Abstract
A summary of the development of extracellular MRI contrast agents during the last twenty years is given. Focal points are chemistry, physico-chemical properties and pharmacokinetic behaviour of gadolinium complexes. The synthesis of acyclic and macrocyclic ligands is described, particularly of derivatives of the ligands DTPA and DOTA. Stability, relaxivity and formulations of the gadolinium complexes are issues of special interest as well as their toxicological and clinical aspects. An outlook on the future development of clinically useful extracellular MRI contrast agents is provided.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
5 References
Sovak M (1984) (ed) Handbook of Experimental Pharmacology: Radiocontrast Agents vol 73 Springer Berlin Heidelberg New York Tokyo
Aeberhard A, Nizza P, Remy J (1962) Int J Radiat Biol 5: 217
Martell EM, Smith RM (1974) (eds) Critical Stability Constants Plenum Press New York London
Perrin DD (1979) Stability Constants of Metal Ion Complexes Pergamon Press Oxford Ney York Toronto Sidney Paris Frankfurt
Schwarzenbach G, Anderess G, Schneider W, Senn H (1955) Helv Chim Acta 38: 1147
Gries H, Miklautz H (1984) Physiol Chem Phys Med NMR 16: 111
Kumar K, Chang CA, Francesconi LC et al. (1994) Inorg Chem 33: 3567
Chang CA (1993) Invest Radiol 28: S21
Claussen C, Laniado M, Schoerner W, Felix R (1985) Am J Neuroradiol 6: 669
Carr DH, Brown J, Bydder GM (1984) Lancet 3: 484
Niendorf HP, Felix R, Laniado M et al. (1985) Radiat Med 3: 7
Niendorf HP, Al Hassan A, Clauss W, Cornelius I (1993) Magn Reson Contrast Imaging 2:12
Niendorf HP, Al Hassan A, Geens V, Clauss W (1994) Invest Radiol 29: S179
Kawano T, Ishijima H, Nakajima T, Aoki J, Endo K (1993) Comput Ass Tomogr 23: 939
Quay SC, US Patent 4,859,451 Paramagnetic contrast agents for MR Imaging
Moore DA, Wallace RA US Patent 5,137,711 Paramagnetic DTPA and EDTA alkoxyalkylamide complexes as MRI agents
Vogler H, Platzek J, Schumann-Giampieri G et al. (1995) Eur J Radiol 21: 1
Tweedle MF, Hagan JJ, Kumar K et al. (1991) Magn Reson Imaging 9: 409
Cacheris WP, Quay SC, Rocklage SM (1990) Magn Reson Imaging 8: 467
Richman JE, Atkins TJ (1974) J Am Chem Soc 96: 2268
Stetter H, Roos EE (1954) Chem Ber 87:566
Stetter H, Marx J (1957) Justus Liebigs Ann Chem 607: 59
Stetter H, Mayer KH (1961) Angew Chem 88: 760
Tsuboyama K, Tsuboyama S, Uzawa J, Kobayashi K, Sakurai T (1977) Tetrahedron Lett 52: 4603
Stetter H, Frank W (1976) Angew Chem 88: 760
Hansen GR, Burg TE (1968) J Heterocycl Chem 5: 305
Cabbiness DK, Margerum DW (1969) J Am Chem Soc 91: 6540
Clay RM, Corr S, Micheloni M, Paoletti P (1984) Inorg Chem 24: 3330
Tweedle MF (1992) Invest Radiol 27: 52
Doucet D, Meyer D, Bonnemain B et al. (1989) In: Runge VM (ed) Enhanced Magnetic Resonance Imaging The C.V. Mosby Company St. Louis Baltimore Toronto: p. 87
Platzek J, Blaszkiewicz P, Gries H, Luger P, Michl G, Mühler-Fahrnow A, Raduechel B, Suelzle D (1997) Inorg Chem 36: 6086
Dishino DD, Delaney EJ, Emswiler JE, Gaughan GT, Prasad JS, Srivastava SK, Tweedle MF (1991) Inorg Chem 30:1265
Toth E, Kiraly R, Platzek J, Raduechel B, Bruecher E (1996) Inorg Chim Acta 249: 191
Chang CA, Kumar K, Tweedle MF Eur Patent 0454078: Dual functioning excipients for metal contrast agents
