Asteropsins B-D, sponge-derived knottins with potential utility as a novel scaffold for oral peptide drugs

Biochimica et Biophysica Acta - General Subjects

Volumn 1840, Issue 3, 2014, Pages 977-984

  Li, Huayue ^a   Bowling, John J ^b,e   Su, Mingzhi ^a   Hong, Jongki ^c   Lee, Bong Jin ^d   Hamann, Mark T ^b   Jung, Jee H ^a  

^a Pusan National University   (South Korea)

^b Center of Applied Electromagnetic System Research (CAESR)   (United States)

^c Kyung Hee University   (South Korea)

^d Seoul National University   (South Korea)

^e ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

Author keywords

Asteropus sp.; Keywords; Knottin; Marine sponge; NMR; Oral peptide drug delivery; Solution structure

Indexed keywords

ASTEROPSIN B; ASTEROPSIN C; ASTEROPSIN D; CHYMOTRYPSIN; ELASTASE; KNOTTIN; PEPSIN A; SCAFFOLD PROTEIN; TRYPSIN; UNCLASSIFIED DRUG;

ARTICLE; BIOAVAILABILITY; CONTROLLED STUDY; ENZYME STABILITY; GASTROINTESTINAL TRACT; HUMAN; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN ISOLATION; PROTEIN TERTIARY STRUCTURE; SEQUENCE ANALYSIS; SPONGE (PORIFERA); STRUCTURAL HOMOLOGY;

ASTEROPUS SP.; KNOTTIN; MARINE SPONGE; NMR; ORAL PEPTIDE DRUG DELIVERY; SOLUTION STRUCTURE;

ADMINISTRATION, ORAL; AMINO ACID SEQUENCE; ANIMALS; CALCIUM; CYSTINE-KNOT MINIPROTEINS; DRUG DISCOVERY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PORIFERA; PROTEIN STABILITY; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY;

EID: 84890462039     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2013.11.001     Document Type: Article

References (46)

