Preparation of no carrier added fluorine-18 labeled 16-fluorohexadecanoic and fluoroacetic acids from highly reactive tetraethylammonium [18F]fluoride

Bosch, A.L.; DeGrado, Timothy R.; Gatley, S.J.

doi:10.1016/0883-2889(86)90118-8

Cited by 14 publications

(1 citation statement)

References 14 publications

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“…Potential entry points for trace impurities are numerous, and controlling them routinely can be a daunting task. Purification of ["Flfluoride by conversion to trimethylsilyl ['8F]fluoride (TMS ['*F]F) is an effective solution to variable fluoride quality (Taves, 1968;Hutchins et al, 1985;Rosenthal et al, 1985;Bosch et al, 1986;Chirakal et al, 1988;Gatley, 1989), but existing procedures have drawbacks which reduce their utility for routine application with cyclotron produced ['* Flfluoride ion. Recovery of the expensive IsO enriched target water, and aqueous hydrolysis of TMS[lsF]F can be problematic with present silylation techniques. The latter drawback has been recognized and a nonaqueous method for cleaving TMS[18F]F with potassium tert-butoxide in acetonitrile has been developed recently (Gatley, 1989).…”

Section: Introductionmentioning

confidence: 99%

Recovery and purification of no-carrier-added [18F]fluoride with bistrimethylsilylsulfate (BTMSS)

Mulholland

1991

International Journal of Radiation Applications and Instrumenta

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No-carrier-added trimethylsilyl[18F]fluoride (TMS[18F]F) was rapidly liberated from a variety of dry supports containing unreactive [18F]fluoride by simply heating with neat bistrimethylsilylsulfate. The supports included calcium phosphate, anion exchange resins, alumina, borosilicate and porous carbon beads, to which [18F]fluoride was applied by absorption or evaporation of aqueous solution. TMS[18F]F was evolved essentially free of entrained moisture or excess silylating agent and was efficiently absorbed and rapidly cleaved to free [18F]fluoride ion by 0.1% benzyltrimethylammonium methoxide in anhydrous methanol. Passage of this solution through a strong cation exchange column provided purified hydrogen[18F]fluoride, which was subsequently trapped on a quaternary 4-aminopyridinium resin and used for heterogeneous nucleophilic radiofluorination of 1,3,4,6-tetraacetyl-beta-mannopyranose-2-triflate in 70% yield. The purified [18F]fluoride was also used for solution phase nucleophilic labeling of ethyl [18F]4-fluorobenzoate following addition of K2 CO3/Kryptofix and DMSO. This approach provides a simplified way to ensure high reactivity in [18F]fluoride ion from cyclotron targets. It also may be used to salvage active [18F]fluoride ion from insoluble complexes and radiofluorination reaction residues.

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Section: Introductionmentioning

confidence: 99%

Recovery and purification of no-carrier-added [18F]fluoride with bistrimethylsilylsulfate (BTMSS)

Mulholland

1991

International Journal of Radiation Applications and Instrumenta

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Synthesis of no-carrier-added [18F]fluoroacetate

Jeong

Lee

Chung

et al. 1997

J Label Compd Radiopharm

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To synthesize no‐carrier‐added potassium [18F]fluoroacetate, O‐mesyl glycolate ethyl ester and O‐tosyl glycolate ethyl ester were synthesized as precursors. These precursors were radiolabeled by reacting with dried tetrabutylammonium [18F]fluoride in the presence of tetrabutylammonium bicarbonate. O‐Mesyl glycolate ethyl ester showed higer 18F incorporation (77.6% at 100 °C) than O‐tosyl glycolate ethyl ester (63.2% at 100 °C). Resulting [18F]fluoroacetate ethyl ester was hydrolyzed quantitatively by heating in 1 M potassium hydroxide solution. The [18F]fluoroacetate was adsorbed to strong anion exchange resin and washed with excess water. Following elution with 1 M sodium bicarbonate solution and passing through Sep‐Pak neutral alumina column, the [18F]fluoroacetate was obtained with 24.5% recovery (non‐decay‐corrected). Total labeling time from drying 18F to final product was 70 to 90 min. © 1997 John Wiley & Sons, Ltd.

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A simple and rapid automated radiosynthesis of [¹⁸F]fluoroacetate

Tang

Wang

et al. 2008

Labelled Comp Radiopharmac

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Preparation of no carrier added fluorine-18 labeled 16-fluorohexadecanoic and fluoroacetic acids from highly reactive tetraethylammonium [18F]fluoride

Cited by 14 publications

References 14 publications

Recovery and purification of no-carrier-added [18F]fluoride with bistrimethylsilylsulfate (BTMSS)

Recovery and purification of no-carrier-added [18F]fluoride with bistrimethylsilylsulfate (BTMSS)

Synthesis of no-carrier-added [18F]fluoroacetate

A simple and rapid automated radiosynthesis of [¹⁸F]fluoroacetate

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Preparation of no carrier added fluorine-18 labeled 16-fluorohexadecanoic and fluoroacetic acids from highly reactive tetraethylammonium [18F]fluoride

Cited by 14 publications

References 14 publications

Recovery and purification of no-carrier-added [18F]fluoride with bistrimethylsilylsulfate (BTMSS)

Recovery and purification of no-carrier-added [18F]fluoride with bistrimethylsilylsulfate (BTMSS)

Synthesis of no-carrier-added [18F]fluoroacetate

A simple and rapid automated radiosynthesis of [18F]fluoroacetate

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A simple and rapid automated radiosynthesis of [¹⁸F]fluoroacetate