Gd-AAZTA-MADEC, an improved blood pool agent for DCE-MRI studies on mice on 1 T scanners(418 views) Longo DL, Arena F, Consolino L, Minazzi P, Geninatti-crich S, Giovenzana GB, Aime S
Biomaterials (ISSN: 0142-9612, 1878-5905electronic, 0142-9612linking), 2015 Oct 16; 75: 47-57.
Keywords: Angiography, Blood Pool Imaging, Dce-Mri, Gadolinium Contrast Agent, Human Serum Albumin, Magnetic Resonance Imaging (mri), Binding Energy, Body Fluids, Lakes, Mammals, Medical Imaging, Pharmacokinetics, Scanning, Tumors, Contrast-Enhanced Images, Magnetic Field Strengths, Pharmacokinetic Profiles, Relaxometric Properties, Deoxycholic Acid, Gadocoletic Acid, Gadofosveset, Gadolinium Aazta Madec, Nuclear Magnetic Resonance Imaging Agent, Unclassified Drug, 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, Melanoma Cell, Molecular Imaging, Mouse, Nonhuman, Nuclear Magnetic Resonance Scanner, Priority Journal, Vascular Tumor, Vascularization,
Affiliations: *** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini (CNR) c/o Molecular Biotechnology Center, Via Nizza 52, 10126, Torino, Italy; Molecular Imaging Center, University of Torino, Via Nizza 52, 10126, Torino, Italy. Electronic address: dario.longo@unito.it., Molecular Imaging Center, University of Torino, Via Nizza 52, 10126, Torino, Italy; Department of Molecular Biotechnology and Health Sciences, University of Torino, Via Nizza 52, 10126, Torino, Italy., Molecular Imaging Center, University of Torino, Via Nizza 52, 10126, Torino, Italy; Department of Molecular Biotechnology and Health Sciences, University of Torino, Via Nizza 52, 10126, Torino, Italy; CAGE Chemicals Srl, Via Bovio 6, 28100, Novara, Italy., Dipartimento di Scienze del Farmaco, Universita del Piemonte Orientale "A. Avogadro" Largo Donegani 2/3, 28100, Novara, Italy; CAGE Chemicals Srl, Via Bovio 6, 28100, Novara, Italy., Istituto di Biostrutture e Bioimmagini (CNR) c/o Molecular Biotechnology Center, Via Nizza 52, 10126, Torino, Italy; Molecular Imaging Center, University of Torino, Via Nizza 52, 10126, Torino, Italy; Department of Molecular Biotechnology and Health Sciences, University of Torino, Via Nizza 52, 10126, Torino, Italy.,
References: Gillies, R.J., Raghunand, N., Karczmar, G.S., Bhujwalla, Z.M., MRI of the tumor microenvironment (2002) J. Magn. Reson Imaging, 16, pp. 430-45
Kiessling, F., Jugold, M., Woenne, E.C., Brix, G., Non-invasive assessment of vessel morphology and function in tumors by magnetic resonance imaging (2007) Eur. Radiol., 17, pp. 2136-2148
Aime, S., Barge, A., Botta, M., Terreno, E., Interactions of lanthanides and their complexes with proteins. Conclusions regarding magnetic resonance imaging (2003) Met. Ions Biol. Syst., 40, pp. 643-682
Jung, K.H., Kim, H.K., Lee, G.H., Gd complexes of macrocyclic diethylenetriaminepentaacetic acid (DTPA) biphenyl-2,2'-bisamides as strong blood-pool magnetic resonance imaging contrast agents (2011) J. Med. Chem., 54, pp. 5385-5394
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 (2014) Inorg. Chem., 53, pp. 6985-6994
Yang, C.T., Chandrasekharan, P., He, T., An intravascular MRI contrast agent based on Gd(DO3A-Lys) for tumor angiography (2014) Biomaterials, 35, pp. 327-336
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 (2005) Chembiochem, 6, pp. 818-820
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! (2011) Contrast Media Mol. Imaging, 6, pp. 421-425
Gossmann, A., Okuhata, Y., Shames, D.M., Prostate cancer tumor grade differentiation with dynamic contrast-enhanced MR imaging in the rat: comparison of macromolecular and small-molecular contrast media-preliminary experience (1999) Radiology, 213, pp. 265-272
