BMIPP-design and development

International Journal of Cardiac Imaging

Volumn 15, Issue 1, 1999, Pages 1-9

  Knapp Jr , F F ^a   Kropp, J ^b  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

^b DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

BMIPP; Methyl branched fatty acids; Myocardial imaging; Radioiodinated fatty acids

Indexed keywords

15 (4 IODOPHENYL) 3 METHYLPENTADECANOIC ACID I 123; 15 (4 IODOPHENYL)PENTADECANOIC ACID; METHYL GROUP; ORGANOTELLURIUM DERIVATIVE;

CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DIAGNOSTIC IMAGING; DRUG ACTIVITY; DRUG DESIGN; DRUG ELIMINATION; DRUG METABOLISM; DRUG RETENTION; DRUG UPTAKE; FATTY ACID METABOLISM; HEART MUSCLE METABOLISM; HUMAN; ISOMER; NONHUMAN; RADIOCARDIOGRAPHY; RAT; REVIEW; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

ANIMALS; DRUG DESIGN; FATTY ACIDS; HEART; HUMANS; IODINE RADIOISOTOPES; IODOBENZENES; ISOMERISM; MYOCARDIUM; RATS; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 0344931805     PISSN: 01679899     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1006147228352     Document Type: Review

References (64)

1. Knapp FF Jr, Kropp J, Franken PR, et al. Pharmacokinetics of radioiodinated fatty acid myocardial imaging agents in animal models and human studies. Quart J Nucl Med 1996; 40: 252-269.
2. Knapp FF Jr, Kropp J. Iodine-123-labeled fatty acids for myocardial single-photon emission tomography: current status and future perspectives. Eur J Nucl Med 1995: 22: 3.
3. Knapp FK Jr. Franken P. Kropp J. Cardiac SPECT with iodine-123-labeled fatty acids: evaluation of myocardial viability with BMIPP. J Nucl Med 1995; 36: 1022-1030.
4. Visser FC, editor. First Workshop on Radiolabelled Free Fatty Acids, Free University Hospital. Amsterdam. The Netherlands, July 6. 1984; Eur Heart J 1985; 6: 1-106.
5. Visser FC, editor. First Workshop on Radiolabelled Free Fatty Acids, Free University Hospital. Amsterdam. The Netherlands, July 6. 1984; Eur Heart J 1985; 6: 1-106.
6. Visser FC, editor. Second Workshop on Radiolabelled Free Fatty Acids. Free University Hospital. Amsterdam. The Netherlands, November 26, 1987; Eur-Amer Commun Nucl Med 1990: 21: 201-266.
7. Visser FC, editor. Second Workshop on Radiolabelled Free Fatty Acids. Free University Hospital. Amsterdam. The Netherlands, November 26, 1987; Eur-Amer Commun Nucl Med 1990: 21: 201-266.
8. Yonekura Y, editor. Third International Workshop on Radioiodinated Free Fatty Acids, Kyoto International Community House. Kyoto. Japan. February 10-11, 1993; Ann Nucl Med 1993; 7: S-II-1-1 16.
9. Yonekura Y, editor. Third International Workshop on Radioiodinated Free Fatty Acids, Kyoto International Community House. Kyoto. Japan. February 10-11, 1993; Ann Nucl Med 1993; 7: S-II-1-1 16.
10. Machulla H-J, Marsmann M, Dutschka KP, et al. Biochemical concept and synthesis of a radioiodinated phenyl fatty acid for in vivo metabolic studies of the myocardium. Eur J Nucl Med 1980; 5: 171-173.
11. Machulla H-J, Marsmann M. Dutschka, et al. Radiopharmaceuticals. I. Synthesis of radioiodinated fatty acids for studying myocardial metabolism. J Radioanalyt Chem 1980; 56: 253-261.
12. Sloof GW, Visser FC, van Eenige MJ, et al. Comparison of uptake, oxidation and lipid distribution of 17-1HA, p-IPPA and DMIPPA in normal canine myocardium. J Nucl Med 1993; 34: 649-657.
