Gd(III)-EPTPAC16, a new self-assembling potential liver MRI contrast agent: In vitro characterization and in vivo animal imaging studies

NMR in Biomedicine

Volumn 21, Issue 4, 2008, Pages 322-336

  Torres, Suzana ^a   Prata, Maria I M ^b   Santos, Ana C ^b   André, João P ^a   Martins, José A ^a   Helm, Lothar ^c   Tóth, Éva ^d   García Martín, Maria L ^e   Rodrigues, Tiago B ^e,f   López Larrubia, Pilar ^e   Cerdán, Sebastián ^e   Geraldes, Carlos F G C ^f  

^a UNIVERSITY OF MINHO   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c EPFL   (Switzerland)

^d CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^e INSTITUTO DE INVESTIGACIONES BIOMÉDICAS ALBERTO SOLS   (Spain)

^f UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

scintigraphy; Contrast agents; Dynamic light scattering; Gadolinium; Liver targeting; Micelles; MRI; Self assembly

Indexed keywords

BIOMEDICAL ENGINEERING; LIGHT SCATTERING; MAGNETIC RESONANCE IMAGING; MICELLES; POLYDISPERSITY; SONICATION;

CONTRAST AGENTSCONTRAST AGENTS; CRITICAL MICELLAR CONCENTRATION (CMC);

MEDICAL IMAGING;

(HYDROXYMETHYLHEXADECANOYL ESTER)ETHYLENEPROPYLENE TRIAMINEPENTA ACETIC ACID SM 153; AMPHOPHILE; CONTRAST MEDIUM; GADOLINIUM (HYDROXYMETHYLHEXADECANOYL ESTER)ETHYLENEPROPYLENE TRIAMINEPENTA ACETIC ACID; GADOLINIUM CHELATE; GADOLINIUM PENTETATE; TRACER; ((HYDROXYMETHYLHEXADECANOYL ESTER)ETHYLENEPROPYLENE TRIAMINEPENTAACETIC ACID)GADOLINIUM(III); CHELATING AGENT; ORGANOMETALLIC COMPOUND; WATER;

ANIMAL EXPERIMENT; ARTICLE; CONCENTRATION RESPONSE; CONTRAST ENHANCEMENT; CONTROLLED STUDY; CORRELATION ANALYSIS; CRITICAL MICELLE CONCENTRATION; DRUG DISTRIBUTION; DRUG RETENTION; DRUG STRUCTURE; DRUG UPTAKE; GAMMA SCINTIGRAPHY; IMAGE ANALYSIS; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; LIGHT SCATTERING; LIVER; LIVER SCINTISCANNING; LUNG; MALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUALITATIVE ANALYSIS; RAT; SPLEEN; STRUCTURE ANALYSIS; ULTRASOUND; WISTAR RAT; ANIMAL; ANTIBODY SPECIFICITY; CHEMISTRY; DRUG EFFECT; LIGHT; METABOLISM; METHODOLOGY; RADIATION SCATTERING; SCINTISCANNING; SOLUTION AND SOLUBILITY; THREE DIMENSIONAL IMAGING; TIME; TISSUE DISTRIBUTION;

ANIMALIA; RATTUS NORVEGICUS;

ANIMALS; CHELATING AGENTS; CONTRAST MEDIA; IMAGING, THREE-DIMENSIONAL; LIGHT; LIVER; MAGNETIC RESONANCE IMAGING; MALE; ORGAN SPECIFICITY; ORGANOMETALLIC COMPOUNDS; RATS; RATS, WISTAR; SCATTERING, RADIATION; SOLUTIONS; SONICATION; TIME FACTORS; TISSUE DISTRIBUTION; WATER;

EID: 44649111266     PISSN: 09523480     EISSN: 10991492     Source Type: Journal    
DOI: 10.1002/nbm.1194     Document Type: Article

References (66)

