Cu(i)-assisted click chemistry strategy for conjugation of non-protected cross-bridged macrocyclic chelators to tumour-targeting peptides

Zhengxin Cai; Barbara T. Y. Li; Edward H. Wong; Gary R. Weisman; Carolyn J. Anderson

doi:10.1039/c4dt03897e

Cu(i)-assisted click chemistry strategy for conjugation of non-protected cross-bridged macrocyclic chelators to tumour-targeting peptides

Dalton Transactions ◽

10.1039/c4dt03897e ◽

2015 ◽

Vol 44 (9) ◽

pp. 3945-3948 ◽

Cited By ~ 15

Author(s):

Zhengxin Cai ◽

Barbara T. Y. Li ◽

Edward H. Wong ◽

Gary R. Weisman ◽

Carolyn J. Anderson

Keyword(s):

Click Chemistry ◽

Tumour Targeting ◽

Pet Radiopharmaceutical ◽

Macrocyclic Chelator

A novel phosphonate-based cross-bridged macrocyclic chelator was efficiently synthesized, clicked with an octreotate analogue, and evaluated as a 64Cu-labelled PET radiopharmaceutical.

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Radiometal-Labelled Macrocyclic Chelator-Derivatised Somatostatin Analogue with Superb Tumour-Targeting Properties and Potential for Receptor-Mediated Internal Radiotherapy

Chemistry - A European Journal ◽

10.1002/(sici)1521-3765(19990702)5:7<1974::aid-chem1974>3.0.co;2-x ◽

1999 ◽

Vol 5 (7) ◽

pp. 1974-1981 ◽

Cited By ~ 211

Author(s):

A. Heppeler ◽

S. Froidevaux ◽

H. R. Mäcke ◽

E. Jermann ◽

M. Béhé ◽

...

Keyword(s):

Somatostatin Analogue ◽

Tumour Targeting ◽

Internal Radiotherapy ◽

Macrocyclic Chelator

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New click chemistry reaction: sulfur fluoride exchange

AccessScience ◽

10.1036/1097-8542.br0902141 ◽

2015 ◽

Keyword(s):

Click Chemistry ◽

Sulfur Fluoride

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Click Chemistry Expedited Radiosynthesis: Sulfur [18F]fluoride Exchange of Aryl Fluorosulfates

10.26434/chemrxiv.10314647.v1 ◽

2019 ◽

Cited By ~ 1

Author(s):

Qinheng Zheng ◽

Hongtao Xu ◽

Hua Wang ◽

Wen-Ge Han Du ◽

Nan Wang ◽

...

Keyword(s):

Click Chemistry ◽

High Performance ◽

Isotopic Exchange ◽

Tumor Imaging ◽

Radiochemical Yield ◽

Exchange Method ◽

Molar Activity ◽

Positron Emission ◽

Sulfur Fluoride

The lack of simple, efficient [18F]fluorination processes and new target-specific organofluorine probes remains the major challenge of fluorine-18-based positron emission tomography (PET). We report here a fast isotopic exchange method for the radiosynthesis of aryl [18F]fluorosulfate based PET agents enabled by the emerging sulfur fluoride exchange (SuFEx) click chemistry. The method has been applied to the fully-automated 18F-radiolabeling of twenty-five structurally diverse aryl fluorosulfates with excellent radiochemical yield (83–100%) and high molar activity (up to 281 GBq µmol–1) at room temperature in 30 seconds. The purification of radiotracers requires no time-consuming high-performance liquid chromatography (HPLC), but rather a simple cartridge filtration. The utility of aryl [18F]fluorosulfate is demonstrated by the in vivo tumor imaging by targeting poly(ADP-ribose) polymerase 1 (PARP1).

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