Preparation of a carbon-11 labelled antibiotic, erythromycin A lactobionate

Reductive N‐alkylation of secondary amines with [2‐11C]acetone

“…[1][2][3] Reductive alkylation reactions with 11 C-labeled carbonyl compounds such as formaldehyde, 4 acetaldehyde 5,6 and acetone 7 have been applied for the synthesis of potential positron emission tomography (PET) tracers and ligands. [8][9][10][11][12][13][14][15] In contrast to the [ 11 C]aldehydes, reductive alkylation reactions using [2-11 C]acetone are limited to primary aliphatic amines (Figure 1), [7][8][9][10][11][12][13][14][15] which generally react faster than primary aromatic and secondary aliphatic amines.…”

A Simple, Rapid Method for the Preparation of [11C]Formaldehyde

“…Due to its versatile oxidation state, [ 11 C]formaldehyde has used in synthesis of compounds otherwise unlabelable, through reductive methylations,[4] ring-closure reactions, [5] and electrophilic aromatic substitutions, [6] among others. [7] However, the widespread development and use of synthetic methods for [ 11 C]formaldehyde in the preparation of PETcompounds has been hindered by access to it. Several methods have been developed for the synthesis of [ 11 C]formaldehyde from [ 11 C]methanol beginning in 1972 here at Brookhaven National Laboratory, [8] improved over time with new catalysts, [9] and quite elegantly synthesized enzymatically.…”

Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

“…The final product required 42 min from the end of [ 11 C]CO 2 production, with a RCY of 4−12% (based on the [ 11 C]CO 2 activity used at the end of proton irradiation). 822,823 12.6.2. Clinical Studies.…”

“…So far, only one natural antibiotic has been labeled and evaluated in vivo for both the above reasons, Erythromycin lactobionate, a macrolide that inhibits protein synthesis. Another compound, daunorubicin, which is classified as an antibiotic but used as a chemotherapeutic compound, has also been labeled. − Daunorubicin, an exogenous compound, is an anthracycline antibiotic initially isolated in the 1950s from a new strain ofStreptomyces peucetiusbacteria. , However, it is mainly used to treat various types of cancers, especially leukemias, through various mechanisms that include anti-mitotic and anti-cytotoxic activities Glycerol, an endogenous compound, is trivalent alcohol produced by the human white adipose tissue (WAT) when an excess of glucose is present .…”