME ACTIVITY; NEUROTOXICITY; NEUROTRANSMITTER RELEASE; NONHUMAN; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; SYNAPTIC TRANSMISSION;

AMINO ACID SEQUENCE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METALLOENDOPEPTIDASES; MOLECULAR STRUCTURE; PEPTIDE LIBRARY; PROTEASE INHIBITORS; SUBSTRATE SPECIFICITY; TETANUS TOXIN;

EID: 0033016862     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981066w     Document Type: Article

References (51)

1. Wellhöner, H. H. Tetanus and botulinum neurotoxin. Handbook of Exp. Pharmacol. 1992, 102, 357-417.
2. Niemann, H. H. In Sourcebook of Bacterial Protein Toxins; Alouf, J. E., Freer, J. H., Eds.; Academic Press: London, 1991; pp 303-348.
3. Montecucco, C.; Papini, E.; Schiavo, G. Bacterial protein toxins penetrate cells via a four-step mechanism. FEBS Lett. 1994, 346, 92-98.
4. Rawlings, N. D.; Barrett, A. J. Evolutionary families of metallopeptidases. Methodol. Enzymol. 1995, 248, 183-228.
5. Lipscomb, W. N.; Sträter, N. Recent advances in zinc enzymology. Chem. Rev. 1996, 96, 2375-2433.
6. Roques, B. P.; Noble, F.; Daugé, V.; Fournié-Zaluski, M.-C.; Beaumont, A. Neutral endopeptidase 24.11: Structure, inhibition, and experimental and clinical pharmacology. Pharmacol. Rev. 1993, 45 (1), 87-146.
7. Matthews, B. Structural Basis of the Action of Thermolysin and Related Zinc Peptidase. Ace. Chem. Res. 1988, 21, 333-340.
8. Li, Y.; Foran, P.; Fairweather, N. F.; de Paiva, A.; Weller, U.; Dougan, G.; Dolly J. O. A single mutation in the recombinant light chain of tetanus toxin abolishes its proteolytic activity and removes the toxicity seen after reconstitution with native heavy chain. Biochemistry 1994, 33, 7014-7020.
9. Yamasaki, S.; Hu, Y.; Binz, T.; Kalkuhl, A.; Kurazono, H.; Tamura T.; Jahn, R.; Kandel, E.; Niemann, H. Synaptobrevin/ vesicle-associated membrane protein (VAMP) of Aplysia californica: structure and proteolysis by tetanus toxin and botulinal neurotoxins type D and F. Proc. Natl. Acad. Sci. U.S.A. 1994, 91 (11), 4688-4692.
10. Borden Lacy, D.; Tepp, W.; Cohen, A. C.; DasGupta, B. R.; Stevens, R. C. Crystal structure of botulinum neurotoxin type A and implications for toxicity. Nature Struct. Biol. 1998, 5, 898-902.
11. Schiavo, G.; Benfenati, F.; Poulain, B.; Rossetto, O.; Polverino de Laureto, P.; DasGupta, B.; Montecucco, C. Tetanus and Botulinum-B neurotoxins block neurotransmitter release by proteolytic cleavage of synaptobrevin. Nature 1992,359 (6398), 832-835.
12. Trimble, W. S.; Cowan, D. M.; Scheller, R. H. VAMP-1: a synaptic vesicle-associated membrane protein. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4538-4542.
13. Baumert, M.; Maycox, P. R.; Navone, F.; De Camilli, P.; Jahn, R. Synaptobrevin: an integral membrane protein present in small synaptic vesicles of rat brain. EMBO J. 1989, 8, 379-384.
14. Südhof, T. C.; Baumert, M.; Perin, M. S.; Jahn, R. A. A synaptic vesicle membrane protein is conserved from mammals to chosophila. Neuron 1989, 2, 1475-1481.
15. Rossetto, O.; Schiavo, G.; Montecucco, C.; Poulain, B.; Deloye, F.; Lozzi, L.; Shone, C. Snare motifs and neurotoxin. Nature 1994, 372, 415-416.
16. Cornille, F.; Martin, L.; Lenoir, C.; Cussac, D.; Roques, B. P.; Fournié-Zaluski, M.-C. Cooperative Exosite-dependent Cleavage of Synaptobrevin by Tetanus Toxin Light Chain. J. Biol. Chem. 1997, 272 (6), 3459-3464.
