Synthesis and in vivo evaluation of 11C‐labeled (1, 7‐dicarba‐closo‐dodecaboran‐1‐yl)‐N‐{[(2S)‐1‐ethylpyrrolidin‐2‐yl]methyl}amide†. (5th December 2013)

• Record Type: Journal Article
• Authors: Gómez‐Vallejo, Vanessa; Vázquez, Naiara; Gona, Kiran Babu; Puigivila, Maria; González, Mikel; Sebastián, Eneko San; Martin, Abraham; Llop, Jordi; Dilworth, Jonathan R.; Pascu, Sofia I.
• Is Part Of: Journal of labelled compounds & radiopharmaceuticals. Volume 57:Number 4(2014)
• Page Start: 209
• Page End: 214
• Publication Date: 2013-12-05
• Subjects: Tracers (Chemistry) -- Periodicals; Radiopharmaceuticals -- Periodicals; 615.8424
• DOI: 10.1002/jlcr.3159
• Languages: English
• ISSNs: 0362-4803

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Boron clusters, and especially dicarba‐<italic>closo</italic>‐dodecaboranes, can be used as hydrophobic pharmacophores in the design of new drugs and radiotracers because of their hydrophobic character, spherical structure, and excellent chemical and photochemical stability. In the present paper, the synthesis and <italic>in vivo</italic> evaluation of <sup>11</sup>C‐labeled (1, 7‐dicarba‐<italic>closo</italic>‐dodecaboran‐1‐yl)‐<italic>N</italic>‐{[(2<italic>S</italic>)‐1‐ethylpyrrolidin‐2‐yl]methyl}amide, an analog of the D<sub>2</sub> receptor ligand [<sup>11</sup>C]raclopride, is described. The radiosynthesis was approached by reaction of the demethylated precursor with [<sup>11</sup>C]CH<sub>3</sub>I in basic media; moderate radiochemical yields (18.2 ± 2.8%, decay corrected), and excellent radiochemical purities (>98%) were obtained in overall synthesis time of ~50 min. <italic>In vivo</italic> assays showed a biodistribution pattern with significant uptake in liver, kidneys and lungs at short times (<italic>t</italic> = 4 min) after administration and increasing accumulation in bladder at longer times (t ≥ 14.5 min). Although brain positron emission tomography scans showed good blood brain barrier penetration, the high unspecific uptake observed in different brain regions impedes its applicability as D<sub>2</sub> receptor ligand. Copyright © 2013 John Wiley & Sons, Ltd.</p> </abstract>