Dicarba α-conotoxin Vc1.1 analogues with differential selectivity for nicotinic acetylcholine and GABAB receptors

ACS Chemical Biology

Volumn 8, Issue 8, 2013, Pages 1815-1821

  Van Lierop, Bianca J ^a   Robinson, Samuel D ^a   Kompella, Shiva N ^b   Belgi, Alessia ^a   McArthur, Jeffrey R ^b   Hung, Andrew ^b   Macraild, Christopher A ^a   Adams, David J ^b   Norton, Raymond S ^a   Robinson, Andrea J ^a  

^a MONASH UNIVERSITY   (Australia)

^b RMIT UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID RECEPTOR; ACETYLCHOLINE; ALPHA CONOTOXIN MII; CALCIUM CHANNEL; CYCLOPEPTIDE; CYSTINE; G PROTEIN COUPLED RECEPTOR; NICOTINIC RECEPTOR;

ANALGESIC ACTIVITY; ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; ISOMER; NERVE CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OOCYTE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RAT; RING CLOSING METATHESIS; XENOPUS;

AMINO ACID SEQUENCE; ANIMALS; CONOTOXINS; GAMMA-AMINOBUTYRIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, BIOLOGICAL; NEURONS; OOCYTES; RATS; RECEPTORS, GABA; RECEPTORS, NICOTINIC; XENOPUS;

EID: 84880874447     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb4002393     Document Type: Article

References (25)

