The development of radioiodinated 3-methyl-branched fatty acids for evaluation of myocardial disease by single photon techniques

Knapp, F. F.; Goodman, Mark M.; Ambrose, K.R.; Som, P.; Brill, A.B.; Yamamoto, Kazutaka; Kubota, Keiichi; Yonekura, Yuriko; Dudczak, Robert; Angelberger, P.; Schmoliner, R

doi:10.1007/978-94-009-3287-6_9

Cited by 9 publications

(6 citation statements)

References 35 publications

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“…1231-BMIPP has been applied to clinical as well as experimental studies for the assessment of myocardial fatty acid metabolism.23 '27-30 121 I-BMIPP has the following favorable biological properties for myocardial SPECT imaging 19 .20: 1)high uptake and prolonged retention in the myocardium; 2) relatively higher heart-to-background count ratio; and 3) rapid blood clearance. 123I-BMIPP is not metabolized by beta-oxidation but is trapped into the triglyceride fraction in the myocardium.…”

Section: Discussionmentioning

confidence: 99%

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Impaired myocardial fatty acid metabolism detected by123I-BMIPP in patients with unstable angina pectoris: Comparison with perfusion imaging by99mTc-sestamibi

Takeishi¹,

Sukekawa

Saito

et al. 1995

Ann Nucl Med

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The present study was undertaken to determine the potential diagnostic value of 123I-BMIPP scintigraphy for the detection of altered myocardial fatty acid metabolism in patients with unstable angina. Both myocardial metabolic imaging with 123I-BMIPP and perfusion imaging with 99mTc-sestamibi were performed at rest in 28 patients with unstable angina in the pain-free state. The regional uptakes of 123I-BMIPP or 99mTc-sestamibi were scored semiquantitatively (0 = normal, 4 = no activity) and compared with the coronary arteriographic findings. Decreased uptakes of 123I-BMIPP were observed in 18 patients, and 11 patients had abnormal 99mTc-sestamibi images. Defect scores of 123I-BMIPP were larger than those of 99mTc-sestamibi (7.8 +/- 2.1 vs. 5.2 +/- 1.9, p < 0.01). The sensitivity for the detection of patients with unstable angina was higher in 123I-BMIPP than in 99mTc-sestamibi (77% vs. 45%, p < 0.01). The site of the decreased 123I-BMIPP uptake corresponded to the most stenotic coronary artery lesion in all patients. Fatty acid metabolic imaging with 123I-BMIPP was more sensitive for detecting myocardial ischemia than perfusion imaging with 99mTc-sestamibi. 123I-BMIPP may be a clue to define the culprit lesion in unstable angina and be helpful to decide the best treatment and guide coronary angioplasty.

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Section: Discussionmentioning

confidence: 99%

“…19 . 20 The goal of the present study was to evaluate the potential diagnostic value of 1231-BMIPP at rest in patients with unstable angina.…”

mentioning

confidence: 95%

Impaired myocardial fatty acid metabolism detected by123I-BMIPP in patients with unstable angina pectoris: Comparison with perfusion imaging by99mTc-sestamibi

Takeishi¹,

Sukekawa

Saito

et al. 1995

Ann Nucl Med

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“…The combined Et2O extracts were washed thoroughly with H2O and dried over anhydrous Na,SO 4 , and the Et2O removed in vacuo to afford 2-(5'-5-phenylpentyl-2'-thienyl)-2-(5'-carboxy-2-thienyl)propane (22; 2.84 g, 94%) as a pale yellow oil; NMR (CDC1 3 Hz, thienyl).…”

Section: -(5 '-5-phenylpentyl-2 '-Thienyl)-2-(5'-carboxy-2 '-Thienylmentioning

confidence: 99%

“…The combined Et20 extracts were washed thoroughly with H2O and dried over anhydrous Na 2 SO4, and the solvent was removed in vacuo. The crude product was purified on a column of silica gel (30 g (3). Thionyl chloride (3.6 g, 0.03 mol) in 10 ml of CHCI, was added dropwise over a 30 min period to a solution of 2 (3.9 g, 0.02 mol) and dimethylaniline (3.6 g, 0.02 mol) in 10 ml of CHCI 3 vigorously stirred at 0-5°C.…”

Section: Preparation Of (P-iodophenyl)dimethyl-substituted Fatty Acidmentioning

confidence: 99%

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Both total chain length and position of dimethyl-branching effect the myocardial uptake and retention of radioiodinated analogues of 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid (DMIPP)

et al. 1996

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Introduction of geminal dimethyl-branching into the 3-position of 15-(p-iodophenyl) pentadecanoic acid (IPPA) significantly delays myocardial clearance in rats and dogs following intravenous administration. Several new analogues of DMIPP have been synthesized and evaluated in fasted rats. The effects of both the position of dimethyl-branching and the total chain-length of 3, 3-dimethyl analogues on heart uptake and clearance kinetics have been studied. In the first series of compounds, two methyl groups were introduced into the 3-, 4-, 6-, or 9- position. Tissue distribution studies of the 15-(p-[I-125] iodophenyl)-analogues demonstrated that the position of dimethyl-branching is an important factor affecting both myocardial specificity and retention. The [I-125] labeled 3,3- and 4,4-DMIPP analogues showed higher myocardial uptake and faster blood clearance than the 6,6- and 9,9-DMIPP analogues [heart, % dose/gm heart: blood), 30 min: 3,3-DMIPP = 5.06 (12:1); 4,4-DMIPP = 8.03 (16.7: 1); 6,6-DMIPP = 2.26 (3.1:1); 9,9-DMIPP = 3.06 (2.77)]. In the second series, the effects of total fatty acid chain length were evaluated with 3,3-dimethyl-substituted analogues with C11, C12, C13, C14, C15, and C19 chain lengths. The C14 and C15 chain length analogues showed the best properties [global heart: blood ratios): 30 min: C11, 0.70 (0.82); C12, 1.25 (0.68); C13, 0.47 (0.90); C14, 1.63 (3.54); C15, 5.06 (12); C19. 1.29 (0.82). These detailed studies have demonstrated that both total chain length and the position of geminal dimethyl-branching are important structural parameters which affect myocardial specificity and retention of omega-(p-iodophenyl)-substituted fatty acid analogues and that 3,3-DMIPP and 4,4-DMIPP are the best candidates with optimal properties for further study.

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Cardiac Metabolism: Positron Emission Tomography Versus Single Photon Emission Computed Tomography

Wall¹

1995

Cardiac Positron Emission Tomography

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The development of radioiodinated 3-methyl-branched fatty acids for evaluation of myocardial disease by single photon techniques

Cited by 9 publications

References 35 publications

Impaired myocardial fatty acid metabolism detected by123I-BMIPP in patients with unstable angina pectoris: Comparison with perfusion imaging by99mTc-sestamibi

Impaired myocardial fatty acid metabolism detected by123I-BMIPP in patients with unstable angina pectoris: Comparison with perfusion imaging by99mTc-sestamibi

Both total chain length and position of dimethyl-branching effect the myocardial uptake and retention of radioiodinated analogues of 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid (DMIPP)

Cardiac Metabolism: Positron Emission Tomography Versus Single Photon Emission Computed Tomography

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