PMID: 2096916Jul 1, 1990Paper

Synthesis and tissue distribution of fluorine-18 labeled trifluorohexadecanoic acids. Considerations in the development of metabolically blocked myocardial imaging agents

Bioconjugate Chemistry
S S PochapskyJ A Katzenellenbogen

Abstract

A versatile method for the synthesis of trifluoro fatty acids, potential metabolically blocked myocardial imaging agents, has been developed. Two trifluorohexadecanoic (palmitic) acids have been prepared [6,6,16-trifluorohexadecanoic acid (I) and 7,7,16-trifluorohexadecanoic acid (II)], each of which bears two of the fluorine atoms as a gem-difluoromethylene unit on the fatty acid chain (at C-6 or C-7) and the third at the omega (C-16) position. The metabolic stability of carbon-fluorine bonds suggests the gem-difluoro group may block the beta-oxidation pathway, while the terminal fluorine could be the site for labeling with fluorine-18. The convergent synthetic approach utilizes a 2-lithio-1,3-dithiane derived from 10-undecenal or 9-decenal, which is alkylated with the OBO (oxabicyclooctyl) ester of 5-bromopentanoic acid or 6-bromohexanoic acid, respectively. Hydroboration-oxidation and alcohol protection are followed by halofluorination to convert the 1,3-dithiane system to a gem-difluoro group. The third fluorine is introduced by fluoride ion displacement of a trifluoromethanesulfonate. This synthesis is adapted to the labeling of these trifluoro fatty acids with the short-lived radionuclide fluorine-18 (t1/2 = 110 min), wit...Continue Reading

References

Jan 1, 1977·The International Journal of Applied Radiation and Isotopes·A K HorschA J Day
Jan 1, 1988·International Journal of Radiation Applications and Instrumentation. Part A, Applied Radiation and Isotopes·M Eisenhut, J Liefhold
Jan 1, 1986·International Journal of Radiation Applications and Instrumentation. Part A, Applied Radiation and Isotopes·J W BrodackJ A Katzenellenbogen
Apr 1, 1985·The International Journal of Applied Radiation and Isotopes·M R KilbournM J Welch
Apr 1, 1983·The International Journal of Applied Radiation and Isotopes·M S BerridgeM J Welch
Dec 1, 1954·Journal of Dental Research·P WALLACE-DURBIN

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Citations

May 1, 1992·International Journal of Radiation Applications and Instrumentation. Part B, Nuclear Medicine and Biology·M G PomperJ A Katzenellenbogen
Jul 20, 2016·Chemistry : a European Journal·Sarah L Clarke, Gerard P McGlacken
Mar 2, 2021·Environmental Science & Technology·Sadjad Fakouri BaygiBernard S Crimmins

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