Synthetic covalently linked dimeric form of h2 relaxin retains native RXFP1 activity and has improved in vitro serum stability

BioMed Research International

Volumn 2015, Issue , 2015, Pages

  Nair, Vinojini B ^a   Bathgate, Ross A D ^a   Separovic, Frances ^a   Samuel, Chrishan S ^b   Hossain, Mohammed Akhter ^a   Wade, John D ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; G PROTEIN COUPLED RECEPTOR; H2 RELAXIN; MACROGOL; MONOMER; PROTEIN RXFP1; PROTEIN VARIANT; RELAXIN; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG; RECEPTOR; RLN2 PROTEIN, HUMAN; RXFP1 PROTEIN, HUMAN;

AMINO ACID ANALYSIS; AMINO ACID SEQUENCE; ARTICLE; CIRCULAR DICHROISM; CLICK CHEMISTRY; CONTROLLED STUDY; COVALENT BOND; DRUG DEGRADATION; DRUG HALF LIFE; DRUG RECEPTOR BINDING; HUMAN; IN VITRO STUDY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OLIGOMERIZATION; PEPTIDE SYNTHESIS; PROTEIN SECONDARY STRUCTURE; PROTEIN STABILITY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID PHASE SYNTHESIS; CHEMISTRY; HEART FAILURE; PROTEIN MULTIMERIZATION; PROTEIN QUATERNARY STRUCTURE;

HEART FAILURE; HUMANS; PROTEIN MULTIMERIZATION; PROTEIN STABILITY; PROTEIN STRUCTURE, QUATERNARY; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, PEPTIDE; RELAXIN;

EID: 84922356169     PISSN: 23146133     EISSN: 23146141     Source Type: Journal    
DOI: 10.1155/2015/731852     Document Type: Article

References (39)