1. Caravan P, Ellison JJ, McMurry TJ, Lauffer RB. Paramagnetic metal complexes as water proton relaxation agents for NMR imaging. Chem. Rev. 1999; 99: 2293-23525.
2. Tóth É, Merbach AE (eds). The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging. Wiley: Chichester, 2001.
3. Tóth É, Helm L, Merbach AE. Relaxivity of MRI contrast agents. Top. Curr Chem. 2002; 221: 61-101.
4. Tóth É, Helm L, Merbach AE. MRI contrast enhancement agents. In Comprehensive Coordination Chemistry II, McCleverty JA, Meyer TJ (eds). Publisher: Elsevier Ltd.: Oxford, UK, 2004; 9: 841-881.
5. Aime S, Botta M, Fasano M, Terreno E. Lanthanide(III) chelates for NMR biomedical applications. Chem. Soc. Rev. 1998; 27: 19-29.
6. Comblin V, Gilsoul D, Hermann M, Humbert V, Jacques V, Mesbari M, Sauvage C, Desreux JF. Designing new MRI contrast agents: a coordination chemistry challenge. Coord. Chem. Rev. 1999; 185-186: 451-470.
7. Gries H. Extracellular MRI contrast agents based on gadolinium. Top. Curr Chem. 2002; 221: 1-24.
8. Aime S, Cabella C, Colombato S, Crich SG, Gianolo E, Maggiori F. Insights into the use of paramagnetic Gd(III) complexes in MR-molecular imaging investigations. J. Magn. Reson. Imaging 2002; 16: 394-406.
9. Tóth É, Burai L, Brücher E, Merbach AE. Tuning water-exchange rates on (carboxymethyl)iminobis(ethylenenitrilo)tetraacetate (DTPA)-type gadolinium(III) complexes. J. Chem. Soc. Dalton Trans. 1997; 1587-1594.
10. André JP, Maecke HR, Tóth É, Merbach AE. Synthesis and physicochemical characterization of a novel precursor for covalently bound macromolecular MRI contrast agents. J. Biol. Inorg. Chem. 1999; 4: 341-347.
11. Ruloff R, Tóth É, Tripier R, Handle H, Merbach AE. Accelerating water exchange for Gd(III) chelates by steric compression around the water binding site. Chem. Commun. 2002; 22: 2630-2631.
12. III complexes with fast water exchange and high thermodynamic stability: potential building blocks for high-relaxivity MRI contrast agents. Chemistry 2003; 9: 3555-3566.
13. III poly(amino carboxylates) by modulation of steric crowding. Dalton Trans. 2005; 2713-2719.
14. Kotek J, Lebdǔková P, Hermann P, van der Elst L, Muller RN, Geraldes CFGC, Maschmeyer T, Lukeš I, Peters JA. Lanthanide(III) complexes of novel mixed carboxylic-phosphorus acid derivatives of diethylenetriamine: a step towards more efficient MRI contrast agents. Chemistry 2003; 9: 5899-5915
15. Corsi DM, van der Elst L, Muller RN, van Bekkum H, Peters JA. Inulin as a carrier for contrast agents in magnetic resonance imaging. Chemistry 2001; 7: 64-71.
16. André JP, Geraldes CFGC, Martins JA, Merbach AE, Prata MIM, Santos AC, de Lima JJP, Tóth É. Lanthanide(III) complexes of glycoconjugates for lectin-mediated medical imaging. Chemistry 2004; 10: 5804-5816.
17. Baía P, André JP, Geraldes CFGC, Martins JA, Merbach AE, Tóth É. Lanthanide(III) chelates of DTPA bis(amide) glycoconjugates: potential imaging agents targeted at the asialoglicoprotein receptor. Eur. J. Inorg. Chem. 2005; 2110-2119.
