A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of 125I-Labeled Molecular Probes
作者： Ran Yan , Kerstin Sander , Eva Galante , Vineeth Rajkumar , Adam Badar
DOI: 10.1021/JA307926G
关键词:
摘要: Nuclear imaging in conjunction with radioactive tracers enables noninvasive measurements of biochemical events vivo. However, access to remains limited due the lack methods for rapid assembly radiolabeled molecules prerequisite biological activity. Herein, we report a one-pot, three-component, copper(II)-mediated reaction azides, alkynes, and [(125)I]iodide yield 5-[(125)I]iodo-1,2,3-triazoles. Using selection azides alkynes combinatorial approach, have synthesized library structurally diverse (125)I-labeled triazoles functionalized bioconjugation groups, fluorescent dyes, biomolecules. Our preliminary evaluation suggests that 5-[(125)I]iodo-1,2,3-triazoles are resistant deiodination vivo, both as small molecular probes antibody conjugates. The ability incorporate iodide into directly from parent makes method broadly applicable offers potential rapidly assemble an array diverse, readily available, building blocks.
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Ganesan Vaidyanathan, Michael R Zalutsky, Synthesis of N -succinimidyl 4-guanidinomethyl-3-[ * I]iodobenzoate: a radio-iodination agent for labeling internalizing proteins and peptides Nature Protocols. ,vol. 2, pp. 282- 286 ,(2007) , 10.1038/NPROT.2007.20
Joseph F. Weiss, Gordon Tollin, John T. Yoke, Reactions of Triethylamine with Copper Halides. II. Internal Oxidation-Reduction of Dichlorobis(triethylamine)copper(II) Inorganic Chemistry. ,vol. 3, pp. 1344- 1348 ,(1964) , 10.1021/IC50020A002
Péter Kele, Xiaohua Li, Martin Link, Krisztina Nagy, András Herner, Krisztián Lőrincz, Szabolcs Béni, Otto S. Wolfbeis, Clickable fluorophores for biological labeling—with or without copper Organic & Biomolecular Chemistry. ,vol. 7, pp. 3486- 3490 ,(2009) , 10.1039/B907741C
Maggie S. Cooper, Michelle T. Ma, Kavitha Sunassee, Karen P. Shaw, Jennifer D. Williams, Rowena L. Paul, Paul S. Donnelly, Philip J. Blower, Comparison of (64)Cu-complexing bifunctional chelators for radioimmunoconjugation: labeling efficiency, specific activity, and in vitro/in vivo stability. Bioconjugate Chemistry. ,vol. 23, pp. 1029- 1039 ,(2012) , 10.1021/BC300037W
Erik Årstad, Per Hoff, Lars Skattebøl, Arne Skretting, Knut Breistøl, Studies on the Synthesis and Biological Properties of Non-Carrier-Added [125I and 131I]-Labeled Arylalkylidenebisphosphonates: Potent Bone-Seekers for Diagnosis and Therapy of Malignant Osseous Lesions Journal of Medicinal Chemistry. ,vol. 46, pp. 3021- 3032 ,(2003) , 10.1021/JM021107V
Yang Zhou, Young-Seung Kim, Xin Yan, Orit Jacobson, Xiaoyuan Chen, Shuang Liu, 64Cu-labeled lissamine rhodamine B: a promising PET radiotracer targeting tumor mitochondria. Molecular Pharmaceutics. ,vol. 8, pp. 1198- 1208 ,(2011) , 10.1021/MP200025M
Lingjun Li, Guisheng Zhang, Anlian Zhu, Lihe Zhang, A convenient preparation of 5-iodo-1,4-disubstituted-1,2,3-triazole: multicomponent one-pot reaction of azide and alkyne mediated by CuI-NBS. Journal of Organic Chemistry. ,vol. 73, pp. 3630- 3633 ,(2008) , 10.1021/JO800035V
Martin Link, Xiaohua Li, Jana Kleim, Otto S. Wolfbeis, Click Chemistry Based Method for the Preparation of Maleinimide‐Type Thiol‐Reactive Labels European Journal of Organic Chemistry. ,vol. 2010, pp. 6922- 6927 ,(2010) , 10.1002/EJOC.201001085
Toshimitsu Okamura, Tatsuya Kikuchi, Kiyoshi Fukushi, Toshiaki Irie, Reactivity of 6-Halopurine Analogs with Glutathione as a Radiotracer for Assessing Function of Multidrug Resistance-Associated Protein 1 Journal of Medicinal Chemistry. ,vol. 52, pp. 7284- 7288 ,(2009) , 10.1021/JM901332C
John T. Yoke, Joseph F. Weiss, Gordon Tollin, Reactions of Triethylamine with Copper(I) and Copper(II) Halides Inorganic Chemistry. ,vol. 2, pp. 1210- 1216 ,(1963) , 10.1021/IC50010A028