A Single-Pot Template Reaction Towards a Manganese-Based T1 Contrast Agent

被引:44
作者
Anbu, Sellamuthu [1 ,2 ]
Hoffmann, Sabrina H. L. [3 ]
Carniato, Fabio [4 ]
Kenning, Lawrence [5 ]
Price, Thomas W. [6 ]
Prior, Timothy J. [2 ]
Botta, Mauro [4 ]
Martins, Andre F. [3 ,7 ]
Stasiuk, Graeme J. [6 ]
机构
[1] Univ Hull, Dept Biomed Sci, Cottingham Rd, Kingston Upon Hull HU6 7RX, N Humberside, England
[2] Univ Hull, Dept Chem, Cottingham Rd, Kingston Upon Hull HU6 7RX, N Humberside, England
[3] Eberhard Karls Univ Tubingen, Werner Siemens Imaging Ctr, Dept Preclin Imaging & Radiopharm, Rontgenweg 13-1, D-72076 Tubingen, Germany
[4] Univ Piemonte Orientale, Dipartimento Sci & Innovaz Tecnol, Viale Teresa Michel 11, I-15121 Alessandria, Italy
[5] Hull Royal Infirm Hosp NHS Trust, MRI Ctr, Anlaby Rd, Kingston Upon Hull HU3 2JZ, N Humberside, England
[6] Kings Coll London, Dept Imaging Chem & Biol, Sch Biomed Engn & Imaging Sci, St Thomas Hosp, Fourth Floor Lambeth Wing, London SE1 7EH, England
[7] Univ Tubingen, Cluster Excellence iFIT EXC 2180 Image Guided & F, Tubingen, Germany
基金
英国工程与自然科学研究理事会;
关键词
bishydrated MnCA; blood pool agents; in  vivo MRI; Mn-based contrast agents; template synthesis; NEPHROGENIC SYSTEMIC FIBROSIS; HUMAN SERUM-ALBUMIN; MN2+ COMPLEXES; WATER EXCHANGE; GADOLINIUM DEPOSITION; MAGNETIC-PROPERTIES; MN(II) CHELATE; MRI; RELAXIVITY; STABILITY;
D O I
10.1002/anie.202100885
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Manganese-based contrast agents (MnCAs) have emerged as suitable alternatives to gadolinium-based contrast agents (GdCAs). However, due to their kinetic lability and laborious synthetic procedures, only a few MnCAs have found clinical MRI application. In this work, we have employed a highly innovative single-pot template synthetic strategy to develop a MnCA, MnLMe, and studied the most important physicochemical properties in vitro. MnLMe displays optimized r(1) relaxivities at both medium (20 and 64 MHz) and high magnetic fields (300 and 400 MHz) and an enhanced r(1)(b)=21.1 mM(-1) s(-1) (20 MHz, 298 K, pH 7.4) upon binding to BSA (K-a=4.2x10(3) M-1). In vivo studies show that MnLMe is cleared intact into the bladder through renal excretion and has a prolonged blood half-life compared to the commercial GdCA Magnevist. MnLMe shows great promise as a novel MRI contrast agent.
引用
收藏
页码:10736 / 10744
页数:9
相关论文
共 100 条
[21]   Manganese(II) Complexes as Potential Contrast Agents for MRI [J].
Drahos, Bohuslav ;
Lukes, Ivan ;
Toth, Eva .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (12) :1975-1986
[22]   Mn2+ Complexes with 12-Membered Pyridine Based Macrocycles Bearing Carboxylate or Phosphonate Pendant Arm: Crystallographic, Thermodynamic, Kinetic, Redox, and 1H/17O Relaxation Studies [J].
Drahos, Bohuslav ;
Kotek, Jan ;
Cisarova, Ivana ;
Hermann, Petr ;
Helm, Lothar ;
Lukes, Ivan ;
Toth, Eva .
INORGANIC CHEMISTRY, 2011, 50 (24) :12785-12801
[23]   Mn2+ complexes of 1-oxa-4,7-diazacyclononane based ligands with acetic, phosphonic and phosphinic acid pendant arms: Stability and relaxation studies [J].
Drahos, Bohuslav ;
Pniok, Miroslav ;
Havlickova, Jana ;
Kotek, Jan ;
Cisarova, Ivana ;
Hermann, Petr ;
Lukes, Ivan ;
Toth, Eva .
DALTON TRANSACTIONS, 2011, 40 (39) :10131-10146
[24]   Mn2+ Complexes with Pyridine-Containing 15-Membered Macrocycles: Thermodynamic, Kinetic, Crystallographic, and 1H/17O Relaxation Studies [J].
Drahos, Bohuslav ;
Kotek, Jan ;
Hermann, Petr ;
Lukes, Ivan ;
Toth, Eva .
INORGANIC CHEMISTRY, 2010, 49 (07) :3224-3238
[25]   High Relaxivity Magnetic Resonance Imaging Contrast Agents Part 1 Impact of Single Donor Atom Substitution on Relaxivity of Serum Albumin-Bound Gadolinium Complexes [J].
Dumas, Stephane ;
Jacques, Vincent ;
Sun, Wei-Chuan ;
Troughton, Jeffrey S. ;
Welch, Joel T. ;
Chasse, Jaclyn M. ;
Schmitt-Willich, Heribert ;
Caravan, Peter .
INVESTIGATIVE RADIOLOGY, 2010, 45 (10) :600-612
[26]   BINDING OF MN2+ TO NUCLEIC ACIDS [J].
EISINGER, J ;
FAWAZEST.F ;
SHULMAN, RG .
JOURNAL OF CHEMICAL PHYSICS, 1965, 42 (01) :43-&
[27]   17O and 1H relaxometric and DFT study of hyperfine coupling constants in [Mn(H2O)6]2+ [J].
Esteban-Gomez, David ;
Cassino, Claudio ;
Botta, Mauro ;
Platas-Iglesias, Carlos .
RSC ADVANCES, 2014, 4 (14) :7094-7103
[28]   Novel MRI contrast agent for molecular imaging of fibrin implications for detecting vulnerable plaques [J].
Flacke, S ;
Fischer, S ;
Scott, MJ ;
Fuhrhop, RJ ;
Allen, JS ;
McLean, M ;
Winter, P ;
Sicard, GA ;
Gaffney, PJ ;
Wickline, SA ;
Lanza, GM .
CIRCULATION, 2001, 104 (11) :1280-1285
[29]   Optimising the relaxivities of Mn2+ complexes by targeting human serum albumin (HSA) [J].
Forgacs, Attila ;
Tei, Lorenzo ;
Baranyai, Zsolt ;
Esteban-Gomez, David ;
Platas-Iglesias, Carlos ;
Botta, Mauro .
DALTON TRANSACTIONS, 2017, 46 (26) :8494-8504
[30]   Developing the family of picolinate ligands for Mn2+ complexation [J].
Forgacs, Attila ;
Pujales-Paradela, Rosa ;
Regueiro-Figueroa, Martin ;
Valencia, Laura ;
Esteban-Gomez, David ;
Botta, Mauro ;
Platas-Iglesias, Carlos .
DALTON TRANSACTIONS, 2017, 46 (05) :1546-1558