Synthesis and in vitro studies of Gd-DTPA derivatives as new potential MRI contrast agents

Tetrahedron Letters

Volumn 51, Issue 18, 2010, Pages 2431-2433

  Sankar, Arigala Uma Ravi ^a,b   Yamasitha, Mitsuji ^a   Srinivasulu, Kambam ^a,b   Ozaki, Nobuhisa ^a   Aoki, Takashi ^a   Fujie, Michio ^a,c   Ogawa, Keisuke ^a   Okada, Shingo ^a   Yamada, Manubu ^a   Tanaka, Yasutaka ^a   Kimura, Motohiko ^a   Toda, Mitsuo ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b Japan Association for the Advancement of Medical Equipment   (Japan)

^c HAMAMATSU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Dendritic ligands; Gd complexes; MRI contrast agents; T1 and r1 values

Indexed keywords

GADOLINIUM PENTETATE; NUCLEAR MAGNETIC RESONANCE IMAGING AGENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77950019636     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.138     Document Type: Article

References (15)

1. Lauffer R.B. Chem. Rev. 87 (1987) 901-927
2. Tweedle M.F. In: Bunzli J.C.G., and Choppin G.R. (Eds). Lanthanide Probes in Life, Chemical, and Earth Sciences (1989), Elsevier, Amsterdam Chapter 5
3. Caravan P., McMurry J.J., and Lauffer R.B. Chem. Rev. 99 (1999) 2293
4. Kabalka G.W., Davis M.A., Moss T.H., Buonocore E., Hubner K., Holmberg E., Maruyama K., and Haung L. Magn. Reson. Med. 19 (1991) 406
5. Takahashi M., Hara Y., Aoshima K., Kurihara H., Oshikawa T., and Yamasitha M. Tetrahedron Lett. 41 (2000) 8485
6. Blish S.W.A., Chowdhury A.H.M.S., Mcpartlin M., Scowen T.J., and Bulman R.A. Polyhedron 14 (1995) 567
7. -.
8. 2O (1.2 g, 3.2 mmol) was added slowly and the reaction was kept at 60 °C and stirred for 24 h. After completion of the reaction water was removed under vacuum and the crude product was dissolved in water and the excess of Gd(III) was removed by using Chelex® resign and checked by use of xylenol orange indicator. After removal of excess Gd(III) the resin was filtered off and under reduced pressure the solvent was removed by rotary-evaporator, dried to obtain pure compound 1a with 90% Yield. MALDI-TOF MS: m/z (%) = 802 (100).
9. Kawa M., and Frechet J.M. J. Chem. Mater. 10 (1998) 286
10. Newkome G.R., Guther R., Moorefield C.N., Cardullo F., Echegoyen L., Perez-Cordero E., and Luftmann H. Angew. Chem., Int. Ed. Engl. 34 (1995) 2023
11. Konings M.S., Dow W.C., Love D.W., Raymond K.N., Quay S.C., and Rocklage S.M. Inorg. Chem. 29 (1990) 1488
12. Lee Y.C., and Lee R.T. Acc. Chem. Res. 28 (1995) 321
13. Zanini D., and Roy R. J. Am. Chem. Soc. 119 (1997) 2088
14. Ozaki N., Sankar A.U.R., Yamasitha M., Aoki T., Tanaka Y., Kimura M., Fujie M., Takehara Y., and Takahara H. Bioorg. Med. Chem. Lett. 20 (2010) 932
15. Formation of 1:1 Gd(III) complex was deduced on the basis of titration experiment, where 0.5, 1.0, or 10.0 equiv of Gd(III) was added relative to the ligands upon complexation.