Technology Commercialization and Partnerships | BSA 08-25: Simple and Rapid Preparation of Isotopically Labeled Formaldehyde

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Category: biotechnology & health

BSA 08-25: Simple and Rapid Preparation of Isotopically Labeled Formaldehyde

BNL Reference Number: BSA 08-25

Patent Status: U.S. Patent Number 8,030,526 was issued on October 4, 2011

Summary

Trimethylamine N-oxide will react with [¹¹C]methyliodide to form [¹¹C]formaldehyde. This new reaction provides a method to access [¹¹C]formaldehyde without the need for special reagents or conditions. It is anticipated that the widespread availability of [¹¹C]formaldehyde will increase the number of compounds that can be labeled with carbon-11 for use in positron emission tomography (PET), a non-invasive way to image molecular interactions in the human body.

Formaldehyde represents a unique reagent for various synthetic routes to drug compounds. Its use as a precursor reagent in the synthesis of ¹¹C labeled positron emission tomography (PET) tracers has been limited due to lack of simple, easily adapted methods of making it from cyclotron-derived ¹¹C- CO₂. This method makes ¹¹C - Formaldehyde a readily available synthetic reagent.

Description

The present invention provides a simple, efficient method for production of radiolabeled formaldehyde. Methods for production of [¹¹C]-formaldehyde (¹¹CH₂O) for use in positron emission tomography (PET) are provided as are methods for synthesis of ¹⁴C, ¹³C, deuterium and tritium labeled formaldehyde.

Benefits

The oxidation state of[¹¹C]-formaldehyde (¹¹CH₂O) provides a way to insert carbon-11 into compounds for use in PET imaging through new routes. Lack of a simple synthetic route for ¹¹CH₂O production has heretofore stymied its routine use. The present invention makes use of commercially available reagents and mild conditions to convert [¹¹C]-methyl iodide (¹¹CH₃I) to [¹¹C]-formaldehyde (¹¹CH_{211C isotopic dilution. The reaction can be readily automated for incorporation into commercial PET tracer synthesis modules.}

Applications and Industries

A wide variety of synthetic routes are possible using ¹¹CH₂O, including reductive methylations, ring-closure reactions, electrophilic aromatic substitutions, Mannich-type condensations, and cyclization reactions. Thus, readily available ¹¹CH₂O enables the development and use of many new radioliglands.