Cyclotides: a patent review

Bibliography

• Craik DJ, Daly NL, Bond T, Waine C. Plant cyclotides: a unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif. J Mol Biol 1999;294:1327-36
   PubMed Web of Science ®Google Scholar
• Craik DJ, Daly NL, Waine C. The cystine knot motif in toxins and implications for drug design. Toxicon 2001;39:43-60
   PubMed Web of Science ®Google Scholar
• Gran L, An oxytocic principle found in Oldenlandia affinis DC. Medd Nor Farm Selsk. 1970;12:173-80
   Google Scholar
• Gran L. Isolation of oxytocic peptides from Oldenlandia affinis by solvent extraction of tetraphenylborate complexes and chromatography on sephadex LH-20. Lloydia 1973;36:207-8
   PubMedGoogle Scholar
• Sletten K, Gran L. Some molecular properties of kalatapeptide B-1. A uterotonic polypeptide isolated from Oldenlandia affinis DC. Medd Nor Farm Selsk 1973;7-8:69-82
   Google Scholar
• Saether O, Craik DJ, Campbell ID, Elucidation of the primary and three-dimensional structure of the uterotonic polypeptide kalata B1. Biochemistry (Mosc) 1995;34:4147-58
   Google Scholar
• Colgrave ML, Craik DJ. Thermal, chemical, and enzymatic stability of the cyclotide kalata B1: the importance of the cyclic cystine knot. Biochemistry (Mosc) 2004;43:5965-75
   Google Scholar
• Gustafson KR, Sowder RCI, Henderson LE, Circulins A and B: novel HIV-inhibitory macrocyclic peptides from the tropical tree Chassalia parvifolia. J Am Chem Soc 1994;116:9337-8
   Web of Science ®Google Scholar
• Witherup KM, Bogusky MJ, Anderson PS, Cyclopsychotride A, A biologically active, 31-residue cyclic peptide isolated from Psychotria longipes. J Nat Prod 1994;57:1619-25
   PubMed Web of Science ®Google Scholar
• Goransson U, Luijendijk T, Johansson S, Seven novel macrocyclic polypeptides from Viola arvensis. J Nat Prod 1999;62:283-6
   PubMed Web of Science ®Google Scholar
• Wang CK, Kaas Q, Chiche L, Craik DJ. CyBase: a database of cyclic protein sequences and structures, with applications in protein discovery and engineering. Nucleic Acids Res 2008;36:D206-10
   PubMed Web of Science ®Google Scholar
• Tam JP, Lu YA, Yang JL, Chiu KW. An unusual structural motif of antimicrobial peptides containing end-to-end macrocycle and cystine-knot disulfides. Proc Natl Acad Sci USA 1999;96:8913-18
   PubMed Web of Science ®Google Scholar
• Nguyen GK, Zhang S, Nguyen NT, Discovery and characterization of novel cyclotides originated from chimeric precursors consisting of albumin-1 chain a and cyclotide domains in the Fabaceae family. J Biol Chem 2011;286:24275-87
   PubMed Web of Science ®Google Scholar
• Poth AG, Colgrave ML, Lyons RE, Discovery of an unusual biosynthetic origin for circular proteins in legumes. Proc Natl Acad Sci USA 2011;108:10127-32
   PubMed Web of Science ®Google Scholar
• Poth AG, Colgrave ML, Philip R, Discovery of cyclotides in the Fabaceae plant family provides new insights into the cyclization, evolution, and distribution of circular proteins. ACS Chem Biol 2011;6:345-55
   PubMed Web of Science ®Google Scholar
• Gruber CW, Elliott AG, Ireland DC, Distribution and evolution of circular miniproteins in flowering plants. Plant Cell 2008;20:2471-83
   PubMed Web of Science ®Google Scholar
• Craik DJ, Cemazar M, Wang CK, Daly NL. The cyclotide family of circular miniproteins: nature's combinatorial peptide template. Biopolymers 2006;84:250-66
   PubMed Web of Science ®Google Scholar
• Gran L. On the effect of a polypeptide isolated from “Kalata-Kalata” (Oldenlandia affinis DC) on the oestrogen dominated uterus. Acta Pharmacol Toxicol 1973;33:400-8
