Optimal cleavage and oxidative folding of α-conotoxin txib as a therapeutic candidate peptide

Marine Drugs

Volumn 11, Issue 9, 2013, Pages 3537-3553

  Wu, Xiaosa ^a   Wu, Yong ^a   Zhu, Furong ^a   Yang, Qiuyuan ^a   Wu, Qianqian ^a   Zhangsun, Dongting ^a   Luo, Sulan ^a  

^a HAINAN UNIVERSITY   (China)

Author keywords

Optimization; Oxidative folding; Therapeutic peptides; conotoxin TxIB

Indexed keywords

ALPHA CONOTOXIN TXIB; CONOTOXIN; CYSTEINE; GLUTATHIONE; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ALPHA HELIX; AMINO ACID SEQUENCE; ARTICLE; BETA SHEET; BETA TURN; CHEMICAL INTERACTION; CONTROLLED STUDY; DISULFIDE BOND; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; OXIDATION; OXIDATION REDUCTION REACTION; PEPTIDE ANALYSIS; PH; PROTEIN CLEAVAGE; PROTEIN FOLDING; REACTION TIME; SOLID PHASE SYNTHESIS; SOLVENT EFFECT; TEMPERATURE SENSITIVITY; TOXIN ANALYSIS; TOXIN STRUCTURE;

CONOTOXINS; HYDROGEN-ION CONCENTRATION; OXIDATION-REDUCTION; PEPTIDES; PROTEIN FOLDING; SALTS; SOLUTIONS; SOLVENTS; TEMPERATURE;

EID: 84885059721     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11093537     Document Type: Article

References (44)

