H4octapa-trastuzumab: Versatile acyclic chelate system for 111In and 177Lu imaging and therapy

Journal of the American Chemical Society

Volumn 135, Issue 34, 2013, Pages 12707-12721

  Price, Eric W ^a,b   Zeglis, Brian M ^c   Cawthray, Jacqueline F ^a,b   Ramogida, Caterina F ^a,b   Ramos, Nicholas ^c   Lewis, Jason S ^c   Adam, Michael J ^b   Orvig, Chris ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b TRIUMF   (Canada)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVITY RATIOS; BI-FUNCTIONAL; OVARIAN CANCERS; RADIOCHEMICAL PURITY; RADIOIMMUNOCONJUGATES; RADIOLABELING; SPECIFIC ACTIVITY; SPECT IMAGING;

CHELATION; SINGLE PHOTON EMISSION COMPUTED TOMOGRAPHY;

MONOCLONAL ANTIBODIES;

CHELATING AGENT; INDIUM 111; LUTETIUM 177; OCTAPA TRASTUZUMAB IN 111; OCTAPA TRASTUZUMAB LU 177; PENTETIC ACID DERIVATIVE; RADIOIMMUNOCONJUGATE; RADIOISOTOPE; TETRAXETAN; TETRAXETAN TRASTUZUMAB IN 111; TETRAXETAN TRASTUZUMAB LU 177; TRASTUZUMAB; UNCLASSIFIED DRUG; 1,4,7,10-TETRAAZACYCLODODECANE- 1,4,7,10-TETRAACETIC ACID; ANTINEOPLASTIC AGENT; ETHYLAMINE; INDIUM; LUTETIUM; MONOCLONAL ANTIBODY; N,N'-((6-CARBOXYLATO)PYRIDIN-2-YL)METHYL)-N,N'-DIACETIC ACID-1,2-DIAMINOETHANE; PYRIDINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; SINGLE HETEROCYCLIC RINGS;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER CELL; CANCER IMMUNOTHERAPY; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; COMPUTER ASSISTED TOMOGRAPHY; DENSITY FUNCTIONAL THEORY; DRUG CONJUGATION; FEMALE; GEOMETRY; HUMAN; HUMAN CELL; IMMUNOREACTIVITY; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; KINETICS; MOUSE; NONHUMAN; NUDE MOUSE; OVARY CANCER; RADIOCHEMISTRY; RADIOIMMUNOTHERAPY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; SPECTROPHOTOMETRY; SYNTHESIS; TARGET ORGAN; THERMODYNAMICS; TISSUE DISTRIBUTION; TUMOR GROWTH; TUMOR XENOGRAFT; ANIMAL; CANCER TRANSPLANTATION; CHEMISTRY; DRUG SCREENING; NEOPLASMS, EXPERIMENTAL; TUMOR CELL CULTURE;

ANIMALS; ANTIBODIES, MONOCLONAL, HUMANIZED; ANTINEOPLASTIC AGENTS; CHELATING AGENTS; ETHYLAMINES; FEMALE; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; INDIUM RADIOISOTOPES; LUTETIUM; MICE; MICE, NUDE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEOPLASM TRANSPLANTATION; NEOPLASMS, EXPERIMENTAL; PYRIDINES; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION; TRASTUZUMAB; TUMOR CELLS, CULTURED; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84883309593     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4049493     Document Type: Article

References (65)

