Synthesis of MRI contrast agents derived from DOTAM-Gly-L-Phe-OH incorporating a disulfide bridge: conjugation to a cell penetrating peptide and preparation of a dimeric agent

Mojmír Suchý; Alex X Li; Robert Bartha; Robert H E Hudson

doi:10.1016/j.bmcl.2010.07.070

Synthesis of MRI contrast agents derived from DOTAM-Gly-L-Phe-OH incorporating a disulfide bridge: conjugation to a cell penetrating peptide and preparation of a dimeric agent

Bioorg Med Chem Lett. 2010 Sep 15;20(18):5521-6. doi: 10.1016/j.bmcl.2010.07.070. Epub 2010 Jul 23.

Authors

Mojmír Suchý¹, Alex X Li, Robert Bartha, Robert H E Hudson

Affiliation

¹ Department of Chemistry, The University of Western Ontario, London, ON, Canada N6A 5B7.

PMID: 20705462
DOI: 10.1016/j.bmcl.2010.07.070

Abstract

A cell penetrating peptide conjugate and dimeric PARACEST MRI contrast agents, based on the DOTAM-Gly-L-Phe-OH scaffold have been prepared in moderate yields using diethyl azodicarboxylate (DEAD) or iodine-mediated disulfide bridge formation as a key step. Magnetic (PARACEST) properties of these agents have been evaluated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetamides / chemical synthesis
Acetamides / chemistry*
Contrast Media / chemical synthesis
Contrast Media / chemistry*
Disulfides / chemical synthesis
Disulfides / chemistry*
Europium / chemistry*
Heterocyclic Compounds, 1-Ring / chemical synthesis
Heterocyclic Compounds, 1-Ring / chemistry*
Magnetic Resonance Imaging / methods*
Magnetics
Peptides / chemical synthesis
Peptides / chemistry*

Substances

1,4,7,10-tetrakis(carbamoylmethyl)-1,4,7,10-tetraazacyclododecane
Acetamides
Contrast Media
Disulfides
Heterocyclic Compounds, 1-Ring
Peptides
Europium