Promising strategies for Gd-based responsive magnetic resonance imaging contrast agents

Current Opinion in Chemical Biology

Volumn 17, Issue 2, 2013, Pages 158-166

  Shen, Clara ^a   New, Elizabeth J ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CONTRAST MEDIUM; GADOLINIUM;

DIAGNOSTIC IMAGING; HUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; REVIEW;

CONTRAST MEDIA; COORDINATION COMPLEXES; GADOLINIUM; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 84876712874     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2012.10.031     Document Type: Review

References (56)

1. Zhang Z.D., Nair S.A., McMurry T.J. Gadolinium meets medicinal chemistry: MRI contrast agent development. Curr Med Chem 2005, 12:751-778.
2. Caravan P., Ellison J.J., McMurry T.J., Lauffer R.B. Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications. Chem Rev 1999, 99:2293-2352.
3. Lauffer R.B. Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: theory and design. Chem Rev 1987, 87:901-927.
4. Moats R.A., Fraser S.E., Meade T.J. A " smart" magnetic resonance imaging agent that reports on specific enzymatic activity. Angew Chem Int Ed Engl 1997, 36:726-728.
5. Gao G.H., Lee J.W., Nguyen M.K., Im G.H., Yang J., Heo H., Jeon P., Park T.G., Lee J.H., Lee D.S. pH-responsive polymeric micelle based on PEG-poly(beta-amino ester)/(amido amine) as intelligent vehicle for magnetic resonance imaging in detection of cerebral ischemic area. J Control Release 2011, 155:11-17.
6. Hasserodt J. Magnetogenic probes that respond to chemical stimuli in an off-on mode. New J Chem 2012, 36:1707-1712.
7. Rolla G.A., Tei L., Fekete M., Arena F., Gianolio E., Botta M. Responsive Mn(II) complexes for potential applications in diagnostic magnetic resonance imaging. Bioorg Med Chem 2011, 19:1115-1122.
8. Bloembergen N., Morgan L.O. Proton relaxation times in paramagnetic solutions effects of electron spin relaxation. J Chem Phys 1961, 34:842-850.
9. Solomon I. Relaxation processes in a system of two spins. Phys Rev 1955, 99:559-565.
10. Raymond K.N., Pierre V.C. Next generation, high relaxivity gadolinium MRI agents†. Bioconj Chem 2004, 16:3-8.
11. Werner E.J., Datta A., Jocher C.J., Raymond K.N. High-relaxivity MRI contrast agents: where coordination chemistry meets medical imaging. Angew Chem Int Ed Engl 2008, 47:8568-8580.
12. Giovenzana G.B., Negri R., Rolla G.A., Tei L. Gd-Aminoethyl-DO3A complexes: a novel class of pH-sensitive MRI contrast agents. Eur J Inorg Chem 2012, 2035-2039.
13. Moriggi L., Yaseen M.A., Helm L., Caravan P. Serum albumin targeted, pH-dependent magnetic resonance relaxation agents. Chemistry 2012, 18:3675-3686.
14. Frullano L., Catana C., Benner T., Sherry A.D., Caravan P. Bimodal MR-PET agent for quantitative pH imaging. Angew Chem Int Ed Engl 2010, 49:2382-2384.
15. Gianolio E., Porto S., Napolitano R., Baroni S., Giovenzana G.B., Aime S. Relaxometric investigations and MRI evaluation of a liposome-loaded pH-responsive gadolinium(III) complex. Inorg Chem 2012, 51:7210-7217.
16. 3+-based MRI contrast agents. Bioorg Med Chem Lett 2012, 22:2798-2802.
17. Mamedov I., Logothetis N.K., Angelovski G. Structure-related variable responses of calcium sensitive MRI probes. Org Biomol Chem 2011, 9:5816-5824.
18. Mishra A., Logothetis N.K., Parker D. Critical in vitro evaluation of responsive MRI contrast agents for calcium and zinc. Chem Eur J 2011, 17:1529-1537.
19. Dong D., Jing X., Zhang X., Hu X., Wu Y., Duan C Gadolinium(III)-fluorescein complex as a dual modal probe for MRI and fluorescence zinc sensing. Tetrahedron 2012, 68:306-310.
