Exploration of the labeling of [11C]tubastatin A at the hydroxamic acid site with [11C]carbon monoxide.
J Labelled Comp Radiopharm
; 59(1): 9-13, 2016 Jan.
Article
em En
| MEDLINE
| ID: mdl-26647018
ABSTRACT
We aimed to label tubastatin A (1) with carbon-11 (t1/2 = 20.4 min) in the hydroxamic acid site to provide a potential radiotracer for imaging histone deacetylase 6 in vivo with positron emission tomography. Initial attempts at a one-pot Pd-mediated insertion of [(11)C]carbon monoxide between the aryl iodide (2) and hydroxylamine gave low radiochemical yields (<5%) of [(11) C]1. Labeling was achieved in useful radiochemical yields (16.1 ± 5.6%, n = 4) through a two-step process based on Pd-mediated insertion of [(11)C]carbon monoxide between the aryl iodide (2) and p-nitrophenol to give the [(11)C]p-nitrophenyl ester ([(11)C]5), followed by ultrasound-assisted hydroxyaminolysis of the activated ester with excess hydroxylamine in a DMSO/THF mixture in the presence of a strong phosphazene base P1-t-Bu. However, success in labeling the hydroxamic acid group of [(11)C]tubastatin A was not transferable to the labeling of three other model hydroxamic acids.
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1
Bases de dados:
MEDLINE
Assunto principal:
Monóxido de Carbono
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Compostos Radiofarmacêuticos
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Ácidos Hidroxâmicos
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Indóis
Idioma:
En
Revista:
J Labelled Comp Radiopharm
Ano de publicação:
2016
Tipo de documento:
Article
País de afiliação:
Estados Unidos