Discovery and applications of naturally occurring cyclic peptides

Drug Discovery Today: Technologies

Volumn 9, Issue 1, 2012, Pages

  Thorstholm, L ^a   Craik, D J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMANITIN; CARNOCYCLIN A; CIRCULARIN A; CIRCULIN; CYCLOPEPTIDE; CYCLOSPORIN; CYCLOVIOLACIN Y1; DEFENSIN; EPITOPE; GARVICIN ML; GASSERICIN A; LACTOCYCLICIN Q; PHALLOCIDIN; RHESUS THETA DEFENSIN 1; SUBTILISIN; SUNFLOWER TRYPSIN INHIBITOR 1; TRICYCLON A; UBEROLYSIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BUTYRIVIBRIO FIBRISOLVENS; CARBON NUCLEAR MAGNETIC RESONANCE; CARNOBACTERIUM MALTAROMATICUM; CLOSTRIDIUM BEIJERINCKII; CYCLIZATION; DRUG DESIGN; ESCHERICHIA COLI; FOOD PRESERVATION; GENE ACTIVATION; HELIANTHUS ANNUUS; HUMAN; LACTOBACILLUS GASSERI; LACTOCOCCUS GARVIEAE; MACACA MULATTA; NITROGEN NUCLEAR MAGNETIC RESONANCE; NONHUMAN; OLDENLANDIA; PSYCHOTRIA; RHIZOBIUM RADIOBACTER; STREPTOCOCCUS UBERIS; SYNTHESIS; VIOLACEAE;

EID: 84865696104     PISSN: None     EISSN: 17406749     Source Type: Journal    
DOI: 10.1016/j.ddtec.2011.07.005     Document Type: Review

References (40)