Marzola, P., Degrassi, A., Calderan, L., Early antiangiogenic activity of SU11248 evaluated in vivo by dynamic contrast-enhanced magnetic resonance imaging in an experimental model of colon carcinoma (2005) Clin. Cancer Res., 11, pp. 5827-5832
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 (2007) Br. J. Cancer, 96, pp. 189-195
Roberts, T.P., Turetschek, K., Preda, A., Tumor microvascular changes to anti-angiogenic treatment assessed by MR contrast media of different molecular weights (2002) Acad. Radiol., 9, pp. S511-S513
Caravan, P., Ellison, J.J., McMurry, T.J., Lauffer, R.B., Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications (1999) Chem. Rev., 99, pp. 2293-2352
Botta, M., Avedano, S., Giovenzana, G.B., Relaxometric study of a series of Monoaqua Gd-III complexes of rigidified EGTA-Like chelators and their noncovalent interaction with human serum albumin (2011) Eur. J. Inorg. Chem., pp. 802-810
Avedano, S., Tei, L., Lombardi, A., Maximizing the relaxivity of HSA-bound gadolinium complexes by simultaneous optimization of rotation and water exchange (2007) Chem. Commun. (Camb), pp. 4726-4728
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 (2009) Chem. Commun. (Camb), pp. 6475-6477
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 (2009) Org. Biomol. Chem., 7, pp. 1120-1131
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 (2011) J. Am. Chem. Soc., 133, pp. 16346-16349
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 (1997) Invest Radiol., 32, pp. 741-747
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 (2002) Acad. Radiol., 9, pp. S491-S494
Gianolio, E., Cabella, C., Colombo Serra, S., B25716/1: a novel albumin-binding Gd-AAZTA MRI contrast agent with improved properties in tumor imaging (2014) J. Biol. Inorg. Chem., 19, pp. 715-726
Anelli, P.L., Brocchetta, M., Lattuada, L., 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 (2009) Org. Process Res. Dev., 13, pp. 739-746
Minazzi, P., Lattuada, L., Menegotto, I.G., Giovenzana, G.B., An enzymatic approach to bifunctional chelating agents (2014) Org. Biomol. Chem., 12, pp. 6915-6921
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 (1998) Synth. Commun., 28, pp. 109-117
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 (1999) J. Biol. Inorg. Chem., 4, pp. 766-774
Aime, S., Calabi, L., Cavallotti, C., [Gd-AAZTA](-): a new structural entry for an improved generation of MRI contrast agents (2004) Inorg. Chem., 43, pp. 7588-7590
Sherry, A.D., Caravan, P., Lenkinski, R.E., Primer on gadolinium chemistry (2009) J. Magn. Reson Imaging, 30, pp. 1240-1248
Werner, E.J., Datta, A., Jocher, C.J., Raymond, K.N., High-relaxivity MRI contrast agents: where coordination chemistry meets medical imaging (2008) Angew. Chem. Int. Ed. Engl., 47, pp. 8568-8580
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 (1999) J. Magn. Reson., 139, pp. 408-421
Curry, S., Lessons from the crystallographic analysis of small molecule binding to human serum albumin (2009) Drug Metab. Pharmacokinet., 24, pp. 342-357
Caravan, P., Parigi, G., Chasse, J.M., Albumin binding, relaxivity, and water exchange kinetics of the diastereoisomers of MS-325, a gadolinium(III)-based magnetic resonance angiography contrast agent (2007) Inorg. Chem., 46, pp. 6632-6639
de Haen, C., Anelli, P.L., Lorusso, V., Gadocoletic acid trisodium salt (b22956/1): a new blood pool magnetic resonance contrast agent with application in coronary angiography (2006) Invest Radiol., 41, pp. 279-291
