Gd-AAZTA-MADEC, an improved blood pool agent for DCE-MRI studies on mice on 1 T scanners

Biomaterials

Volumn 75, Issue , 2016, Pages 47-57

  Longo, Dario Livio ^a,b   Arena, Francesca ^b   Consolino, Lorena ^b,d   Minazzi, Paolo ^c,d   Geninatti Crich, Simonetta ^b   Giovenzana, Giovanni Battista ^c,d   Aime, Silvio ^a,b  

^a CNR   (Italy)

^b UNIVERSITY OF TURIN   (Italy)

^c UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^d CAGE Chemicals Srl   (Italy)

Author keywords

Angiography; Blood pool imaging; DCE MRI; Gadolinium contrast agent; Human serum albumin; Magnetic resonance imaging (MRI)

Indexed keywords

ANGIOGRAPHY; BINDING ENERGY; BLOOD; GADOLINIUM COMPOUNDS; IMAGE ENHANCEMENT; LAKES; MAMMALS; MEDICAL IMAGING; PHARMACOKINETICS; SCANNING; TUMORS;

BLOOD POOL IMAGING; CONTRAST-ENHANCED IMAGES; DCE-MRI; GADOLINIUM CONTRAST AGENTS; HUMAN SERUM ALBUMINS; MAGNETIC FIELD STRENGTHS; PHARMACOKINETIC PROFILES; RELAXOMETRIC PROPERTIES;

MAGNETIC RESONANCE IMAGING;

ALBUMIN; DEOXYCHOLIC ACID; GADOCOLETIC ACID; GADOFOSVESET; GADOLINIUM AAZTA MADEC; HUMAN SERUM ALBUMIN; NUCLEAR MAGNETIC RESONANCE IMAGING AGENT; UNCLASSIFIED DRUG; CHOLIC ACID DERIVATIVE; CONTRAST MEDIUM; COORDINATION COMPOUND; GD-AAZTA-MADEC; PROTEIN BINDING; PROTON; SERUM ALBUMIN; WATER;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; BLOOD VESSEL PERMEABILITY; CLINICAL ASSESSMENT; COMPARATIVE STUDY; CONTRAST ENHANCEMENT; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG DESIGN; DRUG SYNTHESIS; DYNAMIC CONTRAST ENHANCED; HYDRATION; IMAGE ANALYSIS; IN VIVO STUDY; MAGNETIC RESONANCE ANGIOGRAPHY; MALE; MELANOMA CELL; MOLECULAR IMAGING; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE SCANNER; PRIORITY JOURNAL; VASCULAR TUMOR; VASCULARIZATION; ANIMAL; BAGG ALBINO MOUSE; BLOOD; C57BL MOUSE; CHEMISTRY; DEVICES; HUMAN; METABOLISM; NEOPLASMS; PROTON NUCLEAR MAGNETIC RESONANCE; RADIONUCLIDE VENTRICULOGRAPHY; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; CHOLIC ACIDS; CONTRAST MEDIA; COORDINATION COMPLEXES; GATED BLOOD-POOL IMAGING; HUMANS; MAGNETIC RESONANCE ANGIOGRAPHY; MAGNETIC RESONANCE IMAGING; MALE; MICE; MICE, INBRED BALB C; MICE, INBRED C57BL; NEOPLASMS; PROTEIN BINDING; PROTON MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SERUM ALBUMIN; TISSUE DISTRIBUTION; WATER;

EID: 84946430664     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2015.10.012     Document Type: Article

References (58)