13. Van Eenige MJ, Visser FC, Duwel CMB, et al. Comparison of 17-1-131 heptadecanoic acid kinetics from externally measured time-activity curves and from serial myocardial biopsies in an open-chest canine model. J Nucl Med 1988; 29: 1934-1942.
14. 123I]-IPPA as a tracer of oxidative metabolism. Circulation 1992; 86 Suppl 1: 1-797.
15. Kropp J, Koehler U, Fehske W, et al. Semiquantification of 15-(p-[I-123]iodophenyl)petadecanoic acid in the detection of coronary artery disease. Ann Nucl Med 1993; 7: SII-67.
16. Goodman MM. Kirsch G. Knapp FF Jr. Synthesis and evaluation of radioiodinated terminal p-iododphenyl-substituted α and β-methyl-branched fatty acids. J Med Chem 1984; 27: 390-397.
17. Knapp JR FF, Goodman MM, Ambrose KR. et al. The development of radioiodinated 3-methyl-branched fatty acids for evaluation of myocardial disease by single photon tomography. In: van der Wall EE. editor. Noninvasive measurement of cardiac metabolism. Martinus Nijhoff Publishers, 1987: 159-202.
18. Knapp FF Jr, Ambrose KR, Callahan AP. Tellurium-123m-labeled isosteres of palmitoleic and oleic acid show high myocardial uptake. In: Proceedings, Second International Symposium on Radiopharmaceuticals, Seattle, WA, March 19-23. 1979; Society of Nuclear Medicine, pp 101-108 (1979).
19. Knapp FF Jr, Ambrose KR. Callahan AP, et al. Effects of chain length and Te-position on the myocardial uptake of Te-123m-labeled fatty acids. J Nucl Med 1981; 22: 988-993.
20. Elmaleh DR. Knapp FF Jr. Yusuda T. et al. Myocardial imaging uith Te-123m-telluraheptadecanoic acid. J Nucl Med 1981; 22: 994-999.
21. Okada RD. Knapp FF Jr, Elmaleh DR, et al. Tellurium-123m-labeled 9-telluraheptadecanoic acid: a new potential cardiac imaging agent. Circulation 1982; 65: 305-310.
22. Knapp FF Jr, Goodman, MM, Callahan AP, et al. New myocardial imaging agents: Stabilization of radioiodine as a terminal vinyl iodide moiety on tellurium fatty acids. J Med Chem 1983: 26: 1293-1300.
23. Strauss HW, Elmaleh DR. Knapp FF Jr. et al. Relationship of modified fatty acid uptake into the myocardium and heteratom position in the molecule. Circulation 1982; 66: PII-109 (Abstract).
24. Goodman MM, Knapp FF Jr, Callahan AP, et al. A new, well-retained myocardial imaging agent: Radioiodinated 15-(p-iodophenyl)-6-telluraheptadecanoic acid. J Nucl Med 1982; 23: 904-908.
25. 131I]iodo-9-telluraheptadecanoic acid-a potential myocardial imaging agent. J Med Chem 1982; 25: 613-618.
26. Goodman MM, Knapp FF Jr, Callahan AP, et al. Radioiodinated 15-(p-iodophenyl)-6-telluraheptadecanoic acid: A new myocardial imaging agent exhibiting prolonged myocardial retention. J Nucl Med 1982; 23: 903-908.
27. Bianco JA, Alpert JS, Paper LA, et al. Accumulation of radioiodinated 15-(p-iodophenyl)-6-tellurapentadecanoic acid in necrotic and ischemic myocardium during acute coronary occlusion and reperfusion. J Amer Coll Card 1984; 4: 80-87.
28. Knapp FF Jr, Srivastava PC, Callahan AP, et al. The effect of tellurium position on the myocardial specificity of radioiodinated 18-iodo-tellura-17-octadecanoic acid analogues. J Med Chem 1984; 27: 57-62.
29. Steinberg D, Herndon JH, Uhlendorf BW, et al. Refsum's disease: Nature of the enzyme defect. Science 1967; 156: 1740-1742.
