The use of 3-methoxymethyl-16β, 17β-epiestriol-O-cyclic sulfone as the precursor in the synthesis of F-18 16α-fluoroestradiol

Lim, Jean-Luc; Zheng, Lei; Berridge, Marc S.; Tewson, Timothy J.

doi:10.1016/s0969-8051(96)00126-6

Cited by 75 publications

(45 citation statements)

References 8 publications

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“…Fluorine is a small halogen in which substitutions can be made at several positions of the estrogen while preserving binding affinities for both ER and SHBG (52,53). Furthermore, 18 F has a sufficiently long half-life to permit multistep synthesis of ligands (52,54) as well as uptake by target tissue and elimination by nontarget tissue during imaging (14,55); in addition, the use of PET permits quantitative imaging of regional receptor binding.…”

Section: Special Considerations For Tumor Receptor Imagingmentioning

confidence: 99%

Tumor Receptor Imaging

Mankoff¹,

Link²,

Linden³

et al. 2008

J Nucl Med

133

111

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Tumor receptors play an important role in carcinogenesis and tumor growth and have been some of the earliest targets for tumorspecific therapy, for example, the estrogen receptor in breast cancer. Knowledge of receptor expression is key for therapy directed at tumor receptors and traditionally has been obtained by assay of biopsy material. Tumor receptor imaging offers complementary information that includes evaluation of the entire tumor burden and characterization of the heterogeneity of tumor receptor expression. The nature of the ligand-receptor interaction poses a challenge for imaging-notably, the requirement for a low molecular concentration of the imaging probe to avoid saturating the receptor and increasing the background because of nonspecific uptake. For this reason, much of the work to date in tumor receptor imaging has been done with radionuclide probes. In this overview of tumor receptor imaging, aspects of receptor biochemistry and biology that underlie tumor receptor imaging are reviewed, with the estrogen-estrogen receptor system in breast cancer as an illustrative example. Examples of progress in radionuclide receptor imaging for 3 receptor systemssteroid receptors, somatostatin receptors, and growth factor receptors-are highlighted, and recent investigations of receptor imaging with other molecular imaging modalities are reviewed.

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Section: Special Considerations For Tumor Receptor Imagingmentioning

confidence: 99%

Tumor Receptor Imaging

Mankoff¹,

Link²,

Linden³

et al. 2008

J Nucl Med

133

111

View full text Add to dashboard Cite

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“…Many researchers have reported that the use of a microwave as a source of heat energy can enable reactions to proceed over much shorter reactions times and in higher yields than they would do under conventional thermal conditions. [3][4][5][6][7][8] Compounds labeled with 18 F are used as positron emission tomography (PET) tracers. The introduction of 18 F atoms into an organic compound (i.e., 18 F-fluorination reactions), however, invariably requires high temperatures and long reaction times because fluoride anions are only weakly nucleophilic.…”

Section: Introductionmentioning

confidence: 99%

“…[3][4][5][6][7][8] Compounds labeled with 18 F are used as positron emission tomography (PET) tracers. The introduction of 18 F atoms into an organic compound (i.e., 18 F-fluorination reactions), however, invariably requires high temperatures and long reaction times because fluoride anions are only weakly nucleophilic. Furthermore, the use of long reaction times for the introduction of 18 F atoms can be problematic because the half-life of 18 F (109.7 min) is very short.…”

Section: Introductionmentioning

confidence: 99%

“…The introduction of 18 F atoms into an organic compound (i.e., 18 F-fluorination reactions), however, invariably requires high temperatures and long reaction times because fluoride anions are only weakly nucleophilic. Furthermore, the use of long reaction times for the introduction of 18 F atoms can be problematic because the half-life of 18 F (109.7 min) is very short. A microwave-based 18 F labeling method was recently reported and has drawn considerable attention from researchers working in a variety of different fields because this new microwave-assisted method improved yields, reduced the generation of side products, and shortened reaction times compared with conventional heating methods such as oil baths and hotplates.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, the use of long reaction times for the introduction of 18 F atoms can be problematic because the half-life of 18 F (109.7 min) is very short. A microwave-based 18 F labeling method was recently reported and has drawn considerable attention from researchers working in a variety of different fields because this new microwave-assisted method improved yields, reduced the generation of side products, and shortened reaction times compared with conventional heating methods such as oil baths and hotplates. [9][10][11][12][13] A microwave reactor developed by Resonance Instrument Inc. (Model 520/521) and CEM (PETWave) has been used exclusively for the synthesis of radiolabelled agents for PET by numerous groups throughout the world.…”

