Carbohydrate-bearing 3-hydroxy-4-pyridinonato complexes of gallium(III) and indium(III)

Bioconjugate Chemistry

Volumn 16, Issue 6, 2005, Pages 1597-1609

  Green, David E ^a,b,d   Ferreira, Cara L ^a,b   Stick, Robert V ^c   Patrick, Brian O ^a   Adam, Michael J ^b   Orvig, Chris ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b TRIUMF   (Canada)

^c UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^d BRITISH COLUMBIA CANCER RESEARCH CENTRE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; GALLIUM COMPOUNDS; INDIUM COMPOUNDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

GALLIUM COMPLEXES; INDIUM COMPLEXES; LIGAND PRECURSORS; METAL CENTRES; NEUTRAL COMPLEXES; NMR-SPECTROSCOPY; PYRIDINONES; SYNTHESISED;

LIGANDS;

3 HYDROXY 4 PYRIDINONATE DERIVATIVE; 8 QUINOLINOL; CARBOHYDRATE; GALLIUM; HYDROXYPYRIDINONE; INDIUM; PENTETIC ACID; PENTETREOTIDE; PYRIDINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; LIGAND BINDING; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 27944440108     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0501808     Document Type: Article

References (38)

1. Bruner, H. D., Hayes, R. L., and Perkinson, J. D. (1953) A study of gallium-72. Summary and conclusions. X. Preliminary data on gallium-67. Radiology 61, 602-613.
2. van der Werff, J. T. (1954) Clinical investigations on the use of radioactive gallium (Ga-66 and Ga-67) in bone diseases. Acta Radiol. 41, 343-347.
3. Hayes, R. L. (1966) Radioisotopes of gallium. U. S. At. Energy Comm., Symp. Ser. 6, 603-618.
4. Goodwin, D. A., Stern, H. S., and Wagner, H. N., Jr. (1967) Indium-113m labeled iron hydroxide particles for lung scanning. J. Nucl. Med. 8, 346.
5. Pal, J., Gacs, J., Torko, J., and Farkas, G. (1967) Clinical experiences in use of In-115m. Strahlentherapie [Sonderb] 65, 63-69.
6. Andersen, C. J., and Welch, M. J. (1999) Radiometal labeled agents (non-technetium) for diagnostic imaging. Chem. Rev. 99, 2219-2234.
7. Luttropp, C. A., Jackson, J. A., Jones, B. J., Sohn, M. H., Lynch, R. E., and Morton, K. A. (1998) Uptake of gallium-67 in transfected cells and tumors absent or enriched in the transferrin receptor. J. Nucl. Med. 39, 1405-1411.
8. de Jong, M., Breeman, W. A. P., Bakker, W. H., Kooij, P. P. M., Bernard, B. F., Hofland, L. J., Visser, T. J., Srinivasan, A., Schmidt, M. A., Erion, J. L., Bugaj, J. E., Macke, H. R., and Krenning, E. P. (1998) Comparison of In-111-labeled somatostatin analogues for tumor scintigraphy and radionuclide therapy. Cancer Res. 58, 437-441.
9. Zhang, Z., Rettig, S. J., and Orvig, C. (1991) Lipophilic coordination compounds: aluminum, gallium, and indium complexes of 1-aryl-3-hydroxy-2-methyl- 4-pyridinones. Inorg. Chem. 30, 509-515.
10. Clevette, D. J., Lyster, D. M., Nelson, W. O., Rihela, T., Webb, G. A., and Orvig, C. (1990) Solution chemistry of gallium and indium 3-hydroxy-4-pyridinone complexes in vitro and in vivo. Inorg. Chem. 29, 667-672.
11. Clevette, D. J., and Orvig, C. (1990) Comparison of ligands of differing denticity and basicity for the in vivo chelation of aluminium and gallium. Polyhedron 9, 151-161.
12. Kruck, T. P. A., and Burrow, T. E. (2002) Synthesis of feralex a novel aluminum/iron chelating compound. J. Inorg. Biochem. 88, 19-24.
13. 186Re(I) tricarbonyl complexes of N-(2′-hydroxybenzyl)-2-amino-2-deoxy-D-glucose. Bioconjugate Chem. 15, 923-926.
14. Starr, T., Obata, M., Fisher, C. L., Bayly, S. R., Green, D. E., Brudziñska, I., Mikata, Y., Patrick, B. O., Adam, M. J., Yano, S., and Orvig, C. (2005) Novel carbohydrate-appended metal complexes for potential use in molecular imaging. Chem. Eur. J. 11, 195-203.
15. 99mTc and Re precursors and fundamental NMR investigations. Chem. Eur. J. 7, 1868-1873.
16. 99mTc ECDG targeted at the multifunctional glucose transport system: feasibility study with rodents. Radiology 226, 465-473.
