Disease relevance of pentadecanoic acid

• To assess the clinical value of 123I fatty acid analog, 123I-beta-methyl iodophenyl pentadecanoic acid (BMIPP) was imaged at rest in coronary patients without prior myocardial infarction [1].
• In a canine model of reversible global ischemia, the residual quantity of 123I was assessed following a bolus injection of 15-p-(123I)-iodophenyl pentadecanoic acid (123I-IPPA) [2].
• Heart uptake and clearance of 123I-15-(p-iodophenyl)-3(R,S)-methyl- pentadecanoic acid (BMIPP) by whole-body scintigraphy in relation to left ventricular ejection fraction (LVEF) was evaluated in 34 patients with ischaemic heart disease [3].
• To assess whether left ventricular myocardial metabolism is affected by the presence of right ventricular pressure overload, we performed 123I-beta-methyl-iodophenyl pentadecanoic acid (123I-BMIPP) and 99Tc(m)-sestamibi (99Tc(m)-MIBI) single photon emission tomography in 24 patients with pulmonary hypertension and in 10 control subjects [4].
• Myocardial turnover of omega-(p123I-Phenyl-) pentadecanoic acid and release of its metabolites into the coronary sinus and peripheral blood has been studied in patients with coronary artery and valvular heart disease [5].

High impact information on pentadecanoic acid

• This iodinated fatty acid analogue, 15-(para-iodophenyl)-3-methyl pentadecanoic acid, was given intravenously at 3 hours of reperfusion following 15 minutes (Group 1, n = 5 dogs) or 60 minutes (Group 2, n = 5 dogs) of left anterior descending coronary artery occlusion [6].
• These latter results are confirmed in the present study, showing that APOC1 transgenic mice exhibit a 50% reduction in the uptake of the fatty acid analog 15-(p-iodophenyl)-3-(R,S)-methyl pentadecanoic acid in white adipose tissue stores [7].
• In vivo, tissue distribution of iodinated, poorly oxidized beta-methyliodophenyl pentadecanoic acid (BMIPP) was examined 2 h after its intravenous injection [8].
• In humans, an association between CD36 deficiency and defective myocardial uptake of the fatty acid analog 15-(p-iodophenyl)-3-(R, S)-methyl pentadecanoic acid (BMIPP) has been reported [9].
• The specificity for fatty acids, as measured by the stimulation of luciferase activity, had a very limited range, with maximal luminescence being obtained with myristic acid and lower responses being observed only with tridecanoic and pentadecanoic acid [10].

Chemical compound and disease context of pentadecanoic acid

• To evaluate the relationship between myocardial perfusion and fatty acid metabolism in canine myocardial infarction, 16 dogs were studied using thallium and 123I-beta-methyl-iodophenyl pentadecanoic acid (BMIPP) [11].
• METHODS: Tissue Doppler imaging and 123I-beta-methyl iodophenyl pentadecanoic acid (123I-BMIPP) myocardial scintigraphy were performed in 15 patients with asymmetric septal hypertrophy (mean age 47 +/- 18 years) and in 12 healthy controls (mean age 43 +/- 10 years) [12].
• The aim of the present study was to prospectively evaluate the potential risk of a first-ever acute myocardial infarction (AMI) in relation to the estimated milk-fat intake, reflected as the proportions of pentadecanoic acid (15 : 0) and heptadecanoic acid (17 : 0) in serum lipid esters [13].
• Clinical value of iodine-123 beta-methyliodophenyl pentadecanoic acid (BMIPP) myocardial single photon emission computed tomography for predicting cardiac death among patients with chronic heart failure [14].

Biological context of pentadecanoic acid

• The Km value for pentadecanoic acid (C15) was the smallest among the saturated fatty acids tested (C10-C18) and that for myristic acid (C14) showed similar enzyme kinetics to those seen for C15 [15].
• We have verified by gas chromatography/mass spectrometry that the products of in vivo biotransformation of pentadecanoic acid by cytochrome P450BM-3 are identical to those formed in cell-free extracts containing the enzyme [16].