1. Cascales, L. and Craik, D.J. (2010) Naturally occurring circular proteins: Distribution, biosynthesis and evolution. Org. Biomol. Chem. 8, 5035-5047
2. Craik, D.J. (2006) Chemistry - seamless proteins tie up their loose ends. Science 311, 1563-1564
3. Walsh, C.T. (2004) Polyketide and nonribosomal peptide antibiotics: Modularity and versatility. Science 303, 1805-1810 (Pubitemid 38374864)
4. Craik, D.J. et al. (2004) Discovery, structure and biological activities of the cyclotides. Curr. Protein Pept. Sci. 5, 297-315 (Pubitemid 39200161)
5. Göransson, U. et al. (2004) Novel strategies for isolation and characterization of cyclotides: The discovery of bioactive macrocyclic plant polypeptides in the Violaceae. Curr. Protein Pept. Sci. 5, 317-329 (Pubitemid 39200162)
6. Maqueda, M. et al. (2008) Genetic features of circular bacteriocins produced by Gram-positive bacteria. FEMS Microbiol. Rev. 32, 2-22 (Pubitemid 350293913)
7. Tang, Y.Q. et al. (1999) A cyclic antimicrobial peptide produced in primate leukocytes by the ligation of two truncated alpha-defensins. Science 286, 498-502
8. Gran, L. (1973) Oxytocic principles of oldenlandia-affinis. Lloydia 36, 174-178
9. Saether, O. et al. (1995) Elucidation of the primary and 3-dimentional structure of the uterotonic polypeptide kalata B1. Biochemistry 34, 4147-4158
10. Viedma, P.M. et al. (2011) Inhibition of spoilage and toxigenic Bacillus species in dough from wheat flour by the cyclic peptide enterocin AS-48. Food Control 22, 756-761
11. Borrero, J. et al. (2011) Characterization of garvicin ML, a novel circular bacteriocin produced by Lactococcus garvieae DCC43, isolated from Mallard ducks (Anas platyrhynchos). Appl. Environ. Microbiol. 77, 369-373
12. Sawa, N. et al. (2009) Identification and characterization of lactocyclicin Q, a novel cyclic bacteriocin produced by Lactococcus sp. strain QU 12. Appl. Environ. Microbiol. 75, 1552-1558
13. Hallen, H.E. et al. (2007) Gene family encoding the major toxins of lethal Amanita mushrooms. Proc. Natl. Acad. Sci. U.S.A. 104, 19097-19101
14. Craik, D.J. et al. (1999) Plant cyclotides: A unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif. J. Mol. Biol. 294, 1327-1336 (Pubitemid 30008803)
15. Gruber, C.W. et al. (2008) Distribution and evolution of circular miniproteins in flowering plants. Plant Cell 20, 2471-2483 (Pubitemid 352844612)
16. Venkataraman, N. et al. (2009) Reawakening retrocyclins: Ancestral human defensins active against HIV-1. PLoS Biol. 7, 720-729
17. Garcia, A.E. et al. (2008) Isolation, synthesis, and antimicrobial activities of naturally occurring theta-defensin isoforms from baboon leukocytes. Infect. Immun. 76, 5883-5891
18. Stegemann, C. et al. (2010) De novo sequencing of two new cyclic thetadefensins from baboon (Papio hamadryas) leukocytes by matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun. Mass Spectrom. 24, 599-604
19. Jiang, S. et al. (2007) Design and synthesis of redox stable analogues of sunflower trypsin inhibitors (SFTI-1) on solid support, potent inhibitors of matriptase. Org. Lett. 9, 9-12
20. Thongyoo, P. et al. (2008) Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides. Org. Biomol. Chem. 6, 1462-1470 (Pubitemid 351469865)
21. Gunasekera, S. et al. (2008) Engineering stabilized vascular endothelial growth factor-A antagonists: Synthesis, structural characterization, and bioactivity of grafted analogues of cyclotides. J. Med. Chem. 51, 7697-7704
22. Clark, R.J. et al. (2005) Engineering stable peptide toxins by means of backbone cyclization: Stabilization of the alpha-conotoxin MII. Proc. Natl. Acad. Sci. U.S.A. 102, 13767-13772 (Pubitemid 41377653)
23. Akcan, M. et al. (2011) Chemical re-engineering of chlorotoxin improves bioconjugation properties for tumor imaging and targeted therapy. J. Med. Chem. 54, 782-787
24. Ireland, D.C. et al. (2010) Isolation, sequencing, and structure-activity relationships of cyclotides. J. Nat. Prod. 73, 1610-1622
25. Poth, A.G. et al. (2011) Discovery of cyclotides in the Fabaceae plant family provides new insights into the cyclization, evolution, and distribution of circular proteins. ACS Chem. Biol. 6, 345-355
26. Daly,N.L. et al. (2011)NMRandprotein structure indrug design: Application to cyclotides and conotoxins. Eur. Biophys. J. Biophys. Lett. 40, 359-370
27. Mylne, J.S. et al. (2011) Albumins and their processing machinery are hijacked for cyclic peptides in sunflower. Nat. Chem. Biol. 7, 257-259
28. Clark, R.J. and Craik, D.J. (2010) Native chemical ligation applied to the synthesis and bioengineering of circular peptides and proteins. Biopolymers 94, 414-422
29. Park, S. et al. (2010)Anefficient approach for the total synthesis of cyclotides by microwave assisted Fmoc-SPPS. Int. J. Pept. Res. Therapeut. 16, 167-176
30. Tam, J.P. et al. (1999) An unusual structural motif of antimicrobial peptides containing end-to-end macrocycle and cystine-knot disulfides. Proc. Natl. Acad. Sci. U.S.A. 96, 8913-8918 (Pubitemid 29374682)
31. Dawson, P.E. et al. (1994) Synthesis of proteins by native chemical ligation. Science 266, 776-779 (Pubitemid 24359280)
32. Marx, U.C. et al. (2003) Enzymatic cyclization of a potent Bowman-Birk protease inhibitor, sunflower trypsin inhibitor-1, and solution structure of an acyclic precursor peptide. J. Biol. Chem. 278, 21782-21789 (Pubitemid 36792582)
33. Dornenburg, H. (2010) Cyclotide synthesis and supply: From plant to bioprocess. Biopolymers 94, 602-610
34. Seydel, P. et al. (2009) Scale-up of Oldenlandia affinis suspension cultures in photobioreactors for cyclotide production. Eng. Life Sci. 9, 219-226
35. Camarero, J.A. et al. (2007) Biosynthesis of a fully functional cyclotide inside living bacterial cells. Chembiochem 8, 1363-1366 (Pubitemid 47300326)
36. Austin, J. et al. (2010) In vivo biosynthesis of an Ala-scan library based on the cyclic peptide SFTI-1. Amino Acids 38, 1313-1322
37. Austin, J. et al. (2009) Biosynthesis and biological screening of a genetically encoded library based on the cyclotide MCoTI-I. Chembiochem 10, 2663-2670
38. Sancheti, H. and Camarero, J.A. (2009) 'Splicing up' drug discovery. Cellbased expression and screening of genetically-encoded libraries of backbone-cyclized polypeptides. Adv. Drug Deliv. Rev. 61, 908-917
39. Puttamadappa, S.S. et al. (2010) Backbone dynamics of cyclotideMCoTI-I free and complexed with trypsin. Angew. Chem. Int. Ed. Engl. 49, 7030-7034
40. Huang, Y.H. et al. (2010) Lysine-scanning mutagenesis reveals an amendable face of the cyclotide kalata B1 for the optimization of nematocidal activity. J. Biol. Chem. 285, 10797-10805