Synthesis and biological activity of new metallocenic angiotensin II analogs

1988 ◽  
Vol 53 (11) ◽  
pp. 2914-2919 ◽  
Author(s):  
Pierrette Maes ◽  
Annie Ricouart ◽  
Emmanuel Escher ◽  
André Tartar ◽  
Christian Sergheraert
Keyword(s):  
Amino Acids ◽  
Biological Activity ◽  
Angiotensin Ii ◽  
Solid Phase ◽  
Rabbit Aorta ◽  
Phase Method ◽  
Solid Phase Method

Analogs of angiotensin II in which phenylalanine in position 8 was replaced with cymantrenylalanine or with its triphenylphosphine photosubstitution product were synthesized by the solid-phase method. On rabbit aorta strips, these peptides were found to be pure antagonists of angiotensin II. Their relative affinities are higher than most other analogs substituted in position 8 with bulky amino-acids.

Synthesis of Peptides with the Solid Phase Method. II. Octapeptide Analogues of Angiotensin II

1974 ◽  
Vol 52 (2) ◽  
pp. 113-119 ◽  
Author(s):  
W. K. Park ◽  
C. Choi ◽  
F. Rioux ◽  
D. Regoli
Keyword(s):  
Blood Pressure ◽  
Biological Activity ◽  
Angiotensin Ii ◽  
Enzymatic Degradation ◽  
Solid Phase ◽  
Paper Electrophoresis ◽  
Antagonistic Effect ◽  
Phase Method ◽  
Solid Phase Method ◽  
Layer Chromatography

Forty-six analogues of angiotensin II were obtained with the solid-phase method for peptide synthesis. The peptides were purified, using the conventional procedures; homogeneity and purity were established after paper, thin-layer chromatography, paper electrophoresis, amino acid analysis, elemental analysis, and enzymatic degradation by aminopeptidase. The biological activity of all compounds was compared with that of angiotensin II on the blood pressure of anesthetized rats. The same test was used to establish the antagonistic effect of several analogues against angiotensin II.

Synthese eines Thymosin β10-Fragments zur Entwicklung spezifischer Antikörper / Synthesis of a Fragment of Thymosin β10 for the Development of Specific Antibodies

1992 ◽  
Vol 47 (8) ◽  
pp. 1170-1174 ◽  
Author(s):  
Susanne Hörger ◽  
Brigitte Gallert ◽  
Hartmut Echner ◽  
Wolfgang Voelter
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Protecting Groups ◽  
Side Chain ◽  
Phase Method ◽  
Preparative Hplc ◽  
Specific Antibodies ◽  
Tert Butyl ◽  
Thymosin Β10 ◽  
Solid Phase Method

The N-terminal fragment 1-12 of thymosin β10 was synthesized by the solid phase method using p-benzyloxybenzyl alcohol/polystyrene/divinylbenzeneresin and N-a-Fmoc amino acids with tert-butyl or Boc side chain protecting groups. Coupling was performed with BOP. The peptide was purified by preparative HPLC.

Antagonistic Analogs of Oxytocin with Substituted Phenylalanine or Tyrosine in Position 2

1994 ◽  
Vol 59 (6) ◽  
pp. 1430-1438 ◽  
Author(s):  
Rudolf Ježek ◽  
Miroslava Žertová ◽  
Jiřina Slaninová ◽  
Pavel Majer ◽  
Zdenko Procházka
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Phase Method ◽  
Inhibiting Activity ◽  
Structure Activity ◽  
Low Degree ◽  
Solid Phase Method ◽  
Pressor Activity ◽  
Agonistic Activity

Solid phase method on p-methylbenzhydrylamine resin was used for the synthesis of seven analogs of oxytocin with non-coded amino acids in position 2. [L-Phe(4-Me)2]oxytocin (I), [D-Phe(4-Me)2]oxytocin (II), [L-Phe(2-Me,4-Et)2]oxytocin (III), [D-Phe(2-Me,4-Et)2]oxytocin (IV), [D-Tyr(Me)2]oxytocin (V), [D-Tyr(Et)2]oxytocin (VI) and [L-Tyr(2-Me)2]oxytocin (VII) were synthesized. All analogs with D-stereoisomer of alkyl or alkoxy substituted phenylalanine possess uterus in vitro inhibiting activity. In the case of L-stereoisomers the structure activity relationship is more complicated. As far as the pressor activity is concerned, the analogs have either very low agonistic activity or low degree of antagonism.

