A proposed EPR approach to evaluating agonist binding site of a peptide receptor

International Journal of Peptide Research and Therapeutics

Volumn 14, Issue 2, 2008, Pages 121-126

  Lopes, Douglas D ^a   Poletti, Erick F ^a   Vieira, Renata F F ^a   Jubilut, Guita N ^a   Oliveira, Laerte ^a   Paiva, Antonio C M ^a   Schreier, Shirley ^b   Nakaie, Clovis R ^a  

^a FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Angiotensin II; EPR; Peptide; Receptor; Spin label; TOAC

Indexed keywords

2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXYL 4 AMINO 4 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; PEPTIDE; RECEPTOR;

AGONIST; AMINO TERMINAL SEQUENCE; ARTICLE; BINDING SITE; ELECTRON SPIN RESONANCE; MOLECULAR INTERACTION; MOLECULAR PROBE; SYNTHESIS;

EID: 43549124578     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-007-9120-1     Document Type: Article

References (33)

1. Barany G, Merrifield RB (1980) The peptides, vol 2. Academic Press Inc., New York
2. Barbosa SR, Cilli EM, Lamy-Freund MT, Castrucci AML, Nakaie CR (1999) First synthesis of a fully active spin-labeled peptide hormone. FEBS Lett 446:45-48
3. Berliner LJ, Reuben J (1989) Spin labeling theory and applications. Plenum Press, New York
4. Cannon B, Polnazek CF, Buttler KW, Erickson LEG, Smith ICP (1975) Fluidity and organization of mitochondrial membrane lipids of brown adipose tissue of cold-adapted rats and hamsters as determined by nitroxide spin probes. Arch Biochem Biophys 167:505-518
5. Catt KJ, Sandberg K, Balla T (1993) In: Raizada MK, Philips MI, Summers C (eds) Cellular and molecular biology of renin-angiotensin system. CRC Press, Boca Raton
6. Cilli EM, Marchetto R, Schreier S, Nakaie CR (1997) Use of spin label EPR spectra to monitor peptide chain aggregation inside resin beads. Tetrahedron Lett 38:517-520
7. Fields GB, Noble RL (1990) Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int J Pept Protein Res 35:161-214
8. Kardos J, Yamamoto K, Hasegawa K, Naike H (2004) Direct measurement of the thermodynamic parameters of amyloid formation by isothermal titration calorimetry. J Biol Chem 279:55308-55314
9. Karim CB, Kirby TL, Zhang Z, Nesmelov Y, Thomas DD (2004) Phospholamban structural dynamics in lipid bilayers probed by a spin label rigidly coupled to the peptide backbone. Proc Natl Acad Sci USA 101:14437-14442
10. Kates SA, Albericio F (2000) Solid phase synthesis. A practical guide. Marcel Dekker, New York, pp 275-330
11. Kivelson D (1960) Theory of ESR linewidths of free radicals. J Chem Phys 33:1094-1106
12. Malavolta L, Nakaie CR (2004) Peptide dissociation in solution or bound to a polymer: comparative solvent effect. Tetrahedron 60:9417-9424
13. Malavolta L, Pinto MRS, Cuvero JH, Nakaie CR (2006) Interpretation of the dissolution of insoluble peptide sequences based on the acid-base properties of solvent. Protein Sci 15:1476-1488
14. Marchetto R, Cilli EM, Jubilut GN, Schreier S, Nakaie CR (2005) Determination of site-site distance and site concentration within polymer beads: a combined swelling-electron paramagnetic resonance study. J Org Chem 70:4561-4568
15. Marchetto R, Schreier S, Nakaie CR (1993) A novel spin-labeled amino acid derivative for use in peptide synthesis: (9-fluorenylmethyloxycarbonyl)-2.2.6. 6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid. J Am Chem Soc 115:11042-11043
16. Marsh D (2006) Orientation of TOAC amino-acid spin labels in α-helices and β-strands. J Magn Res 180:305-310
17. McNulty JC, Silapie JL, Carnevali M, Farrar CT, Griffin RG, Formaggio F, Crisma M, Toniolo C, Milhauser GL (2000) Electron spin resonance of TOAC labeled peptides: folding transitions and high frequency spectroscopy. Biopolymers 55:479-485
18. Nakaie CR, Goissis G, Schreier S, Paiva ACM (1981) pH dependence of ESR spectra of nitroxide containing ionizable groups. Braz J Med Biol Res 14:173-180
19. Nakaie CR, Malavolta L, Schreier S, Trovatti E, Marchetto R (2006) Direct electron paramagnetic resonance monitoring of the peptide synthesis coupling reaction in polymeric support. Polymer 47:4531-4536
20. Nakaie CR, Schreier S, Paiva ACM (1983) Synthesis and properties of spin-labeled angiotensin derivatives. Biochim Biophys Acta 742:63-71
21. Nakaie CR, Silva EG, Cilli EM, Marchetto R, Schreier S, Paiva TB, Paiva ACM (2002) Synthesis and pharmacological properties of TOAC-labeled angiotensin and bradykinin analogues. Peptides 23:65-70
22. Oliveira E, Cilli EM, Miranda A, Jubilut GN, Albericio F, Andreu D, Paiva ACM, Schreier S, Tominaga M, Nakaie CR (2002) Monitoring the chemical assembly of a transmembrane bradykinin receptor fragment: correlation between resin solvation, peptide chain mobility and rate of coupling. Eur J Org Chem 21:3686-3694
23. Oliveira L, Costa-Neto CM, Nakaie CR, Schreier S, Shimuta SI, Paiva ACM (2007) The angiotensin II AT1 receptor structure-activity correlations in the light of rhodopsin structure. Physiol Rev 87:565-592
24. Oliveira L, Paiva ACM, Vriend G (1999) A low resolution model for the interaction of G proteins with G-protein coupled receptors. Protein Eng 12:1087-1095
25. Paul M, Mehr AP, Kreutz R (2006) Physiology of local rennin-angiotensin systems. Physiol Rev 86:747-803
26. Pertinhez TA, Nakaie CR, Paiva ACM, Schreier S (1997) Spin-labeled extracellular loop from a seven-transmembrane helix receptor: studies in solution and interaction with model membranes. Biopolymers 42:821-829
27. Rassat A, Rey P (1967) Nitroxydes 23 Préparation dàminoacides radicalaires et de leurs sels complexes. Bull Soc Chim Fr 3:815-817
28. Rizos AK, Tsikalas I, Morikis D, Galanakis P, Spyrouias GA, Krambovitis E (2003) Light scattering characterization of synthetic MUC-1 peptides and their behavior in dilute solutions. Int J Mol Med 12:559-563
29. Schreier S, Barbosa SR, Casallanovo F, Vieira RFF, Cilli EM, Paiva ACM, Nakaie CR (2004) Conformational basis for the biological activity of TOAC-labeled angiotensin II and bradykinin: electron paramagnetic resonance, circular dichroism and fluorescence studies. Biopolymers 74:389-402
30. (10)-helical conformation of alanine-based peptides in aqueous solution: an electron spin resonance investigation. J Am Chem Soc 117:10555-10562
31. Teixeira LGD, Bersanetti PA, Schreier S, Carmona AK, Nakaie CR (2007) Analogues containing the paramagnetic amino acid TOAC as substrates for angiotensin converting enzyme. FEBS Lett 581:2411-2415
32. α-tetrasubstituted α-amino acid, is an excellent tool in material science and biochemistry. Biopolymers 47:153-158
33. α,α- disubstituted glycine. J Pept Sci 1:45-57