Section: Introductionmentioning

confidence: 99%

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Development of a resonant‐type microwave reactor and its application to the synthesis of positron emission tomography radiopharmaceuticals

Kimura

Yagi

Ohneda³

et al. 2014

Labelled Comp Radiopharmac

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Microwave technology has been successfully applied to enhance the effectiveness of radiolabeling reactions. The use of a microwave as a source of heat energy can allow chemical reactions to proceed over much shorter reaction times and in higher yields than they would do under conventional thermal conditions. A microwave reactor developed by Resonance Instrument Inc. (Model 520/521) and CEM (PETWave) has been used exclusively for the synthesis of radiolabeled agents for positron emission tomography by numerous groups throughout the world. In this study, we have developed a novel resonant-type microwave reactor powered by a solid-state device and confirmed that this system can focus microwave power on a small amount of reaction solution. Furthermore, we have demonstrated the rapid and facile radiosynthesis of 16α-[(18)F]fluoroestradiol, 4-[(18)F]fluoro-N-[2-(1-methoxyphenyl)-1-piperazinyl]ethyl-N-2-pyridinylbenzamide, and N-succinimidyl 4-[(18)F]fluorobenzoate using our newly developed microwave reactor.

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Herstellung und Charakterisierung der Sulfamate von Estra-3,17ξ-diolen. Schnelle Umsetzung von 16α-Fluorestradiol zum 16α-Fluorestradiol-3,17β-disulfamat

Römer¹,

Steinbach

Kasch

et al. 1999

J. prakt. Chem.

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Sulfamate von 3-Hydroxy-estra-1,3,5(10)-trienen waren erstmals in den siebziger Jahren Gegenstand von Publikationen [1 -4]. Jene Untersuchungen hatten das Ziel, die orale Verfügbarkeit natürlicher und synthetischer Steroide für die Kontrazeption zu verbessern. Bemerkenswerte Erkenntnisse rückten diese Verbindungsklasse in jüngster Vergangenheit wieder in den Blickpunkt. So wurden von Reed et al. [5] die steroidsulfatasehemmende Wirkung und von Elger et al. [6] eine verbesserte Bioverfügbarkeit und Wirkungsverstärkung von Estrogensulfamaten festgestellt. Bei oraler Gabe wurde eine verminderte Metabolisierungsrate ermittelt [6]. Da Steroidsulfatase in entzündeten Geweben und vor allem in Krebszellen überdimensional angereichert wird, eröffnen diese Erkenntnisse neue Wege für die Therapie und Prävention, z.B. bei der Krebsbekämpfung von Mamma-Tumoren [5], bei der Substitutionstherapie [6] und der oralen Kontrazeption mittels Estrogenen [7]. Es wurden eigene detaillierte Untersuchungen zur Estrogenität und Sulfatasehemmwirkung von Estrogensulfamaten durchgeführt. Darin wurde gezeigt, daß Verbindungen vom Typ des Estradiol-disulfamats und des 16-Halogen-estradiol-disulfamats stärkere Sulfatasehemmung aufweisen als alle bisher bekannten Sulfataseinhibitoren und darüber hinaus Preparation and Characterization of the Sulphamates of Estra-3,17ξ-diols. Rapid Conversion of 16α-Fluoroestradiol into 16α-Fluoroestradiol-3,17β-disulphamatesulphatase favoured 16α-[ 18 F]fluorestradiol-3,17 β-disulphamate to a new radio-pharmaceutical which should be appropriate to image the active sites of sulphatase by positron emission tomography. The preparation of 16α-[ 18 F]fluoroestradiol-3,17 β-disulphamate requires a simple and rapid procedure. The conditions for such a procedure were also elaborated using non-radioactive substances.574

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The use of 3-methoxymethyl-16β, 17β-epiestriol-O-cyclic sulfone as the precursor in the synthesis of F-18 16α-fluoroestradiol

Cited by 75 publications

References 8 publications

Tumor Receptor Imaging

Tumor Receptor Imaging

Development of a resonant‐type microwave reactor and its application to the synthesis of positron emission tomography radiopharmaceuticals

Herstellung und Charakterisierung der Sulfamate von Estra-3,17ξ-diolen. Schnelle Umsetzung von 16α-Fluorestradiol zum 16α-Fluorestradiol-3,17β-disulfamat

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