18. Aime S, Botta M, Crich SG, Giovenzana G, Palmisano G, Sisti M. Novel paramagnetic macromolecular complexes derived from the linkage of a macrocyclic Gd(III) complex to polyamino acids through a squaric acid moiety. Bioconjugate Chem. 1999; 10: 192-199.
19. Tóth É, Pubanz D, Vauthey S, Helm L, Merbach AE. The role of water exchange in attaining maximum relaxivities for dendrimeric MRI contrast agents. Chemistry 1996; 2: 1607-1915.
20. Laus S, Sour A, Ruloff R, Tóth É, Merbach AE. Rotational dynamics account for pH-dependent relaxivities of PAMAM dendrimeric, Gd-based potential MRI contrast agents. Chemistry 2005; 11: 3064-3076.
21. 17O NMR relaxometric investigations on two gadolinium(III) DTPA-like chelates endowed with high binding affinity to human serum albumin. J. Biol. Inorg. Chem. 1999; 4: 766-774.
22. Muller RN, Radüchel B, Laurent S, Platzek J, Piérart C, Mareski P, Vander Elst L. Physicochemical characterization of MS-325, a new gadolinium complex, by multinuclear relaxometry. Eur. J. Inorg. Chem. 1999; 1949-1955.
23. Aime S, Gianolio E, Terreno E, Giovenzana GB, Pagliarin R, Sisti M, Palmisano G, Botta M, Lowe MP, Parker D. Ternary Gd(III)L-HSA adducts: evidence for the replacement of inner-sphere water molecules by coordinating groups of the protein. Implications for the design of contrast agents for MRI. J. Biol. Inorg. Chem. 2000; 5: 488-497.
24. Moghini SM, Hunter AC, Murray JC. Long-circulating and target-specific nanoparticles: theory to practice. Pharm. Rev. 2001; 53: 283-318.
25. Torchilin VP, Lukyanov AN, Gao ZG, Papahadjopoulos-Sternberg B. Immunomicelles: targeted pharmaceutical carriers for poorly soluble drugs. Proc. Natl. Acad. Sci. USA. 2003; 100: 6039-6044.
26. Wang J, Mongayt D, Torchilin VP. Polymeric micelles for delivery of poorly soluble drugs: preparation and anticancer activity in vitro of paclitaxel incorporated into mixed micelles based on poly (ethylene glycol)-lipid conjugate and positively charged lipids. J. Drug. Targeting. 2005; 13: 73-80.
27. Mulder WJM, Strijkers GJ, van Tilborg GAF, Griffioen AW, Nicolay K. Lipid-based nanoparticles for contrast-enhanced MRI and molecular imaging. NMR Biomed 2006; 19: 142-164.
28. Lanza GM, Winter PM, Hughes MS, Caruthers SD, Marsh JN, Morawski AM, Schmieder AH, Scott MJ, Fuhrhop RW, Zhang H, Hu G, Lacy EK, Allen JS, Wickline SA. Molecular imaging and therapy: new paradigms for 21(st) century medicine, polymeric drug delivery I: particulate drug carriers. ACS Symposium Series 2006; 923: 295-311.
29. Kostarelos K, Emfietzoglon D. Liposomes as carriers of radionuclides: from imaging to therapy. J. Liposome Res. 1999; 9: 429-460.
30. Torchilin VP, Kamenetsky MDF, Wolff GL. CT visualization of blood pool in rats by using long-circulating, iodine-containing micelles. Acad. Radiol. 1999; 6: 61-65.
31. Goins B, Phillips WT, Klipper R. Blood-pool imaging using technetium-99m-labeled liposomes. J. Nucl. Med. 1996; 37: 1374-1379.
32. Phillips WT, Klipper R, Gains B. Novel method of greatly enhanced delivery of liposomes to lymph nodes. J. Pharm. Exp. Thert. 2000; 295: 309-313.
33. Lukyanov AN, Hartner WC, Torchilin VP. Tumor-targeted liposomes: doxorubicin-loaded long-circulating liposomes modified with anti-cancer antibody. J. Control Release 2004; 94: 187-193.
