Release of toxic Gd3+ ions to tumour cells by vitamin B12 bioconjugates

Chemistry - A European Journal

Volumn 15, Issue 32, 2009, Pages 7980-7989

  Siega, Patrizia ^a   Wuerges, Jochen ^a   Arena, Francesca ^b   Gianolio, Eliana ^b   Fedosov, Sergey N ^c   Dreos, Renata ^a   Geremia, Silvano ^a   Aime, Silvio ^b   Randaccio, Lucio ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

^b UNIVERSITY OF TURIN   (Italy)

^c AARHUS UNIVERSITY   (Denmark)

Author keywords

Bioinorganic chemistry; Cobalamines; Drug delivery; Drug design; Vitamins

Indexed keywords

AFFINITY BINDING; BIOCONJUGATES; BIOINORGANIC CHEMISTRY; CARBOXYLATE GROUPS; CELL VIABILITY; COBALAMINES; CRYSTALLISATION; CYTOTOXIC; DRUG DESIGN; GD-DTPA; GD3+ IONS; IN-CELL; IN-SITU; IN-VITRO; TIME-SCALES; TRANSPORT PROTEINS; TRIETHYLENETETRAMINE; TUMOUR CELLS; VITAMIN B;

ACIDS; AMINES; BIOCHEMISTRY; BIOMOLECULES; CARBOXYLATION; CELL MEMBRANES; CRYSTAL STRUCTURE; DRUG DELIVERY; ESTERIFICATION; ESTERS; HYDROLYSIS; IONS; NUTRITION; SULFUR COMPOUNDS; TOXIC MATERIALS; TUMORS; VITAMINS;

GADOLINIUM;

2 (4 IODOPHENYL) 3 (4 NITROPHENYL) 5 (2,4 DISULFOPHENYL) 2H TETRAZOLIUM; 2-(4-IODOPHENYL)-3-(4-NITROPHENYL)-5-(2,4-DISULFOPHENYL)-2H-TETRAZOLIUM; CATION; CYANOCOBALAMIN; DIAGNOSTIC AGENT; DRUG DERIVATIVE; GADOLINIUM; GADOLINIUM PENTETATE; GD DTPA CNCBL; GD TTHA CNCBL; GD-DTPA-CNCBL; GD-TTHA-CNCBL; ORGANOMETALLIC COMPOUND; TETRAZOLIUM; TRYPAN BLUE;

ARTICLE; CELL STRAIN K 562; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HUMAN; SYNTHESIS; TUMOR CELL CULTURE; X RAY CRYSTALLOGRAPHY;

CATIONS; CRYSTALLOGRAPHY, X-RAY; GADOLINIUM; GADOLINIUM DTPA; HUMANS; K562 CELLS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; TETRAZOLIUM SALTS; TRYPAN BLUE; TUMOR CELLS, CULTURED; VITAMIN B 12;

EID: 68349101066     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802680     Document Type: Article

References (32)