20. Li W.-S., Luo J., Chen Z.-N. A gadolinium(III) complex with 8-amidequinoline based ligand as copper(II) ion responsive contrast agent. Dalton Trans 2011, 40:484-488.
21. 2-: a new MRI contrast agent for copper ion sensing. Dalton Trans 2011, 40:5018-5025.
22. Zhang X.L., Jing X., Liu T., Han G., Li H.Q., Duan C.Y. Dual-functional gadolinium-based copper(II) probe for selective magnetic resonance imaging and fluorescence sensing. Inorg Chem 2012, 51:2325-2331.
23. Que E.L., Gianolio E., Baker S.L., Aime S., Chang C.J. A copper-activated magnetic resonance imaging contrast agent with improved turn-on relaxivity response and anion compatibility. Dalton Trans 2010, 39:469-476.
24. Que E.L., New E.J., Chang C.J. A cell-permeable gadolinium contrast agent for magnetic resonance imaging of copper in a Menkes disease model. Chem Sci 2012, 3:1829-1834.
25. Kubicek V., Vitha T., Kotek J., Hermann P., Vander Elst L., Muller R.N., Lukes I., Peters J.A. Towards MRI contrast agents responsive to Ca(II) and Mg(II) ions: metal-induced oligomerization of dota-bisphosphonate conjugates. Contrast Media Mol Imaging 2010, 5:294-296.
26. Mamedov I., Canals S., Henig J., Beyerlein M., Murayama Y., Mayer H.A., Logothetis N.K., Angelovski G. In vivo characterization of a smart MRI agent that displays an inverse response to calcium concentration. ACS Chem Neurosc 2010, 1:819-828.
27. 2+ sensing. Chem Commun 2012, 48:4085-4087.
28. Surman A.J., Bonnet C.S., Lowe M.P., Kenny G.D., Bell J.D., Toth E., Vilar R. A pyrophosphate-responsive gadolinium(III) MRI contrast agent. Chem Eur J 2011, 17:223-230.
29. 2+ responsive bimodal magnetic resonance imaging and fluorescent imaging probe based on a gadolinium(III) complex. Inorg Chem 2012, 51:9508-9516.
30. Gringeri C.V., Menchise V., Rizzitelli S., Cittadino E., Catanzaro V., Dati G., Chaabane L., Digilio G., Aime S. Novel Gd(III)-based probes for MR molecular imaging of matrix metalloproteinases. Contrast Media Mol Imaging 2012, 7:175-184.
31. 1H MRI probe with self-immolative linker as a versatile tool for detection of enzymes. Contrast Media Mol Imaging 2012, 7:478-483.
32. Xu W., Lu Y. A smart magnetic resonance imaging contrast agent responsive to adenosine based on a DNA aptamer-conjugated gadolinium complex. Chem Commun 2011, 47:4998-5000.
33. Duan C.-Y. A hexanuclear gadolinium-organic octahedron as a sensitive MRI contrast agent for selectively imaging glucosamine in aqueous media. Chem Commun 2012.
34. Shuhendler A.J., Staruch R., Oakden W., Gordijo C.R., Rauth A.M., Stanisz G.J., Chopra R., Wu X.Y. Thermally-triggered 'off-on-off' response of gadolinium-hydrogel-lipid hybrid nanoparticles defines a customizable temperature window for non-invasive magnetic resonance imaging thermometry. J Control Release 2012, 157:478-484.
35. Liang G., Ronald J., Chen Y., Ye D., Pandit P., Ma M.L., Rutt B., Rao J. Controlled self-assembling of gadolinium nanoparticles as smart molecular magnetic resonance imaging contrast agents. Angew Chem Int Ed Engl 2011, 50:6283-6286.
36. Martinelli J., Fekete M., Tei L., Botta M. Cleavable beta-cyclodextrin nanocapsules incorporating Gd-III-chelates as bioresponsive MRI probes. Chem Commun 2011, 47:3144-3146.
37. Xiao Y., Wu Y.J., Zhang W.J., Li X.J., Pei F.K. Research progress of magnetic resonance imaging contrast agents. Fenxi Huaxue/Chin J Anal Chem 2011, 39:757-764.
38. Lowe M.P., Parker D., Reany O., Aime S., Botta M., Castellano G., Gianolio E., Pagliarin R. pH-Dependent modulation of relaxivity and luminescence in macrocyclic gadolinium and europium complexes based on reversible intramolecular sulfonamide ligation. J Am Chem Soc 2001, 123:7601-7609.
