Microwave-assisted (radio)halogenation of nitroimidazole-based Hypoxia markers

Kumar, Piyush; Wiebe, Leonard I.; Aşıkoğlu, Makbule; Tandon, Manju; McEwan, A. J. B.

doi:10.1016/s0969-8043(02)00185-9

Cited by 25 publications

(17 citation statements)

References 7 publications

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“…[ 18 F] FAZA is now routinely produced by substitution of the tosyl group at the 5-position of the precursor with 18 F. [ 131 I] IAZA, the iodo analog of FAZA, has also been synthesized by the tosyl- 131 I substitution reaction [21]. Using a similar method (Fig.…”

Section: Discussionmentioning

confidence: 99%

“…The reaction time of 15 min is 24 times shorter than that required for the [ 131 I] IAZGP preparation via the 131 I–I exchange reaction [15]. Owing to this effectiveness, the use of the nucleophilic substitution method becomes advantageous when IAZGP is labeled with a relatively short-lived nuclide such as 123 I, the half-life of which is 13 h. In the aforementioned [ 131 I]IAZA synthesis, a microwave-assisted heating technique was applied [21]. The authors pointed out, however, that microwave heating was less effective for the 131 I–I exchange reaction compared to the tosyl- 131 I substitution.…”

Section: Discussionmentioning

confidence: 99%

“…The tosylate precursor (B, Fig. 1) was also synthesized at the same facility according to Kumar et al [21] starting with 1-(β-D-galactopyranosyl)-2-nitroimidazole (A, Fig. 1).…”

Section: Methodsmentioning

confidence: 99%

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Radiosynthesis of [131I]IAZGP via nucleophilic substitution and its biological evaluation as a hypoxia marker — is specific activity a factor influencing hypoxia-mapping ability of a hypoxia marker?

Suehiro

Burgman

Carlin

et al. 2009

Nuclear Medicine and Biology

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Introduction-The hypoxia marker IAZGP, 1-(6-deoxy-6-iodo-β-D-galactopyranosyl)-2-nitroimidazole, has been labeled with 123 I/ 124 I/ 125 I/ 131 I via iodine-radioiodine exchange, which gives the radiotracer in a specific activity of 10-90 MBq/μmol. We synthesized the same radiotracer possessing several hundred to thousand times higher specific activity (high-SA IAZGP) via nucleophilic substitution and compared its biological behavior with that of conventionally produced IAZGP (low-SA IAZGP) to determine if specific activity is a factor influencing cell uptake kinetics, biodistribution and intratumor microregional localization of the radiotracer. Conclusions-Radiolabeled IAZGP produced via nucleophilic substitution is validated as an exogenous hypoxia marker. Specific activity does not appear to influence the in vivo hypoxiamapping ability of the radiotracer. Methods

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Radiosynthesis of [131I]IAZGP via nucleophilic substitution and its biological evaluation as a hypoxia marker — is specific activity a factor influencing hypoxia-mapping ability of a hypoxia marker?

Suehiro

Burgman

Carlin

et al. 2009

Nuclear Medicine and Biology

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“…Recently, several investigators reported improved radiochemical yields and reduced overall synthesis time by using microwave (Dolle, et al, 1999;Kahn, et al, 2006;Kumar, et al, 2002). Some of these reports stress the importance of selecting appropriate solvent for microwave assisted reactions.…”

Section: Discussionmentioning

confidence: 99%

A remote controlled system for the preparation of 7α-[18F]fluoro-17α-methyl 5α-dihydrotestosterone ([18F]FMDHT) using microwave

Garg

Lynch

Doke

et al. 2008

Applied Radiation and Isotopes

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For non-invasive imaging of the prostate cancer, we synthesized 7α-fluoro-17α-methyl 5α-dihydrotestosterone ([ 18 F]FMDHT) for androgen receptor mediated PET imaging. Preliminary in vitro and in vivo evaluations of this compound show promise. We designed and implemented a remote controlled system for reliable, efficient, and safe handling of radioactivity during the radiochemical synthesis of [ 18 F]FMDHT. The key features of this report are the microwave assisted radiochemical synthesis, increased radiochemical yields, improved radiochemical purity, reduced overall synthesis time, and remote controlled automation of the entire synthesis. The overall synthesis using microwave reaction took 60 -70 min and provided the desired product in 20 -30% radiochemical yields with >99% radiochemical purity.

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“…The software modification required to perform the synthesis of [ 18 F]-FAZA was made possible by the use of an Excel spreadsheet programming tool provided by GEMS-Coincidence [114]. Microwave-assisted fluorination of the tosylate precursor has been reported [115]. [116].…”

Section: [ 18 F]fluoroazomycin Arabinosidementioning

confidence: 99%

PET radiopharmaceuticals for metabolic imaging in oncology

Wiebe

2004

International Congress Series

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Microwave-assisted (radio)halogenation of nitroimidazole-based Hypoxia markers

Cited by 25 publications

References 7 publications

Radiosynthesis of [131I]IAZGP via nucleophilic substitution and its biological evaluation as a hypoxia marker — is specific activity a factor influencing hypoxia-mapping ability of a hypoxia marker?

Radiosynthesis of [131I]IAZGP via nucleophilic substitution and its biological evaluation as a hypoxia marker — is specific activity a factor influencing hypoxia-mapping ability of a hypoxia marker?

A remote controlled system for the preparation of 7α-[18F]fluoro-17α-methyl 5α-dihydrotestosterone ([18F]FMDHT) using microwave

PET radiopharmaceuticals for metabolic imaging in oncology

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