Synthesis and in vivo evaluation of new contrast agents for cardiac MRI

Journal of Medicinal Chemistry

Volumn 42, Issue 15, 1999, Pages 2852-2861

  Saab Ismail, Nada H ^a   Simor, Tamás ^a   Gaszner, Balázs ^a   Lóránd, Tamás ^a   Szöllösy, Márta ^a   Elgavish, Gabriel A ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTRAST MEDIUM; GADOLINIUM; GADOLINIUM PENTETATE; GADOTERIC ACID; TRIENTINE;

ARTICLE; CONTRAST ENHANCEMENT; HEART FUNCTION; HEART MUSCLE; HYDROPHILICITY; IN VIVO STUDY; LIFESPAN; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING;

ANIMALS; CONTRAST MEDIA; FERRETS; HEART; MAGNETIC RESONANCE IMAGING; ORGANOMETALLIC COMPOUNDS; PENTETIC ACID; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033614930     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980454v     Document Type: Article

References (28)

1. Gotto, A. M.; Farmer, J. A. Risk Factors for Coronary Artery Disease. In Heart Disease: A Textbook of Cardiovascular Medicine; Braunwald, E., Ed.; WB Saunders: Philadelphia, PA, 1988; p 1153.
2. de Roos, A.; van der Wall, E. E.; Burschke, A. V.; van Voorthuisen, A. E. Magnetic Resonance Imaging in the Diagnosis and Evaluation of Mycardial Infraction. Magn. Reson. Q. 1992, 7, 191-207.
3. Budinger, T. F. NMR in Vivo Studies; Comparison with Other Noninvasive Imaging Techniques. In Nuclear Magnetic Resonance (NMR) Imaging; Partain, C. L., James, A. E., Jr., Rollo, F. D., Price, R. R., Eds.; WB Saunders: Philadelphia, PA, 1983; pp 357-374.
4. Lauterbur, P. C. Image Formation by Induced Local Interactions: Examples Employing Nuclear Magnetic Resonance. Clin. Orthop. Related Res. 1973, 244, 3-6.
5. Bakal, C. A.; Strauss, H. W. Radionuclide Imaging. In Noninvasive Cardiac Imaging; Morganroth, J., Parisi, A. F., Pohost, G. E., Eds.; Year Book Medical Publishers Inc.; Chicago, London, 1983; pp 21-52.
6. Cooke, P.; Morris, P. G. The effects of NMR exposure on living organisms. II. A Genetic Study of Human Lymphocytes. Br. J. Radiol. 1981, 54, 622-625.
7. Canby, R. C.; Elgavish, G. A.; Pohost, G. M. Paramagnetic NMR Contrast Agents for Cardiovascular Imaging. In New Concepts Cardiac Imaging; Pohost, G. M., Ed.; Yearbook Medical Publishers Inc.: Chicago, London, 1987; pp 315-342.
8. Reuben, J.; Elgavish, G. A. Shift Reagents and the NMR of Paramagnetic Lanthanide Complexes. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Jr., Eyring, L., Eds.; Noth-Holland Publishing Co.: Amesterdam, New York, Oxford, 1979; Vol. 4, pp 483-514.
9. 7Li NMR Studies of ion Transport across the Membrane of Phosphatidylcholine Vesicles. FEBS Lett. 1978, 90, 357-360.
10. Reuben, J. Bioinorganic Chemistry: Lanthanides as Probes in Systems of Biological Interest In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Jr., Eyring, L., Eds.; Noth-Holland Publishing Co.: Amesterdam, New York, Oxford, 1979; Vol. 4, pp 515-585.
11. Carr, D. H.; Brown, J.; Bydder, G. M.; Steiner, R. E.; Weinmann, H. J.; Speck, U.; Hall, A. S.; Young, I. R. Gadolinium-DTPA as a Contrast Agent in MRI: Initial Clinical Experience in 20 Patients. Am. J. Roent. 1984, 143 (2), 215-224.
