Protocol abstract


Nature Protocols 3, 341 - 350 (2008)
Published online: 14 February 2008 | doi:10.1038/nprot.2007.529

Subject Categories: Imaging | Isolation, purification and separation | Pharmacology and toxicology | Synthetic chemistry

Preparation of magnetic resonance contrast agents activated by bold beta-galactosidase

Lauren M Urbanczyk-Pearson1 & Thomas J Meade1


The preparation of beta-EgadMe and alpha-EgadMe, magnetic resonance (MR) contrast agents that can be used for in vivo detection of beta-galactosidase, is described. Diastereomerically pure beta-EgadMe can be synthesized by kinetically resolving the starting material as described in Step 1. The total time for the preparation of the racemic mixture of beta-EgadMe is about 8 d, and the total time for an diastereomerically resolved agent is about 9 d. The final metallated agent is stable at room temperature as a solid or in aqueous buffer (pH 5.5–10) indefinitely. Diastereomerically pure alpha-EgadMe can be prepared by beginning the synthesis with enantiomerically pure bromopropionic acid. The total time for the preparation of racemic alpha-EgadMe or diastereomerically pure alpha-EgadMe is about 8 d. The final metallated agent is stable at room temperature as a solid or in aqueous buffer (pH 5.5–10) indefinitely.

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  1. Department of Chemistry, Department of Biochemistry and Molecular and Cell Biology, Department of Neurobiology and Physiology, Department of Radiology, Northwestern University, Evanston, Illinois 60201, USA.

Correspondence to: Thomas J Meade1 e-mail: tmeade@northwestern.edu

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