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Title: Synthesis of no carrier added F-18 16-fluorohexadecanoic acid (FHDA) and investigation of its labeled metabolites and its kinetics in the heart

Abstract

No carrier added FHDA was prepared via saponification of the product of silver oxide assisted reaction of near-anhydrous tetraethylammonium fluoride with methyl 16-iodohexadecanoate. The labeled fatty acid was injected into isolated perfused rat hearts. Coronary perfusate was collected for 4-9 minutes, when hearts were chilled and homogenized. F-18 in perfusate was analysed by HPLC (NH column; 50mM amm. acetate in 50% acetonitrile). Material with the same retention time as F-18 fluoroacetate (prepared by F-for-I exchange with ethyl iodoacetate) was found. Some F-18 stuck permanently to the column and was assigned as fluoride since the same fraction of label in perfusate was retained on alumina columns eluted with water. Anion exchange HPLC (SAX column; 20mM pot. phosphate, pH 7) of homogenates gave peaks corresponding to fluoroacetate plus fluoride and minor peaks which could be fluoroacetylCoA and fluorocitrate. The authors interpret their data as follows. Beta-oxidation of FHDA results in fluoroacetylCoA which either undergoes ''lethal synthesis'' to fluorocitrate or is hydrolysed to fluoroacetate which diffuses out of the heart. The source of the fluoride is not yet clear, but could complicate interpretation of FHDA kinetics measured in vivo with positron tomography. Clearance of label from FHDA in isolated perfused hearts was fastermore » than for labeled 16-iodohexadecanoic acid, indicating that the F-18 tracer may be a more sensitive probe of myocardial fatty acid metabolism.« less

Authors:
; ; ; ;
Publication Date:
Research Org.:
Dept. of Medical Physics, Univ. of Wisconsin, Madison, WI
OSTI Identifier:
6793566
Alternate Identifier(s):
OSTI ID: 6793566
Report Number(s):
CONF-840619-
Journal ID: CODEN: JNMEA; TRN: 87-010801
Resource Type:
Conference
Resource Relation:
Journal Name: J. Nucl. Med.; (United States); Journal Volume: 25:5; Conference: 31. annual meeting of the Society of Nuclear Medicine, Los Angeles, CA, USA, 5 Jun 1984
Country of Publication:
United States
Language:
English
Subject:
62 RADIOLOGY AND NUCLEAR MEDICINE; HEXADECANOIC ACID; FLUORINATION; LABELLING; METABOLITES; RADIOPHARMACEUTICALS; CHEMICAL PREPARATION; AMMONIUM FLUORIDES; DIAGNOSTIC USES; FLUORINE 18; ION EXCHANGE CHROMATOGRAPHY; LIQUID COLUMN CHROMATOGRAPHY; MONOCARBOXYLIC ACIDS; MYOCARDIUM; PERFUSED ORGANS; RATS; RETENTION; SAPONIFICATION; SILVER OXIDES; TRACER TECHNIQUES; AMMONIUM COMPOUNDS; ANIMALS; BETA DECAY RADIOISOTOPES; BETA-PLUS DECAY RADIOISOTOPES; BODY; CARBOXYLIC ACIDS; CARDIOVASCULAR SYSTEM; CHALCOGENIDES; CHEMICAL REACTIONS; CHROMATOGRAPHY; DECOMPOSITION; DRUGS; FLUORIDES; FLUORINE COMPOUNDS; FLUORINE ISOTOPES; HALIDES; HALOGEN COMPOUNDS; HALOGENATION; HEART; HOURS LIVING RADIOISOTOPES; HYDROLYSIS; ISOTOPE APPLICATIONS; ISOTOPES; LABELLED COMPOUNDS; LIGHT NUCLEI; LYSIS; MAMMALS; MUSCLES; NUCLEI; ODD-ODD NUCLEI; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANS; OXIDES; OXYGEN COMPOUNDS; RADIOISOTOPES; RODENTS; SEPARATION PROCESSES; SILVER COMPOUNDS; SOLVOLYSIS; SYNTHESIS; TRANSITION ELEMENT COMPOUNDS; USES; VERTEBRATES 550601* -- Medicine-- Unsealed Radionuclides in Diagnostics

Citation Formats

DeGrado, T.R., Bernstein, D.R., Gatley, S.J., Ng, C.K., and Holden, J.E. Synthesis of no carrier added F-18 16-fluorohexadecanoic acid (FHDA) and investigation of its labeled metabolites and its kinetics in the heart. United States: N. p., 1984. Web.
DeGrado, T.R., Bernstein, D.R., Gatley, S.J., Ng, C.K., & Holden, J.E. Synthesis of no carrier added F-18 16-fluorohexadecanoic acid (FHDA) and investigation of its labeled metabolites and its kinetics in the heart. United States.
DeGrado, T.R., Bernstein, D.R., Gatley, S.J., Ng, C.K., and Holden, J.E. Sun . "Synthesis of no carrier added F-18 16-fluorohexadecanoic acid (FHDA) and investigation of its labeled metabolites and its kinetics in the heart". United States. doi:.
@article{osti_6793566,
title = {Synthesis of no carrier added F-18 16-fluorohexadecanoic acid (FHDA) and investigation of its labeled metabolites and its kinetics in the heart},
author = {DeGrado, T.R. and Bernstein, D.R. and Gatley, S.J. and Ng, C.K. and Holden, J.E.},
abstractNote = {No carrier added FHDA was prepared via saponification of the product of silver oxide assisted reaction of near-anhydrous tetraethylammonium fluoride with methyl 16-iodohexadecanoate. The labeled fatty acid was injected into isolated perfused rat hearts. Coronary perfusate was collected for 4-9 minutes, when hearts were chilled and homogenized. F-18 in perfusate was analysed by HPLC (NH column; 50mM amm. acetate in 50% acetonitrile). Material with the same retention time as F-18 fluoroacetate (prepared by F-for-I exchange with ethyl iodoacetate) was found. Some F-18 stuck permanently to the column and was assigned as fluoride since the same fraction of label in perfusate was retained on alumina columns eluted with water. Anion exchange HPLC (SAX column; 20mM pot. phosphate, pH 7) of homogenates gave peaks corresponding to fluoroacetate plus fluoride and minor peaks which could be fluoroacetylCoA and fluorocitrate. The authors interpret their data as follows. Beta-oxidation of FHDA results in fluoroacetylCoA which either undergoes ''lethal synthesis'' to fluorocitrate or is hydrolysed to fluoroacetate which diffuses out of the heart. The source of the fluoride is not yet clear, but could complicate interpretation of FHDA kinetics measured in vivo with positron tomography. Clearance of label from FHDA in isolated perfused hearts was faster than for labeled 16-iodohexadecanoic acid, indicating that the F-18 tracer may be a more sensitive probe of myocardial fatty acid metabolism.},
doi = {},
journal = {J. Nucl. Med.; (United States)},
number = ,
volume = 25:5,
place = {United States},
year = {Sun Jan 01 00:00:00 EST 1984},
month = {Sun Jan 01 00:00:00 EST 1984}
}

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