MA-NOTMP: A Triazacyclononane Trimethylphosphinate Based Bifunctional Chelator for Gallium Radiolabelling of Biomolecules

ChemMedChem

Volumn 10, Issue 9, 2015, Pages 1475-1479

  Poty, Sophie ^a   Désogère, Pauline ^a   Šimeček, Jakub ^b   Bernhard, Claire ^a   Goncalves, Victor ^a   Goze, Christine ^a   Boschetti, Frédéric ^c   Notni, Johannes ^b   Wester, Hans J ^b   Denat, Franck ^a  

^a UNIVERSITÉ BOURGOGNE FRANCHE COMTÉ   (France)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c CheMatech   (France)

Author keywords

bombesin; gallium; phosphinates; radiolabelling; triazacyclononane

Indexed keywords

BOMBESIN DERIVATIVE; GALLIUM; 1,4,7-TRIAZACYCLONONANE-1,4,7-TRIS(METHYLENE METHYLPHOSPHINIC ACID); BOMBESIN; BOMBESIN RECEPTOR; CHELATING AGENT; HETEROCYCLIC COMPOUND; METHYLAMINOTRIAZACYCLONONANE TRIMETHYLPHOSPHINATE; ORGANOPHOSPHORUS COMPOUND; PHOSPHINIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; SINGLE HETEROCYCLIC RINGS; TRIAZACYCLONONANE;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; CHROMATOGRAPHY; COMPLEX FORMATION; DRUG CONJUGATION; DRUG HALF LIFE; DRUG PURIFICATION; DRUG SOLUBILITY; HUMAN; HYDROGENATION; HYDROGENOLYSIS; IN VITRO STUDY; ISOTOPE LABELING; MOLECULAR IMAGING; NONHUMAN; PH; PLASMA CLEARANCE; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION TIME; ANIMAL; BRAIN CORTEX; CHEMISTRY; METABOLISM; PROCEDURES; RAT; SYNTHESIS; TEMPERATURE;

ANIMALS; AZA COMPOUNDS; BOMBESIN; CEREBRAL CORTEX; CHELATING AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; GALLIUM RADIOISOTOPES; HETEROCYCLIC COMPOUNDS, 1-RING; HYDROGEN-ION CONCENTRATION; ISOTOPE LABELING; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHINIC ACIDS; PIPERIDINES; RADIOPHARMACEUTICALS; RATS; RECEPTORS, BOMBESIN; TEMPERATURE;

EID: 84940459852     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201500198     Document Type: Article

References (38)