1. Rösch, F.; Baum, R. P. Dalton Trans. 2011, 40, 6104-6111
2. Zeglis, B. M.; Lewis, J. S. Dalton Trans. 2011, 40, 6168-6195
3. Wadas, T. J.; Wong, E. H.; Weisman, G. R.; Anderson, C. J. Chem. Rev. 2010, 110, 2858-2902
4. Deri, M. A.; Zeglis, B. M.; Francesconi, L. C.; Lewis, J. S. Nucl. Med. Biol. 2013, 40, 3-14
5. Zeglis, B. M.; Mohindra, P.; Weissmann, G. I.; Divilov, V.; Hilderbrand, S. A.; Weissleder, R.; Lewis, J. S. Bioconjugate Chem. 2011, 22, 2048-2059
6. Bartholoma, M. D.; Louie, A. S.; Valliant, J. F.; Zubieta, J. Chem. Rev. 2010, 110, 2903-2920
7. Ramogida, C. F.; Orvig, C. Chem. Commun. 2013, 49, 4720-4739
8. Holland, J. P.; Williamson, M. J.; Lewis, J. S. Mol. Imaging 2010, 9, 1-20
9. Holland, J. P.; Divilov, V.; Bander, N. H.; Smith-Jones, P. M.; Larson, S. M.; Lewis, J. S. J. Nucl. Med. 2010, 51, 1293-1300
10. Boswell, C. A.; Brechbiel, M. W. Nucl. Med. Biol. 2007, 34, 757-778
11. Vermeer, A. W. P.; Norde, W. Biophys. J. 2000, 78, 394-404
12. Stimmel, J. B.; Kull, F. C., Jr Nucl. Med. Biol. 1998, 25, 117-125
13. Stimmel, J. B.; Stockstill, M. E.; Kull, F. C. Bioconjugate Chem. 1995, 6, 219-225
14. Camera, L.; Kinuya, S.; Garmestani, K.; Wu, C.; Brechbiel, M. W.; Pai, L. H.; McMurry, T. J.; Gansow, O. A.; Pastan, I.; Paik, C. H.; Carrasquillo, J. A. J. Nucl. Med. 1994, 35, 882-889
15. Harrison, A.; Walker, C. A.; Parker, D.; Jankowski, K. J.; Cox, J. P. L.; Craig, A. S.; Sansom, J. M.; Beeley, N. R. A.; Boyce, R. A.; Chaplin, L.; Eaton, M. A. W.; Farnsworth, A. P. H.; Millar, K.; Millican, A. T.; Randall, A. M.; Rhind, S. K.; Secher, D. S.; Turner, A. Int. J. Radiat. Appl. Instrum., Part B 1991, 18, 469-476
16. Cooper, M. S.; Ma, M. T.; Sunassee, K.; Shaw, K. P.; Williams, J. D.; Paul, R. L.; Donnelly, P. S.; Blower, P. J. Bioconjugate Chem. 2012, 23, 1029-1039
17. Martell, A. E.; Smith, R. M. Critical Stability Constants; Plenum Press: New York, 1974-1989; Vols. 1-6.
18. Hancock, R. D. J. Chem. Educ. 1992, 69, 615-621
19. Liu, S.; Pietryka, J.; Ellars, C. E.; Edwards, D. S. Bioconjugate Chem. 2002, 13, 902-913
20. Liu, S.; Edwards, D. S. Bioconjugate Chem. 2000, 12, 7-34
21. Kukis, D. L.; DeNardo, S. J.; DeNardo, G. L.; O'Donnell, R. T.; Meares, C. F. J. Nucl. Med. 1998, 39, 2105-2110
22. Jang, Y. H.; Blanco, M.; Dasgupta, S.; Keire, D. A.; Shively, J. E.; Goddard, W. A. J. Am. Chem. Soc. 1999, 121, 6142-6151
23. Milenic, D. E.; Garmestani, K.; Chappell, L. L.; Dadachova, E.; Yordanov, A.; Ma, D.; Schlom, J.; Brechbiel, M. W. Nucl. Med. Biol. 2002, 29, 431-442
24. Kang, C. S.; Sun, X.; Jia, F.; Song, H. A.; Chen, Y.; Lewis, M.; Chong, H.-S. Bioconjugate Chem. 2012, 23, 1775-1782
25. Chappell, L. L.; Ma, D.; Milenic, D. E.; Garmestani, K.; Venditto, V.; Beitzel, M. P.; Brechbiel, M. W. Nucl. Med. Biol. 2003, 30, 581-595
26. Rasaneh, S.; Rajabi, H.; Babaei, M. H.; Johari Daha, F. J. Labelled Compd. Radiopharm. 2010, 53, 575-579
27. Förster, G. J.; Engelbach, M. J.; Brockmann, J. J.; Reber, H. J.; Buchholz, H. G.; Mäcke, H. R.; Rösch, F. R.; Herzog, H. R.; Bartenstein, P. R. Eur. J. Nucl. Med. 2001, 28, 1743-1750
28. Wu, C.; Kobayashi, H.; Sun, B.; Yoo, T. M.; Paik, C. H.; Gansow, O. A.; Carrasquillo, J. A.; Pastan, I.; Brechbiel, M. W. Bioorg. Med. Chem. 1997, 5, 1925-1934
29. Brechbiel, M. W.; Gansow, O. A.; Atcher, R. W.; Schlom, J.; Esteban, J.; Simpson, D.; Colcher, D. Inorg. Chem. 1986, 25, 2772-2781
30. Boros, E.; Ferreira, C. L.; Cawthray, J. F.; Price, E. W.; Patrick, B. O.; Wester, D. W.; Adam, M. J.; Orvig, C. J. Am. Chem. Soc. 2010, 132, 15726-15733
31. Boros, E.; Ferreira, C. L.; Yapp, D. T. T.; Gill, R. K.; Price, E. W.; Adam, M. J.; Orvig, C. Nucl. Med. Biol. 2012, 39, 785-794
