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

Karin A. Stephenson, Sangeeta Ray Banerjee, Nicole McFarlane, Douglas R. Boreham, Kevin P. Maresca, John W. Babich, Jon A Zubieta, John F. Valliant

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2060-2066
Number of pages7
JournalCanadian Journal of Chemistry
Volume83
Issue number12
DOIs
StatePublished - Dec 2005

Fingerprint

Molecular imaging
Peptides
Screening
Ligands
Radiopharmaceuticals
Metal complexes
Resins
Derivatives

Keywords

  • Peptides
  • Radiopharmaceuticals
  • Rhenium
  • Solid-phase synthesis
  • Technetium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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. / Stephenson, Karin A.; Banerjee, Sangeeta Ray; McFarlane, Nicole; Boreham, Douglas R.; Maresca, Kevin P.; Babich, John W.; Zubieta, Jon A; Valliant, John F.

In: Canadian Journal of Chemistry, Vol. 83, No. 12, 12.2005, p. 2060-2066.

Research output: Contribution to journalArticle

Stephenson, Karin A. ; Banerjee, Sangeeta Ray ; McFarlane, Nicole ; Boreham, Douglas R. ; Maresca, Kevin P. ; Babich, John W. ; Zubieta, Jon A ; Valliant, John F. / 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. In: Canadian Journal of Chemistry. 2005 ; Vol. 83, No. 12. pp. 2060-2066.
@article{4c38106ca88a44f9b2bdab21a3423be4,
title = "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",
abstract = "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.",
keywords = "Peptides, Radiopharmaceuticals, Rhenium, Solid-phase synthesis, Technetium",
author = "Stephenson, {Karin A.} and Banerjee, {Sangeeta Ray} and Nicole McFarlane and Boreham, {Douglas R.} and Maresca, {Kevin P.} and Babich, {John W.} and Zubieta, {Jon A} and Valliant, {John F.}",
year = "2005",
month = "12",
doi = "10.1139/v05-224",
language = "English (US)",
volume = "83",
pages = "2060--2066",
journal = "Canadian Journal of Chemistry",
issn = "0008-4042",
publisher = "National Research Council of Canada",
number = "12",

}

TY - JOUR

T1 - 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

AU - Stephenson, Karin A.

AU - Banerjee, Sangeeta Ray

AU - McFarlane, Nicole

AU - Boreham, Douglas R.

AU - Maresca, Kevin P.

AU - Babich, John W.

AU - Zubieta, Jon A

AU - Valliant, John F.

PY - 2005/12

Y1 - 2005/12

N2 - 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.

AB - 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.

KW - Peptides

KW - Radiopharmaceuticals

KW - Rhenium

KW - Solid-phase synthesis

KW - Technetium

UR - http://www.scopus.com/inward/record.url?scp=33744467703&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33744467703&partnerID=8YFLogxK

U2 - 10.1139/v05-224

DO - 10.1139/v05-224

M3 - Article

AN - SCOPUS:33744467703

VL - 83

SP - 2060

EP - 2066

JO - Canadian Journal of Chemistry

JF - Canadian Journal of Chemistry

SN - 0008-4042

IS - 12

ER -