1. F. L. Hisaw, "Experimental relaxation of the pubic ligament of the guinea-pig", Proceedings of the Society for Experimental Biology and Medicine, vol. 23, pp. 611-613, 1926.
2. M. A. Hossain and J. D. Wade, "Theroles of the A- and B-chains of human relaxin-2 and -3 on their biological activity", Current Protein and Peptide Science, vol. 11, no. 8, pp. 719-724, 2010.
3. R. A. D. Bathgate, M. L. Halls, E. T. Van Der Westhuizen, G. E. Callander, M. Kocan, and R. J. Summers, "Relaxin family peptides and their receptors", Physiological Reviews, vol. 93, no. 1, pp. 405-480, 2013.
4. G. D. Bryant-Greenwood, "Relaxin as a new hormone", Endocrine Reviews, vol. 3, no. 1, pp. 62-90, 1982.
5. R. A. Bathgate, R. Ivell, B. M. Sanborn, O. D. Sherwood, and R. J. Summers, "International union of pharmacology LVII: recommendations for the nomenclature of receptors for relaxin family peptides", Pharmacological Reviews, vol. 58, no. 1, pp. 7-31, 2006.
6. X.-J. Du, R. A. D. Bathgate, C. S. Samuel, A. M. Dart, and R. J. Summers, "Cardiovascular effects of relaxin: from basic science to clinical therapy", Nature Reviews Cardiology, vol. 7, no. 1, pp. 48-58, 2010.
7. F. Shabanpoor, F. Separovic, and J. D. Wade, "Thehuman insulin superfamily of polypeptide hormones", Vitamins and Hormones, vol. 80, pp. 1-31, 2009.
8. C. Eigenbrot, M. Randal, C. Quan, J. Burnier, L. O'Connell, and E. A. A. Rinderknecht Kossiakoff, "X-ray structure of human relaxin at 1.5 A", Journal of Molecular Biology, vol. 221, no. 1, pp. 15-21, 1991.
9. S. J. Shire, L. A. Holladay, and E. Rinderknecht, "Self-association of human and porcine relaxin as assessed by analytical ultracentrifugation and circular dichroism", Biochemistry, vol. 30, no. 31, pp. 7703-7711, 1991.
10. K. Huus, S. Havelund, H. B. Olsen, M. Van De Weert, and S. Frokjaer, "Thermal dissociation and unfolding of insulin", Biochemistry, vol. 44, no. 33, pp. 11171-11177, 2005.
11. J. Brange and L. Langkjoer, "Insulin structure and stability", Pharmaceutical biotechnology, vol. 5, pp. 315-350, 1993.
12. T. N. Vinther, M. Norrman, H. M. Strauss et al., "Novel covalently linked insulin dimer engineered to investigate the function of insulin dimerization", PLoS ONE, vol. 7, no. 2, Article ID e30882, 2012.
13. J. R. Teerlink, G. Cotter, B. A. Davison et al., "Serelaxin, recombinant human relaxin-2, for treatment of acute heart failure (RELAX-AHF): a randomised placebo-controlled trial", The Lancet, vol. 381, no. 9860, pp. 29-39, 2013.
14. S. A. Chen, A. J. Perlman, N. Spanski et al., "The pharmacokinetics of recombinant human relaxin in nonpregnant women after intravenous, intravaginal, and intracervical administration", Pharmaceutical Research, vol. 10, no. 6, pp. 834-838, 1993.
15. S. A. Chen, B. Reed, T. Nguyen, N. Gaylord, G. B. Fuller, and J. Mordenti, "The pharmacokinetics and absorption of recombinant human relaxin in nonpregnant rabbits and rhesus monkeys after intravenous and intravaginal administration", Pharmaceutical Research, vol. 10, no. 2, pp. 223-227, 1993.
16. C. S. Samuel, F. Lin, M. A. Hossain et al., "Improved chemical synthesis and demonstration of the relaxin receptor binding affinity and biological activity of mouse relaxin", Biochemistry, vol. 46, no. 18, pp. 5374-5381, 2007.
17. F. Shabanpoor, R. A. D. Bathgate, A. Belgi et al., "Site-specific conjugation of a lanthanide chelator and its effects on the chemical synthesis and receptor binding affinity of human relaxin-2 hormone", Biochemical and Biophysical Research Communications, vol. 420, no. 2, pp. 253-256, 2012.
18. L. J. Chan, C. M. Smith, B. E. Chua et al., "Synthesisoffluorescent analogs of relaxin family peptides and their preliminary in vitro and in vivo characterization", Frontiers in Chemistry, vol. 1, Article 30, 2013.
19. L. V. Najbar, D. J. Craik, J. D. Wade, D. Salvatore, and M. J. McLeish, "Conformational analysis of LYS (11-36), a peptide derived from the β-sheet region of T4 lysozyme, in TFE and SDS", Biochemistry, vol. 36, no. 38, pp. 11525-11533, 1997.
