Chemical synthesis of MT1 and MT7 muscarinic toxins: Critical role of Arg-34 in their interaction with M1 muscarinic receptor

Molecular Pharmacology

Volumn 63, Issue 1, 2003, Pages 26-35

  Mourier, Gilles ^a   Dutertre, Sébastien ^a   Fruchart Gaillard, Carole ^a   Ménez, André ^a   Servent, Denis ^a  

^a DIF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; ATROPINE; METHYLSCOPOLAMINE; MUSCARINIC M1 RECEPTOR; MUSCARINIC TOXIN 1; MUSCARINIC TOXIN 2; RECEPTOR SUBTYPE; SNAKE VENOM; TRITIUM; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING SITE; DISSOCIATION; MOLECULAR RECOGNITION; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; RECEPTOR BINDING; SYNTHESIS; TOXIN ANALYSIS; TOXIN SYNTHESIS;

AMINO ACID SEQUENCE; ANIMALS; ARGININE; BINDING SITES; CHO CELLS; COBRA VENOMS; CRICETINAE; ELAPID VENOMS; HUMANS; MOLECULAR SEQUENCE DATA; PROTEIN CONFORMATION; RECEPTOR, MUSCARINIC M1; RECEPTORS, MUSCARINIC; SEQUENCE HOMOLOGY, AMINO ACID; TRANSFECTION;

EID: 0037218331     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.63.1.26     Document Type: Article

References (39)

