Molecular recognition of sugars by lanthanide (III) complexes of a conjugate of N,N-bis[2-[bis[2-(1, 1-dimethylethoxy)-2-oxoethyl]amino]ethyl]glycine and phenylboronic acid

Contrast Media and Molecular Imaging

Volumn 2, Issue 4, 2007, Pages 163-171

  Battistini, Elisa ^a,b   Mortillaro, Armando ^a,b   Aime, Silvio ^b   Peters, Joop A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UNIVERSITY OF TURIN   (Italy)

Author keywords

Carbohydrates; Diabetes; MRI contrast agents; Phenylboronic acid

Indexed keywords

BENZENEBORONIC ACID; CONTRAST MEDIUM; GADOLINIUM PENTETATE; HUMAN SERUM ALBUMIN; LANTHANIDE N,N BIS[2 [BIS[2 (1,1 DIMETHYLETHOXY) 2 OXOETHYL]AMINO]ETHYL]GLYCINE; SUGAR; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; BORON 11 NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; OXYGEN 17 NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

BORONIC ACIDS; CARBOHYDRATES; CONTRAST MEDIA; FRUCTOSAMINE; GADOLINIUM; GADOLINIUM DTPA; GLUCOSE; HUMANS; LANTHANOID SERIES ELEMENTS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; PENTETIC ACID; SERUM ALBUMIN;

EID: 35148842024     PISSN: 15554309     EISSN: 15554317     Source Type: Journal    
DOI: 10.1002/cmmi.141     Document Type: Article

References (35)

1. Merbach AE, Tóth É. The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging. Wiley: Chichester, 2001.
2. Caravan P, Ellison JJ, McMurry TJ, Laufer RB. Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications. Chem. Rev. 1999; 99: 2293-2352.
3. Jacques V, Desreux JF. New classes of MRI contrast agents. Top. Curr. Chem. 2002; 221: 123-164.
4. Weissleder R, Mahmood U. Molecular imaging. Radiology 2001; 219: 316-333.
5. Davis AP, Wareham RS. Carbohydrate recognition through noncovalent interactions: a challenge for biomimetic and supramolecular chemistry. Angew. Chem., Int. Edn Engl. 1999; 38: 2979-2996.
6. Haseley SR. Carbohydrate recognition: a nascent technology for the detection of bioanalytes. Anal. Chim. Acta 2002; 457: 39-45.
7. James TD, Shinkal S. Artificial receptors as chemosensors for carbohydrates. Top. Curr. Chem. 2002; 218: 159-200.
8. Böeseken J, Rossem A van. Configuration of ring systems. Recl. Trav. Chim. Pay-Bas 1912; 30: 392-406.
9. Böeseken J. Position in space of the hydroxyl groups of polyhydroxy compounds. Configuration of the saturated glycols and of the α- and β-glucoses. Berichte der Deutschen Chemische Gesellschaft 1914; 46: 2612-2628.
10. Kuivila HG, Keough AH, Soboczenski EJ. Areneboronates from diols and polyols. J. Org. Chem. 1954; 19: 780-783.
11. 11B NMR. Tetrahedron 1984; 40: 2901-2911.
12. Edwards JO, Sederstrom RJ. The thermodynamics of ionization of benzeneboronic acid. Phys. Chem. 1961; 65: 862-863.
13. Burgemeister T, Grobe-Einsler R, Grotstollen R, Mannschreck A, Wulff G. On the chemistry of binding sites. Part I. Fast thermal breaking and formation of a B-N bond in 2-(aminomethyl) benzeneboronates. Chem. Ber. 1981; 114: 3403-3411.
14. Mulla HR, Agard RJ, Basu A. 3-Methoxycarbonyl-5-nitrophenyl boronic acid: high affinity diol recognition at neutral pH. Bioorg. Med. Chem. Lett. 2004; 14: 25-27.
15. Aime S, Botta M, Dastrú W, Fasano M, Panero M. Synthesis and characterization of a novel DTPA-like gadolinium(III) complex: a potential reagent for the determination of glycated proteins by water proton NMR relaxation measurements. Inorg. Chem. 1993; 32: 2068-2071.
16. Zhang S, Trokowski R, Sherry AD. A paramagnetic CEST agent for imaging glucose by MRI. J. Am. Chem. Soc. 2003; 125: 15288-15289.
17. Frullano L, Robovec J, Aime S, Maschmeyer T, Prata MI, Pedroso de Lima JJ, Geraldes CFGC, Peters JA. Towards targeted MRI: new MRI contrast agents for sialic acid detection. Chem. Eur. J. 2004; 10: 5205-5217.
18. Djanashvili K, Frullano L, Peters JA. Molecular recognition of sialic acid end groups by phenylboronates. Chem. Eur. J. 2005; 11: 4010-4018.
19. 160Tb complexes for molecular recognition of glycoproteins expressed on tumor cells. Contrast Media Mol. Imaging 2007; 2: 35-41.
20. Anelli PL, Fedeli F, Gazzotti O, Lattuada L, Lux G, Rebasti F. L-Glutamic acid and L-lysine as useful building blocks for the preparation of bifunctional DTPA-like ligands. Bioconj. Chem. 1999; 10: 137-140.
21. Barge A, Cravotto G, Gianolio E, Fedeli F. How to determine free Gd and free ligand in solution of Gd chelates. A technical note. Contrast. Med. Mol. Imag. 2006; 1: 184-186.
22. 13C NMR spectroscopy. Carbohydr. Res. 1994; 253: 1-12.
23. Wit G de. PhD Thesis, Delft University of Technology, Delft, 1979.
24. C-C coupling constants as a structural probe. J. Am. Chem. Soc. 1995; 117: 1479-1484.
25. Bielecki M, Eggert H, Norrild JC. A fluorescent glucose sensor binding covalently to all five hydroxy groups of α-D-glucofuranose. A reinvestigation. J. Chem. Soc. Perkin 1: 1999; 449.
26. Mapple SR, Allerhand A. Detailed tautomeric equilibrium of aqueous D-glucose. Observation of six tautomers by ultrahigh resolution carbon-13 NMR. J. Am. Chem. Soc. 1987; 109: 3168-3169.
27. 11B NMR spectroscopy. Carbohydr. Lett. 1995; 1: 223-230.
28. Rohovec J, Maschmeyer T, Aime S, Peters JA. The structure of the sugar residue in glycated human serum albumin and its molecular recognition by phenylboronate. Chem. Eur. J. 2003; 9: 2193-2199.
29. Botta M. Second coordination sphere water molecules and relaxivity of gadolinium(III) complexes: implications for MRI contrast agents. Eur. J. Inorg. Chem. 2000; 399-407.
30. Solomon I. Relaxation processes in a system of two spins. Phys. Rev. 1955; 99: 559-565.
31. Bloembergen N. Proton relaxation times in paramagnetic solutions. J. Chem. Phys. 1957; 27: 572-573.
32. Bloembergen N, Morgan LO. Proton relaxation times in paramagnetic solutions. Effects of electron spin relaxation. J. Chem. Phys. 1961; 34: 842-850.
33. 1 processes. J. Chem. Phys. 1978; 68: 4034-4037.
34. Swift TJ, Connick RE. NMR (nuclear magnetic resonance)-relaxation mechanisms of O17 in aqueous solutions of paramagnetic cations and the lifetime of water molecules in the first coordination sphere. J. Chem. Phys. 1962; 37: 307-320.
35. 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.