Rational design, synthesis, and evaluation of tetrahydroxamic acid chelators for stable complexation of zirconium(IV)

Chemistry - A European Journal

Volumn 20, Issue 19, 2014, Pages 5584-5591

  Guérard, François ^a   Lee, Yong Sok ^b   Brechbiel, Martin W ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

chelates; imaging agents; ligand design; quantum chemistry; zirconium

Indexed keywords

CAVITY RESONATORS; CHELATION; COMPLEXATION; MEDICAL APPLICATIONS; MEDICAL IMAGING; NUCLEAR MEDICINE; QUANTUM CHEMISTRY; ZIRCONIUM COMPOUNDS;

BIOMEDICAL APPLICATIONS; CHELATES; COMPLEXATION PROCESS; IMAGING AGENT; LIGAND DESIGN; QUANTUM CHEMICAL CALCULATIONS; QUANTUM CHEMICAL STUDIES; RING CLOSING METATHESIS;

ZIRCONIUM;

EID: 84899963307     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201304115     Document Type: Article

References (30)

1. M. Tredwell, V. Gouverneur, Angew. Chem. 2012, 124, 11590-11602
2. Angew. Chem. Int. Ed. 2012, 51, 11426-11437
3. Z. Li, P. S. Conti, Adv. Drug Delivery Rev. 2010, 62, 1031-1051.
4. T. J. Wadas, E. H. Wong, G. R. Weisman, C. J. Anderson, Chem. Rev. 2010, 110, 2858-2902
5. Y. Zhou, K. E. Baidoo, M. W. Brechbiel, Adv. Drug Delivery Rev. 2013, 65, 1098-1111
6. T. K. Nayak, M. W. Brechbiel, Bioconjugate Chem. 2009, 20, 825-841.
7. G. Fischer, U. Seibold, R. Schirrmacher, B. Wängler, C. Wängler, Molecules 2013, 18, 6469-6490.
8. R. Codd, Coord. Chem. Rev. 2008, 252, 1387-1408.
9. M. J. W. D. Vosjan, L. R. Perk, G. W. M. Visser, M. Budde, P. Jurek, G. E. Kiefer, G. A. M. S. vanDongen, Nat. Protoc. 2010, 5, 739-743.
10. B. M. Zeglis, P. Mohindra, G. I. Weissmann, V. Divilov, S. A. Hilderbrand, R. Weissleder, J. S. Lewis, Bioconjugate Chem. 2011, 22, 2048-2059.
11. M. A. Deri, B. M. Zeglis, L. C. Francesconi, J. S. Lewis, Nucl. Med. Biol. 2013, 40, 3-14
12. J. P. Holland, M. J. Evans, S. L. Rice, J. Wongvipat, C. L. Sawyers, J. S. Lewis, Nat. Med. 2012, 18, 1586-1591.
13. T. K. Nayak, K. Garmestani, D. E. Milenic, M. W. Brechbiel, J. Nucl. Med. 2012, 53, 113-120
14. D. S. Abou, T. Ku, P. M. Smith-Jones, Nucl. Med. Biol. 2011, 38, 675-681.
15. L. R. Perk, M. J. W. D. Vosjan, G. W. M. Visser, M. Budde, P. Jurek, G. E. Kiefer, G. A. M. S. vanDongen, Eur. J. Nucl. Med. Mol. Imaging 2010, 37, 250-259.
16. J. N. Tinianow, H. S. Gill, A. Ogasawara, J. E. Flores, A. N. Vanderbilt, E. Luis, R. Vandlen, M. Darwish, J. R. Junutula, S.-P. Williams, J. Marik, Nucl. Med. Biol. 2010, 37, 289-297.
17. E. W. Price, B. M. Zeglis, J. S. Lewis, M. J. Adam, C. Orvig, Dalton Trans. 2014, 43, 119-131.
18. F. Guérard, Y.-S. Lee, R. Tripier, L. P. Szajek, J. R. Deschamps, M. W. Brechbiel, Chem. Commun. 2013, 49, 1002-1004.
19. D. J. Cram, Angew. Chem. 1986, 98, 1041-1060
20. Angew. Chem. Int. Ed. Engl. 1986, 25, 1039-1057.
21. S. Liu, D. S. Edwards, Bioconjugate Chem. 2001, 12, 7-34.
22. A. S. Reddy, M. S. Kumar, G. R. Reddy, Tetrahedron Lett. 2000, 41, 6285-6288.
23. J. Prášilová, J. Havlíček, J. Inorg. Nucl. Chem. 1970, 32, 953-960.
24. Y. Zhao, D. G. Truhlar, J. Chem. Phys. 2006, 125, 194101-194118.
25. W. R. Wadt, P. J. Hay, J. Chem. Phys. 1985, 82, 284-298.
26. Gaussian 09 (RevisionA.02), M.J. Frisch G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery,Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian Inc., Wallingford CT, 2009.
27. IV in water at pH7 in the absence of strong ligand at high dilution, as reported previously. See:, A. Veyland, L. Dupont, J. Pierrard, J. Rimbault, M. Aplincourt, Eur. J. Inorg. Chem. 1998, 1765-1770.
28. M. P. Neu, J. H. Matonic, C. E. Ruggiero, B. L. Scott, Angew. Chem. 2000, 112, 1501-1503
29. Angew. Chem. Int. Ed. 2000, 39, 1442-1444.
30. J. P. Holland, Y. Sheh, J. S. Lewis, Nucl. Med. Biol. 2009, 36, 729-739.