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(4-[18F]Fluoro-3-iodobenzyl)guanidine, a Potential MIBG Analog for Positron Emission Tomography

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    (4-[18F]Fluoro-3-iodobenzyl)guanidine, a Potential MIBG Analog for Positron Emission Tomography
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 1994, 37, 21, 3655–3662
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    https://doi.org/10.1021/jm00047a022
    Published October 1, 1994
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    This article is cited by 47 publications.

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    3. Byung Chul Lee,, Jin-Young Paik,, Dae Yoon Chi,, Kyung-Han Lee, and, Yearn Seong Choe. Potential and Practical Adrenomedullary PET Radiopharmaceuticals as an Alternative to m-Iodobenzylguanidine:  m-(ω-[18F]Fluoroalkyl)benzylguanidines. Bioconjugate Chemistry 2004, 15 (1) , 104-111. https://doi.org/10.1021/bc034115e
    4. Ganesan Vaidyanathan,, Sriram Shankar,, Donna J. Affleck,, Philip C. Welsh,, Susan K. Slade, and, Michael R. Zalutsky. Biological Evaluation of Ring- and Side-Chain-Substituted m-Iodobenzylguanidine Analogues. Bioconjugate Chemistry 2001, 12 (5) , 798-806. https://doi.org/10.1021/bc010032r
    5. Ganesan Vaidyanathan,, Michael R. Zalutsky, and, Timothy R. DeGrado. Iodopyridine-for-Iodobenzene Substitution for Use with Low Molecular Weight Radiopharmaceuticals:  Application to m-Iodobenzylguanidine. Bioconjugate Chemistry 1998, 9 (6) , 758-764. https://doi.org/10.1021/bc980037x
    6. Ganesan Vaidyanathan and, Michael R. Zalutsky. A New Route to Guanidines from Bromoalkanes. The Journal of Organic Chemistry 1997, 62 (14) , 4867-4869. https://doi.org/10.1021/jo9704164
    7. Ganesan Vaidyanathan,, Donna J. Affleck, and, Michael R. Zalutsky. No-Carrier-Added (4-Fluoro-3-[131I]iodobenzyl)guanidine and (3-[211At]Astato-4-fluorobenzyl)guanidine. Bioconjugate Chemistry 1996, 7 (1) , 102-107. https://doi.org/10.1021/bc950078i
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    14. Stephen J. Lokitz, Sudha Garg, Rachid Nazih, Pradeep K. Garg. Whole Body PET Imaging with a Norepinephrine Transporter Probe 4-[18F]Fluorobenzylguanidine: Biodistribution and Radiation Dosimetry. Molecular Imaging and Biology 2019, 21 (4) , 686-695. https://doi.org/10.1007/s11307-018-1280-1
    15. Ravi Kant Gupta, Rakesh Kumar. Molecular Imaging in Neuroblastoma. 2019, 133-145. https://doi.org/10.1016/B978-0-12-812005-7.00008-4
    16. Aiko Yamaguchi, Hirofumi Hanaoka, Tetsuya Higuchi, Yoshito Tsushima. Radiolabeled (4-Fluoro-3-Iodobenzyl)Guanidine Improves Imaging and Targeted Radionuclide Therapy of Norepinephrine Transporter–Expressing Tumors. Journal of Nuclear Medicine 2018, 59 (5) , 815-821. https://doi.org/10.2967/jnumed.117.201525
    17. Ralf Schirrmacher, Björn Wängler, Justin Bailey, Vadim Bernard-Gauthier, Esther Schirrmacher, Carmen Wängler. Small Prosthetic Groups in 18 F-Radiochemistry: Useful Auxiliaries for the Design of 18 F-PET Tracers. Seminars in Nuclear Medicine 2017, 47 (5) , 474-492. https://doi.org/10.1053/j.semnuclmed.2017.07.001
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    19. Ganesan Vaidyanathan, Darryl McDougald, Eftychia Koumarianou, Jaeyeon Choi, Marc Hens, Michael R. Zalutsky. Synthesis and evaluation of 4-[18F]fluoropropoxy-3-iodobenzylguanidine ([18F]FPOIBG): A novel 18F-labeled analogue of MIBG. Nuclear Medicine and Biology 2015, 42 (8) , 673-684. https://doi.org/10.1016/j.nucmedbio.2015.04.005
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    23. Susan E. Sharp, Michael J. Gelfand, Barry L. Shulkin. Neuroblastoma: Functional Imaging. 2014, 429-445. https://doi.org/10.1007/978-1-4614-9551-2_19
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    25. Susan E. Sharp, Michael J. Gelfand, Barry L. Shulkin. Pediatrics: Diagnosis of Neuroblastoma. Seminars in Nuclear Medicine 2011, 41 (5) , 345-353. https://doi.org/10.1053/j.semnuclmed.2011.05.001
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    27. T. L. Ross, H. J. Wester. 18F: Labeling Chemistry and Labeled Compounds. 2011, 2021-2071. https://doi.org/10.1007/978-1-4419-0720-2_42