12. Lauffer, R. B. Paramagnetic Metal Complexes as Water Proton Relaxation Agents for NMR Imaging: Theory and Design. Chem. Rev. 1987, 87, 901-927.
13. Runge, V. M., Claussen, C., Felix, R., James, A. E., Jr., Eds. Contrast Agents in Magnetic Resonance Imaging; Excerpta Medica: Princeton, NJ, 1986.
14. Van Wagoner, M.; O'Toole, M.; Worah, D.; Leese, P. T.; Quay, S. C. A Phase I Clinical Trial with Gadolinium Injection, a Nonionic Magnetic Resonance Imaging Enhancement Agent. Invest. Radiol. 1991, 26, 980-986.
15. Runge, V. M.; Bronen, R. A.; Davis, K. R. Efficacy of Gadoteridol for Magnetic Resonance Imaging of the Brain and Spine. Invest. Radiol. 1992, 27 (1), S22-S32.
16. Wolf, G. L.; Fobben, E. S. The Tissue Proton T1 and T2 Response to Gadolinium DTPA Injection in Rabbits. A Potential Renal Contrast Agent for NMR Imaging. Invest. Radiol. 1984, 19, 324-328.
17. Saeed, M.; Wendland, M. F.; Tomei, E.; Rocklage, S. N.; Quay, S. C.; Moseley, M. E.; Wolfe, C.; Higgins, C. B. Demarcation of Myocardial Ischemia: Magentic Susceptibility Effect of Contrast Medium in MR Imaging. Radiology 1989, 173 (3), 763-767.
18. Kang, S. I.; Ranganathan, R. S.; Emswiler, J. E.; Kumar, K.; Gougoutas, J. Z.; Malley, M. F.; Tweedle, M. F. Synthesis, Characterization, and Crystal Structure of the Gadolinium (III) Chelate of (1R,4R,7R)-α,α′,α″-trimethyl-1,4,7,10- tetraazacycododecane-1,4,7-triacetic acid (DO3MA). Inorg. Chem. 1993, 32, 2912-2918.
19. 3+ Protein-Chelate Conjugates. Magn. Reson. Med. 1986, 3 (4), 541-548.
20. Evans, J. R.; Gunton, R. W.; Baker, R. G. Use of Radioiodinated Fatty Acid for Photoscans of the Heart. Circ. Res. 1965, 16, 1-10.
21. 131I-labeled Oleic Acid. Radiology 1973, 108, 195-196.
22. Kim, S. K.; Pohost, G. M.; Elgavish, G. A. Fatty Acyl Iminopolycarboxylates: Lipophilic Bifunctional Contrast Agents for NMR Imaging. Magn. Reson. Med. 1991, 22, 57-67.
23. Kim, S. K.; Pohost, G. M.; Elgavish, G. A. Gadolinium Complexes of [(Myristoryloxy)propyl] diethylenetriaminetetracetate: New Lipophilic, Fatty Acyl Conjugated NMR Contrast Agents. Bioconjugate Chem. 1992, 3 (1), 20-26.
24. Simor, T.; Chu, W.-J.; Johson, L.; Safranko, A.; Doyle, M.; Pohost, G. M.; Elgavish, G. A. In vivo MRI Visualization of Acute Myocardial Ischemia and Reperfusion in Ferrets by the Persistent Action of the Contrast Agent Gd(BME-DTTA). Circulation 1995, 92 (12), 3549-3559.
25. Chu, W.-J.; Simor, T.; Elgavish, G. A. In vivo Characterization of Gd(BME-DTTA), a Myocardial MRI Contrast Agent: Tissue Distribution of its MRI Intensity Enhancement and its Effect on Heart Function. NMR Biomed. 1997, 10, 87-92.
26. 2+ Complexes. Magn. Reson. Med. 1984, 1 (4), 496-501.
27. Larrabee, A. L. Time-dependent Changes in the Size Distribution of Distearoyl Phosphatidylcholine Vesicles. Biochemistry 1979, 18 (15), 3321-3326.
28. Weinmann, H. J.; Grier, H. Paramagnetic Contrast Media in NMR Tomography-Basic Properties and Experimental Studies in Animals. Magn. Reson. Med. 1984, 1, 271-272.