32. Boros, E.; Cawthray, J. F.; Ferreira, C. L.; Patrick, B. O.; Adam, M. J.; Orvig, C. Inorg. Chem. 2012, 51, 6279-6284
33. Price, E. W.; Cawthray, J. F.; Bailey, G. A.; Ferreira, C. L.; Boros, E.; Adam, M. J.; Orvig, C. J. Am. Chem. Soc. 2012, 134, 8670-8683
34. Boros, E.; Lin, Y.-H. S.; Ferreira, C. L.; Patrick, B. O.; Hafeli, U. O.; Adam, M. J.; Orvig, C. Dalton Trans. 2011, 40, 6253-6259
35. Boros, E.; Ferreira, C. L.; Patrick, B. O.; Adam, M. J.; Orvig, C. Nucl. Med. Biol. 2011, 38, 1165-1174
36. Bailey, G. A.; Price, E. W.; Zeglis, B. M.; Ferreira, C. L.; Boros, E.; Lacasse, M. J.; Patrick, B. O.; Lewis, J. S.; Adam, M. J.; Orvig, C. Inorg. Chem. 2012, 51
37. Platas-Iglesias, C.; Mato-Iglesias, M.; Djanashvili, K.; Muller, R. N.; Elst, L. V.; Peters, J. A.; de Blas, A.; Rodríguez-Blas, T. Chem.-Eur. J. 2004, 10, 3579-3590
38. Ferreiros-Martinez, R.; Esteban-Gomez, D.; Platas-Iglesias, C.; Blas, A. d.; Rodriguez-Blas, T. Dalton Trans. 2008, 5754-5765
39. Masuda, R.; Oishi, S.; Ohno, H.; Kimura, H.; Saji, H.; Fujii, N. Bioorg. Med. Chem. 2011, 19, 3216-3220
40. Dioury, F.; Guéné, E.; Scala-Roulleau, A. D.; Ferroud, C.; Guy, A.; Port, M. Tetrahedron Lett. 2005, 46, 611-613
41. Favre-Réguillon, A.; Segat-Dioury, F.; Nait-Bouda, L.; Cosma, C.; Siaugue, J.-M.; Foos, J.; Guy, A. Synlett 2000, 2000, 0868-0871
42. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374
43. Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785-7811
44. Viola, N. A.; Rarig, R. S., Jr; Ouellette, W.; Doyle, R. P. Polyhedron 2006, 25, 3457-3462
45. Tóth, EÌ.; Brücher, E. Inorg. Chim. Acta 1994, 221, 165-167
46. Cacheris, W. P.; Nickle, S. K.; Sherry, A. D. Inorg. Chem. 1987, 26, 958-960
47. Loncin, M. F.; Desreux, J. F.; Merciny, E. Inorg. Chem. 1986, 25, 2646-2648
48. Anderegg, G.; Arnaud-Neu, F.; Delgado, R.; Felcman, J.; Popov, K. Pure Appl. Chem. 2005, 77, 1445-1495
49. Šimeček, J.; Schulz, M.; Notni, J.; Plutnar, J.; Kubíček, V.; Havlíčková, J.; Hermann, P. Inorg. Chem. 2011, 51, 577-590
50. Šimeček, J.; Hermann, P.; Wester, H.-J.; Notni, J. ChemMedChem 2013, 8, 95-103
51. Thorek, D. L. J.; Abou, D. S.; Beattie, B. J.; Bartlett, R. M.; Huang, R.; Zanzonico, P. B.; Grimm, J. J. Nucl. Med. 2012, 53, 1438-1445
52. Kumar Mishra, A.; Panwar, P.; Chopra, M.; Kumar Sharma, R.; Chatal, J.-F. New J. Chem. 2003, 27, 1054-1058
53. Gran, G. Analyst 1952, 77, 661-671
54. Duckworth, P. Private communication.
55. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753
56. Baes, C. F., Jr.; Mesmer, R. E. Wiley-Interscience: New York, 1976.
57. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Ö. Farkas; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.;; Fox, D. J. Gaussian 09, Revision A.1, Gaussian, Inc.: Wallingford CT, 2009.
58. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
59. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
60. Cao, X.; Dolg, M. J. Chem. Phys. 2001, 115, 7348-7355
61. Holland, J. P.; Caldas-Lopes, E.; Divilov, V.; Longo, V. A.; Taldone, T.; Zatorska, D.; Chiosis, G.; Lewis, J. S. PLoS One 2010, 5, e8859
62. Anderson, C. J.; Connett, J. M.; Schwarz, S. W.; Rocque, P. A.; Guo, L. W.; Philpott, G. W.; Zinn, K. R.; Meares, C. F.; Welch, M. J. J. Nucl. Med. 1992, 33, 1685-1691
63. Anderson, C. J.; Schwarz, S. W.; Connett, J. M.; Cutler, P. D.; Guo, L. W.; Germain, C. J.; Philpott, G. W.; Zinn, K. R.; Greiner, D. P.; Meares, C. F.; Welch, M. J. J. Nucl. Med. 1995, 36, 850-858
64. Lindmo, T.; Boven, E.; Cuttitta, F.; Fedorko, J.; Bunn, P. A., Jr. J. Immunol. Methods 1984, 72, 77-89
65. Lindmo, T.; Bunn, P. A., Jr. Methods Enzymol. 1986, 121, 678-691