1. R. Banerjee, S. W. Ragsdale, Annu. Rev. Biochem. 2003, 72, 209247.
2. R. Waibel, H. Treichler, N. G. Schaefer, D. R. van Staveren, S. Mundwiler, S. Kunze, M. Küenzi, R. Alberto, J. Nüesch, A. Knuth, H. Moch, R. Schibli, P. A. Schubiger, Cancer Res. 2008, 68, 29042911.
3. R. Banerjee, ACS Chem. Biol. 2006, 2, 149-159.
4. M. Wolters, A. Strahle, A. Hahn, Prev. Med. 2004, 39, 1256-1266.
5. 12 (Ed.: R. Banerje), Wiley, New York, 1999, pp. 385-410.
6. G. Russell-Jones, K. McTavish, J. McEwan, J. Rice, D. Nowotnik, J. Inorg. Biochem. 2004, 98, 1625-1633.
7. G. R. McLean, P. M. Pathare, D. S. Wilbur, A. C. Morgan, S. V. Woodhouse, J. W. Schrader, H. J. Ziltener, Cancer Res. 1997, 57, 4015-4022.
8. D. A. Collins, H. P. C. Hogenkamp, J. Nucl. Med. 1997, 38, 717-723.
9. D. A. Collins, H. P. C. Hogenkamp, M. K. O'Connor, S. Naylor, L. M. Benson, T. J. Hardyman, L. M. Thorson, Mayo Clin. Proc. 2000, 75, 568-580.
10. C. C. Smeltzer, M. J. Cannon, P. R. Pinson, J. D. Munger, F. G. West, C. B. Grissom, Org. Lett. 2001, 3, 799-801.
11. J. M. McGreevy, M. J. Cannon, C. B. Grissom, J. Surg. Res. 2003, 111, 38-44.
12. J. D. Bagnato, A. L. Eilers, R. A. Horton, C. B. Grissom, J. Org. Chem. 2004, 69, 8987-8996.
13. T. Amagasaki, R. Green, D.W. Jacobsen, Blood 1990, 76, 13801386.
14. D. A. Collins, H. P. C. Hogenkamp, M. K. O'Connor, S. Naylor, L. M. Benson, T. J. Hardyman, L. M. Thorson, Mayo Clin. Proc. 2000, 75, 568-580.
15. D.A. Collins, H.P.C. Hogenkamp, M.W. Gebhard, Mayo Clin. Proc. 1999, 74, 687-691.
16. J. Wuerges, G. Garau, S. Geremia, S. N. Fedosov, T. E. Petersen, L. Randaccio, Proc Natl Acad Sci USA 2006, 103, 4386-4391.
17. J. Wuerges, S. Geremia, L. Randaccio, Biochem. J. 2007, 403, 431440.
18. J. Reubi, J. C. Schaer, B. Waser, S. Wenger, A. Heppeler, J. S. Schmitt, H. R. Maecke, Eur. J. Nucl. Med. Mol. Imaging 2000, 27, 273-282.
19. J. Wuerges, S. Geremia, S. N. Fedosov, L. Randaccio, IUBMB Life 2007, 59, 722-729.
20. T. Toraya, K. Ohashi, H. Ueno, S. Fukui, Bioinorg. Chem. 1975, 4, 245-255.
21. A. M. Calafat, L. G. Marzilli, J. Am. Chem. Soc. 1993, 115, 91829190.
22. R. H. Horton, J. D. Bagnato, C. B. Grissom, J. Org. Chem. 2003, 68, 7108-7111.
23. R. B. Hannak, S. Gschösser, K. Wurst, B. Kräutler, Monatsh. Chem. 2007, 138, 899-907.
24. P. Caravan, Chem. Soc. Rev. 2006, 35, 512-523.
25. A. Bianchi, L. Calabi, F. Corana, S. Fontana, P. Losi, A. Maiocchi, L. Paleari, B. Valtancoli, Coord. Chem. Rev. 2000, 204, 309-393.
26. A. D. Sherry, W. P. Cacheris, K.-T. Kuan, Magn. Reson. Med. 1988, 8, 180-190.
27. S.N. Fedosov, C.B. Grissom, N.U. Fedosova, S.K. Moestrup, E. Nexø, T. E. Petersen, FEBS J. 2006, 273, 4742-4753.
28. P. Mendes, Trends Biochem. Sci. 1997, 22, 361-363.
29. S. N. Fedosov, N. U. Fedosova, B. Kräutler, E. Nexø, T. E. Petersen, Biochemistry 2007, 46, 6446-6458.
30. C. Cabella, S. Geninatti Crich, D. Corpillo, A. Barge, C. Girelli, E. Bruno, V. Lorusso, F. Uggeri, S. Aime, Contrast Media Mol. Imaging 2006, 2, 23-29.
31. Z. Baranyai, E. Gianolio , K. Ramalingam , R. Swenson, R. Ranganathan , E. Brucher, S. Aime, Contrast Media Mol. Imaging 2007, 2, 94-102.
32. G. M. Sheldrick, T. R. Schneider, Methods Enzymol. 1997, 277, 319343.