Synthesis and pharmacological properties of TOAC-labeled angiotensin and bradykinin analogs

Synthesis and pharmacological properties of TOAC-labeled angiotensin and bradykinin analogs

Author Nakaie, Clovis Ryuichi Autor UNIFESP Google Scholar
Silva, Eneida de Gusmão Autor UNIFESP Google Scholar
Cilli, Eduardo Maffud Autor UNIFESP Google Scholar
Marchetto, Reinaldo Autor UNIFESP Google Scholar
Schreier, Shirley Autor UNIFESP Google Scholar
Paiva, Therezinha Bandiera Autor UNIFESP Google Scholar
Paiva, Antonio Cechelli de Mattos Autor UNIFESP Google Scholar
Institution Universidade Federal de São Paulo (UNIFESP)
Universidade de São Paulo (USP)
Abstract Angiotensin II (AngII) and bradykinin (BK) derivatives containing the TOAC (2,2,6,6-tetramethylpiperidine-N-oxyl-4-amino-4-carboxylic acid) spin label were synthesized by solid phase methodology. Ammonium hydroxide (pH 10, 50degreesC, 1 h) was the best means for reverting nitroxide protonation occurring during peptide cleavage. EPR spectra yielded rotational correlation times for internally labeled analogs that were nearly twice as large as those of N-terminally labeled analogs. Except for TOAC(1)-AngII and TOAC(0)-BK, which showed high intrinsic activities, other derivatives were inactive in smooth muscle preparations. These active paramagnetic analogs may be useful for conformational studies in solution and in the presence of model and biological membranes. (C) 2002 Elsevier Science Inc. All rights reserved.
Keywords angiotensin analogs
bradykinin analogs
peptide synthesis
spin labeled peptides
TOAC spin label
electron paramagnetic resonance
Language English
Date 2002-01-01
Published in Peptides. New York: Elsevier B.V., v. 23, n. 1, p. 65-70, 2002.
ISSN 0196-9781 (Sherpa/Romeo, impact factor)
Publisher Elsevier B.V.
Extent 65-70
Access rights Closed access
Type Article
Web of Science ID WOS:000173678100009

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