30. Bergström S, Bergström B, Tryding N, et al. Intestinal absorption of and metabolism of 2,2-dimethylstearic acid in the rat. Biochem J 1954; 58: 604-608.
31. Avigan J, Steinberg D, Gutman A, et al. Alpha decarboxylation, an important pathway for degradation of phytanic acid in animals. Biochem Biophys Res Commun 1966; 24: 838-844.
32. Hull FE, Waugh RA, Malone M, et al. Synthesis of ordinary and β-hydroxy fatty acids by heart mitochondria. Arch Biochem Biophys 1972; 149: 69-90.
33. Yonekura Y, Brill AB, Som P, et al. Regional myocardial substrate uptake in hypertensive rats: a quantitative autoradiographic measurement. Science 1985; 227: 1494-1496.
34. 131I)iodophenyl-β-methylpentadecanoic acid in normotensive and hypertensive rats. J Nucl Med 1986; 27: 1178-1183.
35. Knapp FK Jr , Kropp J, Goodman MM. et al. The development of iodine-123-methyl-branched fatty acids and their applications in nuclear cardiology. Ann Nucl Med 1993; 7: 1-14.
36. Livne E, Elmalch DR. Barlai-Kovach MM, et al. Radioiodinated beta-methyl phenyl fatty acids as potential tracers for myocardial imaging and metabolism, Eur Heart J 1985; 6: 85-90.
37. Dudzack R, Schmoliner R, Angelberger P. et al. Structurally-modified fatty acids-clinical potential as tracers of metabolism. Eur J Nucl Med 1986; 12: S45-48.
38. Kropp JH, Eisenhut M, Lehmann WD, et al. Pharmacokinetics and metabolism of the methyl-branched fatty acid (BMIPP) in animals and man. J Nucl Med (submitted).
39. Knapp FF Jr, Goodman MM, Kirsch G. Iodine-123-labeled 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid (DMIPP): a useful new agent to evaluate myocardial fatty acid uptake. J Nucl Med 1986; 27: 521-531.
40. Yamamichi Y, Kusuoka H, Morishita K, et al. Metabolism of iodine-123-BMIPP in perfused rat hearts. J Nucl Med 1995; 36: 1043-50.
41. Hosokawa R, Nohara R, Okuda K, et al. Cardiac metabolism of I-123-β-methyl-p-iodophenylpentadecanoic acid (I-123-BMIPP) in normal dogs and those pre-treated with carnitine palmitoyltransferase I inhibitor (Etomoxir): Contribution of α- and β-oxidation. J Nucl Med 1995; 36:137p (Abstract).
42. Knapp FF Jr, Reske SN, Kirsch G, et al. Radioiodinated methyl-branched fatty acids-evaluation of catabolites formed in vivo. NucCompact 1990; 21: 229-231.
43. Knapp FF Jr, Kohlen S, Kolkmeier J, et al. Formation of metabolites from methyl-branched fatty acids by isolated Langendorff rat heart system. In: Proceedings, European Nuclear Medicine Congress 1987, Budapest, Hungary, August 24-28, 1997; Schattauer Verlag, Stuttgart, pp 596-599. 1988.
44. Kropp J, Eisenhut M, Lehmann WD, et al. Metabolism of the fatty acid BMIPP. J Nucl Med 1998; 39: 47p.
45. Kropp J, Ambrose KR, Knapp FF Jr, et al. Incorporation of radioiodinated IPPA and BMIPP fatty acid analogues into complex lipids from isolated rat hearts. Nucl Med Biol 1992; 19: 283-288.
46. Ambrose KR, Owen BA, Goodman MM, et al. Evaluation of the metabolism in rat hearts of two new radioiodinated 3-methyl-branched fatty acid myocardial imaging agents. Eur J Nucl Med 1987l 12: 486-491.
47. Ambrose KR, Owen BA, Callahan AP, et al. Effects of fasting on the myocardial subcellular and lipid distribution of terminal p-iodophenyl-substituted fatty acids in rats. J Nucl Med Biol 1988; 15: 695-700.
