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

被引:11
作者
Chilla, Satya Narayana Murthy [1 ,2 ]
Laurent, Sophie [1 ,2 ]
Elst, Luce Vander [1 ,2 ,3 ]
Muller, Robert N. [1 ,2 ,3 ]
机构
[1] Univ Mons, Dept Gen Organ & Biomed Chem NMR, B-7000 Mons, Belgium
[2] Univ Mons, Mol Imaging Lab, B-7000 Mons, Belgium
[3] CMMI, B-6041 Gosselies, Belgium
关键词
Imaging agents; Macrocyclic ligands; Gadolinium; Relaxivity; Gd-DOTA; ALKALINE-EARTH METAL; FAST WATER EXCHANGE; COMPLEXES; GADOLINIUM; RELAXIVITY; DESIGN; SENSITIVITY; MODULATION; STABILITY; LIGANDS;
D O I
10.1016/j.tet.2014.06.126
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the present work a modular pathway towards the synthesis of a new versatile MRI contrast agent is reported and its physico-chemical properties are described. Two different functional groups were attached on two arms of the gadolinium 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetate (DOTA) in order to get a platform able to bind one probe designed to target specific biological marker and a fluorescent molecule likely to be used for optical imaging. The nuclear magnetic relaxation dispersion (NMRD) profile, the oxygen-17 relaxometric NMR study and stability assessment versus transmetalation of the Gd-complex show that this new contrast agent has a relaxivity and transmetalation stability similar to Gd-DOTA. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5450 / 5454
页数:5
相关论文
共 31 条
  • [1] Synthesis and NMR studies of three pyridine-containing triaza macrocyclic triacetate ligands and their complexes with lanthanide ions
    Aime, S
    Botta, M
    Crich, SG
    Giovenzana, GB
    Jommi, G
    Pagliarin, R
    Sisti, M
    [J]. INORGANIC CHEMISTRY, 1997, 36 (14) : 2992 - 3000
  • [2] [Gd-AAZTA]-:: A new structural entry for an improved generation of MRI contrast agents
    Aime, S
    Calabi, L
    Cavallotti, C
    Gianolio, E
    Giovenzana, GB
    Losi, P
    Maiocchi, A
    Palmisano, G
    Sisti, M
    [J]. INORGANIC CHEMISTRY, 2004, 43 (24) : 7588 - 7590
  • [3] AIME S, 2006, Patent No. 2006002873
  • [4] Properties, Solution State Behavior, and Crystal Structures of Chelates of DOTMA
    Aime, Silvio
    Botta, Mauro
    Garda, Zoltan
    Kucera, Benjamin E.
    Tircso, Gyula
    Young, Victor G.
    Woods, Mark
    [J]. INORGANIC CHEMISTRY, 2011, 50 (17) : 7955 - 7965
  • [5] Pushing the Sensitivity Envelope of Lanthanide-Based Magnetic Resonance Imaging (MRI) Contrast Agents for Molecular Imaging Applications
    Aime, Silvio
    Castelli, Daniela Delli
    Crich, Simonetta Geninatti
    Gianolio, Eliana
    Terreno, Enzo
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (07) : 822 - 831
  • [6] Monopropionate analogues of DOTA4- and DTPA5-:: kinetics of formation and dissociation of their lanthanide(III) complexes
    Balogh, Edina
    Tripier, Raphael
    Fouskova, Petra
    Reviriego, Felipe
    Handel, Henri
    Toth, Eva
    [J]. DALTON TRANSACTIONS, 2007, (32) : 3572 - 3581
  • [7] Synthesis, potentiometry, and NMR studies of two new 1,7-disubstituted tetraazacyclododecanes and their complexes formed with lanthanide, alkaline earth metal, Mn2+, and Zn2+ ions
    Burai, L
    Ren, JM
    Kovacs, Z
    Brucher, E
    Sherry, AD
    [J]. INORGANIC CHEMISTRY, 1998, 37 (01) : 69 - 75
  • [8] THERMODYNAMIC STUDY OF LANTHANIDE COMPLEXES OF 1,4,7-TRIAZACYCLONONANE-N,N',N''-TRIACETIC ACID AND 1,4,7,10-TETRAAZACYCLODODECANE-N,N',N'',N'''-TETRAACETIC ACID
    CACHERIS, WP
    NICKLE, SK
    SHERRY, AD
    [J]. INORGANIC CHEMISTRY, 1987, 26 (06) : 958 - 960
  • [9] Gadolinium(III) chelates as MRI contrast agents: Structure, dynamics, and applications
    Caravan, P
    Ellison, JJ
    McMurry, TJ
    Lauffer, RB
    [J]. CHEMICAL REVIEWS, 1999, 99 (09) : 2293 - 2352
  • [10] Strategies for increasing the sensitivity of gadolinium based MRI contrast agents
    Caravan, Peter
    [J]. CHEMICAL SOCIETY REVIEWS, 2006, 35 (06) : 512 - 523