Multimodal chelation platform for near-infrared fluorescence/nuclear imaging

Journal of Medicinal Chemistry

Volumn 56, Issue 2, 2013, Pages 406-416

  Ghosh, Sukhen C ^a   Ghosh, Pradip ^a   Wilganowski, Nathaniel ^a   Robinson, Holly ^a   Hall, Mary A ^a   Dickinson, Gabriel ^a   Pinkston, Ken L ^a   Harvey, Barrett R ^a   Sevick Muraca, Eva M ^a   Azhdarinia, Ali ^a  

^a UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2',2'' [10 (6 IRDYE 800CW HEXYL AMIDE)] 1,4,7,10 TETRAAZACYCLODODECA 1,4,7 TRIYL)TRIACETIC ACID CU 64; 2,2',2'' [10 (6 IRDYE 800CW HEXYL AMIDE)] 1,4,7,10 TETRAAZACYCLODODECA 1,4,7 TRIYL)TRIACETIC ACID GA 68; CHELATING AGENT; EPITHELIAL CELL ADHESION MOLECULE; EPITHELIAL CELL ADHESION MOLECULE MONOCLONAL ANTIBODY 2,2',2'' [10 (6 IRDYE 800CW HEXYL AMIDE)] 1,4,7,10 TETRAAZACYCLODODECA 1,4,7 TRIYL)TRIACETIC ACID CU 64; EPITHELIAL CELL ADHESION MOLECULE MONOCLONAL ANTIBODY 2,2',2'' [10 (6 IRDYE 800CW HEXYL AMIDE)] 1,4,7,10 TETRAAZACYCLODODECA 1,4,7 TRIYL)TRIACETIC ACID GA 68; FLUORESCENT DYE; MONOCLONAL ANTIBODY; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BLADDER; CHELATION; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG LIVER LEVEL; DRUG STABILITY; DRUG SYNTHESIS; DRUG TISSUE LEVEL; FEMALE; FLUORESCENCE IMAGING; HEART; IMMUNOREACTIVITY; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY; LIVER CLEARANCE; MALE; MOUSE; MULTIMODAL CHELATION; MUSCLE; NEAR INFRARED FLUORESCENCE IMAGING; NONHUMAN; PROTEIN EXPRESSION; RADIOCHEMISTRY;

ANIMALS; ANTIGENS, NEOPLASM; CELL ADHESION MOLECULES; CHELATING AGENTS; DIAGNOSTIC IMAGING; FLUORESCENCE; FLUORESCENT DYES; HUMANS; MALE; MICE; PROSTATIC NEOPLASMS; RADIOISOTOPES;

EID: 84872794907     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300906g     Document Type: Article

References (41)