Schumann H, Boettger UA, Zietzke K, Hemling H, Kociok-Koehn G, Pickardt J, Hahn FE, Zschunke A, Schiefner B, Gries H, Raduechel B, Platzek J (1997) Chem Ber/Receul 130:267
Atkins TJ, Richman JE (1978) Organic Synthesis 58:87
Love D, Dow WC, Himmelsbach RJ, Watson AD, Rocklage SM WO 91/05672: Multi-site metal chelating agents
Krejcarek GE, Tucker KL (1977) Biochem Biophys Res Commun 77: 581
Watson AD US Patent 5,914,095: Polychelants containing amide bonds
Gries H, Radüchel B, Speck U, Weinmann HJ Eur Patent 0255471: Makrocyclische Verbindungen
Krause W, Maier FK, Bauer M, Press W-R, Schumann-Giampieri G, Platzek J, Schmitt-Willich H WO 96/05167: Dimer DTPA derivatives and their metal complexes
Ohnichi S, McConnell HM (1965) J Am Chem Soc 87: 2293
Keana JFW (1978) Chem Rev 78: 37
Berliner LJ (1976 and 1979) Spin labeling, theory and applications Vol 1 and 2 Academic Press, New York
Lovin J, Wesbey GE, Engelstad BL (1984) Invest Radiol 19: S24
Swartz HM, Bennett H, Brown R et al. (1985) Radiology 157: 100
Rozantsev EG, Krinatzkaya LA (1985) Tetrahedron 21: 491
Gries H, Niedballa U, Weinmann H-J US Patent 4,925,652: Nitroxyl compounds, and diagnostic media based thereon useful for enhancing NMR imaging
Brasch RC, London DA, Wesbey GE et al. (1983) Radiology 147: 773
Leunbach I WO 93/02711: Use of persistent free-radicals in magnetic resonance imaging
Solomon I (1955) J Chem Phys 99: 559
Bloembergen N (1957) J Chem Phys 101: 572
Lauffer RB (1987) Chem Rev 87: 901
Koenig SH, Kellar KE (1995) Magn Reson Med 34: 227
Chang CA, Brittain HG, Telser J, Tweedle MF (1990) Inorg Chem 29: 4468
Kaufman JA, Geller SC, Petersen MJ (1994) Am J Roentgenol 163: 203
Prince MR, Narasimham DL, Stanley C (1995) Vasc Surg 21: 656
Di Chiro G, Knop RH, Girton ME (1985) Radiology 157: 373
Di Chiro G, Girton ME, Frank JA (1986) Radiology 160: 221
Baum H, Kuehnert A, Sundermayer R (1987) Roentgenbläter 40: 293
Hajek PC, Sartoris DJ, Gylys-Merin V (1990) Invest Radiol 25: 179
Chandnani VP, Ho C, Chu P (1991) Radiology 178: 557
Kramer J, Stiglbauer R, Engel A, Prayer L, Imhof H (1992) 16: 254
Lehninger AL (1975) Biochemistry 2nd ed Worth New York
Weinmann H-J, Press W-R, Gries H (1990) Invest Radiol 25: S49
Harpur ES, Worath D, Hals PA (1993) Invest Radiol 28: S28
Weinmann H-J, Gries H, Speck U (1989) In: Runge VM (ed) Enhanced Magnetic Resonance Imaging; The C.V. Mosby Company St. Louis Baltimore Toronto p. 74
Yamada K, Ushio Y, Hayakawa T (1982) J Neurosurg 57: 394
Weinmann H-J, Laniado M, Muetzel W (1984) Physiol Chem Phys Med NMR 16:167
Van Wagoner M, Worah D (1993) Invest Rdiol 28: S44
Staks T, Schumann-Giampieri G, Frenzel T (1994) Invest Radiol 29: 709
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2002 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Gries, H. (2002). Extracellular MRI Contrast Agents Based on Gadolinium. In: Krause, W. (eds) Contrast Agents I. Topics in Current Chemistry, vol 221. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-45733-X_1
Download citation
DOI: https://doi.org/10.1007/3-540-45733-X_1
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-42247-1
Online ISBN: 978-3-540-45733-6
eBook Packages: Springer Book Archive