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
来源：
TETRAHEDRON | 2014年 / 70卷 / 35期
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
[11]   Protein-Targeted Gadolinium-Based Magnetic Resonance Imaging (MRI) Contrast Agents: Design and Mechanism of Action [J].
Caravan, Peter .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (07) :851-862
[12]   Gd-Hydroxypyridinone (HOPO)-Based High-Relaxivity Magnetic Resonance Imaging (MRI) Contrast Agents [J].
Datta, Ankona ;
Raymond, Kenneth N. .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (07) :938-947
[13]   A convenient synthesis of novel bifunctional prochelators for coupling to bioactive peptides for radiometal labelling [J].
Eisenwiener, KP ;
Powell, P ;
Mäcke, HR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (18) :2133-2135
[14]   A multinuclear MR study of Gd-EOB-DTPA: Comprehensive preclinical characterization of an organ specific MRI contrast agent [J].
Elst, LV ;
Maton, F ;
Laurent, S ;
Seghi, F ;
Chapelle, F ;
Muller, RN .
MAGNETIC RESONANCE IN MEDICINE, 1997, 38 (04) :604-614
[15]   Gd(DO3A-N-α-aminopropionate): a versatile and easily available synthon with optimized water exchange for the synthesis of high relaxivity, targeted MRI contrast agents [J].
Ferreira, Miguel F. ;
Martins, Andre F. ;
Martins, Jose A. ;
Ferreira, Paula M. ;
Toth, Eva ;
Geraldes, Carlos F. G. C. .
CHEMICAL COMMUNICATIONS, 2009, (42) :6475-6477
[16]   Gadolinium(III) complexes as MRI contrast agents:: ligand design and properties of the complexes [J].
Hermann, Petr ;
Kotek, Jan ;
Kubicek, Vojtech ;
Lukes, Ivan .
DALTON TRANSACTIONS, 2008, (23) :3027-3047
[17]  
HOLMBERG C, 1927, CHEM BER, V60, P2197
[18]   Alkaline earth metal and lanthanide(III) complexes of ligands based upon 1,4,7,10-tetraazacyclododecane-1,7-bis(acetic acid) [J].
Huskens, J ;
Torres, DA ;
Kovacs, Z ;
Andre, JP ;
Geraldes, CFGC ;
Sherry, AD .
INORGANIC CHEMISTRY, 1997, 36 (07) :1495-1503
[19]   THERMODYNAMIC AND KINETIC DATA FOR MACROCYCLE INTERACTION WITH CATIONS AND ANIONS [J].
IZATT, RM ;
PAWLAK, K ;
BRADSHAW, JS ;
BRUENING, RL .
CHEMICAL REVIEWS, 1991, 91 (08) :1721-2085
[20]   Fine-tuning water exchange on GdIII poly(amino carboxylates) by modulation of steric crowding [J].
Jászberényi, Z ;
Sour, A ;
Tóth, É ;
Benmelouka, M ;
Merbach, AE .
DALTON TRANSACTIONS, 2005, (16) :2713-2719
1234