Tris(pyrone) chelates of Gd(III) as high solubility MRI-CA

被引:35
作者
Puerta, DT
Botta, M
Jocher, CJ
Werner, EJ
Avedano, S
Raymond, KN
Cohen, SM [1 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[3] Univ Eastern Piedmont A Avogadro, Dept Environm & Life Sci, I-15100 Alessandria, Italy
关键词
D O I
10.1021/ja057954f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two tripodal, hexadentate pyrone-based chelators have been prepared. These ligands form stable, soluble complexes with gadolinium(III). The complexes show aqueous stability comparable to that of [Gd(DTPA)]2- at pH 7.4. Evaluation by relaxometry shows that these complexes have two inner-sphere water molecules and a very fast water exchange rate. The solution behavior of these complexes suggests that they may be attractive as high relaxivity, next-generation magnetic resonance imaging contrast agents. Copyright © 2006 American Chemical Society.
引用
收藏
页码:2222 / 2223
页数:2
相关论文
共 15 条
[1]   Gadolinium(III) chelates as MRI contrast agents: Structure, dynamics, and applications [J].
Caravan, P ;
Ellison, JJ ;
McMurry, TJ ;
Lauffer, RB .
CHEMICAL REVIEWS, 1999, 99 (09) :2293-2352
[2]   Mixed hydroxypyridinonate ligands as iron chelators [J].
Cohen, SM ;
O'Sullivan, B ;
Raymond, KN .
INORGANIC CHEMISTRY, 2000, 39 (19) :4339-4346
[3]   Syntheses and relaxation properties of mixed gadolinium hydroxypyridinonate MRI contrast agents [J].
Cohen, SM ;
Xu, JD ;
Radkov, E ;
Raymond, KN ;
Botta, M ;
Barge, A ;
Aime, S .
INORGANIC CHEMISTRY, 2000, 39 (25) :5747-5756
[4]   Toward optimized high-relaxivity MRI agents: The effect of ligand basicity on the thermodynamic stability of hexadentate hydroxypyridonate/catecholate gadolinium(III) complexes [J].
Doble, DMJ ;
Melchior, M ;
O'Sullivan, B ;
Siering, C ;
Xu, JD ;
Pierre, VC ;
Raymond, KN .
INORGANIC CHEMISTRY, 2003, 42 (16) :4930-4937
[5]   Optimization of the relaxivity of MRI contrast agents:: Effect of poly(ethylene glycol) chains on the water-exchange rates of GdIII complexes [J].
Doble, DMJ ;
Botta, M ;
Wang, J ;
Aime, S ;
Barge, A ;
Raymond, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10758-10759
[6]   Synthesis of homochiral tris(2-alkyl-2-aminoethyl)amine derivatives from chiral α-amino aldehydes and their application in the synthesis of water soluble chelators [J].
Hajela, SP ;
Johnson, AR ;
Xu, JD ;
Sunderland, CJ ;
Cohen, SM ;
Caulder, DL ;
Raymond, KN .
INORGANIC CHEMISTRY, 2001, 40 (13) :3208-3216
[7]   Synthesis of a ligand based upon a new entry into the 3-hydroxy-N-alkyl-2(1H)-pyridinone ring system and thermodynamic evaluation of its gadolinium complex [J].
Johnson, AR ;
O'Sullivan, B ;
Raymond, KN .
INORGANIC CHEMISTRY, 2000, 39 (12) :2652-2660
[8]   Synthesis of 2-amido-3-hydroxypyridin-4(1H)-ones:: Novel iron chelators with enhanced pFe3+ values [J].
Liu, ZD ;
Piyamongkol, S ;
Liu, DY ;
Khodr, HH ;
Lu, SL ;
Hider, RC .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) :563-573
[9]   The highest water exchange rate ever measured for a Gd(III) chelate [J].
Mato-Iglesias, M ;
Platas-Iglesias, C ;
Djanashvili, K ;
Peters, JA ;
Tóth, V ;
Balogh, E ;
Muller, RN ;
Elst, LV ;
de Blas, A ;
Rodríguez-Blas, T .
CHEMICAL COMMUNICATIONS, 2005, (37) :4729-4731
[10]   The monoethyl ester of meconic acid is an active site inhibitor of HCVNS5B RNA-dependent RNA polymerase [J].
Pace, P ;
Nizi, E ;
Pacini, B ;
Pesci, S ;
Matassa, V ;
De Francesco, R ;
Altamura, S ;
Summa, V .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (12) :3257-3261