Study of Thermodynamic and Kinetic Stability of Transition Metal and Lanthanide Complexes of DTPA Analogues with a Phosphorus Acid Pendant Arm

Kotek, Jan; Kálmán, Ferenc K.; Hermann, Petr; Brücher, Ernő; Binnemans, Koen; Lukeš, Ivan

doi:10.1002/ejic.200501114

Cited by 32 publications

(21 citation statements)

References 29 publications

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“…From the basic side, for P-DTPA and DTPA, the first and second protonation processes take place at the nitrogen atoms of the ligand backbone. The third protonation site involves the protonation of the phosphonate and central carboxylate groups, respectively (6,13,14). Finally, further protonations occur at the nitrogen atom and carboxylate pendant arms.…”

Section: Complexation and Protonation Properties Of The H 6 Np-dtpa Lmentioning

confidence: 98%

“…Finally, further protonations occur at the nitrogen atom and carboxylate pendant arms. In general, the presence of the phosphonate groups in open-chain or macrocyclic amino-polycarboxylate ligands increases the basicity of the amine-N-atoms because the deprotonated phosphonate moiety and the protonated nitrogen form strong H-bonds (13,15). In the case of NP-DTPA the protonation of the central nitrogen occurs at extremely high pH (logK H 1 ¼ 12.88).…”

Section: Complexation and Protonation Properties Of The H 6 Np-dtpa Lmentioning

confidence: 98%

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The effects of intramolecular H‐bond formation on the stability constant and water exchange rate of the Gd(III)‐diethylenetriamine‐N′‐(3‐amino‐1,1‐propylenephosphonic)‐N, N,N″,N″‐tetraacetate complex

Baranyai

Gianolio

Ramalingam

et al. 2007

Contrast Media & Molecular

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The binding interaction of metal chelates to biological macromolecules, though driven by properly devoted recognition synthons, may cause dramatic changes in some property associated with the coordination cage such as the thermodynamic stability or the exchange rate of the metal coordinated water. Such changes are due to electrostatic and H-bonding interactions involving atoms of the coordination cage and atoms of the biological molecule at the binding site. To mimic this type of H-bonding interactions, lanthanide(III) complexes with a DTPA-monophosphonate ligand bearing a propylamino moiety (H6NP-DTPA) were synthesized. Their thermodynamic stabilities and the exchange lifetime of the coordinated water molecule (for the Gd-complex) were compared with those of the analog complexes with DTPA and the parent DTPA-monophosphonate derivative (H6P-DTPA). It was found that the intramolecular H-bond between the epsilon-amino group and the phosphonate moiety in NP-DTPA complexes causes displacements of electric charges in their coordination cage that are markedly pH dependent. In turn, this affects the characteristic properties of the coordination cage. In particular it results in a marked elongation of the exchange lifetime of the coordinated water molecule.

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Section: Complexation and Protonation Properties Of The H 6 Np-dtpa Lmentioning

confidence: 98%

Section: Complexation and Protonation Properties Of The H 6 Np-dtpa Lmentioning

confidence: 98%

The effects of intramolecular H‐bond formation on the stability constant and water exchange rate of the Gd(III)‐diethylenetriamine‐N′‐(3‐amino‐1,1‐propylenephosphonic)‐N, N,N″,N″‐tetraacetate complex

Baranyai

Gianolio

Ramalingam

et al. 2007

Contrast Media & Molecular

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show abstract

“…This is probably due to the higher basicity of the phosphonate group compared to the carboxylate (the complex will be protonated at a pH around 7). The increased steric crowding around the central metal ion, particularly in the presence of the bulky phenylphosphinate moiety, may also increase the lability of the complex [28]. Replacement of one, two, or three carboxylates of DTPA with amide groups leads to the mono-, bis-, and trisamides of DTPA.…”

Section: Inertness Of Complexes Of Open Chain Ligands (Edta Dtpa Anmentioning

confidence: 99%

Stability and Toxicity of Contrast Agents

Brücher

Tircsó

Baranyai

et al. 2013

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging

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Magnetic Resonance Imaging (MRI) derives directly from the phenomenon of Nuclear Magnetic Resonance (NMR [1][2][3][4]), which is widely used by chemists to determine molecular structure. The word "nuclear" was dropped in the switch to imaging to avoid alarming patients as NMR has nothing to do with radioactivity. This book is intended mainly for chemists, who are generally familiar with the NMR spectra. After a brief overview of the technique explaining the notion of relaxation time and saturation transfer used in MRI, we will describe localization techniques, which are less well-known in chemistry. The purpose of this short chapter is not to provide a complete theory of MRI [5][6][7][8], but to understand the rest of the book concerning the action of contrast agents. We will not go into the theoretical background of the phenomena, and while it is important to have some understanding of quantum mechanics, it is not our purpose to develop this aspect. This is a "nuts and bolts" description of MRI. Whenever possible, we refer to chemists' knowledge of NMR (for example, "2D NMR"). Theoretical basis of NMR Short description of NMRIn most cases, MRI focuses on one type of atomic nucleus, that of hydrogen in H 2 O. We will therefore only use this nucleus, termed the " 1 H proton."The physical phenomenon of NMR lies at the boundary between "conventional" and "quantum" treatment due to the small transition energies involved. Traditionally, the 1 H proton can be considered as a charged

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“…Examples are modifications by replacement of carboxylic groups by phosphinic or phosphonic groups (DTTA P or DTTAP R , Chart 5.3) [224,225] or by extension of one of the ethylene bridges or pendant acetate groups with a CH 2 group (DTTA-N-CE or DTTA-N -CE, EPTPA) [226][227][228][229][230].…”

Section: Expanded Dtpa Derivatives and Phosphonate Analogsmentioning

confidence: 99%

Structure, Dynamics, and Computational Studies of Lanthanide‐Based Contrast Agents

Peters

Djanashvili

Geraldes

et al. 2013

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging

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Study of Thermodynamic and Kinetic Stability of Transition Metal and Lanthanide Complexes of DTPA Analogues with a Phosphorus Acid Pendant Arm

Cited by 32 publications

References 29 publications

The effects of intramolecular H‐bond formation on the stability constant and water exchange rate of the Gd(III)‐diethylenetriamine‐N′‐(3‐amino‐1,1‐propylenephosphonic)‐N, N,N″,N″‐tetraacetate complex

The effects of intramolecular H‐bond formation on the stability constant and water exchange rate of the Gd(III)‐diethylenetriamine‐N′‐(3‐amino‐1,1‐propylenephosphonic)‐N, N,N″,N″‐tetraacetate complex

Stability and Toxicity of Contrast Agents

Structure, Dynamics, and Computational Studies of Lanthanide‐Based Contrast Agents

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