1. Histed, S. N.; Lindenberg, M. L.; Mena, E.; Turkbey, B.; Choyke, P. L.; Kurdziel, K. A. Review of functional/anatomical imaging in oncology Nucl. Med. Commun. 2012, 33, 349-361
2. Culver, J.; Akers, W.; Achilefu, S. Multimodality molecular imaging with combined optical and SPECT/PET modalities J. Nucl. Med. 2008, 49, 169-172
3. Sevick-Muraca, E. M. Translation of near-infrared fluorescence imaging technologies: emerging clinical applications Annu. Rev. Med. 2012, 63, 217-231
4. Gioux, S.; Choi, H. S.; Frangioni, J. V. Image-guided surgery using invisible near-infrared light: fundamentals of clinical translation Mol. Imaging 2010, 9, 237-255
5. van Dam, G. M.; Themelis, G.; Crane, L. M.; Harlaar, N. J.; Pleijhuis, R. G.; Kelder, W.; Sarantopoulos, A.; de Jong, J. S.; Arts, H. J.; van der Zee, A. G.; Bart, J.; Low, P. S.; Ntziachristos, V. Intraoperative tumor-specific fluorescence imaging in ovarian cancer by folate receptor-α targeting: first in-human results Nat. Med. 2011, 17, 1315-1319
6. Sevick-Muraca, E. M.; Sharma, R.; Rasmussen, J. C.; Marshall, M. V.; Wendt, J. A.; Pham, H. Q.; Bonefas, E.; Houston, J. P.; Sampath, L.; Adams, K. E.; Blanchard, D. K.; Fisher, R. E.; Chiang, S. B.; Elledge, R.; Mawad, M. E. Imaging of lymph flow in breast cancer patients after microdose administration of a near-infrared fluorophore: feasibility study Radiology 2008, 246, 734-741
7. Buckle, T.; Chin, P. T.; van Leeuwen, F. W. (Non-targeted) radioactive/fluorescent nanoparticles and their potential in combined pre-and intraoperative imaging during sentinel lymph node resection Nanotechnology 2010, 21, 482001
8. Azhdarinia, A.; Ghosh, P.; Ghosh, S.; Wilganowski, N.; Sevick-Muraca, E. M. Dual-labeling strategies for nuclear and fluorescence molecular imaging: a review and analysis Mol. Imaging Biol. 2012, 14, 261-276
9. Kuil, J.; Velders, A. H.; van Leeuwen, F. W. Multimodal tumor-targeting peptides functionalized with both a radio-and a fluorescent label Bioconjugate Chem. 2010, 21, 1709-1719
10. Sampath, L.; Kwon, S.; Hall, M. A.; Price, R. E.; Sevick-Muraca, E. M. Detection of cancer metastases with a dual-labeled near-infrared/positron emission tomography imaging agent Transl. Oncol. 2010, 3, 307-217
11. Zhang, Y.; Hong, H.; Engle, J. W.; Yang, Y.; Theuer, C. P.; Barnhart, T. E.; Cai, W. Positron emission tomography and optical imaging of tumor CD105 expression with a dual-labeled monoclonal antibody Mol. Pharm. 2012, 9, 645-653
12. Hall, M. A.; Kwon, S.; Robinson, H.; Lachance, P. A.; Azhdarinia, A.; Ranganathan, R.; Price, R. E.; Chan, W.; Sevick-Muraca, E. M. Imaging prostate cancer lymph node metastases with a multimodality contrast agent Prostate 2012, 72, 129-146
13. Garanger, E.; Aikawa, E.; Reynolds, F.; Weissleder, R.; Josephson, L. Simplified syntheses of complex multifunctional nanomaterials Chem. Commun. (Cambridge, U. K.) 2008, 4792-4794
14. Xu, H.; Baidoo, K.; Gunn, A. J.; Boswell, C. A.; Milenic, D. E.; Choyke, P. L.; Brechbiel, M. W. Design, synthesis, and characterization of a dual modality positron emission tomography and fluorescence imaging agent for monoclonal antibody tumor-targeted imaging J. Med. Chem. 2007, 50, 4759-4765
15. Liu, S.; Li, D.; Huang, C. W.; Yap, L. P.; Park, R.; Shan, H.; Li, Z.; Conti, P. S. Efficient construction of PET/fluorescence probe based on sarcophagine cage: an opportunity to integrate diagnosis with treatment Mol. Imaging Biol. 2012, 14, 718-724
16. Sherry, A. D.; Caravan, P.; Lenkinski, R. E. Primer on gadolinium chemistry J. Magn. Reson. Imaging 2009, 30, 1240-1248
17. 68Ga-DOTA-Tyr3-octreotide PET for assessing response to somatostatin-receptor-mediated radionuclide therapy J. Nucl. Med. 2009, 50, 1427-1434
18. 90Y-labeled somatostatin analogs J. Nucl. Med. 2005, 46 (Suppl. 1) 13S-17S
19. Bodei, L.; Cremonesi, M.; Grana, C. M.; Fazio, N.; Iodice, S.; Baio, S. M.; Bartolomei, M.; Lombardo, D.; Ferrari, M. E.; Sansovini, M.; Chinol, M.; Paganelli, G. Peptide receptor radionuclide therapy with (177)Lu-DOTATATE: the IEO phase I-II study Eur. J. Nucl. Med. Mol. Imaging 2011, 38, 2125-2135
20. 68Ga for medical application J. Nucl. Med. 2007, 48, 1741-1748
21. Wadas, T. J.; Wong, E. H.; Weisman, G. R.; Anderson, C. J. Copper chelation chemistry and its role in copper radiopharmaceuticals Curr. Pharm. Des. 2007, 13, 3-16
22. 64Cu-DOTA- conatumumab: a PET tracer for in vivo imaging of death receptor 5 J. Nucl. Med. 2011, 52, 942-949
