Peptide-peptoid hybrids based on (1-11)-parathyroid hormone analogs

被引:4
作者
Caporale, A. [1 ]
Schievano, E. [1 ]
Peggion, E. [1 ]
机构
[1] Univ Padua, Inst Biomol Chem, CNR, Dept Chem Sci, I-35131 Padua, Italy
关键词
N-substituted glycine; peptidomimetics; PTH analogs; conformation; bioactivities; N-SUBSTITUTED GLYCINES; PARATHYROID-HORMONE; PTH(1-11) ANALOGS; IDENTIFICATION; DRUG; LIBRARY; DESIGN; MINIMIZATION; AGONISTS; SPECTRA;
D O I
10.1002/psc.1265
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of peptide-peptoid hybrids, containing N-substituted glycines, were synthesized based on the H-Aib-Val-Aib-Glu-Ile-Gln-Leu-Nle-His-Gln-Har-NH2 (Har = Homoarginine) as the parent parathyroid hormone (1-11) analog. The compounds were pharmacologically characterized in their agonistic activity at the parathyroid hormone 1 receptor. Copyright (c) 2010 European Peptide Society and John Wiley & Sons, Ltd.
引用
收藏
页码:480 / 485
页数:6
相关论文
共 49 条
[1]   Converting a peptide into a drug: Strategies to improve stability and bioavailability [J].
Adessi, C ;
Soto, C .
CURRENT MEDICINAL CHEMISTRY, 2002, 9 (09) :963-978
[2]   Bioactive N-terminal undecapeptides derived from parathyroid hormone:: the role of α-helicity [J].
Barazza, A ;
Wittelsberger, A ;
Fiori, N ;
Schievano, E ;
Mammi, S ;
Toniolo, C ;
Alexander, JM ;
Rosenblatt, M ;
Peggion, E ;
Chorev, M .
JOURNAL OF PEPTIDE RESEARCH, 2005, 65 (01) :23-35
[3]   Trifluoroethanol and colleagues: cosolvents come of age. Recent studies with peptides and proteins [J].
Buck, M .
QUARTERLY REVIEWS OF BIOPHYSICS, 1998, 31 (03) :297-355
[4]   Role of the guanidine group in the N-terminal fragment of PTH(1-11) [J].
Caporale, Andrea ;
Woznica, Iwona ;
Schievano, Elisabetta ;
Mammi, Stefano ;
Peggion, Evaristo .
AMINO ACIDS, 2010, 38 (04) :1269-1275
[5]   Structure-function relationship studies of PTH(1-11) analogues containing D-amino acids [J].
Caporale, Andrea ;
Biondi, Barbara ;
Schievano, Elisabetta ;
Wittelsberger, Angela ;
Mammi, Stefano ;
Peggion, Evaristo .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2009, 611 (1-3) :1-7
[6]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[7]   Major histocompatibility complex class II binding characteristics of peptoid-peptide hybrids [J].
de Haan, EC ;
Wauben, MHM ;
Grosfeld-Stulemeyer, MC ;
Kruijtzer, JAW ;
Liskamp, RMJ ;
Moret, EE .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (06) :1939-1945
[8]   Peptoid dendrimers-microwave-assisted solid-phase synthesis and transfection agent evaluation [J].
Diaz-Mochon, Juan J. ;
Fara, Mario A. ;
Sanchez-Martin, Rosario M. ;
Bradley, Mark .
TETRAHEDRON LETTERS, 2008, 49 (05) :923-926
[10]   Structure-function relationship studies of PTH(1-11) analogues containing sterically hindered dipeptide mimetics [J].
Fiori, Nereo ;
Caporale, Andrea ;
Schievano, Elisabetta ;
Mammi, Stefano ;
Geyer, Armin ;
Tremmel, Peter ;
Wittelsberger, Angela ;
Woznica, Iwona ;
Chorev, Michael ;
Peggion, Evaristo .
JOURNAL OF PEPTIDE SCIENCE, 2007, 13 (08) :504-512