Lanthanide(III) Complexes of Tris(amide) PCTA Derivatives as Potential Bimodal Magnetic Resonance and Optical Imaging Agents

Rojas‐Quijano, Federico A.; Benyó, Enikő Tircsóné; Tircsó, Gyula; Kálmán, Ferenc K.; Baranyai, Zsolt; Aime, Silvio; Sherry, A. Dean

doi:10.1002/chem.200901095

Cited by 37 publications

(24 citation statements)

References 67 publications

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“…The concentration of the MnCl 2 , CuCl 2 and ZnCl 2 solutions was determined by using standardized Na 2 H 2 EDTA solution and eriochrome black T (Mn(II)), murexide (Cu(II) and xylenolorange (Zn(II)) as indicator. The ligands were either prepared by following literature procedures (DOTAM, DO3A, DO3P, PCTA, ODO3A, PC3AM Gly ) (Amorim et al, 1988 ; Maumela et al, 1995 ; Aime et al, 1997 ; Siaugue et al, 2000 ; Sun et al, 2003 ; Rojas-Quijano et al, 2009 ; Nithyakumar and Alexander, 2016 ) or obtained from commercial sources (DO3AM H - CheMatech, Dijon (France)). The PC3AM H and PC3AM Pip ligands were prepared by alkylating the pyclen macrocycle prepared according to literature description (Stetter et al, 1981 ) with a suitable bromoacetamide derivative (see the Supplementary Material for the detailed synthesis and analytical data) available from commercial sources or prepared by following literature synthesis (Kaupang and Bonge-Hansen, 2013 ).…”

Section: Methodsmentioning

confidence: 99%

Effect of the Nature of Donor Atoms on the Thermodynamic, Kinetic and Relaxation Properties of Mn(II) Complexes Formed With Some Trisubstituted 12-Membered Macrocyclic Ligands

et al. 2018

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During the past few years increasing attention has been devoted to Mn(II) complexes as possible substitutes for Gd(III) complexes as contrast agents in MRI. Equilibrium (log KMnL or pMn value), kinetic parameters (rates and half-lives of dissociation) and relaxivity of the Mn(II) complexes formed with 12-membered macrocyclic ligands were studied. The ligands were selected in a way to gain information on how the ligand rigidity, the nature of the donor atoms in the macrocycle (pyridine N, amine N, and etheric O atom), the nature of the pendant arms (carboxylates, phosphonates, primary, secondary and tertiary amides) affect the physicochemical parameters of the Mn(II) complexes. As expected, decreasing the denticity of DOTA (to afford DO3A) resulted in a drop in the stability and inertness of [Mn(DO3A)]− compared to [Mn(DOTA)]2−. This decrease can be compensated partially by incorporating the fourth nitrogen atom into a pyridine ring (e.g., PCTA) or by replacement with an etheric oxygen atom (ODO3A). Moreover, the substitution of primary amides for acetates resulted in a noticeable drop in the stability constant (PC3AMH), but it increased as the primary amides (PC3AMH) were replaced by secondary (PC3AMGly) or tertiary amide (PC3AMPip) pendants. The inertness of the Mn(II) complexes behaved alike as the rates of acid catalyzed dissociation increased going from DOTA (k1 = 0.040 M−1s−1) to DO3A (k1 = 0.45 M−1s−1). However, the rates of acid catalyzed dissociation decreased from 0.112 M−1s−1 observed for the anionic Mn(II) complex of PCTA to 0.0107 M−1s−1 and 0.00458 M−1s−1 for the cationic Mn(II) complexes of PC3AMH and PC3AMPip ligands, respectively. In spite of its lower denticity (as compared to DOTA) the sterically more hindered amide complex ([Mn(PC3AMPip)]2+) displays surprisingly high conditional stability (pMn = 8.86 vs. pMn = 9.74 for [Mn(PCTA)]−) and excellent kinetic inertness. The substitution of phosphonates for the acetate pendant arms (DOTP and DO3P), however, resulted in a noticeable drop in the conditional stability as well as dissociation kinetic parameters of the corresponding Mn(II) complexes ([Mn(DOTP)]6− and [Mn(DO3P)]4−) underlining that the phosphonate pedant should not be considered as a suitable building block for further ligand design while the tertiary amide moiety will likely have some implications in this respect in the future.

