Synthesis of Novel Non‐Isoprenoid Phenolic Acids and 3‐Alkylpyridines

Jain, Subhash C.; Kumar, Rohtash; Goswami, Rajeev; Pandey, Mukesh K.; Khurana, Shilpi; Rohatgi, Leena; Gyanda, Kapil

doi:10.1002/chin.200535278

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“…To synthesize the labeling precursor for 4 , 1,14-tetradecadioic acid was converted to 1,14-tetradecane diol ( 6 ) in two steps: esterification using absolute methanol and catalytic amount of sulfuric acid followed by LAH (lithium aluminum hydride) reduction in THF(tetrahydrofuran) 11 . The obtained diol was refluxed with 48% aq.…”

Section: Resultsmentioning

confidence: 99%

Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

et al. 2012

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In-vivo imaging of regional fatty acid oxidation (FAO) rates would have considerable potential for evaluation of mammalian diseases. We have synthe sized and evaluated 18F-labeled thia fatty acid analogues as metabolically trapped FAO probes to understand the effect of chain length, degree of unsaturation and placement of the thia-substituent on myocardial uptake and retention. 18-[18F]fluoro-4-thia-(9Z)-octadec-9-enoic acid (3) showed excellent heart:background radioactivity concentration ratios along with highest retention in heart and liver. Pretreatment of rats with the CPT-1 inhibitor, POCA, caused >80% reduction in myocardial uptake of 16-[18F]fluoro-4-thia-hexadecanoic acid (2), and 3 indicating high specificity for FAO. In contrast, 18-[18F]fluoro-4-thia-octadecanoic acid (4), showed dramatically reduced myocardial uptake and blunted response to POCA. 18-[18F]fluoro-6-thia-octadecanoic acid (5), showed moderate myocardial uptake and no sensitivity of myocardial uptake to POCA. The results demonstrate relationships between structures of 18F-labelled thia fatty acid and uptake, and their utility as FAO probes in various tissues.

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Section: Resultsmentioning

confidence: 99%

Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

et al. 2012

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Synthesis of Novel Non‐Isoprenoid Phenolic Acids and 3‐Alkylpyridines

Cited by 1 publication

References 12 publications

Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

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Synthesis of Novel Non‐Isoprenoid Phenolic Acids and 3‐Alkylpyridines

Cited by 1 publication

References 12 publications

Structure Dependence of Long-Chain [18F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

Structure Dependence of Long-Chain [18F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

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Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes