Bifunctional Gd(III) and Tb(III) chelates based on a pyridine-bis(iminodiacetate) platform, suitable contrast agents for magnetic resonance and optical imaging - 2014
Bifunctional Gd(III) and Tb(III) chelates based on a pyridine-bis(iminodiacetate) platform, suitable contrast agents for magnetic resonance and optical imaging
CMMI - Centre de Recherche en Microscopie et Imagerie Médicale
Disciplines :
Chemistry
Author, co-author :
Laurent, Sophie ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Vander Elst, Luce ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Galaup, C.
Leygue, N.
Boutry, Sébastien ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Picard, C.
Muller, Robert ; Université de Mons > Faculté de Médecine et de Pharmacie > FMP - Service du Doyen
Language :
English
Title :
Bifunctional Gd(III) and Tb(III) chelates based on a pyridine-bis(iminodiacetate) platform, suitable contrast agents for magnetic resonance and optical imaging
Publication date :
01 January 2014
Journal title :
Contrast Media and Molecular Imaging
ISSN :
1555-4309
eISSN :
1555-4317
Publisher :
John Wiley & Sons, Hoboken, United States - New Jersey
Volume :
9
Pages :
300-312
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
M108 - Chimie générale, organique et biomédicale
Research institute :
R550 - Institut des Sciences et Technologies de la Santé R100 - Institut des Biosciences
Tóth E, Helm L, Merbach AE. Relaxivity of gadolinium(III) complexes: theory and mechanism. In The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Merbach AS, Helm L, Tóth E (eds). John Wiley & Sons: Chichester, 2013; 25-82.
Sammes PG, Yahioglu G. Modern bioassays using metal chelates as luminescent probes. Nat Prod Rep 1996;13:1-28.
Jacquier A, Higgins CB, Saeed M. MR imaging in assessing cardiovascular interventions and myocardial injury. Contrast Media Mol Imag 2007;2:1-15.
Bunzli J-CG. Lanthanide luminescence for biomedical analyses and imaging. Chem Rev 2010;110:2729-2755.
Chan KW-Y, Wong W-T. Small molecular gadolinium(III) complexes as MRI contrast agents for diagnostic imaging. Coord Chem Rev 2007;251:2428-2451.
Brunet E, Juanes O, Rodriguez-Ubis J-C. Supramolecularly organized lanthanide complexes for efficient metal excitation and luminescence as sensors in organic and biological applications. Curr Chem Biol 2007;1:11-39.
Laurent S, Vander Elst L, Wautier M, Galaup C, Muller RN, Picard C. In vitro characterization of the Gd complex of [2, 6-pyridinediylbis(methylene nitrilo)] tetraacetic acid (PMN-tetraacetic acid) and of its Eu analogue, suitable bimodal contrast agents for MRI and optical imaging. Bioorg Med Chem Lett 2007;17:6230-6233.
Chellquist EM, Searle R. An LC method for measuring complex formation equilibria by competitive chelation. J Pharm Biomed Anal 1993;11(10):985-992.
Wedeking P, Kumar K, Tweedle MF. Dissociation of gadolinium chelates in mice: relationship to chemical characteristics. Magn Reson Imag 1992;10:641-648.
Martikkala E, Lehmusto M, Lilja M, Rozwandowicz-Jansen A, Lunden J, Tomohiro T, Hänninen P, Petäjä-Repo U, Härmä H. Cell-based β2-adrenergic receptor-ligand binding assay using synthesized europium-labeled ligands and time-resolved fluorescence. Anal Biochem 2009;392:103-109.
Gunanathan C, Pais A, Furman-Haran E, Seger D, Eyal E, Mukhopadhyay S, Ben-David Y, Leitus G, Cohen H, Vilan A, Degani H, Milstein D. Water-soluble contrast agents targeted at the estrogen receptor for molecular magnetic resonance imaging. Bioconjug Chem 2007;18:1361-1365.
Féau C, Klein E, Kerth P, Lebeau L. Synthesis of a coumarin-based europium complex for bioanalyte labeling. Bioorg Med Chem Lett 2007;17:1499-1503.
Havas F, Leygue N, Danel M, Mestre B, Galaup C, Picard C. 6, 6'-Dimethyl-2, 2'-bipyridine-4-ester a pivotal synthon for building tethered bipyridine ligands. Tetrahedron 2009;65:7673-7686.
Maindron N, Poupart S, Hamon M, Langlois J-B, Plé N, Jean L, Romieu A, Renard P-Y. Synthesis and luminescence properties of new red-shifted absorption lanthanide(III) chelates suitable for peptide and protein labelling. Org Biomol Chem 2011;9:2357-2370.
Takalo H, Mukkala V-M, Meriö L, Rodriguez-Ubis J-C, Sedano R, Juanes O, Brunet E. Development of luminescent terbium(III) chelates for protein labelling: effect of triplet state energy level. Helv Chim Acta 1997;80:372-387.
Mukkala V-M, Sund C, Kwiatkowski M, Pasanen P, Högberg M, Kankare J, Takalo H. New heteroatomic complexing agents and luminescence of their europium(III) and terbium(III) chelates. Helv Chim Acta 1992;75:1621-1632.
