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

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.

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

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19872317 ◽

1987 ◽

Vol 52 (9) ◽

pp. 2317-2325 ◽

Cited By ~ 5

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.

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

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2005.11.040 ◽

2006 ◽

Vol 16 (5) ◽

pp. 1392-1396 ◽

Cited By ~ 12

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

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

Peptides ◽

10.1016/j.peptides.2020.170320 ◽

2020 ◽

Vol 129 ◽

pp. 170320 ◽

Cited By ~ 1

Author(s):

Maria Sidorova ◽

Irina Studneva ◽

Valery Bushuev ◽

Marina Pal’keeva ◽

Alexander Molokoedov ◽

...

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Biological Properties ◽

Phase Synthesis

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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

Canadian Journal of Chemistry ◽

10.1139/v05-224 ◽

2005 ◽

Vol 83 (12) ◽

pp. 2060-2066 ◽

Cited By ~ 10

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 peptidechelate 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 metalchelate complexes, the Re complex of a chelatepeptide 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.

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