Multifunctional Clickable Reagents for Rapid Bioorthogonal Astatination and Radio-Crosslinking

Overview

Journal Chempluschem

Specialty Chemistry

Date 2019 Nov 5

PMID 31681526

Citations 6

Authors

Christoph Denk

Martin Wilkovitsch

Emma Aneheim

Matthias M Herth

Holger Jensen

Sture Lindegren

Hannes Mikula

Affiliations

Soon will be listed here.

Abstract

In the past decade, several developments have expanded the chemical toolbox for astatination and the preparation of At-labeled radiopharmaceuticals. However, there is still a need for advanced methods for the synthesis of astatinated (bio)molecules to address challenges such as limited in vivo stability. Herein, we report the development of multifunctional At-labeled reagents that can be prepared by applying a modular and versatile click approach for rapid assembly. The introduction of tetrazines as bioorthogonal tags enables rapid radiolabeling and radio-crosslinking, which is demonstrated by steric shielding of At to significantly increase label stability in human blood plasma.

Citing Articles

Solid-Phase Synthesis of -Tetrazines.

Alghamdi Z, Klausen M, Gambardella A, Lilienkampf A, Bradley M Org Lett. 2023; 25(17):3104-3108.

PMID: 37083299 PMC: 10167685. DOI: 10.1021/acs.orglett.3c00955.

Recent Advances in the Development of Tetrazine Ligation Tools for Pretargeted Nuclear Imaging.

Garcia-Vazquez R, Battisti U, Herth M Pharmaceuticals (Basel). 2022; 15(6).

PMID: 35745604 PMC: 9227058. DOI: 10.3390/ph15060685.

Uncovering the Key Role of Distortion in Bioorthogonal Tetrazine Tools That Defy the Reactivity/Stability Trade-Off.

Svatunek D, Wilkovitsch M, Hartmann L, Houk K, Mikula H J Am Chem Soc. 2022; 144(18):8171-8177.

PMID: 35500228 PMC: 9100665. DOI: 10.1021/jacs.2c01056.

Origin of Increased Reactivity in Rhenium-Mediated Cycloadditions of Tetrazines.

Turlik A, Houk K, Svatunek D J Org Chem. 2021; 86(18):13129-13133.

PMID: 34468143 PMC: 8453624. DOI: 10.1021/acs.joc.1c01564.

Multifunctional Clickable Reagents for Rapid Bioorthogonal Astatination and Radio-Crosslinking.

Denk C, Wilkovitsch M, Aneheim E, Herth M, Jensen H, Lindegren S Chempluschem. 2019; 84(7):775-778.

PMID: 31681526 PMC: 6813637. DOI: 10.1002/cplu.201900114.

References

Hadley S, Wilbur D, Gray M, Atcher R . Astatine-211 labeling of an antimelanoma antibody and its Fab fragment using N-succinimidyl p-astatobenzoate: comparisons in vivo with the p-[125I]iodobenzoyl conjugate. Bioconjug Chem. 1991; 2(3):171-9. DOI: 10.1021/bc00009a006. View

Meyer J, Adumeau P, Lewis J, Zeglis B . Click Chemistry and Radiochemistry: The First 10 Years. Bioconjug Chem. 2016; 27(12):2791-2807. PMC: 5193009. DOI: 10.1021/acs.bioconjchem.6b00561. View

Reilly S, Makvandi M, Xu K, Mach R . Rapid Cu-Catalyzed [At]Astatination and [I]Iodination of Boronic Esters at Room Temperature. Org Lett. 2018; 20(7):1752-1755. PMC: 5973503. DOI: 10.1021/acs.orglett.8b00232. View

Rossin R, Renart Verkerk P, van den Bosch S, Vulders R, Verel I, Lub J . In vivo chemistry for pretargeted tumor imaging in live mice. Angew Chem Int Ed Engl. 2010; 49(19):3375-8. DOI: 10.1002/anie.200906294. View

Yan R, Sander K, Galante E, Rajkumar V, Badar A, Robson M . A one-pot three-component radiochemical reaction for rapid assembly of 125I-labeled molecular probes. J Am Chem Soc. 2012; 135(2):703-9. DOI: 10.1021/ja307926g. View

Zeng D, Zeglis B, Lewis J, Anderson C . The growing impact of bioorthogonal click chemistry on the development of radiopharmaceuticals. J Nucl Med. 2013; 54(6):829-32. PMC: 4151560. DOI: 10.2967/jnumed.112.115550. View

Poty S, Membreno R, Glaser J, Ragupathi A, Scholz W, Zeglis B . The inverse electron-demand Diels-Alder reaction as a new methodology for the synthesis of Ac-labelled radioimmunoconjugates. Chem Commun (Camb). 2018; 54(21):2599-2602. PMC: 5843558. DOI: 10.1039/c7cc09129j. View

Aneheim E, Foreman M, Jensen H, Lindegren S . N-[2-(maleimido)ethyl]-3-(trimethylstannyl)benzamide, a molecule for radiohalogenation of proteins and peptides. Appl Radiat Isot. 2014; 96:1-5. DOI: 10.1016/j.apradiso.2014.11.007. View

Xing Y, Zhao J, Conti P, Chen K . Radiolabeled nanoparticles for multimodality tumor imaging. Theranostics. 2014; 4(3):290-306. PMC: 3915092. DOI: 10.7150/thno.7341. View

10.