The Analogs of [D-Har8]Vasopressin with Di- and Trisubstituted Phenylalanine in Position 2; Synthesis and Some Biological Properties

1993 ◽  
Vol 58 (11) ◽  
pp. 2751-2760 ◽  
Author(s):  
Miroslava Žertová ◽  
Zdenko Procházka ◽  
Jiřina Slaninová ◽  
Tomislav Barth ◽  
Pavel Majer ◽  
...  
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Biological Properties ◽  
Phase Method ◽  
Antidiuretic Activity ◽  
Solid Phase Method

Four analogs of vasopressin with non-coded amino acids D-homoarginine (in position 8) and 2,6-di- or 2,4,6-trisubstituted L- or D-phenylalanine (in position 2) were synthesized using the solid phase method on p-methylbenzhydrylamine resin. All the analogs were found to be uterotonic inhibitors, the most potent one in vitro and in vivo being [D-Phe(2,4,6-triMe)2,D-Har8]vasopressin with pA2 values equal to 8.1 and 7.5, respectively. All of them had negligible antidiuretic activity and were weak pressor inhibitors.

Synthesis and biological activity in GPI test of scyliorhinin I and its analogues modified in position 8 by Leu, Sar and Pro residues

1991 ◽  
Vol 56 (9) ◽  
pp. 1957-1962 ◽  
Author(s):  
Krzysztof Rolka ◽  
Gotfryd Kupryszewski ◽  
Piotr Janas ◽  
Jarosław Myszor ◽  
Zbigniew S. Herman
Keyword(s):  
Biological Activity ◽  
Guinea Pig ◽  
Solid Phase ◽  
Phase Method ◽  
Guinea Pig Ileum ◽  
Tachykinin Receptor ◽  
Solid Phase Method ◽  
One Step ◽  
Agonistic Activity ◽  
The Hill

Three analogues of scyliorhinin I with Gly in position 8 substituted with Leu, Sar and Pro residues, were synthesized by the solid-phase method. The agonistic activity was determined on isolated guinea pig ileum. Analogues with Sar and Pro in position 8 appeared to be significantly more active than scyliorhinin I and the analogues with Leu in this position. For all analogues the Hill cooperativity coefficient is much lower than one suggesting that the interaction of these peptides with tachykinin receptor(s) in not a one-step reaction.

scholarly journals A simple and traceless solid phase method simplifies the assembly of large peptides and the access to challenging proteins

2017 ◽  
Vol 8 (8) ◽  
pp. 5362-5370 ◽  
Author(s):  
N. Ollivier ◽  
R. Desmet ◽  
H. Drobecq ◽  
A. Blanpain ◽  
E. Boll ◽  
...  
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Biologically Active ◽  
Phase Method ◽  
Active Protein ◽  
Solid Phase Method

We show that the combination of solid phase and solution ligation techniques facilitates the production of a challenging and biologically active protein made of 180 amino acids.

Synthesis of peptides by the solid-phase method. III. Bradykinin: fragments and analogs

1978 ◽  
Vol 56 (2) ◽  
pp. 92-100 ◽  
Author(s):  
W. K. Park ◽  
S. A. St-Pierre ◽  
J. Barabé ◽  
D. Regoli
Keyword(s):  
Solid Phase ◽  
Rabbit Aorta ◽  
Paper Electrophoresis ◽  
Phase Method ◽  
Biological Assays ◽  
Anaesthetized Rats ◽  
Solid Phase Method ◽  
Specific Receptors ◽  
Layer Chromatography