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    29. Ingrid Koslowsky, John Mercer, Frank Wuest. Synthesis and application of 4-[18F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers. Organic & Biomolecular Chemistry 2010, 8 (20) , 4730. https://doi.org/10.1039/c0ob00255k
    30. Susan E. Sharp, Barry L. Shulkin, Michael J. Gelfand, Shelia Salisbury, Wayne L. Furman. 123 I-MIBG Scintigraphy and 18 F-FDG PET in Neuroblastoma. Journal of Nuclear Medicine 2009, 50 (8) , 1237-1243. https://doi.org/10.2967/jnumed.108.060467
    31. Susan E. Sharp, Michael J. Gelfand, Barry L. Shulkin. PET/CT in the Evaluation of Neuroblastoma. PET Clinics 2008, 3 (4) , 551-561. https://doi.org/10.1016/j.cpet.2009.03.006
    32. Klaus Kopka, Otmar Schober, Stefan Wagner. 18F-labelled cardiac PET tracers: selected probes for the molecular imaging of transporters, receptors and proteases. Basic Research in Cardiology 2008, 103 (2) , 131-143. https://doi.org/10.1007/s00395-008-0703-6
    33. Klaus Kopka, Stefan Wagner, Michael Schäfers, Andreas Faust, Otmar Schober, Günter Haufe. 18F‐Labeled PET‐Tracers for Cardiological Imaging. 2008, 85-139. https://doi.org/10.1016/B978-0-444-53086-8.00003-5
    34. Johannes Ermert, Thomas Ludwig, René Gail, Heinz H. Coenen. [18F]Fluorophenyl organometallics as intermediates of no-carrier-added 18F-fluoroarylation reactions. Journal of Organometallic Chemistry 2007, 692 (19) , 4084-4092. https://doi.org/10.1016/j.jorganchem.2007.06.009
    35. Ganesan Vaidyanathan, Donna J. Affleck, Kevin L. Alston, Xiao-Guang Zhao, Marc Hens, Duncan H. Hunter, John Babich, Michael R. Zalutsky. A kit method for the high level synthesis of [211At]MABG. Bioorganic & Medicinal Chemistry 2007, 15 (10) , 3430-3436. https://doi.org/10.1016/j.bmc.2007.03.016
    36. Barry L. Shulkin. Neuroblastoma. 2006, 243-255. https://doi.org/10.1007/0-387-34641-4_13
    37. Ganesan Vaidyanathan, Donna J. Affleck, Kevin L. Alston, Philip Welsh, Michael R. Zalutsky. Catabolism of 4-fluoro-3-iodobenzylguanidine and meta-iodobenzylguanidine by SK-N-SH neuroblastoma cells. Nuclear Medicine Communications 2004, 25 (9) , 947-955. https://doi.org/10.1097/00006231-200409000-00013
    38. . 18F: Labeling Chemistry and Labeled Compounds. 2003, 1465-1507. https://doi.org/10.1007/0-387-30682-X_34
    39. B. C. Lee, Y. S. Choe, K. H. Lee, B.‐T. Kim, D. Y. Chi. New potential and practical mibg analogs for pet: meta ‐(3‐[ 18 F]Fluoroalkyl)benzylguanidines. Journal of Labelled Compounds and Radiopharmaceuticals 2001, 44 (S1) https://doi.org/10.1002/jlcr.25804401143
    40. B. Shapiro, L. M. Fig, M. D. Gross, B. L. Shulkin, J. C. Sisson. Neuroendocrine Tumors. 1999, 3-31. https://doi.org/10.1007/978-3-642-58643-9_1
    41. Timothy R DeGrado, Shuyan Wang. Transcapillary Transport of Metaiodobenzylguanidine (MIBG) in Isolated Rat Heart. Nuclear Medicine and Biology 1998, 25 (5) , 455-465. https://doi.org/10.1016/S0969-8051(98)00015-8
    42. Albert D. Windhorst, Rob Leurs, Wiro M.P.B. Menge, Henk Timmerman, Jacobus D.M. Herscheid. Synthesis of radioligands for the histamine H3 receptor. 1998, 159-174. https://doi.org/10.1016/S0165-7208(98)80029-9
    43. . XIIth international symposium on radiopharmaceutical chemistry: Abstracts and programme. Journal of Labelled Compounds and Radiopharmaceuticals 1997, 595-669. https://doi.org/10.1002/jlcr.2580400901
    44. Göran Westerberg, Bengt Långström. Synthesis of meta-iodobenzyl [11C]guanidine. Journal of Labelled Compounds and Radiopharmaceuticals 1997, 39 (6) , 525-529. https://doi.org/10.1002/(SICI)1099-1344(199706)39:6<525::AID-JLCR998>3.0.CO;2-9
    45. Ganesan Vaidyanathan, Henry S. Friedman, Stephen T. Keir, Michael R. Zalutsky. Evaluation of meta-[211At]astatobenzylguanidine in an athymic mouse human neuroblastoma xenograft model. Nuclear Medicine and Biology 1996, 23 (6) , 851-856. https://doi.org/10.1016/0969-8051(96)00115-1
    46. David M. Raffel, James R. Corbett, Markus Schwaiger, Donald M. Wieland. Mechanism-based strategies for mapping heart sympathetic nerve function. Nuclear Medicine and Biology 1995, 22 (8) , 1019-1026. https://doi.org/10.1016/0969-8051(95)02025-X
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    Cite this: J. Med. Chem. 1994, 37, 21, 3655–3662
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    https://doi.org/10.1021/jm00047a022
    Published October 1, 1994
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