Charier S, Ruel O, Baudin J-B, Alcor D, Allemand J-F, Meglio A, Jullien L, Valeur B. Photophysics of a series of efficient fluorescent pH probes for dual-emission-wavelength measurements in aqueous solutions. Chem Eur J 2006;12:1097-1113.
Autiéro H, Bazin H, Mathis G. Novel rare earth metal cryptates which are not very sensitive to the fluorescence quenching. PCT Int. Appl., WO 096877; Chem Abstr, 136:50664, 2001.
Feely WE, Beavers EM. Cyanation of amine oxide salts. A new synthesis of cyanopyridines. J Am Chem Soc 1959;81:4004-4007.
Liu P, Chen Y, Deng J, Tu Y. An efficient method for the preparation of benzylic bromides. Synthesis 2001;14:2078-2080.
Laumonier C, Segers J, Laurent S, Michel A, Coppée F, Belayew A, Vander Elst L, Muller RN. A New peptidic vector for molecular imaging of apoptosis, identified by phage display technology. J Biomol Screen 2006;11:537-545.
Solomon I. Relaxation processes in a system of two spins. Phys Rev 1955;99:559-565.
Bloembergen N. Proton relaxation times in paramagnetic solutions. J Chem Phys 1957;27:572-573.
Freed JH. Dynamic effects of pair correlation functions on spin relaxation by translational diffusion in liquids. II. Finite jumps and independent T1 processes. J Chem Phys 1978;68:4034-4037.
Vander Elst L, Raynal I, Port M, Tisnès P, Muller RN. In vitro relaxometric and luminescence characterization of P792 (Gadomelitol, Vistarem®), an efficient and rapid clearance blood pool MRI contrast agent. Eur J Inorg Chem 2005;6:1142-1148.
Laurent S, Vander Elst L, Muller RN. Comparative study of the physicochemical properties of six clinical low molecular weight gadolinium contrast agents. Contrast Media Mol Imag 2006;1:128-137.
Kang SI, Ranganathan RS, Emswiler JE, Kumar K, Gougoutas JZ, Malley MF, Tweedle MF. Synthesis, characterization, and crystal structure of the gadolinium(III) chelate of (1R, 4R, 7R)-α, α′, α′′-trimethyl-1, 4, 7, 10-tetraazacyclododecane-1, 4, 7-triacetic acid (DO3MA). Inorg Chem 1993;32:2912-2918.
Port M, Raynal I, Vander Elst L, Muller RN, Dioury F, Ferroud C, Guy A. Impact of rigidification on relaxometric properties of a tricyclic tetraazatriacetic gadolinium chelate. Contrast Med Mol Imag 2006;1:121-127.
Laurent S, Botteman F, Vander Elst L, Muller RN. Optimising the design of paramagnetic MRI contrast agents: influence of backbone substitution on the water exchange rate of Gd-DTPA derivatives. Magn Reson Mater Phys, Biol Med 2004;16:235-245.
Powell DH, Ni Dhubhghaill OM, Pubanz D, Helm L, Lebedev YS, Schlaepfer W, Merbach AE. Structural and dynamic parameters obtained from 17O NMR, EPR, and NMRD studies of monomeric and dimeric Gd3+ complexes of interest in magnetic resonance imaging: an integrated and theoretically self-consistent approach. J Am Chem Soc 1996;118:9333-9346.
Livramento JB, Sour A, Borel A, Merbach AE, Toth E. A Starburst-shaped heterometallic compound incorporating six densely packed Gd3+ ions. Chem Eur J 2006;12:989-1003.
Zhang S, Jiang X, Sherry AD. Modulation of the lifetime of water bound to lanthanide metal ions in complexes with ligands derived from 1, 4, 7, 10-tetraazacyclododecane tetraacetate (DOTA). Helv Chim Acta 2005;88:923-935.
Aime S, Botta M, Fasano M, Terreno E. Lanthanide(III) chelates for NMR biomedical applications. Chem Soc Rev 1998;27:19-29.
Laurent S, Henoumont C, Vander Elst L, Muller RN. Synthesis and physicochemical characterisation of Gd-DTPA derivatives as contrast agents for MRI. Eur J Inorg Chem 2012;12:1889-1915.
Laurent S, Vander Elst L, Henoumont C, Muller RN. How to measure the transmetallation of a gadolinium complex. Contrast Media Mol Imag 2010;5:305-308.
Jung K-H, Kim H-K, Lee GH, Kang D-S, Park J-A, Kim KM, Chang Y, Kim T-J. Gd complexes of macrocyclic diethylenetriaminepentaacetic acid (DTPA) biphenyl-2, 20-bisamides as strong blood-pool magnetic resonance imaging contrast agents. J Med Chem 2011;54:5385-5394.
Silvério S, Torres S, Martins AF, Martins JA, André JP, Helm L, Prata MIM, Santos AC, Geraldes CFGC. Lanthanide chelates of (bis)-hydroxymethyl-substituted DTTA with potential application as contrast agents in magnetic resonance imaging. Dalton Trans 2009;24:4656-4670.
