A gadolinium triacetic monoamide DOTA derivative with a methanethiosulfonate anchor group. Relaxivity properties and conjugation with albumin and thiolated particles

Contrast Media and Molecular Imaging

Volumn 2, Issue 1, 2007, Pages 24-34

  Thonon, David ^a   Jacques, Vincent ^a   Desreux, Jean F ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

Albumin; Disulfide link; Methanethiosulfonate; Nuclear magnetic relaxation dispersion; Relaxivity; Thiolated silica particles; Water exchange

Indexed keywords

(2 AMINOETHYL)METHANESULFONOTHIOATE; 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; 2 (2 BROMOACETAMIDO)ETHYLMETHANESULFONOTHIOATE; 2,2',2'' [10 [2 [2 (METHYLSULFONYLTHIO)ETHYLAMINO] 2 OXOETHYL] 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7 TRIYL]TRIACETIC ACID; ALBUMIN; BOVINE SERUM ALBUMIN; CONTRAST MEDIUM; DISULFIDE; GADOLINIUM; NANOPARTICLE; OXYGEN 17; SILICON DIOXIDE; TRI TERT BUTYL 2,2',2'' [10 [2 [2 (METHYLSULFONYLTHIO)ETHYLAMINO] 2 OXOETHYL] 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7 TRIYL]TRIACETATE; UNCLASSIFIED DRUG; ALBUMINOID; CROSS LINKING REAGENT; DIAGNOSTIC AGENT; GADOLINIUM 1,4,7,10-TETRAAZACYCLODODECANE-N,N',N'',N'''-TETRAACETATE; GADOTERIC ACID; HETEROCYCLIC COMPOUND; MESYLIC ACID DERIVATIVE; METHANETHIOSULFONATE; ORGANOMETALLIC COMPOUND; THIOL DERIVATIVE;

ARTICLE; CHEMICAL BOND; COVALENT BOND; DRUG CONJUGATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE ANALYSIS; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; PARTICLE SIZE; PRIORITY JOURNAL; STRUCTURE ANALYSIS; CHEMISTRY; EVALUATION; IMAGE ENHANCEMENT; MAGNETISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALBUMINS; CONTRAST MEDIA; CROSS-LINKING REAGENTS; HETEROCYCLIC COMPOUNDS; IMAGE ENHANCEMENT; MAGNETIC RESONANCE IMAGING; MAGNETIC RESONANCE SPECTROSCOPY; MAGNETICS; MESYLATES; ORGANOMETALLIC COMPOUNDS; PARTICLE SIZE; SULFHYDRYL COMPOUNDS;

EID: 34147123210     PISSN: 15554309     EISSN: 15554317     Source Type: Journal    
DOI: 10.1002/cmmi.121     Document Type: Article

References (49)

1. Caravan P, Ellison JJ, McMurry TJ, Lauffer RB. Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications. Chem. Rev. 1999; 99: 2293-2352.
2. Toth E, Helm L, Merbach AE. Relaxivity of MRI agents. In Topics in Current Chemistry 222, Contrast Agents I, Werner K (ed.) Springer: Berlin. 2002; 62-101
3. Lu Z-R. POly(L-glutamic acid) Gd(III)-DOTA conjugate with a degradable spacer for megnetic resonance imaging. Bioconjugate Chem. 2003; 14: 715-719.
4. Aime S, Botta M, Fasano M, Crich SG, 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.
5. Aime S, Botta M, Crich SG, Giovenzana GB, Pagliari R, Piccinini M, Sisti M, Terreno E. Towards MRI contrast agents of improved efficacy. NMR relaxometric investigations of the binding interaction to HSA of a novel heptadentate macrocyclic triphosphonate Gd(III) complex. J. Biol. Inorg. Chem. 1997; 2: 470-479.
6. Caravan P, Cloutier NJ, Greenfield MT, McDermid SA, Dunham SU, Bulte JWM, Amedio JCJ, Looby Rl, Supkowski RM, Horrocks WD, Jr., McMurry TJ, Lauffer RB. The interaction of MS-325 with human serum albumin and its effect on proton relaxation rates. J. Am. Chem. Soc. 2002; 124: 3152-3162.
7. Zong Y, Guo J, Ke T, Mohs AM, Parker DL, Lu Z-R. Effect of size and charge on pharmacokinetics and in vivo MRI contrast enhancement of biodegradable polydisulfide Gd(III) complexes. J. Control. Release 2006; 112: 350-356.
8. Raghunand N, Jagadish B, Trouard TP, Galons J-P.Gillies RJ, Mash EA. Redox-sensitive contrast agents for MR1 based on reversible hinding of thiols to serum albumin. Magn. Reson. Med. 2006; 55: 1272-1280.
9. Mattila K, Siltainsuu J, Balaspiri L, Ora M, L6nnberg H. Derivatization of phosphopeptides with mercapto- and amino-functionalized conjugate groups by phosphate elimination and subsequent Michael addition. Org. Biol. Chem. 2005; 3: 3039-3044.
10. Bruice TW, Kenyon GL. Novel alkyl alkanethiolsuphonate sulfhydryl reagents. modification of derivatives Of L-Cysteine. J. Protein Chem. 1982; 1: 47-58.
11. Kenyon GL, Bruice TW. Novel sulfhydryl reagents. Meth.Enzymol. (Enzyme Struct. Part E) 1977; 47: 407-430.
12. Toth E, Burai L, Brücher E, Merbach AE, Paight ES. Tuning water-exchange rates on (carboxymethyl)iminobis(ethylenenitrilo) tetracetate (DTPA)-type gadolinium(III) complexes. J. Chem. Soc. Dalton Trans. 1997; 1587-1594
13. Schultze LM, Bulls AR. Polyazacycloalkane Compounds. US Patent 56313681997; 1-8.
14. Wilson JM, Wu D, Motiu-DeGrood R, Hupe DJ. A spectrophotometric method for studying the rates of reaction of disulfides with protein thiol groups applied to bovine serum albumin. J. Am. Chem. Soc. 1980; 102: 359-363.
15. Lowry OH, Rosebrough JJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951; 193: 265-275.
16. Hirayama K, Akashi S, Furuya M, Fukuhara K. Rapid confirmation and revision of the primary structure of bovine serum albumin by ESIMS and Frit-FAB LC/MS. Biochem. Biophys. Res. Commun. 1990; 173: 639-646.
17. Janatova J, Fuller JK, Hunter MJ. The Heterogeneity of bovine albumin with respect to sulhydryl and dimer content. J. Biol. Chem. 1968; 243: 3612-3622.
18. Wong SY, Guile GR, Dwek RA, Arsequell G. Synthetic glycosylation of proteins using N-(β-saccharide) iodoacetamides: applications in site-specific glycosylation and solid-phase enzymic oligosaccharide synthesis. Biochem. J. 1994; 300: 843-850.
19. Ellman GL. Tissue suffhydryl groups. Arch. Biochem. Biophys. 1959; 82: 70-77.
20. Allen LH, Matijevic E. Stability of colloidal silica. I. Effect of simple electrolytes. J. Colloid Interface Sci. 1969; 31: 287-296.
21. Kowalewski J, Kruk D, Parigi G. NMR relaxation in solution of paramagnetic complexes: recent theoretical progress for S > 1. Adv. Inorg. Chem. 2005; 57: 42-104.
22. Banci L, Bertini I, Luchinat C. Nuclear and Electron Relaxation. VCH: Weinheim, 1991.
23. van Eldik R, Bertini I. Relaxometry of water-metal ion interactions. Adv. Inorg. Chem. 2005; 57: 1-479.
24. Merbach AE, Toth E. The Chemistry of Contrast Agents in Medical Magnetic Resonance Intaging. Wiley: Chichester, 2001.
25. 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. 21999; 493-503.