34. Kellar KE, Henricks PM, Hollister R, Koenig SH, Eck J, Wei D. High relaxivity linear Gd(DTPA)-polymer conjugates: the role of hydrophobic interactions. Magn. Reson. Med. 1997; 38: 712-716.
35. Duarte MG, Gil MH, Peters JA, Vander Elst L, Collet JM, Muller RN, Geraldes CFGC. Synthesis, characterization, and relaxivity of two linear Gd(DTPA)-polymer conjugates. Bioconj. Chem. 2001; 12: 170-177.
36. Tóth É, Helm L, Kellar KE, Merbach AE. Gd(DTPA-bisamide)alkyl copolymers: a hint for the formation of MRI contrast agents with very high relaxivity. Chemistry 1999; 5: 1202-1211.
37. André JP, Tóth É, Fischer H, Seelig A, Mäcke H, Merbach AE. High relaxivity for monomeric Gd(DOTA)-based MRI contrast agents, thanks to micellar self-organization. Chemistry 1999; 5: 2977-2983.
38. Nicolle GM, Tóth É, Eisenwiener KP, Mäcke HR, Merbach AE. From monomers to micelles: investigation of the parameters influencing proton relaxivity. J. Biol. Inorg. Chem. 2002; 7: 757-769.
39. Gløgård C, Hovland R, Fossheim SL, Aasen AJ, Klaveness J. Synthesis and physicochemical characterisation of new amphiphilic gadolinium DO3A complexes as contrast agents for MRI. J. Chem. Soc., Perkin Trans. 2000; 2: 1047-1052.
40. 3+ complex of a fatty acid analogue of DOTP binds to multiple albumin sites with variable water relaxivities. Inorg. Chem. 2001; 40: 6580-6587.
41. Li X, Zhang S, Zhao P, Kovacs Z, Sherry AD. Synthesis and NMR studies of new DOTP-like lanthanide(III) complexes containing a hydrophobic substituent on one phosphonate side arm. Inorg. Chem. 2001; 40: 6572-6579.
42. Hovland R, Gløgård C, Aasen AJ, Klaveness J. Preparation and in vitro evaluation of a novel amphiphilic GdPCTA-[12] derivative: a micellar MRI contrast agent. Org. Biomol. Chem. 2003; 1: 644-647.
43. 8S paramagnetic centres in molecular assemblies: possible effect of their proximity on the water proton relaxivity. Magn. Reson. Chem. 2003; 41: 794-799.
44. Tournier H, Hyacinthe R, Schneider M. Gadolinium-containing mixed micelle formulations: a new class of blood pool MRI/MRA contrast agents. Acad. Radiol. 2002; 202 (Suppl. 1): S20-S28.
45. Gløgård C, Stensrud G, Klaveness J. Novel high relaxivity colloidal particles based on the specific phase organisation of amphiphilic gadolinium chelates with cholesterol. Int. J. Pharm. 2003; 253: 39-48.
46. Gløgård C. Liposomes as carriers of amphiphilic gadolinium chelates: the effect of membrane composition on incorporation efficacy and in vitro relaxivity. Int. J. Pharm. 2002; 233: 131-140.
47. Lattuada L, Lux G. Synthesis of Gd-DTPA-cholesterol: a new lipophilic gadolinium complex as a potential MRI contrast agent. Tetrahedron Lett 2003; 44: 3893-3895.
48. 2-. Eur. J. Inorg. Chem. 2003; 3021-3027.
49. Parac-Vogt TN, Kimpe K, Laurent S, Piérart C, Vander Elst L, Muller RN, Binnemans K. Gadolinium DTPA-monoamide complexes incorporated into mixed micelles as possible MRI contrast agents. Eur. J. Inorg. Chem. 2004; 3538-3543.