   PubMedGoogle Scholar
• Goransson U, Sjogren M, Svangard E, Reversible antifouling effect of the cyclotide cycloviolacin O2 against barnacles. J Nat Prod 2004;67:1287-90
   PubMed Web of Science ®Google Scholar
• Herrmann A, Burman R, Mylne J, The alpine violet, Viola biflora, is a rich source of cyclotides with potent cytotoxicity. Phytochemistry 2008;69:939-52
   PubMed Web of Science ®Google Scholar
• Lindholm P, Göransson U, Johansson S, Cyclotides: a novel type of cytotoxic agents. Mol Cancer Ther 2002;1:365-9
   PubMed Web of Science ®Google Scholar
• Svangard E, Goransson U, Hocaoglu Z, Cytotoxic cyclotides from Viola tricolor. J Nat Prod 2004;67:144-7
   PubMed Web of Science ®Google Scholar
• Burman R, Svedlund E, Felth J, Evaluation of toxicity and anti-tumour activity of cycloviolacin O2 in mice. Biopolymers Pept Sci 2010;94:626-34
   PubMed Web of Science ®Google Scholar
• Gerlach SL, Rathinakumar R, Chakravarty G, Anticancer and chemosensitizing abilities of cycloviolacin O2 from Viola odorata and psyle cyclotides from Psychotria leptothyrsa. Biopolymers 2010;94:617-25
   PubMedGoogle Scholar
• Craik DJ. Circling the enemy: cyclic proteins in plant defence. Trends Plant Sci 2009;14:328-35
   PubMed Web of Science ®Google Scholar
• Gruber CW, Cemazar M, Anderson MA, Craik DJ. Insecticidal plant cyclotides and related cystine knot toxins. Toxicon 2007;49:561-75
   PubMed Web of Science ®Google Scholar
• Jennings C, West J, Waine C, Biosynthesis and insecticidal properties of plant cyclotides: the cyclic knotted proteins from Oldenlandia affinis. Proc Natl Acad Sci USA 2001;98:10614-19
   PubMed Web of Science ®Google Scholar
• Colgrave ML, Kotze AC, Ireland DC, The anthelmintic activity of the cyclotides: natural variants with enhanced activity. ChemBioChem 2008;9:1939-45
   PubMed Web of Science ®Google Scholar
• Colgrave ML, Kotze AC, Kopp S, Anthelmintic activity of cyclotides: In vitro studies with canine and human hookworms. Acta Trop 2009;109:163-6
   PubMed Web of Science ®Google Scholar
• Plan MR, Saska I, Cagauan AG, Craik DJ. Backbone cyclised peptides from plants show molluscicidal activity against the rice pest Pomacea canaliculata (golden apple snail). J Agric Food Chem 2008;56:5237-41
   PubMed Web of Science ®Google Scholar
• Barbeta BL, Marshall AT, Gillon AD, Plant cyclotides disrupt epithelial cells in the midgut of lepidopteran larvae. Proc Natl Acad Sci USA 2008;105:1221-5
   PubMed Web of Science ®Google Scholar
• Adessi C, Soto C. Converting a peptide into a drug: strategies to improve stability and bioavailability. Curr Med Chem 2002;9:963-78
   PubMed Web of Science ®Google Scholar
• Tam JP, Lu Y-A. A biomimetic strategy in the synthesis and fragmentation of cyclic protein. Protein Sci 1998;7:1583-92
   PubMed Web of Science ®Google Scholar
• Daly NL, Love S, Alewood PF, Craik DJ. Chemical synthesis and folding pathways of large cyclic polypeptides: studies of the cystine knot polypeptide kalata B1. Biochemistry (Mosc) 1999;38:10606-14
   Google Scholar
• Craik DJ, Cemazar M, Daly NL. The chemistry and biology of cyclotides. Curr Opin Drug Discov Devel 2007;10:176-84
   PubMed Web of Science ®Google Scholar
• Dawson PE, Muir TW, Clark-Lewis I, Kent SB. Synthesis of proteins by native chemical ligation. Science 1994;266:776-9
   PubMed Web of Science ®Google Scholar
• Tam JP, Lu YA, Liu CF, Shao J. Peptide synthesis using unprotected peptides through orthogonal coupling methods. Proc Natl Acad Sci USA 1995;92:12485-9
   PubMed Web of Science ®Google Scholar
