Synthesis and characterization of a new lanthanide based MRI contrast agent, potential and versatile tracer for multimodal imaging

Tetrahedron

Volumn 70, Issue 35, 2014, Pages 5450-5454

  Chilla, Satya Narayana Murthy ^a   Laurent, Sophie ^a   Vander Elst, Luce ^a,b   Muller, Robert N ^a,b  

^a UNIVERSITY OF MONS   (Belgium)

^b Center for Microscopy and Molecular Imaging   (Belgium)

Author keywords

Imaging agents Macrocyclic ligands Gadolinium Relaxivity Gd DOTA

Indexed keywords

2 [7 ( 5 AMINO 1 CARBOXYPENTYL) 4,10 BIS(CARBOXYMETHYL) 1,4,7,10 TETRAAZACYCLODODECAN 1 YL]SUCCINIC ACID; ACETIC ACID DERIVATIVE; BENZYL 6 [[(BENZYLOXY) CARBONYL]AMINO] 2 BROMOHEXANOATE; BIOLOGICAL MARKER; BROMINE DERIVATIVE; CARBOXYLIC ACID; DIBENZYL 2 BROMOSUCCINATE; DIBENZYL 2 [4,10 BIS(2 TERT BUTOXY 2 OXOETHYL) 1,4,7,10 TETRAAZACYCLODODECAN 1 YL]SUCCINATE; DIBENZYL 2 [7 [1 [(BENZYLOXY)CARBONYL] 5 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL] 4,10 BIS (2 TERT BUTOXY 2 OXOETHYL) 1,4,7,10 TETRAAZACYCLODODECAN 1 YL]SUCCINATE; GADOLINIUM; GADOTERIC ACID; HEXANOIC ACID DERIVATIVE; LANTHANIDE; MACROCYCLIC COMPOUND; NITROGEN DERIVATIVE; NUCLEAR MAGNETIC RESONANCE IMAGING AGENT; OXYGEN 17; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DEBENZYLATION; DRUG SYNTHESIS; HYDROGENOLYSIS; HYDROLYSIS; MOLECULAR WEIGHT; MULTIMODAL IMAGING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; REVERSED PHASE LIQUID CHROMATOGRAPHY; STEREOSPECIFICITY; TEMPERATURE DEPENDENCE;

EID: 84949114876     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.06.126     Document Type: Article

References (31)

1. R.B. Lauffer Chem. Rev. 87 1987 901 927
2. P. Caravan, J.J. Ellison, T.J. McMurry, and R.B. Lauffer Chem. Rev. 99 1999 2293 2352
3. P. Hermann, J. Kotek, V. Kubícek, and I. Lukes Dalton Trans. 2008 3027 3047
4. S. Laurent, C. Henoumont, L. Vander Elst, and R.N. Muller Eur. J. Inorg. Chem. 2012 2035 2039
5. P. Caravan Chem. Soc. Rev. 35 2006 512 523
6. S. Aime, D. Castelli, S. GeninattiCrich, E. Gianolio, and E. Terreno Acc. Chem. Res. 42 2009 822 831
7. E. Toth, L. Helm, and A.E. Merbach The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging 2nd ed. 2013 Wiley United Kingdom
8. P. Caravan Acc. Chem. Res. 42 2009 851 862
9. A.J.L. Villaraza, A. Bumb, and M.W. Brechbiel Chem. Rev. 110 2010 2921 2959
10. S. Aime, M. Botta, S. Geninatti Crich, G.B. Giovenzana, G. Jommi, R. Pagliarin, and M. Sisti Inorg. Chem. 36 1997 2992 3000
11. S. Aime, L. Calabi, C. Cavallotti, E. Gianolio, G.B. Giovenzana, P. Losi, A. Maiocchi, G. Palmisano, and M. Sisti Inorg. Chem. 43 2004 7588 7590
12. A. Datta, and K.N. Raymond Acc. Chem. Res. 42 2009 938 947
13. R. Ruloff, E. Toth, R. Scopelliti, R. Tripier, H. Handel, and A.E. Merbach Chem. Commun. 2002 2630 2631
14. S. Laus, R. Ruloff, E. Toth, and A.E. Merbach Chem. - Eur. J. 9 2003 3555 3566
15. S. Laurent, L. Vander Elst, A. Vroman, and R.N. Muller Helv. Chim. Acta 90 2007 562 573
16. Z. Jaszberenyi, A. Sour, E. Toth, M. Benmelouka, and A.E. Merbach Dalton Trans. 2005 2713 2719
17. E. Balogh, R. Tripier, P. Fouskova, F. Reviriego, H. Handel, and É. Toth Dalton Trans. 2007 3572 3581
18. S. Laurent, L. Vander Elst, F. Copoix, and R.N. Muller Invest. Radiol. 36 2001 115 122
19. R.M. Izatt, K. Pawlak, J.S. Bradshaw, and R.L. Bruening Chem. Rev. 91 1991 1721 2085
20. L. Burai, J. Ren, Z. Kovacs, E. Brucher, and A.D. Sherry Inorg. Chem. 37 1998 69 75
21. M.P. Lowe, D. Parker, O. Reany, S. Aime, M. Botta, G. Castellano, E. Gianolio, and R. Pagliarin J. Am. Chem. Soc. 123 2001 7601 7609
22. K.-P. Eisenwiener, P. Powell, and H.R. Macke Bioorg. Med. Chem. Lett. 10 2000 2133 2135
23. J. Huskens, A.D. Sherry, D.A. Torres, Z. Kovacs, J.P. Andre, and C.F.G.C. Geraldes Inorg. Chem. 36 1997 1495 1503
24. Z. Kovacs, and A.D. Sherry Synthesis 1997 759 763
25. C. Holmberg Chem. Ber. 60 1927 2197 2199
26. Aime, S.; Galli, M.; Luciano, L.; Morosini, P.; Uggeri, F., Int. Patent WO2006002873, 2006.
27. F. Ferreira, F. Martins, J. Martins, M. Ferreira, E. Toth, and F.G.C. Geraldes Chem. Commun. 2009 6475 6477
28. L. Vander Elst, F. Maton, S. Laurent, F. Seghi, F. Chapelle, and R.N. Muller Magn. Reson. Med. 38 1997 604 614
29. S. Aime, M. Botta, Z. Garda, B.E. Kucera, G. Tircso, V.G. Young, and M. Woods Inorg. Chem. 50 2011 7955 7965
30. S. Laurent, L. Vander Elst, and R.N. Muller Contrast Med. Mol. Imaging 1 2006 128 137
31. W.P. Cacheris, S.K. Nickle, and A.D. Sherry Inorg. Chem. 26 1987 958 960