17. Pellizari, R.; Rossetto, O.; Lozzi, L.; Giovedi, S.; Johnson, E.; Shone, C. C.; Montecucco, C. Structural determinants of the specificity for synaptic vesicle-associated membrane protein/ synaptobrevin of tetanus and botulinum type B and G neurotoxins. J. Biol. Chem. 1996, 271, 20353-20358.
18. Foran, P.; Shone, C. C.; Dolly, J. O. Differences in the protease activities of tetanus and botulinum B toxins revealed by the cleavage of vesicle-associated membrane protein and various sized fragments. Biochemistry 1994, 33, 15365-15374.
19. Cornille, F.; Goudreau, N.; Ficheux, D.; Niemann, H.; Roques, B. P. Solid-phase synthesis, conformational analysis and in vitro cleavage of synthetic human synaptobrevin II 1-93 by tetanus toxin L chain. Eur. J. Biochem. 1994, 222 (1), 173-181.
20. 3H]-noradrenaline release by the light chain of tetanus toxin. Naunyn-Schmiedebergs Arch. Pharmacol. 1992, 346 (3), 358-361.
21. Schiavo, G.; Poulain, B.; Rossetto, O.; Benfenati, F.; Tauc, L.; Montecucco, C. Tetanus toxin is a zinc protein and its inhibition of neurotransmitter release and protease activity depend on zinc. EMBO J. 11, 3577-3583.
22. Martin, L.; Coric, P.; Cornille, F.; Roques, B. P.; Fournié-Zaluski, M.-C. β-Aminothiols inhibit the Zn-metallopeptidase activity of tetanus toxin light chain. J. Med. Chem. 1998, 41, 3450-3460.
23. Gordon, E. M.; Godfrey, J. D.; Delaney, N. G.; Asaad, M. M.; Von Langen, D.; Cushman, D. W. Design of novel inhibitors of aminopeptidases. Synthesis of peptide-derived diamino thiols and sulfur replacement analogues of bestatin. J. Med. Chem. 1988, 31, 2199-2211.
24. Bischoff, L.; David, C.; Martin, L.; Meudal, H.; Roques, B. P.; Fournié-Zaluski, M.-C. 2,4-Dinitrophenyl 4-methoxybenzyl disulfide: a new efficient reagent for the electrophilic sulfenylation of β-amino ester enolates. J. Org. Chem. 1997, 62, 4848-4850.
25. Brown, W. G. Reductions by lithium aluminum hydride. Org. React. 1951, 6, 469-509.
26. Mancuso, A. J.; Swern, D. Activated dimethyl sulfoxide: useful reagents for synthesis. Synthesis 1981, 165-184.
27. Wadsworth, W. S.; Emmons, W. D. The utility of phosphonate carbanions in olefin synthesis. J. Am. Chem. Soc. 1961, 83, 1733-1738.
28. Davies, S. G.; Ichihara, O. Asymmetric synthesis of R-β-amino butanoic acid and S-β-tyrosine: homochiral lithium amide equivalents for Michael additions to α,β-unsaturated esters. Tetrahedron: Asym. 1991, 2 (3), 183-186.
29. Burke, A. J.; Davies, S. G.; Hedgecock, C. J. R. Asymmetric synthesis of (2S,3S)- and (2R,3S)-2,3-diaminobutanoic acids, nonprotein amino acid diastereomers found in a number of peptide antibiotics. Synlett 1996, 621-622.
30. Shibata, N.; Baldwin, J. E.; Jacobs, A.; Wood, M. E. Electrophilic sulfenylation in a stereocontrolled synthesis of protected (2R,3R)-3-mercaptoaspartic acid from L-aspartic acid. Tetrahedron 1996, 52 (39), 12839-12852.
31. Lu, G.-S.; Mojsov, S.; Tam, J. P.; Merrifield, R. B. Improved Synthesis of 4-Alkoxybenzyl Alcohol Resin. J. Org. Chem. 1981, 46, 3433-3436.
32. Pearson, D. A.; Blanchette, M.; Baker, M.; Guindon, C. A. Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis. Tetrahedron Lett. 1989, 30 (21), 2739-2742.
33. Sakakibara, S.; Shimonishi, Y.; Kishida, Y.; Okada, M.; Sugihara, H. Use of anhydrous hydrogen fluoride in peptide synthesis. I. Behavior of various protective groups in anhydrous hydrogen fluoride. Bull. Chem. Soc. Jpn. 1967, 40 (9), 2164-2167.
