Role of the guanidine group in the N-terminal fragment of PTH(1-11)

被引:5
作者
Caporale, Andrea [1 ]
Woznica, Iwona [2 ]
Schievano, Elisabetta [1 ]
Mammi, Stefano [1 ]
Peggion, Evaristo [1 ]
机构
[1] Univ Padua, CNR, Inst Biomol Chem, Dept Chem Sci, I-35131 Padua, Italy
[2] Tufts Univ, Sch Med, Dept Physiol, Boston, MA 02111 USA
关键词
SPPS; CD; Peptidomimetics; PTH; PARATHYROID-HORMONE RECEPTOR; MOLECULAR CHARACTERIZATION; PTH/PTHRP RECEPTOR; BINDING MECHANISM; PEPTIDE; PROTEIN; ANALOGS; CONFORMATION; MINIMIZATION; ANTAGONISTS;
D O I
10.1007/s00726-009-0337-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
070307 [化学生物学]; 071010 [生物化学与分子生物学];
摘要
A series of PTH hybrids containing a diamine [NH(2)(CH(2)) (n) NH(2); n = 4, 5, 6] in the C-terminal position was synthesized based on the H-Aib-Val-Aib-Glu-Ile-Gln-Leu-Nle-His-Gln-Har-NH(2) (Har = homoarginine) template. The compounds were pharmacologically characterized at PTH1R receptors for agonist activity.
引用
收藏
页码:1269 / 1275
页数:7
相关论文
共 34 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]
CAPORALE A, 2006, P 29 EUR PEPT S GDAN, P424
[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]
EFFECT OF TERTIARY BASES ON O-BENZOTRIAZOLYLURONIUM SALT-INDUCED PEPTIDE SEGMENT COUPLING [J].
CARPINO, LA ;
EL-FAHAM, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :695-698
[7]
ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A ;
MINOR, CA ;
ALBERICIO, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203
[8]
1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[9]
Turn-on switch in parathyroid hormone receptor by a two-step parathyroid hormone binding mechanism [J].
Castro, M ;
Nikolaev, VO ;
Palm, D ;
Lohse, MJ ;
Vilardaga, JP .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (44) :16084-16089
[10]
Altered selectivity of parathyroid hormone (PTH) and PTH-Related protein (PTHrP) for distinct conformations of the PTH/PTHrP receptor [J].
Dean, Thomas ;
Vilardaga, Jean-Pierre ;
Potts, John T., Jr. ;
Gardella, Thomas J. .
MOLECULAR ENDOCRINOLOGY, 2008, 22 (01) :156-166