26. Botta M, Quici S, Pozzi G, Marzanni G, Pagliarin R, Barra S, Crich SG. NMR relaxometric study of new GdIII macrocyclic complexes and their interaction with human serum albumin. Org. Biol. Chem. 2004; 2: 570-577.
27. 17 in aqueous solutions of paramagnetic cations and the lifetime of water molecules in the first coordination sphere. J. Chem. Phys. 1962; 37: 307-320.
28. Paris J, Gameiro C, Humblet V, Mohapatra PK, Jacques V, Desreux JF. Auto-assembling of ditopic macrocyclic lanthanide chelates with transition metal ions. rigid multimetallic high relaxivity contrast agents for magnetic resonance imaging. Inorg. Chem. 2006; 1.
29. Vander Elst L, Sessoye A, Laurent S, Muller RN. Can the theoretical fitting of the proton-nuclear-magnetic-relaxation-dispersion (proton NMRD) curves of paramagnetic complexes be improved by independent measurement of their self-diffusion coefficients? Helv. Chim. Acta 2005; 88: 574-587.
30. 3+ complexes of interest in magnetic resonance imaging: an integrated and theoretically self-consistent approach. J. Am. Chem. Soc. 1996; 118: 9333-9346.
31. Terreno E, Boniforte P, Botta M, Fedeli F, Milone L, Mortillaro A, Aime S. The water-exchange rate in neutral heptadentate DO3A-like GdIII complexes: effect of the basicity at the macrocyclic nitrogen site. Eur. J. Inorg. Chem. 2003; 3530-3533
32. Bertini I, Galas O, Luchinat C, Parigi G. A computer program for the calculation of paramagnetic enhancements of nuclear-relaxation rates in slowly rotating systems. J. Magn. Reson. A 1995; 113: 151-158.
33. Anelli PL, Bertini I, Fragai M, Lattuada L, Luchinat C, Parigi G. Suffonamide-functionalized gadolinium, DTPA complexes as possible contrast agents for MRI: a relaxometric investigation. Eur. J. Inorg. Chem. 2000; 625-630.
34. Bligh SWA, Chowdhury AHMS, Kennedy D, Luchinat C, Parigi G. Non-ionic bulky Gd(III) DPTA-bisamide complexes as potential contrast agents for magnetic resonance imaging. Magn. Reson. Med. 1999; 41: 767-773.
35. 1H NMR and EPR simultaneous analysis. J. Am. Chem. Soc. 2002; 124: 2042-2048.
36. III chelates. Chem. Eur. J. 2001; 7: 5262-5269.
37. Kruk D, Nilsson T, Kowalewski J. Nuclear spin relaxation in paramagnetic systems with zero-field splitting and arbitrary electron spin. Phys. Chem. Chem. Phys. 2001; 3: 4907-4917.
38. Zhang Z, Greenfield MT, Spiller M, McMurry TJ, Lauffer RB, Caravan P. Multilocus binding increases the relaxivity of protein-bound MRI contrast agents. Angew. Chem., Int. Edn Engl. 2005; 44: 6766-6769.
39. Schaefle N, Sharp R. Electron spin relaxation due to reorientation of a permanent zero field splitting tensor. J. Chem. Phys. 2004; 121: 5387-5394.
40. Kruk D, Kowalewski J. Nuclear spin relaxation in paramagnetic systems systems (S > 1) under fast rotation conditions. J. Magn. Reson. 2003; 162: 229-240.
41. Wilhelm C, Billotey C, Roger J, Pons JN, Bacri J-C, Gazeau F. Intracellular uptake of anionic superparamagnetic nanoparticles as a function of their surface coating. Biomaterials 2003; 24: 1001-1011.
42. Cleland WW. Dithiothreitol, a new protective agent for SH groups. Biochemistry 1964; 3: 480-482.
43. Barra PB, Sasa K, Ueki T, Takeda K. Ciruclar dichroism study of the conformational stability of sulfhydryl-blocked bovine serum albumin. Int. J. Biochem. 1989; 21: 857-862.
44. Meister A, Anderson ME. Glutathione. A. Rev. Biochem. 2006; 52: 655-709.
45. Vina J, Sastre J, Asensi M, Packer L. Asssay of blood glutathione oxidation during physical exercise. Meth. Enzymol. 1995; 237-243.
46. Prudencio M, Rohovec J, Peters JA, Tocheva E, Boulanger MJ, Murphy MEP, Huokes HJ, Mosters W, Impagliazzo A, Ubbink M. A caged lanthanide complex as a paramagnetic shift agent for protein NMR. Chem. Eur J. 2004; 10: 3252-3260.
47. Ge P, Selvin PR. Thiol-reactive luminescent lanthanide chelates. Part 2. Bioconjug. Chem. 2003; 14: 870-876.
48. Moran JK, Greiner DP, Meares CF. Improved synthesis of 6-p(bromoacetamido)benzyll-1,4,8,11-tetraazacyclotetradecane- N,N′,N″,-tetraacetic acid and development of a thin-layer assay for thiol-reactive bifunctional chelating agents. Bioconjug. Chem. 1995; 6: 296-301.
49. Karlin A, Akabas MH. Substituted-cysteine accessibility method. Meth. Enzymol. 1998; 293: 123-145.