DOTMA-based amides (DOTMAMs) as a platform for the development of PARACEST MRI contrast agents

Document Type

Article

Publication Date

1-1-2016

Journal

RSC Advances

Volume

6

Issue

67

First Page

62647

Last Page

62655

URL with Digital Object Identifier

10.1039/c6ra11741d

Abstract

A synthetic methodology leading to previously unknown DOTMA-based secondary amides (DOTMAMs) has been developed. Alkylation of cyclen with l-lactic acid-derived pseudohalides was used as a key step affording the alkyl- and aryl-decorated DOTMAMs. Amino acid-decorated DOTMAMs were obtained via peptide coupling between DOTMA and protected amino acids. Metallation of the DOTMAMs ligand with Tm3+ gave complexes exhibiting proximal amide proton based paramagnetic CEST effects at <-50 ppm relative to water.

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