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 (2003) Radiology, 227, pp. 802-808
Fasano, M., Curry, S., Terreno, E., The extraordinary ligand binding properties of human serum albumin (2005) IUBMB Life, 57, pp. 787-796
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 (1996) J. Biol. Inorg. Chem., 1, pp. 312-319
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 (2007) Chemistry, 13, pp. 5785-5797
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 (2013) Inorg. Chem., 52, pp. 8436-8450
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 (2005) J. Med. Chem., 48, pp. 3874-3877
Aime, S., Caravan, P., Biodistribution of gadolinium-based contrast agents, including gadolinium deposition (2009) J. Magn. Reson. Imaging, 30, pp. 1259-1267
Richardson, O.C., Bane, O., Scott, M.L., Gadofosveset-based biomarker of tissue albumin concentration: Technical validation in vitro and feasibility in vivo (2015) Magn. Reson. Med., 73, pp. 244-253
Laurent, S., Elst, L.V., Muller, R.N., Comparative study of the physicochemical properties of six clinical low molecular weight gadolinium contrast agents (2006) Contrast Media Mol. Imaging, 1, pp. 128-137
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 (2012) Chem. a Eur. J., 18, pp. 16426-16435
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 (2009) Chem. a Eur. J., 15, pp. 1696-1705
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 (2005) Angew. Chem. Int. Ed. Engl., 44, pp. 6766-6769
Manus, L.M., Mastarone, D.J., Waters, E.A., Gd(III)-nanodiamond conjugates for MRI contrast enhancement (2010) Nano Lett., 10, pp. 484-489
Song, Y., Kohlmeir, E.K., Meade, T.J., Synthesis of multimeric MR contrast agents for cellular imaging (2008) J. Am. Chem. Soc., 130, pp. 6662-6663
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 (2008) J. Am. Chem. Soc., 130, pp. 2546-2552
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 (2007) Inorg. Chem., 46, pp. 3576-3584
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 (2006) Invest Radiol., 41, pp. 229-243
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 (2007) Clin. Cancer Res., 13, pp. 3449-3459
Longo, D.L., Dastru, W., Consolino, L., Cluster analysis of quantitative parametric maps from DCE-MRI: application in evaluating heterogeneity of tumor response to antiangiogenic treatment (2015) Magn. Reson Imaging, 33, pp. 725-736
Gugliotta, G., Botta, M., Tei, L., AAZTA-based bifunctional chelating agents for the synthesis of multimeric/dendrimeric MRI contrast agents (2010) Org. Biomol. Chem., 8, pp. 4569-4574
Lim, J., Turkbey, B., Bernardo, M., Gadolinium MRI contrast agents based on triazine dendrimers: relaxivity and in vivo pharmacokinetics (2012) Bioconjug. Chem., 23, pp. 2291-2299
Zhu, W., Artemov, D., Biocompatible blood pool MRI contrast agents based on hyaluronan (2011) Contrast Media Mol. Imaging, 6, pp. 61-68
Boschi, F., Marzola, P., Sandri, M., Tumor microvasculature observed using different contrast agents: a comparison between Gd-DTPA-albumin and B-22956/1 in an experimental model of mammary carcinoma (2008) MAGMA, 21, pp. 169-176
Bandini, S., Curcio, C., Macagno, M., Early onset and enhanced growth of autochthonous mammary carcinomas in C3-deficient Her2/neu transgenic mice (2013) Oncoimmunology, 2, p. e26137
Schmid, A., Schmitz, J., Mannheim, J.G., Feasibility of sequential PET/MRI using a state-of-the-art small animal PET and a 1 T benchtop MRI (2013) Mol. Imaging Biol., 15, pp. 155-165
Gd-AAZTA-MADEC, an improved blood pool agent for DCE-MRI studies on mice on 1 T scanners