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Title: Radiolabeled dimethyl branched long chain fatty acid for heart imaging

Abstract

A radiolabeled long chain fatty acid for heart imaging that has dimethyl branching at one of the carbons of the chain which inhibits the extent to which oxidation can occur. The closer to the carboxyl the branching is positioned, the more limited the oxidation, thereby resulting in prolonged retention of the radiolabeled compound in the heart.

Inventors:
 [1];  [2];  [3]
  1. (Oak Ridge, TN)
  2. (Knoxville, TN)
  3. (Woippy, FR)
Publication Date:
Research Org.:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN
OSTI Identifier:
866686
Patent Number(s):
US 4764358
Application Number:
06/868,480
Assignee:
United States of America as represented by United States (Washington, DC) ORNL
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
radiolabeled; dimethyl; branched; chain; fatty; acid; heart; imaging; branching; carbons; inhibits; extent; oxidation; occur; closer; carboxyl; positioned; limited; resulting; prolonged; retention; compound; fatty acid; prolonged retention; chain fatty; heart imaging; radiolabeled compound; /424/999/

Citation Formats

Knapp, Jr., Furn F., Goodman, Mark M., and Kirsch, Gilbert. Radiolabeled dimethyl branched long chain fatty acid for heart imaging. United States: N. p., 1988. Web.
Knapp, Jr., Furn F., Goodman, Mark M., & Kirsch, Gilbert. Radiolabeled dimethyl branched long chain fatty acid for heart imaging. United States.
Knapp, Jr., Furn F., Goodman, Mark M., and Kirsch, Gilbert. 1988. "Radiolabeled dimethyl branched long chain fatty acid for heart imaging". United States. doi:. https://www.osti.gov/servlets/purl/866686.
@article{osti_866686,
title = {Radiolabeled dimethyl branched long chain fatty acid for heart imaging},
author = {Knapp, Jr., Furn F. and Goodman, Mark M. and Kirsch, Gilbert},
abstractNote = {A radiolabeled long chain fatty acid for heart imaging that has dimethyl branching at one of the carbons of the chain which inhibits the extent to which oxidation can occur. The closer to the carboxyl the branching is positioned, the more limited the oxidation, thereby resulting in prolonged retention of the radiolabeled compound in the heart.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = 1988,
month = 8
}

Patent:

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  • This patent describes a radiolabeled long chain fatty acid for heart imaging that has dimentyl branching at one of the carbons of the chain which inhibits the extent to which oxidation can occur. The closer to the carboxyl the branching is positioned, the more limited the oxidation, thereby resulting in prolonged retention of the radiolabeled compound in the heart.
  • The synthetic method for the preparation of (E)-19-iodo-3,3-dimethyl-18-nonadecenoic acid (DMIVN) involved introduction of substituents into the 2- and 5-positions of a thiophene ring followed by sulfur extrusion of a 2,5-dialkyl thiophene derivative to provide a key 3,3-dimethyl-branched fatty acid intermediate, 17-iodo-3,3-dimethylheptadecanoic acid. Myocardial subcellular distribution studies of the /sup 125/I-labeled DMIVN in fasted rats showed a higher association of radioactivity with the microsomes when compared to the results obtained with the 19-carbon straight chain analogue. With the nonfasted rats the distribution profiles of the two analogues showed differences that seemed to correlate with the differences in myocardial retention that fastingmore » and feeding can induce. 5 refs., 3 figs., 2 tabs.« less
  • Extracorporeal membrane oxygenation (ECMO) supports infants and children with severe cardiopulmonary compromise. Nutritional support for these children includes provision of medium- and long-chain fatty acids (FAs). However, ECMO induces a stress response, which could limit the capacity for FA oxidation. Metabolic impairment could induce new or exacerbate existing myocardial dysfunction. Using a clinically relevant piglet model, we tested the hypothesis that ECMO maintains the myocardial capacity for FA oxidation and preserves myocardial energy state. Provision of 13-Carbon labeled medium-chain FA (octanoate), longchain free FAs (LCFAs), and lactate into systemic circulation showed that ECMO promoted relative increases in myocardial LCFA oxidationmore » while inhibiting lactate oxidation. Loading of these labeled substrates at high dose into the left coronary artery demonstrated metabolic flexibility as the heart preferentially oxidized octanoate. ECMO preserved this octanoate metabolic response, but also promoted LCFA oxidation and inhibited lactate utilization. Rapid upregulation of pyruvate dehydrogenase kinase-4 (PDK4) protein appeared to participate in this metabolic shift during ECMO. ECMO also increased relative flux from lactate to alanine further supporting the role for pyruvate dehydrogenase inhibition by PDK4. High dose substrate loading during ECMO also elevated the myocardial energy state indexed by phosphocreatine to ATP ratio. ECMO promotes LCFA oxidation in immature hearts, while maintaining myocardial energy state. These data support the appropriateness of FA provision during ECMO support for the immature heart.« less
  • No abstract prepared.