Towards Targeted MRI: New MRI Contrast Agents for Sialic Acid Detection

The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L1 and L2) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consis...

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Published in:	Chemistry : a European journal Vol. 10; no. 20; pp. 5205 - 5217
Main Authors:	Frullano, Luca, Rohovec, Jan, Aime, Silvio, Maschmeyer, Thomas, Prata, M. Isabel, de Lima, J. J. Pedroso, Geraldes, Carlos F. G. C., Peters, Joop A.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 11.10.2004 WILEY‐VCH Verlag Wiley
Subjects:	borates Boronic Acids - chemistry carbohydrates Carbohydrates - chemistry Cations - chemistry Chemistry Chemistry, Multidisciplinary Contrast Media - analysis Contrast Media - chemistry drug design Gadolinium - chemistry Hydrogen-Ion Concentration lanthanides Ligands magnetic resonance imaging Magnetic Resonance Imaging - methods Molecular Structure N-Acetylneuraminic Acid - analysis N-Acetylneuraminic Acid - chemistry Pentetic Acid - chemistry Physical Sciences Science & Technology Temperature Titrimetry Water carbohydrates magnetic resonance imaging AQUEOUS-SOLUTIONS DESIGN drug design borates COMPLEXES PARAMAGNETIC SOLUTIONS lanthanides NMR GLUCOSE CHEMISTRY SITES PROTON RELAXATION TIMES BINDING
ISSN:	0947-6539, 1521-3765
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Abstract	The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L1 and L2) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA‐bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd3+ complexes of these two ligands were evaluated. The relaxivity of the GdL1 complex has a significant second‐sphere contribution at pH values above the pKa of its phenylboronic acid moiety. The interaction of the Gd3+ complexes of L1 and L2 with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL2 with sialic acid has the higher conditional formation constant (50.43±4.61 M−1 at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes (153SmL1 and 153SmL2) with C6 glioma rat cells. 153SmL2 in particular is retained on the cell surface in significant amounts. Selective molecular recognition of N‐acetylneuraminic acid residues (Neu5Ac; see scheme) on cell walls was achieved by the lanthanide complexes of two DTPA‐bisamide ligands (L1 and L2). Both ligands were designed with boronate functions that recognize the diol group in the side chain of Neu5Ac, and positively charged functions that interact with the Neu5Ac carboxylate group.
AbstractList	The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L-1 and L-2) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA-bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd3+ complexes of these two ligands were evaluated. The relaxivity of the GdL1 complex has a significant second-sphere contribution at pH values above the pK(a) of its phenylboronic acid moiety. The interaction of the Gd3+ complexes of L-1 and L-2 with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL2 with sialic acid has the higher conditional formation constant (50.43 +/- 4.61 m(-1) at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes ((SmL1)-Sm-153 and (SmL2)-Sm-153) with C6 glioma rat cells. (SmL2)-Sm-153 in particular is retained on the cell surface in significant amounts. The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L1 and L2) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA‐bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd3+ complexes of these two ligands were evaluated. The relaxivity of the GdL1 complex has a significant second‐sphere contribution at pH values above the pKa of its phenylboronic acid moiety. The interaction of the Gd3+ complexes of L1 and L2 with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL2 with sialic acid has the higher conditional formation constant (50.43±4.61 M−1 at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes (153SmL1 and 153SmL2) with C6 glioma rat cells. 153SmL2 in particular is retained on the cell surface in significant amounts. Selective molecular recognition of N‐acetylneuraminic acid residues (Neu5Ac; see scheme) on cell walls was achieved by the lanthanide complexes of two DTPA‐bisamide ligands (L1 and L2). Both ligands were designed with boronate functions that recognize the diol group in the side chain of Neu5Ac, and positively charged functions that interact with the Neu5Ac carboxylate group. The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L1 and L2) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA-bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd3+ complexes of these two ligands were evaluated. The relaxivity of the GdL1 complex has a significant second-sphere contribution at pH values above the pKa of its phenylboronic acid moiety. The interaction of the Gd3+ complexes of L1 and L2 with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL2 with sialic acid has the higher conditional formation constant (50.43+/-4.61 M(-1) at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes (153SmL1 and 153SmL2) with C6 glioma rat cells. 153SmL2 in particular is retained on the cell surface in significant amounts.The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L1 and L2) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA-bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd3+ complexes of these two ligands were evaluated. The relaxivity of the GdL1 complex has a significant second-sphere contribution at pH values above the pKa of its phenylboronic acid moiety. The interaction of the Gd3+ complexes of L1 and L2 with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL2 with sialic acid has the higher conditional formation constant (50.43+/-4.61 M(-1) at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes (153SmL1 and 153SmL2) with C6 glioma rat cells. 153SmL2 in particular is retained on the cell surface in significant amounts. The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L 1 and L 2 ) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA‐bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd 3+ complexes of these two ligands were evaluated. The relaxivity of the GdL 1 complex has a significant second‐sphere contribution at pH values above the p K a of its phenylboronic acid moiety. The interaction of the Gd 3+ complexes of L 1 and L 2 with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL 2 with sialic acid has the higher conditional formation constant (50.43±4.61 M −1 at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes ( 153 SmL 1 and 153 SmL 2 ) with C6 glioma rat cells. 153 SmL 2 in particular is retained on the cell surface in significant amounts. The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L1 and L2) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA-bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd3+ complexes of these two ligands were evaluated. The relaxivity of the GdL1 complex has a significant second-sphere contribution at pH values above the pKa of its phenylboronic acid moiety. The interaction of the Gd3+ complexes of L1 and L2 with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL2 with sialic acid has the higher conditional formation constant (50.43+/-4.61 M(-1) at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes (153SmL1 and 153SmL2) with C6 glioma rat cells. 153SmL2 in particular is retained on the cell surface in significant amounts.
Author	de Lima, J. J. Pedroso Frullano, Luca Maschmeyer, Thomas Prata, M. Isabel Peters, Joop A. Geraldes, Carlos F. G. C. Rohovec, Jan Aime, Silvio
Author_xml	– sequence: 1 givenname: Luca surname: Frullano fullname: Frullano, Luca organization: Laboratory of Applied Organic Chemistry and Catalysis, Julianalaan 136, 2628 BL Delft, The Netherlands, Fax: (+31) 15-278-4289 – sequence: 2 givenname: Jan surname: Rohovec fullname: Rohovec, Jan organization: Department of Chemistry, Universita Karlova, 12840 Prague, Czech Republic – sequence: 3 givenname: Silvio surname: Aime fullname: Aime, Silvio organization: Dipartimento di Chimica I.F.M. Università di Torino, 10125 Torino, Italy – sequence: 4 givenname: Thomas surname: Maschmeyer fullname: Maschmeyer, Thomas organization: Laboratory of Applied Organic Chemistry and Catalysis, Julianalaan 136, 2628 BL Delft, The Netherlands, Fax: (+31) 15-278-4289 – sequence: 5 givenname: M. Isabel surname: Prata fullname: Prata, M. Isabel organization: Department of Biophysics of the Faculty of Medicine, University of Coimbra, 3000 Coimbra, Portugal – sequence: 6 givenname: J. J. Pedroso surname: de Lima fullname: de Lima, J. J. Pedroso organization: Department of Biophysics of the Faculty of Medicine, University of Coimbra, 3000 Coimbra, Portugal – sequence: 7 givenname: Carlos F. G. C. surname: Geraldes fullname: Geraldes, Carlos F. G. C. organization: Departamento de Ciências e Tecnologica e Centro Neurociências, Universidade de Coimbra, 3049 Coimbra, Portugal – sequence: 8 givenname: Joop A. surname: Peters fullname: Peters, Joop A. email: j.a.peters@tnw.tudelft.nl organization: Laboratory of Applied Organic Chemistry and Catalysis, Julianalaan 136, 2628 BL Delft, The Netherlands, Fax: (+31) 15-278-4289
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Keywords	carbohydrates magnetic resonance imaging AQUEOUS-SOLUTIONS DESIGN drug design borates COMPLEXES PARAMAGNETIC SOLUTIONS lanthanides NMR GLUCOSE CHEMISTRY SITES PROTON RELAXATION TIMES BINDING
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Snippet	The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new...
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SubjectTerms	borates Boronic Acids - chemistry carbohydrates Carbohydrates - chemistry Cations - chemistry Chemistry Chemistry, Multidisciplinary Contrast Media - analysis Contrast Media - chemistry drug design Gadolinium - chemistry Hydrogen-Ion Concentration lanthanides Ligands magnetic resonance imaging Magnetic Resonance Imaging - methods Molecular Structure N-Acetylneuraminic Acid - analysis N-Acetylneuraminic Acid - chemistry Pentetic Acid - chemistry Physical Sciences Science & Technology Temperature Titrimetry Water
Title	Towards Targeted MRI: New MRI Contrast Agents for Sialic Acid Detection
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