1. C. J. Anderson, M. J. Welch, Chem. Rev. 1999, 99, 2219-2234.
2. I. Velikyan, Theranostics 2014, 4, 47-80
3. F. Rösch, Appl. Radiat. Isot. 2013, 76, 24-30.
4. T. J. Wadas, E. H. Wong, G. R. Weisman, C. J. Anderson, Chem. Rev. 2010, 110, 2858-2902.
5. A. S. Craig, D. Parker, H. Adams, N. A. Bailey, J. Chem. Soc. Chem. Commun. 1989, 1793-1794
6. E. R. Price, C. Orvig, Chem. Soc. Rev. 2014, 43, 260-290.
7. C. J. Mathias, Y. Sun, M. J. Welch, M. A. Green, J. A. Thomas, K. R. Wade, A. E. Martell, Nucl. Med. Biol. 1988, 15, 69-81
8. J. Schuhmacher, G. Klívenyi, W. E. Hull, R. Matys, H. Hauser, H. Kalthoff, W. H. Schmiegel, W. Maier-Borst, S. Matzku, Nucl. Med. Biol. 1992, 19, 809-824
9. G. Tircsõ, E. T. Benyõ, E. H. Suh, P. Jurek, G. E. Kiefer, A. D. Sherry, Z. Kovács, Bioconjugate Chem. 2009, 20, 565-575
10. C. L. Ferreira, E. Lamsa, M. Woods, Y. Duan, P. Fernando, C. Bensimon, M. Kordos, K. Guenther, P. Jurek, G. E. Kiefer, Bioconjugate Chem. 2010, 21, 531-536
11. C. L. Ferreira, D. T. T. Yapp, D. Mandel, R. K. Gill, E. Boros, M. Q. Wong, P. Jurek, G. E. Kiefer, Bioconjugate Chem. 2012, 23, 2239-2246.
12. E. Cole, D. Parker, G. Ferguson, J. F. Gallagher, B. Kaitner, J. Chem. Soc. Chem. Commun. 1991, 1473-1475
13. E. Cole, R. C. B. Copley, J. A. K. Howard, D. Parker, G. Ferguson, J. F. Gallagher, B. Kaitner, A. Harrison, L. Royle, J. Chem. Soc. Dalton Trans. 1994, 1619-1625.
14. J. Notni, P. Hermann, J. Havlíčková, J. Kotek, V. Kubíček, J. Plutnar, N. Loktionova, P. J. Riss, F. Rösch, I. Lukeš, Chem. Eur. J. 2010, 16, 7174-7185
15. J. Notni, J. Šimeček, P. Hermann, H. J. Wester, Chem. Eur. J. 2011, 17, 14718-14722
16. J. Šimeček, M. Schulz, J. Notni, J. Plutnar, V. Kubíček, J. Havlíčková, P. Hermann, Inorg. Chem. 2012, 51, 577-590.
17. J. Notni, K. Pohle, H. J. Wester, Nucl. Med. Biol. 2013, 40, 33-41
18. J. Notni, P. Hermann, I. Dregely, H. J. Wester, Chem. Eur. J. 2013, 19, 12602-12606
19. J. Notni, J. Plutnar, H. J. Wester, EJNMMI Res. 2012, 2, 13.
20. J. Šimeček, O. Zemek, P. Hermann, H. J. Wester, J. Notni, ChemMedChem 2012, 7, 1375-1378
21. J. Šimeček, O. Zemek, P. Hermann, J. Notni, H. J. Wester, Mol. Pharm. 2014, 11, 3893-3903
22. J. Notni, J. Šimeček, H. J. Wester, ChemMedChem 2014, 9, 1107-1115.
23. K. P. Eisenwiener, P. Powell, H. R. Mäcke, Bioorg. Med. Chem. Lett. 2000, 10, 2133-2135
24. C. Bernhard, M. Moreau, D. Lhenry, C. Goze, F. Boschetti, Y. Rousselin, F. Brunotte, F. Denat, Chem. Eur. J. 2012, 18, 7834-7841.
25. K. P. Eisenwiener, M. I. M. Prata, I. Buschmann, H. W. Zhang, A. C. Santos, S. Wenger, J. C. Reubi, H. R. Mäcke, Bioconjugate Chem. 2002, 13, 530-541.
26. P. Désogère, Y. Rousselin, S. Poty, C. Bernhard, C. Goze, F. Boschetti, F. Denat, Eur. J. Org. Chem. 2014, 7831-7838
27. F. Denat, Y. Rousselin, P. Désogère, F. Boschetti, C. Bernhard, (Université de Bourgogne, CNRS, Dijon cedex), Int. PCT Pub. No. WO2014079953 A1, 2014.
28. J. Huskens, A. D. Sherry, J. Am. Chem. Soc. 1996, 118, 4396-4404.
29. J. Seemann, B. P. Waldron, F. Roesch, D. Parker, ChemMedChem 2015, 10, 1019-1026.
30. I. Velikyan, H. R. Mäcke, B. Langstrom, Bionconjugate Chem. 2008, 19, 569-573.
31. J. D. G. Correia, A. Paulo, P. D. Raposinbo, I. Santos, Dalton Trans. 2011, 40, 6144-6167
32. M. Fani, H. R. Maëcke, S. M. Okarvi, Theranostics 2012, 2, 481-501.
33. R. Varshney, P. P. Hazari, P. Fernandez, J. Schulz, M. Allard, A. K. Mishra, Theranostics, Gallium-68, and Other Radionuclides (Eds.:, R. P. Baum, F. Rösch,), Springer-Verlag, Berlin, Heidelberg, 2013, pp. 221-252.
34. V. Sancho, A. Di Florio, T. W. Moody, R. T. Jensen, Curr. Drug Delivery 2011, 8, 79-134.
35. A. F. Prasanphanich, P. K. Nanda, T. L. Rold, L. Ma, M. R. Lewis, J. C. Garrison, T. J. Hoffman, G. L. Sieckman, S. D. Figueroa, C. J. Smith, Proc. Natl. Acad. Sci. USA 2007, 104, 12462-12467
36. M. Asti, M. Iori, P. C. Capponi, G. Atti, S. Rubagotti, R. Martin, A. Brennauer, M. Müller, R. Bergmann, P. A. Erbe, A. Versari, Nucl. Med. Biol. 2014, 41, 24-35.
37. J. Šimeček, J. Notni, T. G. Kapp, H. Kessler, H. J. Wester, Mol. Pharm. 2014, 11, 1687-1695.
38. H. Zhang, J. Schuhmacher, B. Waser, D. Wild, M. Eisenhut, J. C. Reubi, H. R. Mäcke, Eur. J. Nucl. Med. Mol. Imaging 2007, 34, 1198-1208.