20. P. G. Scott, C. M. Dodd, E. M. Bergmann, J. K. Sheehan, and P. N. Bishop, "Crystal structure of the biglycan dimer and evidence that dimerization is essential for folding and stability of class I small leucine-rich repeat proteoglycans", Journal of Biological Chemistry, vol. 281, no. 19, pp. 13324-13332, 2006.
21. M. A. Hossain, A. Belgi, F. Lin et al., "Use of a temporary "solubilizing" peptide tag for the Fmoc solid-phase synthesis of human insulin glargine via use of regioselective disulfide bond formation", Bioconjugate Chemistry, vol. 20, no. 7, pp. 1390-1396, 2009.
22. M. A. Hossain, R. A. D. Bathgate, C. K. Kong et al., "Synthesis, conformation, and activity of human insulin-like peptide 5(INSL5)", Chem Bio Chem, vol. 9, no. 11, pp. 1816-1822, 2008.
23. M. A. Hossain, K. J. Rosengren, S. Zhang et al., "Solid phase synthesis and structural analysis of novel A-chain dicarba analogs of human relaxin-3 (INSL7) that exhibit full biological activity", Organic and Biomolecular Chemistry, vol. 7, no. 8, pp. 1547-1553, 2009.
24. M. P. Del Borgo, R. A. Hughes, and J. D. Wade, "Conformationally constrained single-chain peptide mimics of relaxin B-chain secondary structure", Journal of Peptide Science, vol. 11, no. 9, pp. 564-571, 2005.
25. J. R. Teerlink, M. Metra, G. M. Felker et al., "Relaxinfor the treatment of patients with acute heart failure (Pre-RELAX-AHF): a multicentre, randomised, placebo-controlled, parallelgroup, dose-finding phase lib study", The Lancet, vol. 373, no. 9673, pp. 1429-1439, 2009.
26. M. Werle and A. Bernkop-Schnurch, "Strategies to improve plasma halflife time of peptide and protein drugs", Amino Acids, vol. 30, no. 4, pp. 351-367, 2006.
27. L. Otvos and J. D. Wade, "Current challenges in peptide-based drug discovery", Frontiers in Chemistry, vol. 2, Article62, 2014.
28. M. W. Fried, M. L. Shiffman, K. Rajender Reddy et al., "Peginterferon alfa-2a plus ribavirin for chronic hepatitis C virus infection", The New England Journal of Medicine, vol. 347, no. 13, pp. 975-982, 2002.
29. J. M. Harris and R. B. Chess, "Effect of pegylation on pharmaceuticals", Nature Reviews Drug Discovery, vol. 2, no. 3, pp. 214-221, 2003.
30. P. Caliceti and F. M. Veronese, "Pharmacokinetic and biodistribution properties of poly (ethylene glycol)-protein conjugates", Advanced Drug Delivery Reviews, vol. 55, no. 10, pp. 1261-1277, 2003.
31. E. R. Gillies and J. M. J. Frechet, "Dendrimers and dendritic polymers in drug delivery", Drug Discovery Today, vol. 10, no. 1, pp. 35-43, 2005.
32. A. J. Sytkowski, E. D. Lunn, K. L. Davis, L. Feldman, and S. Siekman, "Human erythropoietin dimers with markedly enhanced in vivo activity", Proceedings of the National Academy of Sciences of the United States of America, vol. 95, no. 3, pp. 1184-1188, 1998.
33. P. B. Noto, G. Abbadessa, M. Cassone et al., "Alternative stabilities of a proline-rich antibacterial peptide in vitro and in vivo", Protein Science, vol. 17, no. 7, pp. 1249-1255, 2008.
34. M. A. Hossain, K. J. Rosengren, C. S. Samuel et al., "The minimal active structure of human relaxin-2", Journal of Biological Chemistry, vol. 286, no. 43, pp. 37555-37565, 2011.
35. M. N. Mathieu, J. D. Wade, G. W. Tregear et al., "Synthesis, conformational studies and biological activity of Na-monobiotinylated rat relaxin", Journal of Peptide Research, vol. 57, no. 5, pp. 374-382, 2001.
36. R. A. Bathgate, A. Hsueh, and O. D. Sherwood, "Physiologyand molecular biology of the relaxin peptide family", in Knobil and Neills Physiology of Reproduction, J. D. Neiil, Ed., pp. 679-768, Academic Press, San Diego, Calif, USA, 2006.
37. M. A. Hossain, C. S. Samuel, C. Binder et al., "The chemically synthesized human relaxin-2 analog, B-R13/17K H2, is an RXFP1 antagonist", Amino Acids, vol. 39, no. 2, pp. 409-416, 2010.
38. T. H. Kim, H. H. Jiang, S. Lee et al., "Mono-PEGylated dimeric exendin-4 as high receptor binding and long-acting conjugates for type 2 anti-diabetes therapeutics", Bioconjugate Chemistry, vol. 22, no. 4, pp. 625-632, 2011.
39. C. Heinis, T. Rutherford, S. Freund, and G. Winter, "Phageencoded combinatorial chemical libraries based on bicyclic peptides", Nature Chemical Biology, vol. 5, no. 7, pp. 502-507, 2009.