A New Strategy for the Preparation of Peptide-Targeted Radiopharmaceuticals Based on an Fmoc-Lysine-Derived Single Amino Acid Chelate (SAAC). Automated Solid-Phase Synthesis, NMR Characterization, and in Vitro Screening of fMLF(SAAC)G and fMLF[(SAAC−Re(CO)3)+]G

2004 ◽  
Vol 15 (1) ◽  
pp. 128-136 ◽  
Author(s):  
Karin A. Stephenson ◽  
Jon Zubieta ◽  
Sangeeta Ray Banerjee ◽  
Murali K. Levadala ◽  
Linda Taggart ◽  
...  
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Single Amino Acid ◽  
In Vitro Screening ◽  
Phase Synthesis ◽  
Nmr Characterization ◽  
New Strategy ◽  
Acid Chelate

Oxytocin analogues with non-coded amino acid residues in position 8: [8-Neopentylglycine]oxytocin and [8-cycloleucine]oxytocin

1987 ◽  
Vol 52 (9) ◽  
pp. 2317-2325 ◽  
Author(s):  
Jan Hlaváček ◽  
Jan Pospíšek ◽  
Jiřina Slaninová ◽  
Walter Y. Chan ◽  
Victor J. Hruby
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Other ◽  
Amino Acid Residues ◽  
Phase Synthesis ◽  
Other Hand ◽  
Fragment Condensation

[8-Neopentylglycine]oxytocin (II) and [8-cycloleucine]oxytocin (III) were prepared by a combination of solid-phase synthesis and fragment condensation. Both analogues exhibited decreased uterotonic potency in vitro, each being about 15-30% that of oxytocin. Analogue II also displayed similarly decreased uterotonic potency in vivo and galactogogic potency. On the other hand, analogue III exhibited almost the same potency as oxytocin in the uterotonic assay in vivo and in the galactogogic assay.

A convenient solid-phase synthesis methodology for preparing peptide-derived molecular imaging agents — Synthesis, characterization, and in vitro screening of Tc(I) – chemotactic peptide conjugates

2005 ◽  
Vol 83 (12) ◽  
pp. 2060-2066 ◽  
Author(s):  
Karin A Stephenson ◽  
Sangeeta Ray Banerjee ◽  
Nicole McFarlane ◽  
Douglas R Boreham ◽  
Kevin P Maresca ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Metal Chelate ◽  
Free Ligand ◽  
Peptide Sequence ◽  
In Vitro Screening ◽  
Chemotactic Peptide ◽  
Phase Synthesis ◽  
Synthesis Strategy

A versatile solid-phase synthesis strategy for preparing peptide–chelate conjugates was developed. The methodology was optimized using a series of ligands, designed to bind Tc(I)/Re(I), and a chemotactic peptide fMFL, which was exploited as a model targeting vector. The peptide derivatives were prepared in parallel using a conventional automated peptide synthesizer in multi-milligram quantities, which provided sufficient material to perform complete characterization, radiolabelling, and in vitro screening studies. Because of the robust nature of the metal–chelate complexes, the Re complex of a chelate–peptide conjugate was prepared on the resin using the same methodology employed to prepare the free ligand conjugates. As such, the reported methodology is amenable to the preparation of libraries of novel Tc radiopharmaceutical ligands and their corresponding Re reference standards in which several factors, including peptide sequence, site of derivatization, and both the type and length of the spacer, can be easily varied.Key words: radiopharmaceuticals, technetium, rhenium, peptides, solid-phase synthesis.

Comparison of the Potency of 8-L-Arginine, 8-D-Arginine and 8-D-Homoarginine Vasopressin Analogs with Substituted Phenylalanine in Position 2

1994 ◽  
Vol 59 (6) ◽  
pp. 1439-1450 ◽  
Author(s):  
Miroslava Žertová ◽  
Jiřina Slaninová ◽  
Zdenko Procházka
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Basic Amino Acid ◽  
The Other ◽  
Side Chain ◽  
Inhibitory Potency ◽  
Phase Synthesis ◽  
Other Hand ◽  
Order Of Magnitude

An analysis of the uterotonic potencies of all analogs having substituted L- or D-tyrosine or -phenylalanine in position 2 and L-arginine, D-arginine or D-homoarginine in position 8 was made. The series of analogs already published was completed by the solid phase synthesis of ten new analogs having L- or D-Phe, L- or D-Phe(2-Et), L- or D-Phe(2,4,6-triMe) or D-Tyr(Me) in position 2 and either L- or D-arginine in position 8. All newly synthesized analogs were found to be uterotonic inhibitors. Deamination increases both the agonistic and antagonistic potency. In the case of phenylalanine analogs the change of configuration from L to D in position 2 enhances the uterotonic inhibition for more than 1 order of magnitude. The L to D change in position 8 enhances the inhibitory potency negligibly. Prolongation of the side chain of the D-basic amino acid in position 8 seems to decrease slightly the inhibitory potency if there is L-substituted amino acid in position 2. On the other hand there is a tendency to the increase of the inhibitory potency if there is D-substituted amino acid in position 2.

A new strategy for total solid-phase synthesis of polymyxins

2015 ◽  
Vol 56 (33) ◽  
pp. 4796-4799 ◽  
Author(s):  
Wei-Liang Xu ◽  
A-Long Cui ◽  
Xin-Xin Hu ◽  
Xue-Fu You ◽  
Zhuo-Rong Li ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Total Solid ◽  
Phase Synthesis ◽  
New Strategy

[MeArg1, NLe10]-apelin-12: Optimization of solid-phase synthesis and evaluation of biological properties in vitro and in vivo

Peptides ◽  
2020 ◽  
Vol 129 ◽  
pp. 170320 ◽  
Author(s):  
Maria Sidorova ◽  
Irina Studneva ◽  
Valery Bushuev ◽  
Marina Pal’keeva ◽  
Alexander Molokoedov ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Properties ◽  
Phase Synthesis

Amino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-Proteinase: solid-Phase synthesis of ornithine analogues

2001 ◽  
Vol 11 (16) ◽  
pp. 2085-2088 ◽  
Author(s):  
Sharon M. Dankwardt ◽  
Robert L. Martin ◽  
Christine S. Chan ◽  
Harold E. Van Wart ◽  
Keith A.M. Walker ◽  
...  
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Solid-Phase Synthesis of Acyclic and Cyclic Amino Acid Derived Urea Peptidomimetics Using Phoxime Resin†

1999 ◽  
Vol 1 (2) ◽  
pp. 163-172 ◽  
Author(s):  
Yoshitomo Hamuro ◽  
William J. Marshall ◽  
Mark A. Scialdone
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Solid-phase synthesis of linear and cyclic peptides containing a calix[4]arene amino acid

2009 ◽  
Vol 50 (26) ◽  
pp. 3450-3453 ◽  
Author(s):  
Laura Baldini ◽  
Francesco Sansone ◽  
Federico Scaravelli ◽  
Chiara Massera ◽  
Alessandro Casnati ◽  
...  
Keyword(s):  
Amino Acid ◽  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis
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