• Daly NL, Clark RJ, Craik DJ. Disulfide folding pathways of cystine knot proteins. Tying the knot within the circular backbone of the cyclotides. J Biol Chem 2003;278:6314-22
   PubMed Web of Science ®Google Scholar
• Goransson U, Craik DJ. Disulfide mapping of the cyclotide kalata B1. Chemical proof of the cyclic cystine knot motif. J Biol Chem 2003;278:48188-96
   PubMed Web of Science ®Google Scholar
• Gunasekera S, Daly NL, Anderson MA, Craik DJ. Chemical synthesis and biosynthesis of the cyclotide family of circular proteins. IUBMB Life 2006;58:515-24
   PubMed Web of Science ®Google Scholar
• Craik DJ, Daly NL. Oxidative folding of the cystine knot motif in cyclotide proteins. Protein Pept Lett 2005;12:147-52
   PubMed Web of Science ®Google Scholar
• Dutton JL, Renda RF, Waine C, Conserved Structural and Sequence Elements Implicated in the Processing of Gene-encoded Circular Proteins. J Biol Chem 2004;279:46858-67
   PubMed Web of Science ®Google Scholar
• Trabi M, Mylne JS, Sando L, Craik DJ. Circular proteins from Melicytus (Violaceae) refine the conserved protein and gene architecture of cyclotides. Org Biomol Chem 2009;7:2378-88
   PubMed Web of Science ®Google Scholar
• Zhang J, Liao B, Craik DJ, Identification of two suites of cyclotide precursor genes from metallophyte Viola baoshanensis: cDNA sequence variation, alternative RNA splicing and potential cyclotide diversity. Gene 2009;431:23-32
   PubMed Web of Science ®Google Scholar
• Dornenburg H. Plant cell culture technology-harnessing a biological approach for competitive cyclotides production. Biotechnol Lett 2008;30:1311-21
   PubMed Web of Science ®Google Scholar
• Dornenburg H. Progress in kalata peptide production via plant cell bioprocessing. Biotechnol J 2009;4:632-45
   PubMedGoogle Scholar
• Dornenburg H. Cyclotide synthesis and supply: from plant to bioprocess. Biopolymers 2010;94:602-10
   Google Scholar
• Dornenburg H, Frickinger P, Seydel P. Plant cell-based processes for cyclotides production. J Biotechnol 2008;135:123-6
   PubMed Web of Science ®Google Scholar
• Seydel P, Dornenburg H. Establishment of in vitro plants, cell and tissue cultures from Oldenlandia affinis for the production of cyclic peptides. Plant Cell Tissue Org Cult 2006;85:247-55
   Web of Science ®Google Scholar
• Seydel P, Gruber CW, Craik DJ, Dornenburg H. Formation of cyclotides and variations in cyclotide expression in Oldenlandia affinis suspension cultures. Appl Microbiol Biotechnol 2007;77:275-84
   PubMed Web of Science ®Google Scholar
• Kimura RH, Tran A-T, Camarero JA. Biosynthesis of the cyclotide kalata B1 by using protein splicing. Angew Chem Int Ed 2006;118:987-90
   Google Scholar
• Camarero JA, Kimura RH, Woo Y-H, Biosynthesis of a fully functional cyclotide inside living bacterial cells. ChemBioChem 2007;8:1363-6
   PubMed Web of Science ®Google Scholar
• Jagadish K, Camarero JA. Cyclotides, a promising molecular scaffold for peptide-based therapeutics. Biopolymers 2010;94:611-16
   PubMedGoogle Scholar
• Marx UC, Korsinczky ML, Schirra HJ, Enzymatic cyclization of a potent Bowman-Birk protease inhibitor, sunflower trypsin inhibitor-1, and solution structure of an acyclic precursor peptide. J Biol Chem 2003;278:21782-9
   PubMed Web of Science ®Google Scholar
• Thongyoo P, Jaulent AM, Tate EW, Leatherbarrow RJ. Immobilized protease-assisted synthesis of engineered cysteine-knot microproteins. ChemBioChem 2007;8:1107-9
   PubMed Web of Science ®Google Scholar
