Transition-metal-free nucleophilic 211At-astatination of spirocyclic aryliodonium ylides

被引:11
作者
Matsuoka, Keitaro [1 ]
Obata, Honoka [1 ,2 ]
Nagatsu, Kotaro [2 ]
Kojima, Masahiro [1 ]
Yoshino, Tatsuhiko [1 ]
Ogawa, Mikako [1 ,3 ]
Matsunaga, Shigeki [1 ,3 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Natl Inst Quantum & Radiol Sci & Technol, Dept Adv Nucl Med Sci, Inst Quantum Med Sci, Chiba 2638555, Japan
[3] Hokkaido Univ, Global Stn Biosurfaces & Drug Discovery, Sapporo, Hokkaido 0600812, Japan
关键词
IODONIUM YLIDES; RADIOFLUORINATION; SUBSTITUTION; RADIOIODINATION; RADIOHALOGENS; ASTATINATION; CHEMISTRY; BEHAVIOR; STEP;
D O I
10.1039/d1ob00789k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The transition-metal-free At-211-astatination of spirocyclic aryliodonium ylides via a nucleophilic aromatic substitution reaction is described. This method enables the preparation of At-211-radiolabeled compounds derived from multi-functionalized molecules and heteroarenes in good to excellent radiochemical yields.
引用
收藏
页码:5525 / 5528
页数:4
相关论文
共 29 条
[1]   Radiohalogens for imaging and therapy [J].
Adam, MJ ;
Wilbur, DS .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :153-163
[2]   Molecular Pathways: Targeted α-Particle Radiation Therapy [J].
Baidoo, Kwamena E. ;
Yong, Kwon ;
Brechbiel, Martin W. .
CLINICAL CANCER RESEARCH, 2013, 19 (03) :530-537
[3]   Investigation on the reactivity of nucleophilic radiohalogens with arylboronic acids in water: access to an efficient single-step method for the radioiodination and astatination of antibodies [J].
Berdal, Marion ;
Gouard, Sebastien ;
Eychenne, Romain ;
Marionneau-Lambot, Severine ;
Croyal, Mikael ;
Faivre-Chauvet, Alain ;
Cherel, Michel ;
Gaschet, Joelle ;
Gestin, Jean-Francois ;
Guerard, Francois .
CHEMICAL SCIENCE, 2021, 12 (04) :1458-1468
[4]   Iodonium ylides for one-step, no-carrier-added radiofluorination of electron rich arenes, exemplified with 4-(([18F] fluorophenoxy)-phenylmethyl) piperidine NET and SERT ligands [J].
Cardinale, Jens ;
Ermert, Johannes ;
Humpert, Sven ;
Coenen, Heinz H. .
RSC ADVANCES, 2014, 4 (33) :17293-17299
[5]   Bifunctional aryliodonium salts for highly efficient radioiodination and astatination of antibodies [J].
Guerard, F. ;
Navarro, L. ;
Lee, Y. -S. ;
Roumesy, A. ;
Alliot, C. ;
Cherel, M. ;
Brechbiel, M. W. ;
Gestin, J. -F. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (21) :5975-5980
[6]   Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts [J].
Guerard, Francois ;
Lee, Yong-Sok ;
Baidoo, Kwamena ;
Gestin, Jean-Francois ;
Brechbiel, Martin W. .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (35) :12332-12339
[7]   Production of [211At]-Astatinated Radiopharmaceuticals and Applications in Targeted α-Particle Therapy [J].
Guerard, Francois ;
Gestin, Jean-Francois ;
Brechbiel, Martin W. .
CANCER BIOTHERAPY AND RADIOPHARMACEUTICALS, 2013, 28 (01) :1-20
[8]   Organocatalyst-assisted Ar-18F bond formation: a universal procedure for direct aromatic radiofluorination [J].
Jakobsson, Jimmy Erik ;
Gronnevik, Gaute ;
Riss, Patrick Johannes .
CHEMICAL COMMUNICATIONS, 2017, 53 (96) :12906-12909
[9]   Synthesis of Functionalized Monoaryl-λ3-iodanes through Chemo- and Site-Selective ipso-Substitution Reactions [J].
Komami, Narumi ;
Matsuoka, Keitaro ;
Nakano, Ayako ;
Kojima, Masahiro ;
Yoshino, Tatsuhiko ;
Matsunaga, Shigeki .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (05) :1217-1220
[10]   Facile 18F labeling of non-activated arenes via a spirocyclic iodonium(III) ylide method and its application in the synthesis of the mGluR5 PET radiopharmaceutical [18F]FPEB [J].
Liang, Steven H. ;
Wang, Lu ;
Stephenson, Nickeisha A. ;
Rotstein, Benjamin H. ;
Vasdev, Neil .
NATURE PROTOCOLS, 2019, 14 (05) :1530-1545