1. Sandall, D. W., Satkunanathan, N., Keays, D. A., Polidano, M. A., Liping, X., Pham, V., Down, J. G., Khalil, Z., Livett, B. G., and Gayler, K. R. (2003) A novel α-conotoxin identified by gene sequencing is active in suppressing the vascular response to selective stimulation of sensory nerves in vivo Biochemistry 42, 6904-6911
2. Satkunanathan, N., Livett, B., Gayler, K., Sandall, D., Down, J., and Khalil, Z. (2005) Alpha-conotoxin Vc1.1 alleviates neuropathic pain and accelerates functional recovery of injured neurones Brain Res. 1059, 149-158
3. Clark, R. J., Fischer, H., Nevin, S. T., Adams, D. J., and Craik, D. J. (2006) The synthesis, structural characterization, and receptor specificity of the α-conotoxin Vc1.1 J. Biol. Chem. 281, 23254-23263
4. Vincler, M., Wittenauer, S., Parker, R., Ellison, M., Olivera, B. M., and McIntosh, J. M. (2006) Molecular mechanism for analgesia involving specific antagonism of α9 α10 nicotinic acetylcholine receptors Proc. Natl. Acad. Sci. U.S.A. 103, 17880-17884
5. B receptor activation J. Neurosci. 28, 10943-10951
6. Callaghan, B. and Adams, D. J. (2010) Analgesic α-conotoxins Vc1.1 and Rg1A inhibit N-type calcium channels in sensory neurons of α9 nicotinic receptor knockout mice Channels 4, 1-4
7. Clark, R. J., Jensen, J., Nevin, S. T., Callaghan, B. P., Adams, D. J., and Craik, D. J. (2010) The engineering of an orally active conotoxin for the treatment of neuropathic pain Angew. Chem., Int. Ed. 49, 6545-6548
8. v2.2) calcium channels by analgesic α-conotoxins J. Biol. Chem. 287, 23948-23957
9. v2.2) calcium channels Br. J. Pharmacol. 166, 486-500
10. Nevin, S. T., Clark, R. J., Klimis, H., Christie, M. J., Craik, D. J., and Adams, D. J. (2007) Are α9 α10 nicotinic acetylcholine receptors a pain target for α-conotoxins? Mol. Pharmacol. 72, 1406-1410
11. Klimis, H., Adams, D. J., Callaghan, B., Nevin, S., Alewood, P. F., Vaughan, C. W., Mozar, C. A., and Cristie, M. J. (2011) A novel mechanism of inhibition of high-voltage activated calcium channels by α-conotoxins contributes to relief of nerve injury-induced neuropathic pain Pain 152, 259-266
12. Livett, B. G., Sandall, D. W., Keays, D., Down, J., Gayler, K. R., Satkunanathan, N., and Khalil, Z. (2006) Therapeutic applications of conotoxins that target the neuronal nicotinic acetylcholine receptor Toxicon 48, 810-829
13. Hossain, M. A., Rosengren, K. J., Bathgate, R. A. D., Tregear, G. W., van Lierop, B. J., Robinson, A. J., and Wade, J. D. (2009) Therapeutic applications of conotoxins that target the neuronal nicotinic acetylcholine receptor Org. Biomol. Chem. 7, 1485-1736
14. MacRaild, C. A., Illesinghe, J., van Lierop, B. J., Townsend, A. L., Chebib, M., Livett, B. G., Robinson, A. J., and Norton, R. S. (2009) Structure and activity of (2,8)-dicarba-(3,12)-cystino α-ImI, an α-conotoxin containing a nonreducible cystine analogue J. Med. Chem. 52, 755-762
15. Zhang, S. D., Hughes, R. A., Bathgate, R. A., Shabanpoor, F., Hossain, M. A., Lin, F., van Lierop, B. J., Robinson, A. J., and Wade, J. D. (2010) Role of the intra-A-chain disulfide bond of insulin-like peptide 3 in binding and activation of its receptor, RXFP2 Peptides 31, 1730-1736
16. Elaridi, J., Patel, J., Jackson, W. R., and Robinson, A. J. (2006) Controlled synthesis of (S, S)-2,7-diaminosuberic Acid: A method for regioselective construction of dicarba analogues of multicystine-containing peptides J. Org. Chem. 71, 7538-7545
17. Halai, R., Clark, R. J., Nevin, S. T., Jensen, J. E., Adams, D. J., and Craik, D. J. (2009) Scanning mutagenesis of α-conotoxin Vc1.1 reveals residues crucial for activity at the α9 α10 nicotinic acetylcholine receptor J. Biol. Chem. 284, 20275-20284
18. Celie, P. H., Kasheverov, I. E., Mordvintsev, D. Y., Hogg, R. C., van Nierop, P., van Elk, R., van Rossum-Fikkert, S. E., Zhmak, M. N., Bertrand, D., Tsetlin, V., Sixma, T. K., and Smit, A. B. (2005) Crystal structure of nicotinic acetylcholine receptor homolog AChBP in complex with an alpha-conotoxin PnIA variant Nat. Struct. Mol. Biol. 12, 582-588
19. 15N chemical shift referencing in biomolecular NMR J. Biomol. NMR 6, 135-140
20. Shen, Y., Delaglio, F., Cornilescu, G., and Bax, A. (2009) TALOS+: A hybrid method for predicting protein torsion angles from NMR chemical shifts J. Biomol. NMR 44, 213-223
21. Güntert, P. (2004) Automated NMR structure calculation with CYANA Methods Mol. Biol. 278, 353-378
22. Koradi, R., Billeter, M., and Wüthrich, K. (1996) MOLMOL: A program for display and analysis of macromolecular structures J. Mol. Graphics 14, 51-55
23. Schwieters, C. D., Kuszewski, J. J., Tjandra, N., and Clore, G. M. (2003) The Xplor-NIH NMR molecular structure determination package J. Magn. Reson. 160, 65-73
24. Linge, J. P. and Nilges, M. (1999) Influence of non-bonded parameters on the quality of NMR structures: a new force-field for NMR structure calculation J. Biomol. NMR 13, 51-59
25. Laskowski, R. A., Rullmann, J. A. C., MacArthur, M. W., Kaptein, R., and Thornton, J. M. (1996) AQUA and PROCHECK-NMR: Programs for checking the quality of protein structures solved by NMR J. Biomol. NMR 8, 477-496