48. Sloof GW, Visser FC, Teerlink T, et al. Incorporation of radioiodinated fatty acids into cardiac phospholipids of normoxic myocardium. Mol Cell Biochem 1992; 116: 79-87.
49. Fujibayashi Y, Yonekura Y, Takemura Y, et al. Myocardial accumulation of iodinated beta-methyl-branched fatty acid analogue, iodine-125-15-(p-iodophenyl)-3-(R,S)-methylpentadecanoic acid (BMIPP), in relation to ATP concentration. J Nucl Med 1990: 31: 1818-1822.
50. Lin Q. Luo H, Mokier FT. et al. Effects of configuration on the myocardial uptake of radioiodinated 3(R)-BMIPP and 3(S)-BMIPP in rats. J Nucl Med 1997: 38: 1434-1440.
51. Knapp FF Jr, Lin Q. Luo H. et al. Preparation and evaluation of 3-methyl isomers of 15-(p-iodophenyl)-3-methylpentadecanoic acid (BMIPP): 3(R)-BMIPP shows greater heart uptake than 3(S)-BMIPP in rats. J Nucl Med 1996; 37: P6 (Abstract).
52. Mokler FT, Lin Q, Luo H, et al. Dual-label studies with [I-125]-3R [I-131]-3S-BMIPP demonstrate similar metabolism in rat tissues. J Nucl Med (submitted).
53. Knapp FF Jr, Kropp J, Franken PR. Radioiodinated BMIPP for myocardial imaging-current status and future perspectives. Nuklearmedizin 1998; 37: S8-11
54. Knapp FF Jr, Mokler FT, Lin Q, et al. Higher heart uptake of 3(R)-BMIPP in rats but similar lipid pool distribution suggests differences in isomae membrane transport. J Nucl Cardiol 1997; 4: S-118 (Abstract).
55. Mokler FT, Lin Q, Luo H, et al. Dual-label study with [I-125]-3(R)-BIMPP and [I-131]-3(S)-BMIPP demonstrates similar metabolism of the two isomers in rat tissues. Eur J Nucl Med 1996; 23: 1139 (Abstract).
56. Cavalier V, Franken PR, Knapp FF Jr, et al. Intra-individual comparison of the 3(R)-BMIPP and 3(S)-BMIPP Isomers in humans. J Nucl Med 1998; 39: 1672-1675.
57. Cavalier V, Franken PR, Knapp FF Jr, et al. Intra-individual comparison of the 3(R)-BMIPP and 3 (S)-BMIPP Isomers in humans. J Nucl Cardiol 1997; 4 Suppl: S113 (Abstract).
58. Franken PR, De Geeter F, Dendale P, et al. Abnormal free fatty acid uptake in subacute myocardial infraction after coronary thrombolysis: correlation with wall motion and inotropic reserve. J Nucl Med 1994; 35: 1758-1765.
59. DeGeeter FF, Franken P, Knapp FF Jr. et al. Relationship between blood flow and fatty acid metabolism in subacute myocardial infarction: a study by means of Tc-99m-Sestamibi and iodine-123-beta-methyl iodophenylpentadecanoic acid. Eur J Nucl Med 1941; 21: 283-291.
60. Kropp J, Köhler U, Knapp FF Jr, et al. 15-(p-[I-123]iodophenyl)-3-R,S-methylpentadecanoic acid to evaluate ischemia in patients with coronary artery disease. Eur J Nucl Med 1991; 18: 650.
61. Kropp J, Jörgens M. Glaenzer K, et al. Evaluation of ischemia and myocardial viability in patients with coronary artery disease(CAD) with iodine-123 labeled 15-(p-iodophenyl)-3-R,S-methylpentadecanoic acid (BMIPP). Ann Nucl Med 1993; 7: 93-100.
62. Diede HE, Rodilla-Sala E, Gunawan J, et al. Identification and characterization of a moncloncal antibody to the membrane fatty acid binding protein. Biochim Biophys Acta 1992; 1125: 13-20.
63. Tanaka T, Sohmiya K, Kawamura K. Is CD36 deficiency an etiology of hereditary cardiomyopathy? J Mol Cell Cardiol 1997; 29: 121-127.
64. Fukuchi K, Nozaki S, Yosizumi T, et al. Enhanced myocardial glucose uptake in individuals with a deficiency in long-chain fatty acid transporter (CD36 deficiency). J Nucl Med 1998; 39: 152P (Abstract).