Toxic Fluorine Compounds. III.<sup>1</sup> ι-Fluoroalcohols

Pattison, F. L. M.; Howell, W. C.; McNAMARA, A. J.; Schneider, James W.; Walker, J. F.

doi:10.1021/jo01113a006

Cited by 66 publications

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“…2-Fluoroethanol was first synthesized by Swarts (1914), but there was no report of its toxicity until its use as a rodenticide was patented in 1935 in Germany (Schrader, 1935). 2-Fluoroethanol has about the same toxicity as fluoroacetate to the rat and its structural relationship to this compound makes it likely that it is toxic for the same reason, namely as a substrate for a lethal synthesis of fluorocitrate (McCombie & Saunders, 1946;Saunders, Stacy & Wilding, 1949;Peters, 1952;Bartlett, D. H. TREBLE 1952;Pattison, Howell, McNamara, Schneider & Walker, 1956).…”

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confidence: 99%

The metabolism of 2-fluoroethanol

Dh¹

1962

Biochemical Journal

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1. Methods of preparation of three distinct fractions of histones have been described and applied to the thymus, spleen and liver of calves and to the liver and spleen of normal and leukaemic rats. 2. No differences in amino acid composition or in N-terminal groups of the same fractions from the different sources were found, outside the probable experimental errors. On the other hand the characteristic analytical differences between the fractions were apparent in all the preparations. 3. The purity of the fractions was examined by starch-gel electrophoresis. Apart from minor bands observed in some cases and probably due to unremoved impurities, no differences of the patterns or of the mobilities were observed which could be ascribed to tissue or species specificity. 4. Some qualification of the above statements are necessary for fractions derived from the Ehrlich ascites tumour. A complete resolution into the fractions was not achieved in this case. We are indebted to the World Health Organization for the award of a Research Fellowship to one of us (L. H.) and to Dr V. Holoubek who made available the histones from leukaemic rat spleen and liver which he had prepared. We also wish to thank Dr D. M. P. Phillips for useful discussions. This investigation has been supported by grants to the

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confidence: 99%

The metabolism of 2-fluoroethanol

Dh¹

1962

Biochemical Journal

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“…Precursors 9–12 were synthesised on the basis of known procedures (see Supplementary Information for full synthesis details) …”

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confidence: 99%

Radiosynthesis of 11-[¹⁸F]fluoroundecyltriphenylphosphonium (MitoF) as a potential mitochondria-specific positron emission tomography radiotracer

Brichard

Larsen

et al. 2013

J. Label Compd. Radiopharm

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Changes in the magnitude of the mitochondrial membrane potential occur in a range of important pathologies. To assess changes in membrane potential in patients, we set out to develop an improved mitochondria-targeted positron emission tomography probe comprising a lipophilic triphenylphosphonium cation attached to a fluorine-18 radionuclide via an 11-carbon alkyl chain, which is well-established to effectively transport to and localise within mitochondria. Here, we describe the radiosynthesis of this probe, 11-[(18) F]fluoroundecyl-triphenylphosphonium (MitoF), from no-carrier-added [(18) F]fluoride and a fully automated synthetic protocol to prepare it in good radiochemical yields (2-3 GBq at end-of-synthesis) and radiochemical purity (97-99%).

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“…The crude product (456 mg) was purified using flash chromatography (Hex/EtOAc 1 : 20) to remove residual starting material. A sample of 9-fluoro-1-nonanol was obtained as a colorless liquid 11 (55 mg, >99% pure by GC-MS …”

Section: Experimental Materialsmentioning

confidence: 99%

In vitro enzymatic oxidation of a fluorine‐tagged sulfido substrate analogue: a ¹⁹F NMR investigation

Tremblay

Buist

Hodgson

et al. 2006

Magnetic Reson in Chemistry

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1H-decoupled 19F NMR has been used to monitor the highly regioselective oxidation of a fluorine-tagged thia-fatty acid derivative by castor stearoyl-ACP delta9 desaturase. The major enzymatic product, after reductive work-up, was identified as 9-fluoro-1-nonanol. This compound could be easily distinguished from substrate and a 9-sulfoxy by-product on the basis of its 19F NMR chemical shift and spiking experiments using authentic standards. Structural assignment of the cleavage product was confirmed by GC-MS analysis of the enzymatic products.

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Toxic Fluorine Compounds. III.¹ ι-Fluoroalcohols

Cited by 66 publications

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The metabolism of 2-fluoroethanol

The metabolism of 2-fluoroethanol

Radiosynthesis of 11-[¹⁸F]fluoroundecyltriphenylphosphonium (MitoF) as a potential mitochondria-specific positron emission tomography radiotracer

In vitro enzymatic oxidation of a fluorine‐tagged sulfido substrate analogue: a ¹⁹F NMR investigation

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Toxic Fluorine Compounds. III.1 ι-Fluoroalcohols

Cited by 66 publications

References 0 publications

The metabolism of 2-fluoroethanol

The metabolism of 2-fluoroethanol

Radiosynthesis of 11-[18F]fluoroundecyltriphenylphosphonium (MitoF) as a potential mitochondria-specific positron emission tomography radiotracer

In vitro enzymatic oxidation of a fluorine‐tagged sulfido substrate analogue: a 19F NMR investigation

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Toxic Fluorine Compounds. III.¹ ι-Fluoroalcohols

Radiosynthesis of 11-[¹⁸F]fluoroundecyltriphenylphosphonium (MitoF) as a potential mitochondria-specific positron emission tomography radiotracer

In vitro enzymatic oxidation of a fluorine‐tagged sulfido substrate analogue: a ¹⁹F NMR investigation