Literature DB >> 23153307

Structure dependence of long-chain [18F]fluorothia fatty acids as myocardial fatty acid oxidation probes.

Mukesh K Pandey1, Anthony P Belanger, Shuyan Wang, Timothy R DeGrado.   

Abstract

In vivo imaging of regional fatty acid oxidation (FAO) rates would have considerable potential for evaluation of mammalian diseases. We have synthesized 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-thiahexadecanoic acid (2) and 3, indicating high specificity for FAO. In contrast, 18-[18F]fluoro-4-thiaoctadecanoic acid (4) showed dramatically reduced myocardial uptake and blunted response to POCA. 18-[18F]Fluoro-6-thiaoctadecanoic acid (5) showed moderate myocardial uptake and no sensitivity of myocardial uptake to POCA. The results demonstrate relationships between structures of 18F-labeled thia fatty acid and uptake and their utility as FAO probes in various tissues.

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Year:  2012        PMID： 23153307      PMCID： PMC3533245          DOI： 10.1021/jm301345v

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  22 in total

1.  Validation of 18F-fluoro-4-thia-palmitate as a PET probe for myocardial fatty acid oxidation: effects of hypoxia and composition of exogenous fatty acids.

Authors:  Timothy R DeGrado; Mehmet T Kitapci; Shuyan Wang; Jun Ying; Gary D Lopaschuk
Journal:  J Nucl Med       Date:  2006-01       Impact factor: 10.057

2.  Long term cardioprotective action of trimetazidine and potential effect on the inflammatory process in patients with ischaemic dilated cardiomyopathy.

Authors:  P Di Napoli; A A Taccardi; A Barsotti
Journal:  Heart       Date:  2005-02       Impact factor: 5.994

Review 3.  Fatty acid oxidation inhibitors in the management of chronic complications of atherosclerosis.

Authors:  Clifford D L Folmes; Alexander S Clanachan; Gary D Lopaschuk
Journal:  Curr Atheroscler Rep       Date:  2005-02       Impact factor: 5.113

4.  Quantitation of myocardial fatty acid metabolism using PET.

Authors:  S R Bergmann; C J Weinheimer; J Markham; P Herrero
Journal:  J Nucl Med       Date:  1996-10       Impact factor: 10.057

5.  Non-beta-oxidizable omega-[18F]fluoro long chain fatty acid analogs show cytochrome P-450-mediated defluorination: implications for the design of PET tracers of myocardial fatty acid utilization.

Authors:  T R DeGrado; D C Moka
Journal:  Int J Rad Appl Instrum B       Date:  1992-04

6.  Radioiodinated beta-methyl phenyl fatty acids as potential tracers for myocardial imaging and metabolism.

Authors:  E Livni; D R Elmaleh; M M Barlai-Kovach; M M Goodman; F F Knapp; H W Strauss
Journal:  Eur Heart J       Date:  1985-08       Impact factor: 29.983

7.  Myocardial uptake of the fatty acid analog 14-fluorine-18-fluoro-6-thia-heptadecanoic acid in comparison to beta-oxidation rates by tritiated palmitate.

Authors:  C K Stone; R A Pooley; T R DeGrado; B Renstrom; R J Nickles; S H Nellis; A J Liedtke; J E Holden
Journal:  J Nucl Med       Date:  1998-10       Impact factor: 10.057

8.  Comparison of fatty acid tracers FTHA and BMIPP during myocardial ischemia and hypoxia.

Authors:  B Renstrom; S Rommelfanger; C K Stone; T R DeGrado; K J Carlson; E Scarbrough; R J Nickles; A J Liedtke; J E Holden
Journal:  J Nucl Med       Date:  1998-10       Impact factor: 10.057

9.  beta-Methyl-15-p-iodophenylpentadecanoic acid metabolism and kinetics in the isolated rat heart.

Authors:  T R DeGrado; J E Holden; C K Ng; D M Raffel; S J Gatley
Journal:  Eur J Nucl Med       Date:  1989

10.  14(R,S)-[18F]fluoro-6-thia-heptadecanoic acid (FTHA): evaluation in mouse of a new probe of myocardial utilization of long chain fatty acids.

Authors:  T R DeGrado; H H Coenen; G Stocklin
Journal:  J Nucl Med       Date:  1991-10       Impact factor: 10.057
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  6 in total

1.  Noninvasive evaluation of fat-carbohydrate metabolic switching in heart and contracting skeletal muscle.

Authors:  Timothy R DeGrado; Mukesh K Pandey; Anthony P Belanger; Falguni Basuli; Aditya Bansal; Shuyan Wang
Journal:  Am J Physiol Endocrinol Metab       Date:  2018-12-04       Impact factor: 4.310

Review 2.  Imaging of myocardial fatty acid oxidation.

Authors:  Kieren J Mather; Timothy R DeGrado
Journal:  Biochim Biophys Acta       Date:  2016-02-27

3.  Global Analysis of Plasma Lipids Identifies Liver-Derived Acylcarnitines as a Fuel Source for Brown Fat Thermogenesis.

Authors:  Judith Simcox; Gisela Geoghegan; John Alan Maschek; Claire L Bensard; Marzia Pasquali; Ren Miao; Sanghoon Lee; Lei Jiang; Ian Huck; Erin E Kershaw; Anthony J Donato; Udayan Apte; Nicola Longo; Jared Rutter; Renate Schreiber; Rudolf Zechner; James Cox; Claudio J Villanueva
Journal:  Cell Metab       Date:  2017-09-05       Impact factor: 27.287

4.  Radiation induced oxidation of [18F]fluorothia fatty acids under cGMP manufacturing conditions.

Authors:  Mukesh K Pandey; Mark S Jacobson; Emily K Groth; Natalie G Tran; Val J Lowe; Timothy R DeGrado
Journal:  Nucl Med Biol       Date:  2019-11-09       Impact factor: 2.408

5.  A Novel Substrate Radiotracer for Molecular Imaging of SIRT2 Expression and Activity with Positron Emission Tomography.

Authors:  Robin E Bonomi; Maxwell Laws; Vadim Popov; Swatabdi Kamal; Shreya Potukutchi; Aleksandr Shavrin; Xin Lu; Nashaat Turkman; Ren-Shyan Liu; Thomas Mangner; Juri G Gelovani
Journal:  Mol Imaging Biol       Date:  2018-08       Impact factor: 3.488

6.  Design, Synthesis, and Preliminary Evaluation of [68Ga]Ga-NOTA-Insulin as a PET Probe in an Alzheimer's Disease Mouse Model.

Authors:  Jillissa C Taubel; Nicholas R Nelson; Aditya Bansal; Geoffrey L Curran; Lushan Wang; Zengtao Wang; Heather M Berg; Cynthia J Vernon; Hoon-Ki Min; Nicholas B Larson; Timothy R DeGrado; Karunya K Kandimalla; Val J Lowe; Mukesh K Pandey
Journal:  Bioconjug Chem       Date:  2022-04-14       Impact factor: 6.069
  6 in total

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