1. Albuquerque, E.X.; Pereira, E.F.; Alkondon, M.; Rogers, S.W. Mammalian nicotinic acetylcholine receptors: From structure to function. Physiol. Rev. 2009, 89, 73-120.
2. Millar, N.S.; Gotti, C. Diversity of vertebrate nicotinic acetylcholine receptors. Neuropharmacology 2009, 56, 237-246.
3. Rose, J.E. Multiple brain pathways and receptors underlying tobacco addiction. Biochem. Pharmacol. 2007, 74, 1263-1270.
4. Quik, M.; Perez, X.A.; Grady, S.R. Role of α6 nicotinic receptors in CNS dopaminergic function: Relevance to addiction and neurological disorders. Biochem. Pharmacol. 2011, 82, 873-882.
5. Luo, S.; Christensen, S.; Zhangsun, D.; Wu, Y.; Hu, Y.; Zhu, X.; Chhabra, S.; Norton, R.S.; McIntosh, J.M. A novel inhibitor of alpha9alpha10 nicotinic acetylcholine receptors from Conus vexillum delineates a new conotoxin superfamily. PLoS ONE 2013, 8, e54648.
6. Lewis, R.J.; Garcia, M.L. Therapeutic potential of venom peptides. Nat. Rev. Drug Discov. 2003, 2, 790-802.
7. Han, T.S.; Teichert, R.W.; Olivera, B.M.; Bulaj, G. Conus venoms - a rich source of peptide-based therapeutics. Curr. Pharm. Des. 2008, 14, 2462-2479.
8. Luo, S.; Akondi, K.B.; Zhangsun, D.; Wu, Y.; Zhu, X.; Hu, Y.; Christensen, S.; Dowell, C.; Daly, N.L.; Craik, D.J.; et al. Atypical alpha-conotoxin LtIA from Conus litteratus targets a novel microsite of the alpha3beta2 nicotinic receptor. J. Biol. Chem. 2010, 285, 12355-12366.
9. Ellison, M.; Haberlandt, C.; Gomez-Casati, M.E.; Watkins, M.; Elgoyhen, A.B.; McIntosh, J.M.; Olivera, B.M. Alpha-RgIA: A novel conotoxin that specifically and potently blocks the alpha9alpha10 nAChR. Biochemistry 2006, 45, 1511-1517.
10. Luo, S.; Kulak, J.M.; Cartier, G.E.; Jacobsen, R.B.; Yoshikami, D.; Olivera, B.M.; McIntosh, J.M. alpha-conotoxin AuIB selectively blocks alpha3 beta4 nicotinic acetylcholine receptors and nicotine-evoked norepinephrine release. J. Neurosci. 1998, 18, 8571-8579.
11. Lopez-Vera, E.; Aguilar, M.B.; Schiavon, E.; Marinzi, C; Ortiz, E.; Restano Cassulini, R.; Batista, C.V.; Possani, L.D.; Heimer de la Cotera, E.P.; Peri, F.; et al. Novel alpha-conotoxins from Conus spurius and the alpha-conotoxin EI share high-affinity potentiation and low-affinity inhibition of nicotinic acetylcholine receptors. FEBS J. 2007, 274, 3972-3985.
12. Klink, R.; de Kerchove d'Exaerde, A.; Zoli, M.; Changeux, J.P. Molecular and physiological diversity of nicotinic acetylcholine receptors in the midbrain dopaminergic nuclei. J. Neurosci. 2001, 21, 1452-1463.
13. Livett, B.G.; Sandall, D.W.; Keays, D.; Down, J.; Gayler, K.R.; Satkunanathan, N.; Khalil, Z. Therapeutic applications of conotoxins that target the neuronal nicotinic acetylcholine receptor. Toxicon 2006, 48, 810-829.
14. Gehrmann, J.; Alewood, P.F.; Craik, D.J. Structure determination of the three disulfide bond isomers of α-conotoxin GI: A model for the role of disulfide bonds in structural stability. J. Mol. Biol. 1998, 278, 401-415.
15. Luo, S.; Zhangsun, D.; Wu, Y.; Zhu, X.; Hu, Y.; McIntyre, M.; Christensen, S.; Akcan, M.; Craik, D.J.; McIntosh, J.M. Characterization of a Novel alpha-Conotoxin from Conus textile that Selectively Targets Alpha6/alpha3beta2betab3 Nicotinic Acetylcholine Receptors. J. Biol. Chem. 2013, 288, 894-902.
16. Guy, CA.; Fields, G.B. Trifluoroacetic acid cleavage and deprotection of resin-bound peptides following synthesis by Fmoc chemistry. Methods Enzymol. 1997, 289, 67-83.
17. Fields, CG.; Fields, G.B. Minimization of tryptophan alkylation following 9-fluorenylmethoxy carbonyl solid-phase peptide synthesis. Tetrahedron Lett. 1993, 34, 6661-6664.
18. King, D.S.; Fields, CG; Fields, G.B. A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis. Int. J. Pept. Protein Res. 1990, 36, 255-266.
19. Pearson, D.A.; Blanchette, M.; Baker, M.L.; Guindon, CA. Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis. Tetrahedron Lett. 1989, 30, 2739-2742.
20. Bulaj, G; Olivera, B.M. Folding of conotoxins: formation of the native disulfide bridges during chemical synthesis and biosynthesis of Conus peptides. Antioxid. Redox Signal. 2008, 10, 141-155.
21. De La Cruz, R.; Whitby, F.G.; Buczek, O.; Bulaj, G. Detergent-assisted oxidative folding of delta-conotoxins. J. Pept. Res. 2003, 61, 202-212.
22. Gyanda, R.; Banerjee, J.; Chang, Y.P.; Phillips, A.M.; Toll, L.; Armishaw, C.J. Oxidative folding and preparation of alpha-conotoxins for use in high-throughput structure-activity relationship studies. J. Pept. Sci. 2012, 19, 16-24.
23. Konermann, L.; Stocks, B.B.; Pan, Y.; Tong, X. Mass spectrometry combined with oxidative labeling for exploring protein structure and folding. Mass Spectrom. Rev. 2010, 29, 651-667.
24. Salamanca, S.; Chang, J.Y. Unfolding and refolding pathways of a major kinetic trap in the oxidative folding of alpha-lactalbumin. Biochemistry 2005, 44, 744-750.
25. Wong, C.T.T.; Taichi, M.; Nishio, H.; Nishiuchi, Y.; Tam, J.P. Optimal Oxidative Folding of the Novel Antimicrobial Cyclotide from Hedyotis biflora Requires High Alcohol Concentrations. Biochemistry 2011, 50, 7275-7283.
26. Gunasekera, S.; Daly, N.L.; Clark, R.J.; Craik, D.J. Dissecting the oxidative folding of circular cystine knot miniproteins. Antioxid. Redox signal. 2009, 11, 971-980.
27. Leta Aboye, T.; Clark, R.J.; Craik, D.J.; Goransson, U. Ultra-stable peptide scaffolds for protein engineering-synthesis and folding of the circular cystine knotted cyclotide cycloviolacin O2. Chembiochem. 2008, 9, 103-113.
28. Steiner, A.M.; Bulaj, G. Optimization of oxidative folding methods for cysteine-rich peptides: a study of conotoxins containing three disulfide bridges. J. Pept. Sci. 2011, 17, 1-7.
29. Fuller, E.; Green, B.R.; Catlin, P.; Buczek, O.; Nielsen, J.S.; Olivera, B.M.; Bulaj, G Oxidative folding of conotoxins sharing an identical disulfide bridging framework. FEBS J. 2005, 272, 1727-1738.
30. Bulaj, G; Buczek, O.; Goodsell, I.; Jimenez, E.C.; Kranski, J.; Nielsen, J.S.; Garrett, J.E.; Olivera, B.M. Efficient oxidative folding of conotoxins and the radiation of venomous cone snails. Proc. Natl. Acad. Sci. USA 2003, 100 (Suppl. 2), 14562-14568.
31. Zhang, R.M.; Snyder, G.H. Factors governing selective formation of specific disulfides in synthetic variants of alpha-conotoxin. Biochemistry 1991, 30, 11343-11348.
32. Nielsen, J.S.; Buczek, P.; Bulaj, G. Cosolvent-assisted oxidative folding of a bicyclic alpha-conotoxin ImI. J. Pept. Sci. 2004, 10, 249-256.
33. Grishin, A.A.; Wang, C.I.; Muttenthaler, M.; Alewood, P.F.; Lewis, R.J.; Adams, D.J. Alpha-conotoxin AuIB isomers exhibit distinct inhibitory mechanisms and differential sensitivity to stoichiometry of alpha3beta4 nicotinic acetylcholine receptors. J. Biol. Chem. 2010, 285, 22254-22263.
34. Clark, R.J.; Daly, N.L.; Halai, R.; Nevin, S.T.; Adams, D.J.; Craik, D.J. The three-dimensional structure of the analgesic alpha-conotoxin, RgIA. FEBS Lett. 2008, 582, 597-602.
35. Anderson, M.E.; Meister, A. Transport and direct utilization of gamma-glutamylcyst(e)ine for glutathione synthesis. Proc. Natl. Acad. Sci. USA 1983, 80, 707-711.
36. Aboye, T.L.; Clark, R.J.; Burman, R.; Roig, M.B.; Craik, D.J.; Goransson, U. Interlocking disulfides in circular proteins: toward efficient oxidative folding of cyclotides. Antioxid. Redox Signal. 2011, 14, 77-86.
37. Kubo, S.; Chino, N.; Kimura, T.; Sakakibara, S. Oxidative folding of omega-conotoxin MVIIC: Effects of temperature and salt. Biopolymers 1996, 38, 733-744.
38. Tam, J.P.; Wu, CR.; Liu, W.; Zhang, J.W. Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and applications. J. Am. Chem. Soc. 1991, 113, 6657-6662.
39. Bulaj, G; Kortemme, T.; Goldenberg, D.P. Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry 1998, 37, 8965-8972.
40. Zhang, J.; Diamond, S.; Arvedson, T.; Sasu, B.J.; Miranda, L.P. Oxidative folding of hepcidin at acidic pH. Biopolymers 2010, 94, 257-264.
41. Kubo, S.; Tanimura, K.; Nishio, H.; Chino, N.; Teshima, T.; Kimura, T.; Nishiuchi, Y. Optimization of the Oxidative Folding Reaction and Disulfide Structure Determination of Human α-Defensin 1, 2, 3 and 5. Int. J. Pept. Res. Ther. 2008, 14, 341-349.
42. Daly, N.L.; Craik, D.J. Acyclic permutants of naturally occurring cyclic proteins Characterization of cystine knot and β-sheet formation in the macrocyclic polypeptide kalata B1. J. Biol. Chem. 2000, 275, 19068-19075.
43. Shimizu, S.; Shimizu, K. Alcohol denaturation: thermodynamic theory of peptide unit solvation. J. Am. Chem. Soc. 1999, 121, 2387-2394.
44. Welker, E.; Narayan, M.; Wedemeyer, W.J.; Scheraga, H.A. Structural determinants of oxidative folding in proteins. Proc. Natl. Acad. Sci. USA 2001, 98, 2312-2316.