39. Que E.L., Chang C.J. Responsive magnetic resonance imaging contrast agents as chemical sensors for metals in biology and medicine. Chem Soc Rev 2010, 39:51-60.
40. Bonnet C.S., Toth E. MRI probes for sensing biologically relevant metal ions. Future Med Chem 2010, 2:367-384.
41. Que E.L., Gianolio E., Baker S.L., Wong A.P., Aime S., Chang C.J. Copper-responsive magnetic resonance imaging contrast agents. J Am Chem Soc 2009, 131:8527-8536.
42. Rae T.D., Schmidt P.J., Pufahl R.A., Culotta V.C., O'Halloran T V. Undetectable intracellular free copper: the requirement of a copper chaperone for superoxide dismutase. Science 1999, 284:805-808.
43. Caravan P., Farrar C.T., Frullano L., Uppal R. Influence of molecular parameters and increasing magnetic field strength on relaxivity of gadolinium- and manganese-based T(1) contrast agents. Contrast Media Mol Imaging 2009, 4:89-100.
44. Nicolle G.M., Tóth é., Schmitt-Willich H., Radüchel B., Merbach A.E. The impact of rigidity and water exchange on the relaxivity of a dendritic MRI contrast agent. Chemistry 2002, 8:1040-1048.
45. Schlemmer H.P., Pichler B.J., Krieg R., Heiss W.D. An integrated MR/PET system: prospective applications. Abdom Imaging 2009, 34:668-674.
46. Kobayashi H., Longmire M.R., Ogawa M., Choyke P.L., Kawamoto S. Multiplexed imaging in cancer diagnosis: applications and future advances. Lancet Oncol 2010, 11:589-595.
47. Drzezga A., Souvatzoglou M., Eiber M., Beer A.J., Furst S., Martinez-Moller A., Nekolla S.G., Ziegler S., Ganter C., Rummeny E.J., et al. First clinical experience with integrated whole-body PET/MR: comparison to PET/CT in patients with oncologic diagnoses. J Nucl Med 2012, 53:845-855.
48. 1 agents. Proc Natl Acad Sci USA 1998, 95:8443-8448.
49. Su W., Mishra R., Pfeuffer J., Wiesmuller K.H., Ugurbil K., Engelmann J. Synthesis and cellular uptake of a MR contrast agent coupled to an antisense peptide nucleic acid - cell-penetrating peptide conjugate. Contrast Media Mol Imaging 2007, 2:42-49.
50. Kamaly N., Kalber T., Ahmad A., Oliver M.H., So P.W., Herlihy A.H., Bell J.D., Jorgensen M.R., Miller A.D. Bimodal paramagnetic and fluorescent liposomes for cellular and tumor magnetic resonance imaging. Bioconjug Chem 2008, 19:118-129.
51. Keliris A., Ziegler T., Mishra R., Pohmann R., Sauer M.G., Ugurbil K., Engelmann J. Synthesis and characterization of a cell-permeable bimodal contrast agent targeting β-galactosidase. Bioorg Med Chem 2011, 19:2529-2540.
52. Rojas-Quijano F.A., Tircsõ G., Tircsõné Benyõ E., Baranyai Z., Tran Hoang H., Kálmán F.K., Gulaka P.K., Kodibagkar V.D., Aime S., Kovács Z., et al. Synthesis and characterization of a hypoxia-sensitive MRI probe. Chemistry 2012, 18:9669-9676.
53. Guenoun J., Koning G.A., Doeswijk G., Bosman L., Wielopolski P.A., Krestin G.P., Bernsen M.R. Cationic Gd-DTPA liposomes for highly efficient labeling of mesenchymal stem cells and cell tracking with MRI. Cell Transplant 2012, 21:191-205.
54. Caravan P., Zhang Z.D. Structure-relaxivity relationships among targeted MR contrast agents. Eur J Inorg Chem 2012, 1916-1923.
55. Wu X.M., Burden-Gulley S.M., Yu G.P., Tan M.Q., Lindner D., Brady-Kalnay S.M., Lu Z.R. Synthesis and evaluation of a peptide targeted small molecular Gd-DOTA monoamide conjugate for MR molecular imaging of prostate cancer. Bioconjug Chem 2012, 23:1548-1556.
56. Geelen T., Paulis L.E.M., Coolen B.F., Nicolay K., Strijkers G.J. Contrast-enhanced MRI of murine myocardial infarction - Part I. NMR Biomed 2012, 25:953-968.