Fujiki K, Yano S, Ito T, Kumagai Y, Murakami Y, Kamigaito O . A One-Pot Three-Component Double-Click Method for Synthesis of [Cu]-Labeled Biomolecular Radiotherapeutics. Sci Rep. 2017; 7(1):1912. PMC: 5432496. DOI: 10.1038/s41598-017-02123-2. View

11.

Steen E, Edem P, Norregaard K, Jorgensen J, Shalgunov V, Kjaer A . Pretargeting in nuclear imaging and radionuclide therapy: Improving efficacy of theranostics and nanomedicines. Biomaterials. 2018; 179:209-245. DOI: 10.1016/j.biomaterials.2018.06.021. View

12.

Aneheim E, Albertsson P, Back T, Jensen H, Palm S, Lindegren S . Automated astatination of biomolecules--a stepping stone towards multicenter clinical trials. Sci Rep. 2015; 5:12025. PMC: 4500947. DOI: 10.1038/srep12025. View

13.

Wilbur D, Chyan M, Nakamae H, Chen Y, Hamlin D, Santos E . Reagents for astatination of biomolecules. 6. An intact antibody conjugated with a maleimido-closo-decaborate(2-) reagent via sulfhydryl groups had considerably higher kidney concentrations than the same antibody conjugated with an.... Bioconjug Chem. 2012; 23(3):409-20. PMC: 3310299. DOI: 10.1021/bc200401b. View

14.

Orozco J, Back T, Kenoyer A, Balkin E, Hamlin D, Wilbur D . Anti-CD45 radioimmunotherapy using (211)At with bone marrow transplantation prolongs survival in a disseminated murine leukemia model. Blood. 2013; 121(18):3759-67. PMC: 3643772. DOI: 10.1182/blood-2012-11-467035. View

15.

Wilbur D, Chyan M, Hamlin D, Nguyen H, Vessella R . Reagents for astatination of biomolecules. 5. Evaluation of hydrazone linkers in (211)At- and (125)I-labeled closo-decaborate(2-) conjugates of Fab' as a means of decreasing kidney retention. Bioconjug Chem. 2011; 22(6):1089-102. PMC: 3116028. DOI: 10.1021/bc1005625. View

16.

Keiko Li H, Morokoshi Y, Nagatsu K, Kamada T, Hasegawa S . Locoregional therapy with α-emitting trastuzumab against peritoneal metastasis of human epidermal growth factor receptor 2-positive gastric cancer in mice. Cancer Sci. 2017; 108(8):1648-1656. PMC: 5543454. DOI: 10.1111/cas.13282. View

17.

Pozzi O, Zalutsky M . Radiopharmaceutical chemistry of targeted radiotherapeutics, part 4: Strategies for At labeling at high activities and radiation doses of At α-particles. Nucl Med Biol. 2016; 46:43-49. PMC: 5285439. DOI: 10.1016/j.nucmedbio.2016.11.009. View

18.

Albu S, Al-Karmi S, Vito A, Dzandzi J, Zlitni A, Beckford-Vera D . (125)I-Tetrazines and Inverse-Electron-Demand Diels-Alder Chemistry: A Convenient Radioiodination Strategy for Biomolecule Labeling, Screening, and Biodistribution Studies. Bioconjug Chem. 2015; 27(1):207-16. DOI: 10.1021/acs.bioconjchem.5b00609. View

19.

Andersson H, Cederkrantz E, Back T, Divgi C, Elgqvist J, Himmelman J . Intraperitoneal alpha-particle radioimmunotherapy of ovarian cancer patients: pharmacokinetics and dosimetry of (211)At-MX35 F(ab')2--a phase I study. J Nucl Med. 2009; 50(7):1153-60. DOI: 10.2967/jnumed.109.062604. View

20.

Goel S, England C, Chen F, Cai W . Positron emission tomography and nanotechnology: A dynamic duo for cancer theranostics. Adv Drug Deliv Rev. 2016; 113:157-176. PMC: 5299094. DOI: 10.1016/j.addr.2016.08.001. View