1. Gillies R.J., Raghunand N., Karczmar G.S., Bhujwalla Z.M. MRI of the tumor microenvironment. J. Magn. Reson Imaging 2002, 16:430-450.
2. Kiessling F., Jugold M., Woenne E.C., Brix G. Non-invasive assessment of vessel morphology and function in tumors by magnetic resonance imaging. Eur. Radiol. 2007, 17:2136-2148.
3. Aime S., Barge A., Botta M., Terreno E. Interactions of lanthanides and their complexes with proteins. Conclusions regarding magnetic resonance imaging. Met. Ions Biol. Syst. 2003, 40:643-682.
4. Jung K.H., Kim H.K., Lee G.H., et al. Gd complexes of macrocyclic diethylenetriaminepentaacetic acid (DTPA) biphenyl-2,2'-bisamides as strong blood-pool magnetic resonance imaging contrast agents. J. Med. Chem. 2011, 54:5385-5394.
5. Boros E., Karimi S., Kenton N., Helm L., Caravan P. Gd(DOTAlaP): exploring the boundaries of fast water exchange in gadolinium-based magnetic resonance imaging contrast agents. Inorg. Chem. 2014, 53:6985-6994.
6. Yang C.T., Chandrasekharan P., He T., et al. An intravascular MRI contrast agent based on Gd(DO3A-Lys) for tumor angiography. Biomaterials 2014, 35:327-336.
7. Aime S., Gianolio E., Longo D., Pagliarin R., Lovazzano C., Sisti M. New insights for pursuing high relaxivity MRI agents from modelling the binding interaction of Gd(III) chelates to HSA. Chembiochem 2005, 6:818-820.
8. Geninatti-Crich S., Szabo I., Alberti D., Longo D., Aime S. MRI of cells and mice at 1 and 7 Tesla with Gd-targeting agents: when the low field is better!. Contrast Media Mol. Imaging 2011, 6:421-425.
9. Gossmann A., Okuhata Y., Shames D.M., et al. Prostate cancer tumor grade differentiation with dynamic contrast-enhanced MR imaging in the rat: comparison of macromolecular and small-molecular contrast media-preliminary experience. Radiology 1999, 213:265-272.
10. Marzola P., Degrassi A., Calderan L., et al. Early antiangiogenic activity of SU11248 evaluated in vivo by dynamic contrast-enhanced magnetic resonance imaging in an experimental model of colon carcinoma. Clin. Cancer Res. 2005, 11:5827-5832.
11. O'Connor J.P., Jackson A., Parker G.J., Jayson G.C. DCE-MRI biomarkers in the clinical evaluation of antiangiogenic and vascular disrupting agents. Br. J. Cancer 2007, 96:189-195.
12. Roberts T.P., Turetschek K., Preda A., et al. Tumor microvascular changes to anti-angiogenic treatment assessed by MR contrast media of different molecular weights. Acad. Radiol. 2002, 9(Suppl. 2):S511-S513.
13. Turetschek K., Preda A., Novikov V., et al. Tumor microvascular changes in antiangiogenic treatment: assessment by magnetic resonance contrast media of different molecular weights. J. Magn. Reson. Imaging 2004, 20:138-144.
14. 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.
15. Botta M., Avedano S., Giovenzana G.B., et al. Relaxometric study of a series of Monoaqua Gd-III complexes of rigidified EGTA-Like chelators and their noncovalent interaction with human serum albumin. Eur. J. Inorg. Chem. 2011, 802-810.
16. Avedano S., Tei L., Lombardi A., et al. Maximizing the relaxivity of HSA-bound gadolinium complexes by simultaneous optimization of rotation and water exchange. Chem. Commun. (Camb) 2007, 4726-4728.
17. Ferreira M.F., Martins A.F., Martins J.A., Ferreira P.M., Toth E., Geraldes C.F. Gd(DO3A-N-alpha-aminopropionate): a versatile and easily available synthon with optimized water exchange for the synthesis of high relaxivity, targeted MRI contrast agents. Chem. Commun. (Camb) 2009, 6475-6477.
18. Elemento E.M., Parker D., Aime S., Gianolio E., Lattuada L. Variation of water exchange dynamics with ligand structure and stereochemistry in lanthanide complexes based on 1,4-diazepine derivatives. Org. Biomol. Chem. 2009, 7:1120-1131.
19. Strauch R.C., Mastarone D.J., Sukerkar P.A., Song Y., Ipsaro J.J., Meade T.J. Reporter protein-targeted probes for magnetic resonance imaging. J. Am. Chem. Soc. 2011, 133:16346-16349.
