Conformational basis for the biological activity of TOAC-labeled angiotensin II and bradykinin: electron paramagnetic resonance, circular dichroism, and fluorescence studies

Biopolymers
Shirley SchreierClóvis R Nakaie

Abstract

N-Terminally and internally labeled analogues of the hormones angiotensin (AII, DRVYIHPF) and bradykinin (BK, RPPGFSPFR) were synthesized containing the paramagnetic amino acid 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid (TOAC). TOAC replaced Asp1 (TOAC1-AII) and Val3 (TOAC3-AII) in AII and was inserted prior to Arg1 (TOAC0-BK) and replacing Pro3 (TOAC3-BK) in BK. The peptide conformational properties were examined as a function of trifluoroethanol (TFE) content and pH. Electron paramagnetic resonance spectra were sensitive to both variables and showed that internally labeled analogues yielded rotational correlation times (tauC) considerably larger than N-terminally labeled ones, evincing the greater freedom of motion of the N-terminus. In TFE, tauC increased due to viscosity effects. Calculation of tau(Cpeptide)/tau(CTOAC) ratios indicated that the peptides acquired more folded conformations. Circular dichroism spectra showed that, except for TOAC1-AII in TFE, the N-terminally labeled analogues displayed a conformational behavior similar to that of the parent peptides. In contrast, under all conditions, the TOAC3 derivatives acquired more restricted conformations. Fluorescence spectra of AII and its derivati...Continue Reading

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Citations

Oct 26, 2012·Amino Acids·Douglas D LopesClovis R Nakaie
Jun 19, 2008·Journal of Biomolecular NMR·Hanna E LindforsMarcellus Ubbink
May 9, 2007·FEBS Letters·Luis Gustavo de Deus TeixeiraClovis Ryuichi Nakaie
May 12, 2005·The Journal of Peptide Research : Official Journal of the American Peptide Society·M CrismaC Toniolo
Jun 26, 2007·Chemistry & Biodiversity·Derek MarshClaudio Toniolo
Oct 24, 2006·Biophysical Journal·Derek MarshClaudio Toniolo
Oct 10, 2006·Biochimica Et Biophysica Acta·Luis G M MoraesAntonio Miranda
Jul 19, 2013·Biochimica Et Biophysica Acta·Marco BortolusAnna Lisa Maniero
Jan 10, 2008·International Immunopharmacology·Edson L SantosJoão B Pesquero
Jul 27, 2011·Regulatory Peptides·Vani X OliveiraAntonio Miranda
Nov 19, 2008·International Journal of Radiation Biology·Daniela T NardiClovis R Nakaie
Apr 3, 2013·Biological & Pharmaceutical Bulletin·Renata de Freitas Fischer VieiraClovis Ryuichi Nakaie

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