Anatomical context of pentadecanoic acid

• Because abnormal fatty acid metabolism and cardiac adrenergic neuronal damage are observed in ischemic myocardium, (123)I-15-(p-iodophenyl)-3-R,S-methyl pentadecanoic acid (BMIPP) and (123)I-metaiodobenzylguanidine (MIBG) have recently been proposed as useful tracers for detection of myocardial damage [17].
• Although grain source had only minimal effects on the fatty acid composition of subcutaneous fat samples, pentadecanoic acid (15:0) was greater (P < 0.05) in fat from steers fed SM3 and Steptoe barley varieties than in fat from steers fed corn [18].
• Myristic acid (C14:0) and pentadecanoic acid (C15:0) in plasma and erythrocyte phospholipids reached a maximum increase in plasma and erythrocyte phospholipids within 2 weeks of initiating the saturated fat-rich diet but were unchanged throughout the 8 week saturated fat diet in buccal cell phospholipids [19].
• As the chylothorax was considered to be due to thoracic duct injury at the time of operation, lymphoscintigraphy was performed by oral administration of I-123 beta-methyl-iodophenyl pentadecanoic acid (BMIPP) [20].

Associations of pentadecanoic acid with other chemical compounds

• On-line liquid chromatography-electrospray ionization-tandem mass spectrometry revealed rapid alpha-oxidation of palmitic acid incubated at 0 degrees C with the purified alpha-oxidation enzyme, leading to (R)-2-hydroperoxypalmitic acid as the major product together with (R)-2-hydroxypalmitic acid, 1-pentadecanal, and pentadecanoic acid [21].
• OBJECTIVE: To determine the clinical and prognostic value of identifying metabolic abnormalities of myocardial fatty acid metabolism in idiopathic dilated cardiomyopathy using iodine-123 beta-methyl-iodophenyl pentadecanoic acid (123I BMIPP) [22].
• The polysaccharides contained pentadecanoic acid and anteisopentadecanoic acid, possibly present as the acyl components [23].
• Potential application of tissue Doppler imaging to assess regional left ventricular diastolic function in patients with hypertrophic cardiomyopathy: comparison with 123I-beta-methyl iodophenyl pentadecanoic acid myocardial scintigraphy [12].
• Impaired cardiac fatty acid uptake, assessed by the radiolabelled fatty acid analogue beta-methyl-p-iodophenyl pentadecanoic acid (I-123-BMIPP), is observed in the myocardium following acute ischaemic events, but the long-term prognostic implication has not been established [24].

Gene context of pentadecanoic acid

• A characteristic C15/C17 ratio was found for different phospholipids and the triglyceride fraction; pentadecanoic acid was the principal odd-numbered fatty acid utilized in the assembly of complex lipids [25].

Analytical, diagnostic and therapeutic context of pentadecanoic acid

• METHODS AND RESULTS: Twenty-eight patients with wall motion abnormalities related to stenosed coronary arteries underwent resting two-dimensional echocardiography and 123I-beta-methyl-iodophenyl pentadecanoic acid single photon emission tomography before coronary angioplasty [26].
• Increased clinical use of 123I-labeled 15-(p-iodophenyl)-3-(R,S)-methyl- pentadecanoic acid ([123I]BMIPP) revealed discordance between BMIPP uptake and that of perfusion agents, which was inexplicable due to the uncertainty of its myocardial metabolism [27].
• The fatty acids of the 33 collected fractions were analysed by gas chromatography after pentadecanoic acid (15:0) was added as an internal standard to quantitate the TG fractions [28].
• (123)iodine labelled beta-methyl-iodophenyl pentadecanoic acid myocardial single photon emission computed tomography showed decreased uptake of the inferior segment in the early image, whereas the delayed images revealed significant fill-in of the tracer in the inferior segment of the myocardium [29].
• Six baboons were injected on different occasions with 123I-labelled para and ortho isomers of 15-(iodophenyl) pentadecanoic acid (123I-pPPA and 123I-oPPA, respectively) for dynamic scintigraphy, followed by a Na123I injection at 30 min for blood background correction [30].

References