50. Accardo A, Tesauro D, Roscigno P, Gianolio E, Paduano L, D'Errico G, Pedone C, Morelli G. Physicochemical properties of mixed micellar aggregates containing CCK peptides and Gd complexes designed as tumor specific contrast agents in MRI. J. Am. Chem. Soc. 2004; 126: 3097-3107.
51. III chelate: tuning the reorientational correlation time and the water exchange rate. Chemistry 2006; 12: 940-948.
52. Zettl H, Portnoy Y, Gottlieb M, Krausch G. Investigation of micelle formation by fluorescence correlation spectroscopy. J. Phys. Chem. 2005; 109: 13397-13401.
53. Perez-Rodriguez M, Varela LM, Garcia M, Mosquera V, Sarmiento F. Conductivity and relative permittivity of sodium n-dodecyl sulfate and n-dodecyl trimethylammonium bromide. Journal of Chemical Engineering Data 1999; 44: 944-947.
54. He X, Liang H, Huang L, Pan C. Complex microstructures of amphiphilic diblock copolymer in dilute solution. J. Phys. Chem. 2004; 108: 1731-1735.
55. Sampson CB. Textbook of Radiopharmacy, Theory and Practice, 3rd edition. Gordon and Breach Science Publishers: London, 1999; chapter 23: 283, 294.
56. Ekeh S, Chu R, Ficken VJ, Allen EW, Ryals CJ. Distributions of perfusion and lung water. Nucl. Med. Biol. 1990; 17: 561-565.
57. Frias JC, Williams KJ, Fischer EW, Fayad ZA. Recombinant HDL-like nanoparticles: a specific contrast agent for MRI of atherosclerotic plaques. J. Am. Chem. Soc. 2004; 126: 16316-16317.
58. Jasanada F, Urizzi P, Suchard JP, LeGaillard F, Fabre G, Nepveu F. Indium-111 labeling of low density lipoproteins with the DTPA-bis(stearylamide): evaluation as a potential radiopharmaceutical for tumor localization. Bioconj Chem. 1996; 7: 72-81.
59. Corbin IR, Li H, Chen J, Lund-Katz S, Zhou R, Glickson JD, Zheng G. Low-density lipoprotein nanoparticles as magnetic resonance imaging contrast agents. Neoplasia 2006; 8: 488-498.
60. Yoshikawa K, Inoue Y, Akahane M, Shimada M, Itoh S, Seno A, Hayashi S. Phantom and animal studies of a new hepatobiliary agent for MR imaging: comparison of GdDTPA-DeA with Gd-EOB-DTPA. J. Magn. Reson. Imaging. 2003; 18: 204-209.
61. III complexes. Eur. J. Inorg. Chem. 2007; in press.
62. Accardo A, Tesauro D, Morelli G, Gianolio E, Aime S, Vaccaro M, Mangiapia G, Paduano L, Schillén K. High relaxivity supramolecular aggregates containing peptides and Gd complexes as contrast agents in MRI. J. Biol. Inorg. Chem. 2007; 12: 267-276.
63. Kabalka GW, Buonocore E, Hubner K, Davis M, Huang L. Gadolinium-labeled liposomes containing paramagnetic amphipatic agents: targeted MRI contrast agents for the liver. Magn. Reson. Med. 1988; 8: 89-95.
64. Chu WJ, Simor T, Elgavish G. In vivo characterization of Gd(BME-DTTA), a myocardial MRI contrast agent: tissue distribution of its MRI intensity enhancement, and its effect on heart function. NMR Biomed. 1977; 10: 87-92.
65. Schuhmann-Giampieri G, Schmitt-Willich H, Press W-R, Negishi C, Weinmann H-J, Speck U. Preclinical evaluation of Gd-EOB-DTPA as a contrast agent in MR imaging of the hepatobiliary systems. Radiology 1992; 183: 59-64.
66. Vittadini G, Felder E, Musu C, Tirone C. Preclinical profile of Gd-BOPTA: a liver specific MRI contrast agent. Invest. Radiol. 1990; 5: S59-S60.