Structure-function relationship studies of PTH(1-11) analogues containing sterically hindered dipeptide mimetics

Journal of Peptide Science

Volumn 13, Issue 8, 2007, Pages 504-512

  Fiori, Nereo ^a   Caporale, Andrea ^a   Schievano, Elisabetta ^a   Mammi, Stefano ^a   Geyer, Armin ^b   Tremmel, Peter ^b   Wittelsberger, Angela ^c   Woznicz, Iwona ^c   Chorev, Michael ^d   Peggion, Evaristo ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

^c TUFTS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Molecular modeling; NMR; Peptide mimetics; PTH

Indexed keywords

3 CARBOXY 6 AMINO 7,5 BICYCLIC THIAZOLIDINLACTAM; LACTAM DERIVATIVE; PARATHYROID HORMONE DERIVATIVE; PARATHYROID HORMONE RECEPTOR 1; PARATHYROID HORMONE[1-11] DERIVATIVE; UNCLASSIFIED DRUG;

ALPHA HELIX; AQUEOUS SOLUTION; ARTICLE; CHEMICAL MODIFICATION; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR DYNAMICS; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

CELL LINE; DIPEPTIDES; HUMANS; ISOMERISM; PARATHYROID HORMONE; PEPTIDE FRAGMENTS; PROTEIN STRUCTURE, SECONDARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34548206701     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.872     Document Type: Article

References (34)