23. Bryan, J. N.; Jia, F.; Mohsin, H.; Sivaguru, G.; Anderson, C. J.; Miller, W. H.; Henry, C. J.; Lewis, M. R. Monoclonal antibodies for copper-64 PET dosimetry and radioimmunotherapy Cancer Biol. Ther. 2011, 11, 1001-1007
24. Houston, J. P.; Ke, S.; Wang, W.; Li, C.; Sevick-Muraca, E. M. Quality analysis of in vivo near-infrared fluorescence and conventional γ images acquired using a dual-labeled tumor-targeting probe J. Biomed. Opt. 2005, 10, 054010
25. Li, C.; Wang, W.; Wu, Q.; Ke, S.; Houston, J.; Sevick-Muraca, E.; Dong, L.; Chow, D.; Charnsangavej, C.; Gelovani, J. G. Dual optical and nuclear imaging in human melanoma xenografts using a single targeted imaging probe Nucl. Med. Biol. 2006, 33, 349-358
26. Adams, K. E.; Ke, S.; Kwon, S.; Liang, F.; Fan, Z.; Lu, Y.; Hirschi, K.; Mawad, M. E.; Barry, M. A.; Sevick-Muraca, E. M. Comparison of visible and near-infrared wavelength-excitable fluorescent dyes for molecular imaging of cancer J. Biomed. Opt. 2007, 12, 024017
27. Marshall, M. V.; Draney, D.; Sevick-Muraca, E. M.; Olive, D. M. Single-dose intravenous toxicity study of IRDye 800CW in Sprague-Dawley rats Mol. Imaging Biol. 2010, 12, 583-594
28. 64Cu radiopharmaceuticals Nucl. Med. Biol. 2010, 37, 57-65
29. Anderson, C. J.; Ferdani, R. Copper-64 radiopharmaceuticals for PET imaging of cancer: advances in preclinical and clinical research Cancer Biother. Radiopharm. 2009, 24, 379-393
30. Dumont, R. A.; Deininger, F.; Haubner, R.; Maecke, H. R.; Weber, W. A.; Fani, M. Novel (64)Cu-and (68)Ga-labeled RGD conjugates show improved PET imaging of α(v)β(3) integrin expression and facile radiosynthesis J. Nucl. Med. 2011, 52, 1276-1284
31. Azhdarinia, A.; Wilganowski, N.; Robinson, H.; Ghosh, P.; Kwon, S.; Lazard, Z. W.; Davis, A. R.; Olmsted-Davis, E.; Sevick-Muraca, E. M. Characterization of chemical, radiochemical and optical properties of a dual-labeled MMP-9 targeting peptide Bioorg. Med. Chem. 2011, 19, 3769-3776
32. Rodenberg, E.; Azhdarinia, A.; Lazard, Z. W.; Hall, M.; Kwon, S. K.; Wilganowski, N.; Salisbury, E. A.; Merched-Sauvage, M.; Olmsted-Davis, E. A.; Sevick-Muraca, E. M.; Davis, A. R. Matrix metalloproteinase-9 is a diagnostic marker of heterotopic ossification in a murine model Tissue Eng., Part A 2011, 17, 2487-2496
33. Rogers, B. E.; Anderson, C. J.; Connett, J. M.; Guo, L. W.; Edwards, W. B.; Sherman, E. L.; Zinn, K. R.; Welch, M. J. Comparison of four bifunctional chelates for radiolabeling monoclonal antibodies with copper radioisotopes: biodistribution and metabolism Bioconjugate Chem. 1996, 7, 511-522
34. Hall, M. A.; Pinkston, K. L.; Wilganowski, N.; Robinson, H.; Ghosh, P.; Azhdarinia, A.; Vazquez-Arreguin, K.; Kolonin, A. M.; Harvey, B. R.; Sevick-Muraca, E. M. Comparison of mAbs targeting epithelial cell adhesion molecule for the detection of prostate cancer lymph node metastases with multimodal contrast agents: quantitative small-animal PET/CT and NIRF J. Nucl. Med. 2012, 53, 1427-1437
35. Weissleder, R.; Tung, C. H.; Mahmood, U.; Bogdanov, A., Jr. In vivo imaging of tumors with protease-activated near-infrared fluorescent probes Nat. Biotechnol. 1999, 17, 375-378
36. Sun, M. M.; Beam, K. S.; Cerveny, C. G.; Hamblett, K. J.; Blackmore, R. S.; Torgov, M. Y.; Handley, F. G.; Ihle, N. C.; Senter, P. D.; Alley, S. C. Reduction-alkylation strategies for the modification of specific monoclonal antibody disulfides Bioconjugage Chem. 2005, 16, 1282-1290
37. Rossin, R.; Verkerk, P. R.; van den Bosch, S. M.; Vulders, R. C.; Verel, I.; Lub, J.; Robillard, M. S. In vivo chemistry for pretargeted tumor imaging in live mice Angew. Chem., Int. Ed. 2010, 49, 3375-3378
38. Williams, A. T. R.; Winfield, S. A.; J.N., M. Relative fluorescence quantum yields using a computer controlled luminescence spectrometer Analyst 1983, 108, 1067-1071
39. Sevick-Muraca, E. M.; Heintzelman, D. L.; Lee, J.; Troy, T. L.; Paithankar, D. Y. Role of higher-order scattering in solutions to the forward and inverse optical-imaging problems in random media Appl. Opt. 1997, 36, 9058-9067
40. Poczatek, R. B.; Myers, R. B.; Manne, U.; Oelschlager, D. K.; Weiss, H. L.; Bostwick, D. G.; Grizzle, W. E. Ep-Cam levels in prostatic adenocarcinoma and prostatic intraepithelial neoplasia J. Urol. 1999, 162, 1462-1466
41. Hall, M. A.; Aldrich, M. B.; Azhdarinia, A.; Lachance, P. A.; Robinson, H.; Hazen, A.; Haviland, D. L.; Sevick-Muraca, E. M. Quantifying multimodal contrast agent biological activity using near-infrared flow cytometry Contrast Media Mol. Imaging 2012, 7, 338-345