20. Parmelee D.J., Walovitch R.C., Ouellet H.S., Lauffer R.B. Preclinical evaluation of the pharmacokinetics, biodistribution, and elimination of MS-325, a blood pool agent for magnetic resonance imaging. Invest Radiol. 1997, 32:741-747.
21. Cavagna F.M., Lorusso V., Anelli P.L., Maggioni F., de Haen C. Preclinical profile and clinical potential of gadocoletic acid trisodium salt (B22956/1), a new intravascular contrast medium for MRI. Acad. Radiol. 2002, 9(Suppl 2):S491-S494.
22. Gianolio E., Cabella C., Colombo Serra S., et al. B25716/1: a novel albumin-binding Gd-AAZTA MRI contrast agent with improved properties in tumor imaging. J. Biol. Inorg. Chem. 2014, 19:715-726.
23. Anelli P.L., Brocchetta M., Lattuada L., et al. Scale-Up of trisodium [(3 beta,5 beta,12(alpha)-3-[[4(S)-4-[Bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]-4-(carboxy-kO)-1-oxabutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) complex under development as a contrast agent for MRI coronary angiography. Org. Process Res. Dev. 2009, 13:739-746.
24. Minazzi P., Lattuada L., Menegotto I.G., Giovenzana G.B. An enzymatic approach to bifunctional chelating agents. Org. Biomol. Chem. 2014, 12:6915-6921.
25. Anelli P.L., Lattuada L., Uggeri F. One-pot Mitsunobu-Staudinger preparation of 3-aminocholan-24-oic acid esters from 3-hydroxycholan-24-oic acid esters. Synth. Commun. 1998, 28:109-117.
26. Aime S., Chiaussa M., Digilio G., Gianolio E., Terreno E. Contrast agents for magnetic resonance angiographic applications: 1H and 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.
27. Aime S., Calabi L., Cavallotti C., et al. [Gd-AAZTA](-): a new structural entry for an improved generation of MRI contrast agents. Inorg. Chem. 2004, 43:7588-7590.
28. Sherry A.D., Caravan P., Lenkinski R.E. Primer on gadolinium chemistry. J. Magn. Reson Imaging 2009, 30:1240-1248.
29. 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.
30. Andrec M., Montelione G.T., Levy R.M. Estimation of dynamic parameters from NMR relaxation data using the Lipari-Szabo model-free approach and Bayesian statistical methods. J. Magn. Reson. 1999, 139:408-421.
31. Curry S. Lessons from the crystallographic analysis of small molecule binding to human serum albumin. Drug Metab. Pharmacokinet. 2009, 24:342-357.
32. Caravan P., Parigi G., Chasse J.M., et al. Albumin binding, relaxivity, and water exchange kinetics of the diastereoisomers of MS-325, a gadolinium(III)-based magnetic resonance angiography contrast agent. Inorg. Chem. 2007, 46:6632-6639.
33. de Haen C., Anelli P.L., Lorusso V., et al. Gadocoletic acid trisodium salt (b22956/1): a new blood pool magnetic resonance contrast agent with application in coronary angiography. Invest Radiol. 2006, 41:279-291.
34. Dirksen M.S., Lamb H.J., Kunz P., Robert P., Corot C., de Roos A. Improved MR coronary angiography with use of a new rapid clearance blood pool contrast agent in pigs. Radiology 2003, 227:802-808.
35. Fasano M., Curry S., Terreno E., et al. The extraordinary ligand binding properties of human serum albumin. IUBMB Life 2005, 57:787-796.
36. Aime S., Botta M., Fasano M., Crich S.G., Terreno E. Gd(III) complexes as contrast agents for magnetic resonance imaging: a proton relaxation enhancement study of the interaction with human serum albumin. J. Biol. Inorg. Chem. 1996, 1:312-319.
37. Gianolio E., Giovenzana G.B., Longo D., Longo I., Menegotto I., Aime S. Relaxometric and modelling studies of the binding of a lipophilic Gd-AAZTA complex to fatted and defatted human serum albumin. Chemistry 2007, 13:5785-5797.
38. Avedano S., Botta M., Haigh J.S., Longo D.L., Woods M. Coupling fast water exchange to slow molecular tumbling in Gd3+ chelates: why faster is not always better. Inorg. Chem. 2013, 52:8436-8450.
