Evidence map›Paper›PMID 23517079›Full record

ArticleInorganic chemistry2013

Is macrocycle a synonym for kinetic inertness in Gd(III) Complexes? Effect of coordinating and noncoordinating substituents on inertness and relaxivity of Gd(III) chelates with DO3A-like ligands.

Miloslav Polasek, Peter Caravan

Abstract read
In one paragraph

Article in Inorganic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.

0numbers the graph read from it
0cells of the map it votes in
15citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

15 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Review
  6. Removal of gadolinium-based contrast agents: adsorption on activated carbon.Environmental science and pollution research international · 2017
    Article
  7. Article
  8. MR imaging probes: design and applications.Dalton transactions (Cambridge, England : 2003) · 2015
    Review
  9. Article
  10. Rapid synthesis of 1,7-bis(Tetrahedron letters · 2014
    Article
  11. Review
  12. Article
  13. Article
  14. Article
  15. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

2 authors.

Miloslav PolasekThe Athinoula A. Martinos Center for Biomedical Imaging, Department of Radiology, Massachusetts General Hospital, Harvard Medical School, 149 Thirteenth Street, Suite 2301, Charlestown, Massachusetts 02129, USA.
Peter Caravan

Funding

Stable, High Relaxivity MRI Contrast AgentsR01EB009062 · NIBIB · MASSACHUSETTS GENERAL HOSPITAL · PI CARAVAN, PETER D · 2009 to 2017
$4.9M
500 MHz NMR Spectrometer for Molecular Imaging ApplicationsS10RR023385 · NCRR · MASSACHUSETTS GENERAL HOSPITAL · PI ROSEN, BRUCE R · 2007 to 2007
$500k
NCRR NIH HHS S10 RR023385NIBIB NIH HHS R01 EB009062NIBIB NIH HHS R01EB009062
6 · The paper itself

Abstract

Gadolinium chelates with octadentate ligands are widely used as contrast agents for magnetic resonance imaging (MRI), with macrocyclic ligands based on DO3A being preferred for the high kinetic inertness of their Gd chelates. A major challenge in the design of new bifunctional MRI probes is the need to control the rotational motion of the chelate, which greatly affects its relaxivity. In this work we explored facile alkylation of a secondary amine in macrocyclic DO3A-like ligands to create a short, achiral linkage to limit the undesired internal motion of chelates within larger molecular constructs. The acetate moiety on the trans nitrogen was also replaced with either a bidentate (ethoxyacetate, L1 or methyl picolinate, L2) or bulky monodentate (methyl phosphonate, L3) donor arm to give octa- or heptadentate ligands, respectively. The resultant Gd(III) complexes were all monohydrated (q = 1) and exhibited water residency times that spanned 2 orders of magnitude (τM = 2190 ± 170, 3500 ± 90, and 12.7 ± 3.8 ns at 37 °C for GdL1, GdL2, and GdL3, respectively). Alkylation of the secondary amine with a noncoordinating biphenyl moiety resulted in coordinatively saturated q = 0 complexes of octadentate ligands L1 and L2. Relaxivities were limited by slow water exchange and/or lack of water coligand. All complexes showed decreased inertness compared to [Gd(DO3A)] despite higher ligand denticity, and inertness was further decreased upon N-alkylation. These results demonstrate that high kinetic inertness and in vivo safety of Gd chelates with macrocyclic ligands should not be generalized.

Indexed as

Biphenyl CompoundsChelating AgentsContrast MediaGadoliniumHeterocyclic Compounds, 1-RingKineticsLigandsMagnetic Resonance ImagingMagnetic Resonance SpectroscopyMotionWater1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acidBiphenyl CompoundsChelating AgentsContrast MediaGadoliniumHeterocyclic Compounds, 1-RingLigandsWater

Identifiers

PMID23517079
PMCPMC3640422

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.