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Section: Methodsmentioning

confidence: 99%

Effect of the Nature of Donor Atoms on the Thermodynamic, Kinetic and Relaxation Properties of Mn(II) Complexes Formed With Some Trisubstituted 12-Membered Macrocyclic Ligands

et al. 2018

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“…An alternative cell labeling strategy that has recently emerged is to label cells with a class of contrast agents that selectively generate contrast through a process termed c hemical e xchange s aturation t ransfer (CEST) [ 18 – 20 ]. CEST agents resonate at unique frequencies offset from water resonance.…”

Section: Conventional Mri Cell Trackingmentioning

confidence: 99%

Cardiac Cell Tracking with MRI Reporter Genes: Welcoming a New Field

Vandsburger

2014

Curr Cardiovasc Imaging Rep

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Research into cell therapy based cardiac repair and regeneration has experienced explosive growth over the last decade, however further progress is hindered by an inability to serially and non-invasively image cell survival and fate decisions following implantation. Recent advances in magnetic resonance imaging (MRI) reporter gene techniques have enabled in vivo imaging of cell survival, proliferation, migration, and differentiation, however this has mostly been performed in stationary tissues. A small series of recent studies has examined the possibility of using MRI reporter genes to track the survival of cells injected into the heart following myocardial infarction. In this review, we seek to frame the emerging field of MRI reporter gene based cardiac cell tracking within the larger framework of the needs of cardiac regeneration therapy and the more established field of MRI cell tracking. While initial studies have demonstrated a promising ability to track the viability and proliferation of cells used for cell therapy, the ultimate goal of MR reporter gene imaging in the heart remains the ability to simultaneously correlate cell fate decisions with additional measures of structural and functional recovery.

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“…All known compounds viz. 2a, 23 3, 24 5a,b, 28 8, 24 14 29 and 24 30 were prepared according to literature procedures. Solvents were dried according to standard procedures and stored over molecular sieves.…”

Section: Experimental Generalmentioning

confidence: 99%

Synthesis and evaluation of ligands with mixed amide and phosphonate, phosphinoxide, and phosphonothioate sites for An(iii)/Ln(iii) extraction

et al. 2012

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Various organophosphorus ligands with a combination of different donor sites were synthesized and evaluated by solvent extraction studies for the complexation of Am(III)/Eu(III). Among the ligands with a glycolamide backbone, those with mixed amide and PQO donor sites and a central oxygen or nitrogen atom showed a reasonable extraction of Am(III) and Eu(III). Ligands with a central oxygen atom exhibited selectivity towards Eu(III), and those with a central nitrogen atom towards Am(III). Ligands with PQS donor sites and a glycolamide backbone did not show any reasonable extraction. Amongst the ligands with a malonamide backbone, high extraction efficiency was observed for the ligand with electron-rich substituents on phosphorus, however, with almost no discrimination between Am(III) and Eu(III). The extraction efficiency of different ligands towards Eu(III) was confirmed by microcalorimetry.

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Lanthanide(III) Complexes of Tris(amide) PCTA Derivatives as Potential Bimodal Magnetic Resonance and Optical Imaging Agents

Cited by 37 publications

References 67 publications

Effect of the Nature of Donor Atoms on the Thermodynamic, Kinetic and Relaxation Properties of Mn(II) Complexes Formed With Some Trisubstituted 12-Membered Macrocyclic Ligands

Effect of the Nature of Donor Atoms on the Thermodynamic, Kinetic and Relaxation Properties of Mn(II) Complexes Formed With Some Trisubstituted 12-Membered Macrocyclic Ligands

Cardiac Cell Tracking with MRI Reporter Genes: Welcoming a New Field

Synthesis and evaluation of ligands with mixed amide and phosphonate, phosphinoxide, and phosphonothioate sites for An(iii)/Ln(iii) extraction

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