• Goransson U, Svangard E, Claeson P, Bohlin L. Novel strategies for isolation and characterization of cyclotides: the discovery of bioactive macrocyclic plant polypeptides in the Violaceae. Curr Protein Pept Sci 2004;5:317-29
   PubMed Web of Science ®Google Scholar
• Ireland DC, Clark RJ, Daly NL, Craik DJ. Isolation, sequencing, and structure-activity relationships of cyclotides. J Nat Prod 2010;73:1610-22
   PubMed Web of Science ®Google Scholar
• Craik DJ, Conibear AC. The chemistry of cyclotides. J Org Chem 2011;76:4805-17
   PubMed Web of Science ®Google Scholar
• Craik DJ, Daly NL. NMR as a tool for elucidating the structures of circular and knotted proteins. Mol Biosyst 2007;3:257-65
   PubMed Web of Science ®Google Scholar
• Chiche L, Heitz A, Gelly JC, Squash inhibitors: from structural motifs to macrocyclic knottins. Curr Protein Pept Sci 2004;5:341-9
   PubMed Web of Science ®Google Scholar
• Daly NL, Craik DJ. Bioactive cystine knot proteins. Curr Opin Chem Biol 2011;15:362-8
   PubMed Web of Science ®Google Scholar
• Henriques ST, Craik DJ. Cyclotides as templates in drug design. Drug Discov Today 2010;15:57-64
   PubMed Web of Science ®Google Scholar
• Garcia AE, Camarero JA. Biological activities of natural and engineered cyclotides, a novel molecular scaffold for peptide-based therapeutics. Curr Mol Pharmacol 2010;3:153-63
   PubMedGoogle Scholar
• The University of Queensland. Cystine knot molecules. US7960340; 2000
   Google Scholar
• The University of Queensland and Hexima Ltd. Novel nucleic acid molecules. WO0134829; 2000
   Google Scholar
• Viogard AB. On-growth inhibiting compounds. WO0004055; 2000
   Google Scholar
• Friedrich-Alexander-Universitat Erlangen-Nurnberg. Method for producing cyclic peptides from in vitro plant cell cultures. WO05108596; 2005
   Google Scholar
• E.I. Du Pont De Nemours & Co. Nucleic acid molecules encoding cyclotide polypeptides and methods of use. US7232939; 2005
   Google Scholar
• NascaCell Technologies. Use of microproteins as tryptase inhibitors. WO06032436; 2005
   Google Scholar
• E.I. Du Pont De Nemours & Co. Insecticidal plant cyclotide with activity against homopteran insects. US7211658; 2005
   Google Scholar
• Pioneer Hi Breed International, Inc. and E.I. Du Pont De Nemours & Co. Maize cyclo1 gene and promoter. WO06076189; 2006
   Google Scholar
• NascaCell Technologies. Dimeric or multimeric microproteins. WO06094813; 2006
   Google Scholar
• Elso Magyar Biodrog Kutato Es Fejleszto FKT. A pharmaceutical composition containing an extract of a medicinal herb belonging to the order of violales. WO2007026185; 2006
   Google Scholar
• Amunix, Inc. Proteinaceous pharmaceuticals and uses thereof. WO2007038619; 2006
   Google Scholar
• Singapore Polytechnic. Novel polypeptides for anti-viral treatment. WO2007149052; 2007
   Google Scholar
• University of Southern California. Compositions and methods for the rapid biosynthesis and in vivo screening of biologically relevant peptides. WO2011005598; 2010
   Google Scholar
• Craik DJ, Mylne JS, Daly NL. Cyclotides: macrocyclic peptides with applications in drug design and agriculture. Cell Mol Life Sci 2010;67:9-16
   PubMed Web of Science ®Google Scholar
• Clark RJ, Daly NL, Craik DJ. Structural plasticity of the cyclic-cystine-knot framework: implications for biological activity and drug design. Biochem J 2006;394:85-93
   PubMed Web of Science ®Google Scholar
• Gunasekera S, Foley FM, Clark RJ, Engineering stabilized vascular endothelial growth factor-A antagonists: synthesis, structural characterization, and bioactivity of grafted analogues of cyclotides. J Med Chem 2008;51:7697-704