34. Barlos, K.; Chatzi, O.; Gatos, D.; Stravropoulos, G. 2-Chlorotrityl chloride resin. Int. J. Pept. Protein Res. 1991, 37, 513-520.
35. Jiracek, J.; Yiotakis, A.; Vincent, B.; Lecoq, A.; Nicolaou, A.; Checler, F.; Dive, V. Development of highly potent and selective phosphonic peptide inhibitors of zinc endopeptidase 24-15 using combinatorial chemistry. J. Biol. Chem. 1993, 270 (37), 21701-21706.
36. Jiracek, J.; Yiotakis, A.; Vincent, B.; Checler, F.; Dive, V. Development of the first potent and selective inhibitor of the zinc endopeptidase neurolysin using a systematic approach based on combinatorial chemistry of phosphinic peptides. J. Biol. Chem. 1996, 271 (32), 19606-19611.
37. Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. General method for rapid synthesis of multicomponent peptide mixtures. Int. J. Pept. Protein Res. 1991, 37, 487-493.
38. Barlos, K.; Gatos, D.; Kutsogianni, S.; Papaphotiou, G.; Poulos, C.; Tsegenidis, T. Solid phase synthesis of partially protected and free peptides containing disulphide bonds by simultaneous cysteine oxidation-release from 2-chlorotrityl resin. Int. J. Pept. Protein Res. 1991, 38, 562-568.
39. Soleilhac, J.-M.; Cornille, F.; Martin, L.; Lenoir, C.; Fournié-Zaluski, M.-C.; Roques, B. P. A Sensitive and Rapid Fluorescence-Based Assay for Determination of Tetanus Toxin Peptidase Activity. Anal. Biochem. 1996, 241, 120-127.
40. Ellman, J. A.; Gallop, M. A. Combinatorial chemistry. Curr. Opin. Chem. Biol. 1998, 2, 317-319.
41. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P.; Gordon, E. M. Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J. Med. Chem. 1994, 37, 1233-1251.
42. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P.; Gordon, E. M. Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J. Med. Chem. 1994, 37, 1385-1401.
43. Kuntz, I. D. Structure-based strategies for design and discovery. Science 1992, 257, 1078-1082.
44. Lybrand, T. P. Ligand-protein docking and rational drug design. Curr. Opin. Struct. Biol. 5, 224-228.
45. Murphy, M. M.; Schullek, J. R.; Gordon, E. M.; Gallop, M. A. Combinatorial organic synthesis of highly functionalized pyrrolidines: identification of a potent angiotensin converting enzyme inhibitor from a mercaptoacyl proline library. J. Am. Chem. Soc. 1995, 117, 7029-7030.
46. Rockwell, A.; Melden, M.; Copeland, R. A.; Hardman, K.; Decicco, C. P.; DeGrado, W. F. Complementarity of combinatorial chemistry and structure-based ligand design: Application to the discovery of novel inhibitors of matrix metalloproteinases. J. Am. Chem. Soc. 1996, 118, 10337-10338.
47. Wyvratt, M. J.; Patchett, A. A. Recent developments in the design of angiotensin-converting enzyme inhibitors. Med. Res. Rev. 1985, 5 (4), 483-531.
48. Chauvel, E. N.; Coric, P.; Llorens-Cortes, C.; Wilk, S.; Roques, B. P.; Fournié-Zaluski, M.-C. Investigation of the active site of aminopeptidase A using a series of new thiol-containig inhibitors. J. Med. Chem. 1994, 37, 1339-1346.
49. Yamasaki, S.; Baumeister, A.; Binz, T.; Blasi, J.; Link, E.; Cornille, F.; Roques, B. P.; Fykse, E.; Südhof, T.; Jahn, R. Cleavage of members of the synaptobrevin/VAMP family by types D and F botulinal neurotoxins and tetanus toxin. J. Biol. Chem. 1994, 269, 12764-12772.
50. Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Réactifs de couplage peptidique IV (1) - L'hiexafluorophosphate de benzotrialzolyl n-oxytrisdimethylamino phosphonium (B.O.P.). Tetrahedron Lett. 1975, 14, 1219-1222.
51. Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Ichihara, O. An expeditious asymmetric synthesis of allophenylnorstatine. Tetrahedron 1994, 50 (13), 3975-3986.