Solid phase synthesis and biological activities of oxytocin carba analogues containing threonine in position 4

1985 ◽  
Vol 50 (2) ◽  
pp. 418-427 ◽  
Author(s):  
Michal Lebl ◽  
Victor J. Hruby ◽  
Jiřina Slaninová ◽  
Tomislav Barth
Keyword(s):  
Biological Activity ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Activities ◽  
High Biological Activity ◽  
Phase Synthesis

Solis phase methodology was developed for the synthesis of carba-analogues of oxytocin. Two known compounds (deamino-1-carba-oxytocin (I) and deamino-6-carba-oxytocin (II)) and two new analogues ([4-threonine]deamino-1-carba-oxytocin (III) and [4-threonine]deamino-6-carba-oxytocin (IV)) were synthesized using different approaches. The latter two compounds were found to possess high biological activity in the rat uterotonic (in vitro and in vivo) and galactogogic (in vivo) assays.

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.

[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

Solid-phase synthesis and in vitro biological activity of a Thr4→Ser4 analog of daptomycin

2015 ◽  
Vol 25 (23) ◽  
pp. 5490-5494 ◽  
Author(s):  
Chuda Raj Lohani ◽  
Robert Taylor ◽  
Michael Palmer ◽  
Scott D. Taylor
Keyword(s):  
Biological Activity ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

scholarly journals A convenient and efficient total solid-phase synthesis of DOTA-functionalized tumor-targeting peptides for PET imaging of cancer

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Subhani M. Okarvi ◽  
Ibrahim AlJammaz
Keyword(s):  
Tumor Targeting ◽  
Chelating Agents ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Cost Effective ◽  
Binding Affinities ◽  
Phase Synthesis ◽  
Metal Chelating

Abstract Introduction An efficient and cost-effective synthesis of the metal chelating agents that couple to tumor-targeting peptides is required to enhance the process of preclinical research toward the clinical translation of molecular imaging agents. DOTA is one of the most widely used macrocyclic ligands for the development of new metal-based imaging and therapeutic agents owing to its ability to form stable and inert complexes under physiological conditions. Although solid-phase synthesis compatible DOTA-tris-(t-Bu ester) is a commercial product, it is expensive and contain chemical impurities. There is a need to explore new and cost-effective methods for the preparation of metal chelating agents, i.e., DOTA, directly on solid support to facilitate rapid, cost-effective, and high purity preparation of DOTA-linked peptides for imaging and therapy. In the present study, we describe a facile synthetic strategy of DOTA preparation and its linkage to peptides directly on solid-phase support. Methods Bombesin (BN) peptides were functionalized with DOTA chelator prepared from cyclen precursor on solid-phase and from commercial DOTA-tris and radiolabeled with 68Ga. In vitro BN/GRP receptor binding affinities of the corresponding radiolabeled peptides were determined by saturation binding assays on human breast MDA-MB-231, MCF7, T47D, and PC3 prostate cancer cells. Pharmacokinetics were studied in Balb/c mice and in vivo tumor targeting in MDA-MB-231 tumor-bearing nude mice. Results DOTA was prepared successfully from cyclen on solid-phase support, linked specifically to BN peptides and resultant DOTA-coupled peptides were radiolabeled efficiently with 68Ga. The binding affinities of all the six BN peptides were comparable and in the low nanomolar range. All 68Ga-labeled peptides showed high metabolic stability in plasma. These radiopeptides exhibited rapid pharmacokinetics in Balb/c mice with excretion mainly through the urinary system. In nude mice, MDA-MB-231 tumor uptake profiles were slightly different; the BN peptide with Ahx spacer and linked to DOTA through cyclen exhibited higher tumor uptake (2.32% ID/g at 1 h post-injection) than other radiolabeled BN peptides investigated in this study. The same leading BN peptide also displayed favorable pharmacokinetic profile in Balb/c mice. The PET images clearly visualized the MDA-MB-231 tumor. Conclusions DOTA prepared from cyclen on solid-phase support showed comparable potency and efficiency to DOTA-tris in both in vitro and in vivo evaluation. The synthetic methodology described here allows versatile, site-specific introduction of DOTA into peptides to facilitate the development of DOTA-linked molecular imaging and therapy agents for clinical translation.

Solid-phase synthesis and biological activities of gastrointestinal hormones: Secretin and motilin

Peptides ◽  
1982 ◽  
Vol 3 (2) ◽  
pp. 137-141 ◽  
Author(s):  
David H. Coy ◽  
Esther J. Coy ◽  
Kae-Yol Lee ◽  
William Y. Chey
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Activities ◽  
Gastrointestinal Hormones ◽  
Phase Synthesis

New Gly-Pro-Glu (GPE) analogues: Expedite solid-phase synthesis and biological activity

2006 ◽  
Vol 16 (5) ◽  
pp. 1392-1396 ◽  
Author(s):  
Sergio A. Alonso De Diego ◽  
Marta Gutiérrez-Rodríguez ◽  
M. Jesús Pérez de Vega ◽  
Diego Casabona ◽  
Carlos Cativiela ◽  
...  
Keyword(s):  
Biological Activity ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Ampullosporin Analogs: Solid Phase Synthesis, Conformational Studies, and Biological Activities

2001 ◽  
pp. 226-227
Author(s):  
Hoai Huong Nguyen ◽  
Diana Imhof ◽  
Brigitte Schlegel ◽  
Albert Härtl ◽  
Matthias Kronen ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Activities ◽  
Phase Synthesis ◽  
Conformational Studies
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