1. C. Pichereau, and C. Allary Therapeutic peptides under the spotlight Eur. BioPharm. Rev. Winter 2005 88 91
2. H. Kolmar Biological diversity and therapeutic potential of natural and engineered cystine knot miniproteins Curr. Opin. Pharmacol. 9 2009 608 614
3. J.A. Getz, J.J. Rice, and P.S. Daugherty Protease-resistant peptide ligands from a knottin scaffold library ACS Chem. Biol. 6 2011 837 844
4. C.T. Wong, D.K. Rowlands, C.H. Wong, T.W. Lo, G.K. Nguyen, H.Y. Li, and J.P. Tam Orally active peptidic bradykinin B1 receptor antagonists engineered from a cyclotide scaffold for inflammatory pain treatment Angew. Chem. Int. Ed. Engl. 51 2012 5620 5624
5. T.L. Aboye, and J.A. Camarero Biological synthesis of circular polypeptides J. Biol. Chem. 287 2012 27026 27032
6. G.P. Miljanich Ziconotide: neuronal calcium channel blocker for treating severe chronic pain Curr. Med. Chem. 11 2004 3029 3040 (Pubitemid 39545572)
7. O. Bogin Venom peptides and their mimetics as potential drugs Modulator 19 2005 14 20
8. L.Y. Chan, S. Gunasekera, S.T. Henriques, N.F. Worth, S.J. Le, R.J. Clark, J.H. Campbell, D.J. Craik, and N.L. Daly Engineering pro-angiogenic peptides using stable, disulfide-rich cyclic scaffolds Blood 118 2011 6709 6717
9. T.L. Aboye, H. Ha, S. Majumder, F. Christ, Z. Debyser, A. Shekhtman, N. Neamati, and J.A. Camarero Design of a novel cyclotide-based CXCR4 antagonist with anti-human immunodeficiency virus (HIV)-1 activity J. Med. Chem. 55 2012 10729 10734
10. Y. Ji, S. Majumder, M. Millard, R. Borra, T. Bi, A.Y. Elnagar, N. Neamati, A. Shekhtman, and J.A. Camarero In vivo activation of the p53 tumor suppressor pathway by an engineered cyclotide J. Am. Chem. Soc. 135 2013 11623 11633
11. A.E. Garcia, and J.A. Camarero Biological activities of natural and engineered cyclotides, a novel molecular scaffold for peptide-based therapeutics Curr. Mol. Pharmacol. 3 2010 153 163
12. K. Jagadish, and J.A. Camarero Cyclotides, a promising molecular scaffold for peptide-based therapeutics Biopolymers 94 2010 611 616
13. M. Werle, T. Schmitz, H.L. Huang, A. Wentzel, H. Kolmar, and A. Bernkop-Schnürch The potential of cystine-knot microproteins as novel pharmacophoric scaffolds in oral peptide drug delivery J. Drug Target. 14 2006 137 146 (Pubitemid 43878822)
14. M. Werle, K. Kafedjiiski, H. Kolmar, and A. Bernkop-Schnürch Evaluation and improvement of the properties of the novel cystine-knot microprotein McoEeTI for oral administration Int. J. Pharm. 332 2007 72 79 (Pubitemid 46227767)
15. M. Werle, H. Kolmar, R. Albrecht, and A. Bernkop-Schnürch Characterisation of the barrier caused by luminally secreted gastro-intestinal proteolytic enzymes for two novel cystine-knot microproteins Amino Acids 35 2008 195 200 (Pubitemid 351799193)
16. J.A. Williams, M. Day, and J.E. Heavner Ziconotide: an update and review Expert. Opin. Pharmacother. 9 2008 1575 1583 (Pubitemid 352005917)
17. K. Zheng, D.M. Lubman, D.T. Rossi, G.D. Nordblom, and C.M. Barksdale Elucidation of peptide metabolism by on-line immunoaffinity liquid chromatography mass spectrometry Rapid Commun. Mass Spectrom. 14 2000 261 269 (Pubitemid 30100852)
18. R.J. Clark, J. Jensen, S.T. Nevin, B.P. Callaghan, D.J. Adams, and D.J. Craik The engineering of an orally active conotoxin for the treatment of neuropathic pain Angew. Chem. Int. Ed. Engl. 49 2010 6545 6548
19. K. Takada, T. Hamada, H. Hirota, Y. Nakao, S. Matsunaga, R.W.M. van Soest, and N. Fusetani Asteropine A, a sialidase-inhibiting conotoxin-like peptide from the marine sponge Asteropus simplex Chem. Biol. 13 2006 569 574
20. 2 + influx Biochim. Biophys. Acta 1830 2013 2591 2599
21. T.D. Goddard, and D.G. Kneller SPARKY 3 2007 University of California San Francisco
22. K. Wüthrich NMR of Proteins and Nucleic Acids 1986 J. Wiley New York
23. D.S. Wishart, B.D. Sykes, and F.M. Richards The chemical shift index: a fast and simple method for the assignment of protein secondary structure through NMR spectroscopy Biochemistry 31 1992 1647 1651
24. 13C chemical-shift data J. Biomol. NMR 4 1994 171 180
25. P. Guntert Automated NMR structure calculation with CYANA Methods Mol. Biol. 278 2004 353 378