   PubMed Web of Science ®Google Scholar
• Thongyoo P, Roque-Rosell N, Leatherbarrow RJ, Tate EW. Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides. Org Biomol Chem 2008;6:1462-70
   PubMed Web of Science ®Google Scholar
• Tan N-H, Zhou J. Plant cyclopeptides. Chem Rev 2006;106:840-95
   PubMed Web of Science ®Google Scholar
• Colgrave ML, Kotze AC, Huang YH, Cyclotides: natural, circular plant peptides that possess significant activity against gastrointestinal nematode parasites of sheep. Biochemistry 2008;47:5581-9
   PubMed Web of Science ®Google Scholar
• Jennings CV, Rosengren KJ, Daly NL, Isolation, solution structure, and insecticidal activity of kalata B2, a circular protein with a twist: do Mobius strips exist in nature? Biochemistry 2005;44:851-60
   PubMed Web of Science ®Google Scholar
• Tam JP, Lu Y-A, Yu Q. Thia zip reaction for synthesis of large cyclic peptides: mechanisms and applications. J Am Chem Soc 1999;121:4316-24
   Google Scholar
• Gustafson KR, McKee TC, Bokesch HR. Anti-HIV cyclotides. Curr Protein Pept Sci 2004;5:331-40
   PubMedGoogle Scholar
• Gustafson KR, Walton LK, Sowder RCI, New circulin macrocyclic polypeptides from Chassalia parvifolia. J Nat Prod 2000;63:176-8
   PubMed Web of Science ®Google Scholar
• Daly NL, Clark RJ, Plan MR, Craik DJ. Kalata B8, a novel antiviral circular protein, exhibits conformational flexibility in the cystine knot motif. Biochem J 2006;393:619-26
   PubMed Web of Science ®Google Scholar
• Daly NL, Craik DJ. Acyclic permutants of naturally occurring cyclic proteins. Characterization of cystine knot and beta -sheet formation in the macrocyclic polypeptide kalata B1. J Biol Chem 2000;275:19068-75
   PubMed Web of Science ®Google Scholar
• Barry DG, Daly NL, Clark RJ, Linearization of a naturally occurring circular protein maintains structure but eliminates hemolytic activity. Biochemistry 2003;42:6688-95
   PubMed Web of Science ®Google Scholar
• Simonsen SM, Sando L, Rosengren KJ, Alanine scanning mutagenesis of the prototypic cyclotide reveals a cluster of residues essential for bioactivity. J Biol Chem 2008;283:9805-13
   PubMed Web of Science ®Google Scholar
• Rice K, Spencer J. Inhibitors of human mast cell serine proteases and potential therapeutic applications. Expert Opin Ther Pat 1999;9:1537-55
   Web of Science ®Google Scholar
• Kolmar H. Biological diversity and therapeutic potential of natural and engineered cystine knot miniproteins. Curr Opin Pharmacol 2009;9:608-14
   PubMed Web of Science ®Google Scholar
• Heitz A, Avrutina O, Le-Nguyen D, Knottin cyclization: impact on structure and dynamics. BMC Struct Biol 2008;8:54
   PubMedGoogle Scholar
• Werle M, Kafedjiiski K, Kolmar H, Bernkop-Schnurch A. Evaluation and improvement of the properties of the novel cystine-knot microprotein McoEeTI for oral administration. Int J Pharm 2007;332:72-9
   PubMed Web of Science ®Google Scholar
• Werle M, Schmitz T, Huang HL, The potential of cystine-knot microproteins as novel pharmacophoric scaffolds in oral peptide drug delivery. J Drug Target 2006;14:137-46
   PubMed Web of Science ®Google Scholar
• Frank SJ. Receptor dimerization in GH and erythropoietin action–it takes two to tango, but how? Endocrinology 2002;143:2-10
   PubMedGoogle Scholar
• Grotzinger J. Molecular mechanisms of cytokine receptor activation. Biochim Biophys Acta 2002;1592:215-23
   PubMed Web of Science ®Google Scholar
• Mellado M, Vila-Coro AJ, Martinez C, Rodriguez-Frade JM. Receptor dimerization: a key step in chemokine signaling. Cell Mol Biol 2001;47:575-82