1. Adem A and Karlsson E (1997) Muscarinic receptor subtype selective toxins. Life Sci 60:1069-1076.
2. Alessandri-Haber N, Lecoq A, Gasparini S, Grangier-Macmath G, Jacquet G, Harvey AL, de Medeiros C, Rowan EG, Gola M, Ménez A, et al. (1999) Mapping the functional anatomy of BgK on Kv1.1, Kv1.2 and Kv1.3. Clues to design analogs with enhanced selectivity. J Biol Chem 274:35653-35659.
3. Altschul SF, Madden TL, Schäffer AA, Zhang J, Zhang Z, Miller W, and Lipman DJ (1997) Gapped BLAST and PSI-BLAST: A new generation of protein database search programs. Nucleic Acids Res 25:3389-3402.
4. Antil S, Servent D, and Ménez A (1999) Variability among the sites by which curaremimetic toxins bind to Torpedo acetylcholine receptor, as revealed by identification of the functional residues of α-cobratoxin. J Biol Chem 274:34851-34858.
5. Antil-Delbeke S, Gaillard C, Tamiya T, Corringer PJ, Changeux JP, Servent D, and Ménez A (2000) Molecular determinants by which a long chain toxin from snake venom interacts with the neuronal α7 nicotinic acetylcholine receptor. J Biol Chem 275:29594-29601.
6. Bradley KN (2000) Muscarinic toxins from the green mamba. Pharmacol Ther 85:87-109.
7. Carpino LA, El-Farham A, Minor C, and Albericio F (1994) Advantageous application to azabenzotriazole-based coupling reagents to solid-phase peptide synthesis. J Chem Soc Chem Commun 201-206.
8. Carsi JM and Potter LT (2000) m1-toxin isotoxins from the green mamba (Dendroaspis angusticeps) that selectively block m1 muscarinic receptors. Toxicon 38:187-198.
9. Cheng Y-C and Prusoff WH (1973) Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 per cent inhibition (150) of an enzymatic reaction. Biochem Pharmacol 22:3099-3108.
10. Drake AF, Dufton MJ, and Hider RC (1980) Circular dichroism of elapidae protein toxins. Eur J Biochem 105:623-630.
11. Eglen RM, Choppin A, Dillon MP, and Hegde S (1999) Muscarinic receptor ligands and their therapeutic potential. Curr Opin Chem Biol 3:426-432.
12. Ellis J and Seidenberg M (2000) Interactions of alcuronium, TMB-8 and other allosteric ligands with muscarinic acetylcholine receptors: Studies with chimeric receptors. Mol Pharmacol 58:1451-1460.
13. Fiordalisi JJ, al-Rabiee R, Chiappinelli VA, and Grant GA. (1994) Site-directed mutagenesis of κ-bungarotoxin: Implications for neuronal receptor specificity. Biochemistry 33:3872-3877.
14. Fruchart-Gaillard C, Gilquin B, Antil-Delbeke S, Le Novère N, Tamiya T, Corringer PJ, Changeux JP, Ménez A, and Servent D (2002) Experimentally-based model of a complex between a snake toxin and the α7 nicotinic acetylcholine receptor. Proc Natl Acad Sci USA 99:3216-3221.
15. Gnagey AL, Seidenberg M, and Ellis J (1999) Site-directed mutagenesis reveals two epitopes involved in the subtype selectivity of the allosteric interactions of gallamine at muscarinic acetylcholine receptors. Mol Pharmacol 56:1245-1253.
16. Guex N and Peitsch MC (1997) SWISS-MODEL and the Swiss-PdbViewer: An environment for comparative protein modelling. Electrophoresis 18:2714-2723.
17. Jerusalinsky D and Harvey AL (1994) Toxins from mamba venoms: Small proteins with selectivities for different subtypes of muscarinic acetylcholine receptors. Trends Pharmacol Sci 15:424-430.
18. Jerusalinsky D, Kornisiuk E, Alfaro P, Quillfeldt J, Ferreira A, Rial VE, Duran R, and Cervenansky C (2000) Muscarinic toxins: Novel pharmacological tools for the muscarinic cholinergic system. Toxicon 38:747-761.
19. Jerusalinsky D, Kornisiuk E, Bernabeu R, Izquierdo I, and Cervenansky C (1995) Muscarinic toxins from the venom of Dendroaspis snakes with agonist-like actions. Toxicon 33:389-397.
20. Kalman K, Pennington MW, Lanigan MD, Nguyen A, Rauer H, Mahnir V, Paschetto K, Kem WR, Grissmer S, Gutman GA, et al. (1998) ShK-Dap22, a potent Kv1.3-specific immunosuppressive polypeptide. J Biol Chem 273:32697-32707.
21. Karlsson E, Jolkonen M, Mulugeta E, Onali P, and Adem A (2000) Snake toxins with high selectivity for subtypes of muscarinic acetylcholine receptors. Biochimie 82:793-806.
22. 1 muscarinic receptors. Mol Pharmacol 60:725-731.
23. 3H]scepolamine and acetylcholine at muscarinic receptor subtypes: Identification of a second allosteric site. Mol Pharmacol 58:194-207.
24. Max SI, Liang JS, and Potter LT (1993) Stable allosteric binding of m1-toxin to m1 muscarinic receptors. Mol Pharmacol 44:1171-1175.
25. Ménez A (1998) Functional architectures of animal toxins: A clue to drug design? Toxicon 36:1557-1572.
26. Ménez A, Servent D, and Gasparini S (2002) The sites by which animal toxins bind to their targets involve two components: A clue for selectivity, evolution and design of proteins, in Perspectives in Molecular Toxinology (Ménez A ed) pp 175-202, John Wiley & Sons, Ltd., New York.
27. Mourier G, Servent D, Zinn-Justin S, and Ménez A (2000) Chemical engineering of a three-fingered toxin with anti-α7 neuronal acetylcholine receptor activity. Protein Engineering 13:217-225.
28. 1 muscarinic receptors. Biochem Biophys Res Commun 271:435-439.
29. Nishiuchi Y, Nishio H, Inui T, Bodi J, and Kimura T (2000) Combined solid-phase and solution approach for the synthesis of large peptides or proteins. J Pept Sci 6:84-93.
30. Olianas MC, Maullu C, Adem A, Mulugeta E, Karlsson E, and Onali P (2000) Inhibition of acetylcholine muscarinic M(1) receptor function by the M(1)-selective ligand muscarinic toxin 7 (MT-7). Br J Pharmacol 131:447-452.
31. Peitsch MC (1995) Protein modeling by E-mail. Biotechnology 13:658-660.
32. Peitsch MC (1996) ProMod and Swiss-Model: Internet-based tools for automated comparative protein modelling. Biochem Soc Trans 24:274-279.
33. Potter LT (2001) Snake toxins that bind specifically to individual subtypes of muscarinic receptors. Life Sci 68, 2541-2547.
34. Racape J, Lecoq A, Romi-Lebrun R, Liu J, Kohler M, Garcia ML, Ménez A, and Gasparini S (2002) Characterization of a novel radiolabeled peptide selective for a subpopulation of voltage-gated potassium channels in mammalian brain. J Biol Chem 277:3886-3893.
35. Rosenthal JA, Levandoski MM, Chang B, Potts JF, Shi Q-L, and Hawrot E (1999) The functional role of positively charged amino acid side chains in α-bungarotoxin revealed by site-directed mutagenesis of a His-tagged recombinant α-bungarotoxin. Biochemistry 38:7847-7855.
36. Segalas I, Roumestand C, Zinn-Justin S, Gilquin B, Menez R, Menez A, and Toma F (1995) Solution structure of a green mamba toxin that activates muscarinic acetylcholine receptors, as studied by nuclear magnetic resonance and molecular modeling. Biochemistry 34:1248-1260.
37. Thompson JD, Higgins DG, and Gibson TJ (1994) CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680.
38. Trémeau O, Lemaire C, Drevet P, Pinkasfeld S, Ducancel F, Boulain JC, and Ménez A (1995) Genetic engineering of snake toxins. The functional site of Erabutoxin a, as delineated by site-directed mutagenesis, includes variant residues. J Biol Chem 270:9362-9369.
39. Waelbroeck M, De Neef P, Domenach V, Vandermeers-Piret MC, and Vandermeers A (1996) Binding of the labelled muscarinic toxin 1251-MT1 to rat brain muscarinic M1 receptors. Eur J Pharmacol 305:187-192.