26. A.T. Brünger, P.D. Adams, G.M. Clore, W.L. DeLano, P. Gros, R.W. Grosse-Kunstleve, J.S. Jiang, J. Kuszewski, M. Nilges, N.S. Pannu, R.J. Read, L.M. Rice, T. Simonson, and G.L. Warren Crystallography & NMR system: a new software suite for macromolecular structure determination Acta Crystallogr. D Biol. Crystallogr. 54 1998 905 921
27. The PyMOL Molecular Graphics System, version 1.3 2010 Schrödinger, LLC
28. R. Koradi, M. Billeter, and K. Wüthrich MOLMOL: a program for display and analysis of macromolecular structures J. Mol. Graph. 14 1996 51 55 (29-32) (Pubitemid 26152976)
29. A. Bhattacharya, R. Tejero, and G.T. Montelione Evaluating protein structures determined by structural genomics consortia Proteins 66 2007 778 795
30. D. Xu, and Y. Zhang Improving the physical realism and structural accuracy of protein models by a two-step atomic-level energy minimization Biophys. J. 101 2011 2525 2534
31. A. Bernkop-Schnürch The use of inhibitory agents to overcome the enzymatic barrier to perorally administered therapeutic peptides and proteins J. Control. Release 52 1998 1 16 (Pubitemid 28123168)
32. H. Li, T.D. Hung, J. Li, C.J. Sim, J. Hong, D.K. Kim, and J.H. Jung Pyroglutamyl dipeptides and tetrahydro-beta-carboline alkaloids from a marine sponge Asteropus sp. Biochem. Syst. Ecol. 38 2010 1049 1051
33. P.N. Lewis, F.A. Momany, and H.A. Scheraga Chain reversals in proteins Biochim. Biophys. Acta 303 1973 211 229
34. C.M. Wilmot, and J.M. Thornton Beta-turns and their distortions: a proposed new nomenclature Protein Eng. 3 1990 479 493 (Pubitemid 20290024)
35. W. Klaus, C. Broger, P. Gerber, and H. Senn Determination of the disulphide bonding pattern in proteins by local and global analysis of nuclear magnetic resonance data. Application to flavoridin J. Mol. Biol. 232 1993 897 906 (Pubitemid 23256981)
36. 13C chemical shift statistics J. Biomol. NMR 24 2002 149 154 (Pubitemid 35414678)
37. J. Ay, K. Hilpert, N. Krauss, J. Schneider-Mergener, and W. Hohne Structure of a hybrid squash inhibitor in complex with porcine pancreatic elastase at 1.8 Å resolution Acta Crystallogr. D Biol. Crystallogr. 59 2003 247 254 (Pubitemid 36224845)
38. Y. Zhu, Q. Huang, M. Qian, Y. Jia, and Y. Tang Crystal structure of the complex formed between bovine beta-trypsin and MCTI-A, a trypsin inhibitor of squash family, at 1.8-Å resolution J. Protein Chem. 18 1999 505 509 (Pubitemid 29473490)
39. D.C. Rees, and W.N. Lipscomb Refined crystal structure of the potato inhibitor complex of carboxypeptidase A at 2.5 Å resolution J. Mol. Biol. 160 1982 475 498
40. R. Kratzner, J.E. Debreczeni, T. Pape, T.R. Schneider, A. Wentzel, H. Kolmar, G.M. Sheldrick, and I. Uson Structure of Ecballium elaterium trypsin inhibitor II (EETI-II): a rigid molecular scaffold Acta Crystallogr. D Biol. Crystallogr. 61 2005 1255 1262 (Pubitemid 43961297)
41. K.J. Nielsen, D. Adams, L. Thomas, T. Bond, P.F. Alewood, D.J. Craik, and R.J. Lewis Structure-activity relationships of omega-conotoxins MVIIA, MVIIC and 14 loop splice hybrids at N and P/Q-type calcium channels J. Mol. Biol. 289 1999 1405 1421 (Pubitemid 29296713)
42. L. Nadasdi, D. Yamashiro, D. Chung, K. Tarczy-Hornoch, P. Adriaenssens, and J. Ramachandran Structure-activity analysis of a Conus peptide blocker of N-type neuronal calcium channels Biochemistry 34 1995 8076 8081
43. D. Li, Y. Xiao, X. Xu, X. Xiong, S. Lu, Z. Liu, Q. Zhu, M. Wang, X. Gu, and S. Liang Structure-activity relationships of hainantoxin-IV and structure determination of active and inactive sodium channel blockers J. Biol. Chem. 279 2004 37734 37740 (Pubitemid 39195487)
44. D.C. Ireland, R.J. Clark, N.L. Daly, and D.J. Craik Isolation, sequencing, and structure-activity relationships of cyclotides J. Nat. Prod. 73 2010 1610 1622
45. L. Cascales, S.T. Henriques, M.C. Kerr, Y.H. Huang, M.J. Sweet, N.L. Daly, and D.J. Craik Identification and characterization of a new family of cell-penetrating peptides: cyclic cell-penetrating peptides J. Biol. Chem. 286 2011 36932 36943
46. J. Contreras, A.Y. Elnagar, S.F. Hamm-Alvarez, and J.A. Camarero Cellular uptake of cyclotide MCoTI-I follows multiple endocytic pathways J. Control. Release 155 2011 134 143