   PubMed Web of Science ®Google Scholar
• Lok S, Foster DC. The structure, biology and potential therapeutic applications of recombinant thrombopoietin. Stem Cells 1994;12:586-98
   PubMed Web of Science ®Google Scholar
• Hunt P. The physiologic role and therapeutic potential of the Mpl-ligand in thrombopoiesis. Stem Cells 1995;13:579-87
   PubMed Web of Science ®Google Scholar
• Kaushansky K. Thrombopoietin: the primary regulator of platelet production. Blood 1995;86:419-31
   PubMed Web of Science ®Google Scholar
• Kuter DJ. Thrombopoietin and thrombopoietin mimetics in the treatment of thrombocytopenia. Annu Rev Med 2009;60:193-206
   PubMed Web of Science ®Google Scholar
• Sancheti H, Camarero JA. “Splicing up” drug discovery. Cell-based expression and screening of genetically-encoded libraries of backbone-cyclized polypeptides. Adv Drug Deliv Rev 2009;61:908-17
   Google Scholar
• Camarero JA, Muir TW. Biosynthesis of a head-to-tail cyclized protein with improved biological activity. J Am Chem Soc 1999;121:5597-8
   Web of Science ®Google Scholar
• Camarero JA, Fushman D, Cowburn D, Muir TW. Peptide chemical ligation inside living cells: in vivo generation of a circular protein domain. Bioorg Med Chem 2001;9:2479-84
   PubMed Web of Science ®Google Scholar
• Austin J, Wang W, Puttamadappa S, Biosynthesis and biological screening of a genetically encoded library based on the cyclotide MCoTI-I. ChemBioChem 2009;10:2663-70
   PubMed Web of Science ®Google Scholar
• Austin J, Kimura RH, Woo YH, Camarero JA. In vivo biosynthesis of an Ala-scan library based on the cyclic peptide SFTI-1. Amino Acids 2010;38:1313-22
   PubMed Web of Science ®Google Scholar
• Luckett S, Garcia RS, Barker JJ, High-resolution structure of a potent, cyclic proteinase inhibitor from sunflower seeds. J Mol Biol 1999;290:525-33
   PubMed Web of Science ®Google Scholar
• Korsinczky ML, Schirra HJ, Rosengren KJ, Solution structures by 1H NMR of the novel cyclic trypsin inhibitor SFTI-1 from sunflower seeds and an acyclic permutant. J Mol Biol 2001;311:579-91
   PubMed Web of Science ®Google Scholar
• Craik DJ. Seamless Proteins tie up their loose ends. Science 2006;311:1563-4
   PubMed Web of Science ®Google Scholar
• Cole AM, Wang W, Waring AJ, Lehrer RI. Retrocyclins: using past as prologue. Curr Protein Pept Sci 2004;5:373-81
   PubMed Web of Science ®Google Scholar
• Maqueda M, Galvez A, Bueno MM, Sanchez-Barrena M. Peptide AS-48: prototype of a new class of cyclic bacteriocins. Curr Protein Pept Sci 2004;5:399-416
   PubMed Web of Science ®Google Scholar
• Selsted ME. Theta-defensins: cyclic antimicrobial peptides produced by binary ligation of truncated alpha-defensins. Curr Protein Pept Sci 2004;5:365-71
   PubMed Web of Science ®Google Scholar
• Trabi M, Craik DJ. Circular proteins - no end in sight. Trends Biochem Sci 2002;27:132-8
   PubMed Web of Science ®Google Scholar
• Mylne JS, Colgrave ML, Daly NL, Albumins and their processing machinery are hijacked for cyclic peptides in sunflower. Nat Chem Biol 2011;7:257-9
   PubMed Web of Science ®Google Scholar
• Koradi R, Billeter M, Wuthrich K. MOLMOL: a program for display and analysis of macromolecular structures. J Mol Graph 1996;14:29-32
   Google Scholar
• Gillon AD, Saska I, Jennings CV, Biosynthesis of circular proteins in plants. Plant J 2008;53:505-15
   PubMed Web of Science ®Google Scholar
• Saska I, Gillon AD, Hatsugai N, An asparaginyl endopeptidase mediates in vivo protein backbone cyclisation. J Biol Chem 2007;282:29721-8
   PubMed Web of Science ®Google Scholar