17. Cramer, F. D. (1962) Methods In Carbohydrate Chemistry (Whistler, R. L., Wolfrom, M. L., Eds.) Vol. I, pp 244-245, Academic Press, New York.
18. Conchie, J., and Levvy, G. A. (1963) Methods In Carbohydrate Chemistry (Whistler, R. L., Wolfrom, M. L., Eds.) Vol. II, pp 335-337, Academic Press, New York.
19. Tsunoda, T., Yamamiya, Y., and Ito, S. (1993) 1,1′-(Azodicarbonyl) dipiperidine-tributylphosphine, a new reagent system for mitsunobu reaction. Tetrahedron Lett. 34, 1639-1642.
20. Nelson, W. O., Rettig, S. J., and Orvig, C. (1989) Aluminum and gallium complexes of 1-ethyl-3-hydroxy-2-methyl-4-pyridinone: a new exoclathrate matrix. Inorg. Chem. 28, 3153-3157.
21. Matsuba, C. A., Nelson, W. O., Rettig, S. J., and Orvig, C. (1988) Neutral water-soluble indium complexes of 3-hydroxy-4-pyrones and 3-hydroxy-4-pyridinones. Inorg. Chem. 27, 3935-3939.
22. Chang, C. H. F., Pitner, T. P., Lenkinski, R. E., and Glickson, J. D. (1977) Carbon-13 Fourier transform nuclear magnetic resonance study of gallium citrate in aqueous solution. Inorg. Chem. 99, 5858-5863.
23. 2O. Eur. J. Inorg. Chem., 1005-1011.
24. Escandar, G. M., Olivieri, A. C., Gonzalez-Sierra, M., Frutos, A. A., and Sala, L. F. (1995) Complexation of aluminum(III), gallium(III) and indium(III) ions with D-gluconic and lactobionic acids - a potentiometric and nuclear magnetic resonance spectroscopic study (Correction, Addition). J. Chem. Soc.-Dalton Trans., 1393-1393.
25. Escandar, G. M., Olivieri, A. C., Gonzalez-Sierra, M., Frutos, A. A., and Sala, L. F. (1995) Complexation of aluminum(III), gallium(III) and indium(III) ions with D-gluconic and lactobionic acids - a potentiometric and nuclear magnetic resonance spectroscopic study. J. Chem. Soc., Dalton Trans. 799-804.
26. Pardridge, W. M., Boado, R. J., and Farrell, C. R. (1990) Brain-type glucose transporter (Glut-1) is selectively localized to the blood-brain-barrier - studies with quantitative western blotting and in situ hybridization. J. Biol. Chem. 265, 18035-18040.
27. Heidren, M., Boermans, H., Friedrich, L., and Siegfried, M. (2001) Molecular cloning and expression of human bile acid β-glucosidase. J. Biol. Chem. 276, 37929-37933.
28. Kempton, J. B., and Withers, S. G. (1992) Mechanism of Agrobacterium β-glucosidase - kinetic studies. Biochemistry 31, 9961-9969.
29. Perrin, D. D., Armarego, W. L. F., and Perrin, D. R. (1980) Purification of laboratory chemicals, Permagon Press, Oxford.
30. Molecular Structure Corporation (2001) d*Trek Area Detector Software. 3200 Research Forest Drive, The Woodlands, TX, 77381.
31. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., and Spagna, R. (1999) SIR97: a new tool for crystal structure determination and refinement. J. Appl. Crystallogr. 32, 115-119.
32. Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., de Gelder, R., Israel, R., and Smits, J. M. M. The DIRDIF-94 Program System, University of Nijmegen, The Netherlands, 1994.
33. Molecular Structure Corporation (1992-1997) teXsan Single-Crystal Structure Analysis Software. 3200 Research Forest Dr., The Woodlands, TX, 77381.
34. Harris, R. L. N. (1976) Potential wool growth inhibitors. Improved syntheses of mimosine and related 4(1H)-pyridones. Auat. J. Chem. 29, 1329-1334.
35. Cramer, F. D. (1963) Methods In Carbohydrate Chemistry (Whistler, R. L., Wolfrom, M. L., Eds.) Vol. II, pp 242-246, Academic Press, New York.
36. Matsuda, K., Tsuchiya, T., Torii, T., and Umezawa, S. (1986) Synthesis of 6-amino-6-deoxy-L-idopyranosides. Bull. Chem. Soc. Jpn. 59, 1397-1401,
37. Rosowsky, A., Yu, C.-S., Uren, J., Lazarus, H., and Wick, M. (1981) Methotrexate analogues. 13. Chemical and pharmacological studies on amide, hydrazide, and hydroxamic acid derivatives of the glutamate side chain. J. Med. Chem. 24, 559-567.
38. Thompson, A., Wolfrom, M. L., and Pacou, E. (1963) Methods In Carbohydrate Chemistry (Whistler, R. L., Wolfrom, M. L., Eds.) Vol. II, pp 215-220, Academic Press, New York.