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Synthesis of the stable isotope labeled antiviral nucleoside analog [8-13C–7,9-15N2]-ganciclovir

✍ Scribed by Naiyu Zheng; Santosh Tilve; Tomoyuki Oe; Steven M. Albelda; Suzanne Wehrli; Ian A. Blair

Publisher
John Wiley and Sons
Year
2006
Tongue
French
Weight
145 KB
Volume
49
Category
Article
ISSN
0022-2135

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✦ Synopsis

Ganciclovir, a nucleoside analog of 2 0 -deoxyguanosine, is a drug used in suicide gene therapy for the treatment of mesothelioma. We required a stable isotope analog of ganciclovir for use in pharmacokinetic studies in order to monitor the systemic exposure of patients to the drug. Therefore, a facile and efficient synthesis of [8-13 C-7,9-15 N 2 ]-ganciclovir, was devised. The synthesis was achieved in 4 steps with 25% total yield using commercially-available [8-13 C-7,9-15 N 2 ]-guanine, without the need for purification of intermediates. The key step of the synthesis involved the coupling of [8-13 C-7,9-15 N 2 ]-guanine with 3-propionyloxy-2-propionyloxy-methoxypropyl propionate. The latter was synthesized from a commercially available dichlorohydrin. Each step of the reaction could be easily monitored by liquid chromatography-mass spectrometry. The structure of the labeled ganciclovir was confirmed using 1 H, 13 C, and 15 N nuclear magnetic resonance spectroscopy.

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