The natural sequence of bradykinin (BK) and 55 fragments or analogs of this peptide were prepared via the solid-phase method. The peptides were purified using ion-exchange (O-carboxymethyl (CM)) and partition (Sephadex G-25) chromatography. The purity of each peptide was established by paper and thin-layer chromatography, paper electrophoresis, amino acid analysis, and biological assays. The compounds were tested in anaesthetized rats (test in vivo) and in two smooth-muscle preparations (rabbit aorta strip, cat ileum strip) in which BK produces contraction by stimulating specific receptors of different types. Some of the new peptides are interesting in that they either resist pulmonary inactivation, or are more potent than BK itself, or antagonize the myotropic effect of BK in rabbit aorta strips.

scholarly journals Amino Acids and Peptides. XXXV. Facile Preparation of p-Nitroanilide Analogs by the Solid-Phase Method.

2000 ◽  
Vol 48 (11) ◽  
pp. 1740-1744 ◽  
Author(s):  
Keiko HOJO ◽  
Mitsuko MAEDA ◽  
Shin IGUCHI ◽  
Timothy SMITH ◽  
Hiroshi OKAMOTO ◽  
...  
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Phase Method ◽  
Solid Phase Method ◽  
Facile Preparation

Site Directed Antisera to the D-2 Polypeptide Subunit of Photosystem II

1987 ◽  
Vol 42 (4) ◽  
pp. 491-498 ◽  
Author(s):  
R. Geiger ◽  
R. J. Berzborn ◽  
B. Depka ◽  
W. Oettmeier ◽  
A. Trebst
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Photosystem Ii ◽  
Amino Acid Sequence ◽  
Solid Phase ◽  
High Titer ◽  
Membrane Surface ◽  
High Sensitivity ◽  
Phase Method ◽  
Solid Phase Method

Three synthetic oligopeptides were used for preparation of antibodies against the D-2 polypeptide of thylakoid membranes. Their sequence was chosen from a model of the folding of the amino acid sequence of the D-2 polypeptide subunit through the membrane that predicted these sequences to be exposed at the membrane surface. For the Merrifield solid-phase method on a fully automated synthesizer the Na-amino group was protected by a fluorenyl-9-methylcarbonyl group. The oligopeptides were coupled to serum albumin by EDAC for immunizations in rabbits. Antisera with high titer were obtained for the two oligopeptides that contained the amino acid sequence of the D-2 protein from amino acid 230 to 235 and from 235 to 241. The antisera reacted with the D-2 polypeptide, separated on SDS gel and agglutinated the thylakoid membrane. It is known that certain photosystem II functions are impaired by short time trypsin treatment of the membrane. The antisera were used to show that under these conditions the D-2 polypeptide in the membrane is very sensitive. The trypsination yielded two cleavage products detected by the two antisera, a 20 kDa fragment blotted by antiserum against amino acids 230 to 235 and a 10 kDa fragment blotted by the antiserum against amino acids 235 to 241. As the polypeptide cleavage occurs between the two epitopes, the trypsin cut is therefore at arginine 234. This supports the prediction that the sequence containing this arginine is the most exposed part of the D-2 polypeptide on the membrane (matrix) surface. It is proposed that the high sensitivity of the D-2 polypeptide accounts for the known effect of membrane trypsination on QA accessibility in photosystem II.

scholarly journals Amino Acids and Peptides. XXXVIII. Facile Synthesis of Laminin-Related Peptide-Poly(Ethylene Glycol) Hybrids by the Solid Phase Method.

2001 ◽  
Vol 49 (4) ◽  
pp. 488-491 ◽  
Author(s):  
Mitsuko MAEDA ◽  
Haruhiko KAMADA ◽  
Keiko HOJO ◽  
Yoko YAMAMOTO ◽  
Shinsaku NAKAGAWA ◽  
...  
Keyword(s):  
Amino Acids ◽  
Ethylene Glycol ◽  
Solid Phase ◽  
Phase Method ◽  
Poly Ethylene Glycol ◽  
Facile Synthesis ◽  
Related Peptide ◽  
Solid Phase Method ◽  
Poly Ethylene
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