39. Thompson M.K., Misselwitz B., Tso L.S., Doble D.M., Schmitt-Willich H., Raymond K.N. In vivo evaluation of gadolinium hydroxypyridonate chelates: initial experience as contrast media in magnetic resonance imaging. J. Med. Chem. 2005, 48:3874-3877.
40. Aime S., Caravan P. Biodistribution of gadolinium-based contrast agents, including gadolinium deposition. J. Magn. Reson. Imaging 2009, 30:1259-1267.
41. Richardson O.C., Bane O., Scott M.L., et al. Gadofosveset-based biomarker of tissue albumin concentration: Technical validation in vitro and feasibility in vivo. Magn. Reson. Med. 2015, 73:244-253.
42. Laurent S., Elst L.V., Muller R.N. Comparative study of the physicochemical properties of six clinical low molecular weight gadolinium contrast agents. Contrast Media Mol. Imaging 2006, 1:128-137.
43. Baranyai Z., Palinkas Z., Uggeri F., Maiocchi A., Aime S., Brucher E. Dissociation kinetics of open-chain and macrocyclic gadolinium(III)-aminopolycarboxylate complexes related to magnetic resonance imaging: catalytic effect of endogenous ligands. Chem. a Eur. J. 2012, 18:16426-16435.
44. Baranyai Z., Uggeri F., Giovenzana G.B., Benyei A., Brucher E., Aime S. Equilibrium and kinetic properties of the lanthanoids(III) and various divalent metal complexes of the heptadentate ligand AAZTA. Chem. a Eur. J. 2009, 15:1696-1705.
45. Zhang Z., Greenfield M.T., Spiller M., McMurry T.J., Lauffer R.B., Caravan P. Multilocus binding increases the relaxivity of protein-bound MRI contrast agents. Angew. Chem. Int. Ed. Engl. 2005, 44:6766-6769.
46. Manus L.M., Mastarone D.J., Waters E.A., et al. Gd(III)-nanodiamond conjugates for MRI contrast enhancement. Nano Lett. 2010, 10:484-489.
47. Song Y., Kohlmeir E.K., Meade T.J. Synthesis of multimeric MR contrast agents for cellular imaging. J. Am. Chem. Soc. 2008, 130:6662-6663.
48. Datta A., Hooker J.M., Botta M., Francis M.B., Aime S., Raymond K.N. High relaxivity gadolinium hydroxypyridonate-viral capsid conjugates: nanosized MRI contrast agents. J. Am. Chem. Soc. 2008, 130:2546-2552.
49. Zech S.G., Eldredge H.B., Lowe M.P., Caravan P. Protein binding to lanthanide(III) complexes can reduce the water exchange rate at the lanthanide. Inorg. Chem. 2007, 46:3576-3584.
50. Eldredge H.B., Spiller M., Chasse J.M., Greenwood M.T., Caravan P. Species dependence on plasma protein binding and relaxivity of the gadolinium-based MRI contrast agent MS-325. Invest Radiol. 2006, 41:229-243.
51. Jackson A., O'Connor J.P., Parker G.J., Jayson G.C. Imaging tumor vascular heterogeneity and angiogenesis using dynamic contrast-enhanced magnetic resonance imaging. Clin. Cancer Res. 2007, 13:3449-3459.
52. Longo D.L., Dastru W., Consolino L., et al. Cluster analysis of quantitative parametric maps from DCE-MRI: application in evaluating heterogeneity of tumor response to antiangiogenic treatment. Magn. Reson Imaging 2015, 33:725-736.
53. Gugliotta G., Botta M., Tei L. AAZTA-based bifunctional chelating agents for the synthesis of multimeric/dendrimeric MRI contrast agents. Org. Biomol. Chem. 2010, 8:4569-4574.
54. Lim J., Turkbey B., Bernardo M., et al. Gadolinium MRI contrast agents based on triazine dendrimers: relaxivity and in vivo pharmacokinetics. Bioconjug. Chem. 2012, 23:2291-2299.
55. Zhu W., Artemov D. Biocompatible blood pool MRI contrast agents based on hyaluronan. Contrast Media Mol. Imaging 2011, 6:61-68.
56. Boschi F., Marzola P., Sandri M., et al. Tumor microvasculature observed using different contrast agents: a comparison between Gd-DTPA-albumin and B-22956/1 in an experimental model of mammary carcinoma. MAGMA 2008, 21:169-176.
57. Bandini S., Curcio C., Macagno M., et al. Early onset and enhanced growth of autochthonous mammary carcinomas in C3-deficient Her2/neu transgenic mice. Oncoimmunology 2013, 2:e26137.
58. Schmid A., Schmitz J., Mannheim J.G., et al. Feasibility of sequential PET/MRI using a state-of-the-art small animal PET and a 1 T benchtop MRI. Mol. Imaging Biol. 2013, 15:155-165.