Laurent S, Parac-Vogt TN, Kimpe K, Thirifays C, Binnemans K, Muller RN, Vander Elst L. Bis(phenylethylamide) derivatives of Gd-DTPA as potential receptor-specific MRI contrast agents. Eur J Inorg Chem 2007;14:2061-2067.
Richardson FS. Terbium(III) and europium(III) ions as luminescent probes and stains for biomolecular systems. Chem Rev 1982;82:541-552.
Sabbatini N, Guardigli M, Lehn J-M. Luminescent lanthanide complexes as photochemical supramolecular devices. Coord Chem Rev 1993;123:201-228.
Armelao L, Quici S, Barigelletti F, Accorsi G, Bottaro G, Cavazzini M, Tondello E. Design of luminescent lanthanide complexes: from molecules to highly efficient photo-emitting materials. Coord Chem Rev 2010;254:487-505.
Supkowski RM, Horrocks WDW Jr. On the determination of the number of water molecules, q, coordinated to europium(III) ions in solution from luminescence decay lifetimes. Inorg Chim Acta 2002;340:44-48.
Beeby A, Clarkson IM, Dickins RS, Faulkner S, Parker D, Royle L, de Sousa AS, Williams JAG, Woods M. Non-radiative deactivation of the excited states of europium, terbium and ytterbium complexes by proximate energy-matched OH, NH and CH oscillators: an improved luminescence method for establishing solution hydration states. J Chem Soc, Perkin Trans 2 1999;3:493-503.
Alpha B, Balzani V, Lehn J-M, Perathoner S, Sabbatini N. Luminescence probes: the Eu3+ and Tb3+cryptates of polypyridine macrobicyclic ligands. Angew Chem Int Ed Engl 1987;26:1266-1267.
Takalo H, Mukkala V-M, Mikola H, Liitti P, Hemmila I. Synthesis of europium(III) chelates suitable for labeling of bioactive molecules. Bioconjug Chem 1994;5:278-282.
Gutierrez F, Tedeschi C, Maron L, Daudey J-P, Poteau R, Azéma J, Tisnès P, Picard C. Quantum chemistry-based interpretations on the lowest triplet state of luminescent lanthanides complexes. Part 1. Relation between the triplet state energy of hydroxamate complexes and their luminescence properties. J Chem Soc Dalton Trans 2004;9:1334-1347.
De Bettencourt-Dias A. Small molecule luminescent lanthanide ion complexes - photophysical characterization and recent developments. Curr Org Chem 2007;11:1460-1480.
Werts MHV, Jukes RTF, Verhoeven JW. The emission spectrum and the radiative lifetime of Eu3+ in luminescent lanthanide complexes. Phys Chem Chem Phys 2002;4:1542-1548.
Nasso I. Complexes d'ions Ln(III) dérivés de ligands à motifs polyaminocarboxylique: synthèse, propriétés luminescentes (EuIII, TbIII) et relaxométriques (GdIII). PhD Thesis, Paul Sabatier University, France, 2006.
Bruce JI, Dickins RS, Govenlock LJ, Gunnlaugsson T, Lopinski S, Lowe MP, Parker D, Peacock RD, Perry JJB, Aime S, Botta M. The selectivity of reversible oxy-anion binding in aqueous solution at a chiral europium and terbium center: signaling of carbonate chelation by changes in the form and circular polarization of luminescence emission. J Am Chem Soc 2000;122:9674-9684.
Dickins RS, Aime S, Batsanov AS, Beeby A, Botta M, Bruce JI, Howard JAK, Love CS, Parker D, Peacock RD, Puschmann H. Structural, luminescence, and NMR studies of the reversible binding of acetate, lactate, citrate, and selected amino acids to chiral diaqua ytterbium, gadolinium, and europium complexes. J Am Chem Soc 2002;124:12697-12705.
Moriggi L, Cannizzo C, Prestinari C, Berrière F, Helm L. Physicochemical properties of the high-field MRI-relevant [Gd(DTTA-Me)(H2O)2]- complex. Inorg Chem 2008;47:8357-8366.
Aime S, Geninatti Crich S, Gianolio E, Giovenzana GB, Tei L, Terreno E. High sensitivity lanthanide(III) based probes for MR-medical imaging. Coord Chem Rev 2006;250:1562-1579
Vallet P. Relaxivity of nitroxide stable free radicals. Evaluation by field cycling method and optimisation, PhD Thesis, University of Mons-Hainaut, Belgium, 1992.
Laurent S, Vander Elst L, Copoix F, Muller RN. Stability of MRI paramagnetic contrast media a proton relaxometric protocol for transmetallation assessment. Invest Radiol 2001;36:115-122.
Nakamaru K. Synthesis, luminescence quantum yields and lifetimes of trischelated ruthenium(II) mixed-ligand complexes including 3, 3'-2, 2'bipyridyl. Bull Chem Soc Jpn 1982;55:2697-2705.
Meech SR, Phillips D. Photophysics of some common fluorescence standarts. J Photochem 1983;23:193-217.