1. Chorev M, Rosenblatt M. The Parathyroids. Raven Press: New York, 1994; 139-156.
2. Scian M, Marin M, Bellanda M, Tou L, Alexander JM, Rosenblatt M, Chorev M, Peggion E, Mammi S. Backbone dynamics of human parathyroid hormone (1-34): flexibility of the central region under different environmental conditions. Biopolymers 2006; 84: 147-160.
3. Shimizu M, Petroni BD, Khatri A, Gardella TJ. Functional evidence for an intramolecular side chain interaction between residues 6 and 10 of receptor-bound parathyroid hormone analogues. Biochemistry 2003; 42: 2282-2290.
4. Tsomaia N, Pellegrini M, Hyde K, Gardella TJ, Mierke DF. Toward parathyroid hormone minimization: conformational studies of cyclic PTH(1-14) analogues. Biochemistry 2004; 43: 690-699.
5. Barazza A, Wittelsberger A, Fiori N, Schievano E, Mammi S, Toniolo C, Alexander JM, Rosenblatt M, Peggion E, Chorev M. Bioactive N-terminal undecapeptides derived from parathyroid hormone: the role of alpha-helicity. J. Pept. Res. 2005; 65: 23-35.
6. Monticelli L, Mammi S, Mierke DF. Molecular characterization of a ligand-tethered parathyroid hormone receptor. Biophys. Chem. 2002; 95: 165-172.
7. Shimizu M, Potts JT Jr., Gardella TJ. Toward parathyroid hormone minimization: conformational studies of cyclic PTH(1-14) analogues. J. Biol. Chem. 2000; 275: 21836-21843.
8. Geyer A, Moser E. Polyol peptidomimetics. Eur. J. Org. Chem. 2000; 7:1113-1120.
9. Hirschmann R. Medicinal chemistry in the golden age of biology: lessons from steroid and peptide research. Angew. Chem. Int. Ed. 1991; 30: 1278-1301.
10. Gante J. Peptidomimetics - tailored enzyme inhibitors. Angew. Chem. Int. Ed. 1994; 33: 1699-1720.
11. Kessler H, Diefenbach B, Finsinger D, Geyer A, Gurrath M, Goodman SL, Hölzemann G, Haubner R, Jonczyk A, Muller G, Graf v. Roedern E, Wermuth J. Design of superactive and selective integrin receptor antagonists containing the RGD sequence. Lett. Pept. Sci. 1995; 2: 155-160.
12. Shimizu M, Guo J, Gardella TJ. Parathyroid hormone (PTH)-(1-14) and -(1-11) analogs conformationally constrained by alpha-aminoisobutyric acid mediate full agonist responses via the juxtamembrane region of the PTH-1 receptor. J. Biol. Chem. 2001; 276:49003-49012.
13. Rosenblatt M, Goltzmann D, Keutmann HT, Tregear GW, Potts JT Jr. Chemical and biological properties of synthetic, sulfur-free analogues of parathyroid hormone. J. Biol. Chem. 1976; 251: 159-164.
14. Frelinger AL, Zull JE. Oxidized forms of parathyroid hormone with biological activity. Separation and characterization of hormone forms oxidized at methionine 8 and methionine 18. J. Biol. Chem. 1984; 259: 5507-5513.
15. Shimizu M, Carter PH, Gardella TJ. Autoactivation of type-1 parathyroid hormone receptors containing a tethered ligand. J. Biol. Chem. 2000; 275: 19456-19460.
16. Shimizu M, Carter PH, Khatri A, Potts JT Jr., Gardella TJ. Enhanced activity in parathyroid hormone-(1-14) and -(1-11): novel peptides for probing ligand-receptor interactions. Endocrinology 2001; 142: 3068-3074.
17. Shimizu M, Dean T, Khatri A, Gardella TJ. Amino-terminal parathyroid hormone fragment analogs containing alpha, alpha-di-alkyl amino acids at positions 1 and 3. J. Bone Miner. Res. 2004; 19:2078-2086.
18. Carpino LA, El-Faham A, Minor CA, Albericio F. Advantageous applications of azabenzotriazole (triazolopyridine)-based coupling reagents to solid-phase peptide synthesis. J. Chem Soc., Chem. Commun. 1994; 201-203.
19. Knorr R, Trzeciak A, Bannwarth W, Gillessen D. New coupling reagents in peptide chemistry. Tetrahedron Lett. 1989; 30: 1927-1930.
20. Carpino LA. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J. Am. Chem. Soc. 1993; 115: 4397-4398.
21. Carpino LA, El-Faham A, Albericio F. Efficiency in peptide coupling: 1-hydroxy-7-azabenzotriazole vs 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine. J. Org. Chem. 1995; 60: 3561-3564.
22. Carpino LA, El-Faham A. Effect of tertiary bases on O-benzotriazolyluronium salt-induced peptide segment coupling. J. Org. Chem. 1994; 59: 695-698.
23. Belvisi L, Bernardi A, Checchia A, Manzoni L, Potenza D, Scolastico C, Castorina M, Cupelli A, Giannini G, Carminati P, Pisano C. Potent integrin antagonists from a small library of RGD-including cyclic pseudopeptides. Org. Lett. 2001; 3: 1001-1004.
24. Yang JT, Wu CS, Martinez HM. Calculation of protein conformation from circular dichroism. Meth. Enzymol. 1986; 130: 208-269.
25. 1H NMR spectra of proteins via double quantum filtering. Biochem. Biophys. Res. Commun. 1983; 117: 479-485.
26. Bax A, Davis DG. MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 1985; 65: 355-360.
27. Griesinger C, Otting G, Wüthrich K, Ernst RR. Clean TOCSY for proton spin system identification in macromolecules. J. Am. Chem. Soc. 1988; 110: 7870-7872.
28. Bull TE. ROESY relaxation theory. J. Magn. Reson. 1988; 80: 470-481.
29. Kabsch W, Sander C. Dictionary of protein secondary structure: pattern recognition of hydrogen-bonded and geometrical features. Biopolymers 1983; 22: 2577-2637.
30. Rose GD, Gierasch LM, Smith JA. Turns in peptides and proteins. Adv. Protein Chem. 1985; 37: 1-109.
31. Wüthrich K. NMR of Proteins and Nucleic Acids. John Wiley & Sons: NewYork, 1986; 117-175.
32. Pastore A, Saudek V. The relationship between chemical shift and secondary structure in proteins. J. Magn. Reson. 1990; 90: 165-176.
33. Hyberts SG, Goldberg MS, Havel TF, Wagner G. The solution structure of eglin c based on measurements of many NOEs and coupling constants and its comparison with X-ray structures. Protein Sci. 1992; 1: 736-751.
34. Tremmel P, Geyer A. Coupled hydrogen-bonding networks in polyhydroxylated peptides. Angew. Chern. Int. Ed. 2004; 43: 5789-5791.