دورية أكاديمية
Synthesis of a metabolically stable modified long-chain fatty acid salt and its photolabile derivative.
| العنوان: | Synthesis of a metabolically stable modified long-chain fatty acid salt and its photolabile derivative. |
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| المؤلفون: | Stoll GH; Institut für Organische Chemie and Biochemie, Universität Freiburg, Germany., Voges R, Gerok W, Kurz G |
| المصدر: | Journal of lipid research [J Lipid Res] 1991 May; Vol. 32 (5), pp. 843-57. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: Elsevier Country of Publication: United States NLM ID: 0376606 Publication Model: Print Cited Medium: Print ISSN: 0022-2275 (Print) Linking ISSN: 00222275 NLM ISO Abbreviation: J Lipid Res Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: 2021- : [New York] : Elsevier Original Publication: Memphis, Lipid Research, inc. |
| مواضيع طبية MeSH: | Neoplasm Proteins* , Nerve Tissue Proteins*, Stearic Acids/*chemical synthesis, Affinity Labels ; Animals ; Biological Transport ; Carrier Proteins/metabolism ; Cells, Cultured ; Chromatography, Thin Layer ; Electrophoresis, Polyacrylamide Gel ; Fatty Acid-Binding Protein 7 ; Fatty Acid-Binding Proteins ; Kinetics ; Liver/metabolism ; Male ; Micelles ; Photolysis ; Rats ; Rats, Inbred Strains ; Stearic Acids/chemistry ; Stearic Acids/metabolism ; Tritium |
| مستخلص: | An analogue of the long-chain fatty acid salt, sodium stearate, was synthesized in which the hydrogen atoms at carbons 2, 3, and 18 were replaced by fluorine. The key step in the synthesis was the addition of 3-iodo-2,2,3,3-tetrafluoropropanoic acid amide to 15,15,15-trifluoro-1-pentadecene. Radioactivity was introduced by catalytic reduction of 2,2,3,3,18,18,18-heptafluoro-4-octadecenoic acid amide with carrier-free tritium gas yielding a product with the specific radioactivity of 2.63 TBq/mmol. The resulting 2,2,3,3,18,18,18-heptafluoro-4-octadecenoic acid has a pKa of about 0.5 and is completely dissociated under normal physiological conditions. The fluorinated fatty acid salt analogue is readily taken up into hepatocytes and proved to be metabolically inert. In an approach to the identification of proteins involved in long-chain fatty acid salt transport across membranes and intracellular compartments, the photolabile derivative 11,11-azo-2,2,3,3,18,18,18-heptafluoro[G-3H]octadecanoic acid sodium salt was synthesized with a specific radioactivity of 2.63 TBq/mmol. Photolysis of the photolabile derivative, using a light source with a maximum emission at 350 nm, occurred with a half-life of 1.5 min. The generated carbene reacted with 14C-labeled methanol and acetonitrile with covalent bond formation of 6-13%. Its efficacy for photoaffinity labeling was demonstrated by incorporation into serum albumin, the extracellular fatty acid salt-binding protein, as well as into the intracellular fatty acid salt-binding protein (FABP) of rat liver with the molecular weight of 14,000. |
| المشرفين على المادة: | 0 (Affinity Labels) 0 (Carrier Proteins) 0 (Fabp7 protein, rat) 0 (Fatty Acid-Binding Protein 7) 0 (Fatty Acid-Binding Proteins) 0 (Micelles) 0 (Neoplasm Proteins) 0 (Nerve Tissue Proteins) 0 (Stearic Acids) 10028-17-8 (Tritium) |
| تواريخ الأحداث: | Date Created: 19910501 Date Completed: 19910819 Latest Revision: 20210217 |
| رمز التحديث: | 20221213 |
| PMID: | 2072043 |
| قاعدة البيانات: | MEDLINE |
| تدمد: | 0022-2275 |
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