Gold-Triggered Uncaging Chemistry in Living Systems

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2017 Jul 13

PMID 28699691

Citations 57

Authors

Ana M Perez-Lopez

Belen Rubio-Ruiz

Victor Sebastian

Lloyd Hamilton

Catherine Adam

Thomas L Bray

Silvia Irusta

Paul M Brennan

Guy C Lloyd-Jones

Dirk Sieger

Jesus Santamaria

Asier Unciti-Broceta

Affiliations

Soon will be listed here.

Abstract

Recent advances in bioorthogonal catalysis are increasing the capacity of researchers to manipulate the fate of molecules in complex biological systems. A bioorthogonal uncaging strategy is presented, which is triggered by heterogeneous gold catalysis and facilitates the activation of a structurally diverse range of therapeutics in cancer cell culture. Furthermore, this solid-supported catalytic system enabled locally controlled release of a fluorescent dye into the brain of a zebrafish for the first time, offering a novel way to modulate the activity of bioorthogonal reagents in the most fragile and complex organs.

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References

Hamilton L, Astell K, Velikova G, Sieger D . A Zebrafish Live Imaging Model Reveals Differential Responses of Microglia Toward Glioblastoma Cells In Vivo. Zebrafish. 2016; 13(6):523-534. PMC: 5124743. DOI: 10.1089/zeb.2016.1339. View

Michel B, Lippert A, Chang C . A reaction-based fluorescent probe for selective imaging of carbon monoxide in living cells using a palladium-mediated carbonylation. J Am Chem Soc. 2012; 134(38):15668-71. DOI: 10.1021/ja307017b. View

Matikonda S, Orsi D, Staudacher V, Jenkins I, Fiedler F, Chen J . Bioorthogonal prodrug activation driven by a strain-promoted 1,3-dipolar cycloaddition. Chem Sci. 2018; 6(2):1212-1218. PMC: 5811098. DOI: 10.1039/c4sc02574a. View

Prescher J, Bertozzi C . Chemistry in living systems. Nat Chem Biol. 2006; 1(1):13-21. DOI: 10.1038/nchembio0605-13. View

Daraee H, Eatemadi A, Abbasi E, Aval S, Kouhi M, Akbarzadeh A . Application of gold nanoparticles in biomedical and drug delivery. Artif Cells Nanomed Biotechnol. 2014; 44(1):410-22. DOI: 10.3109/21691401.2014.955107. View

Tsubokura K, Vong K, Pradipta A, Ogura A, Urano S, Tahara T . In Vivo Gold Complex Catalysis within Live Mice. Angew Chem Int Ed Engl. 2017; 56(13):3579-3584. DOI: 10.1002/anie.201610273. View

Patterson D, Nazarova L, Prescher J . Finding the right (bioorthogonal) chemistry. ACS Chem Biol. 2014; 9(3):592-605. DOI: 10.1021/cb400828a. View

Furstner A, Davies P . Catalytic carbophilic activation: catalysis by platinum and gold pi acids. Angew Chem Int Ed Engl. 2007; 46(19):3410-49. DOI: 10.1002/anie.200604335. View

Sletten E, Bertozzi C . Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl. 2009; 48(38):6974-98. PMC: 2864149. DOI: 10.1002/anie.200900942. View

10.

Hsu H, Trantow B, Waymouth R, Wender P . Bioorthogonal Catalysis: A General Method To Evaluate Metal-Catalyzed Reactions in Real Time in Living Systems Using a Cellular Luciferase Reporter System. Bioconjug Chem. 2015; 27(2):376-82. PMC: 4772775. DOI: 10.1021/acs.bioconjchem.5b00469. View

11.

Yang M, Li J, Chen P . Transition metal-mediated bioorthogonal protein chemistry in living cells. Chem Soc Rev. 2014; 43(18):6511-26. DOI: 10.1039/c4cs00117f. View

12.

Tomas-Gamasa M, Martinez-Calvo M, Couceiro J, Mascarenas J . Transition metal catalysis in the mitochondria of living cells. Nat Commun. 2016; 7:12538. PMC: 5023949. DOI: 10.1038/ncomms12538. View

13.

Vericat C, Vela M, Benitez G, Carro P, Salvarezza R . Self-assembled monolayers of thiols and dithiols on gold: new challenges for a well-known system. Chem Soc Rev. 2010; 39(5):1805-34. DOI: 10.1039/b907301a. View

14.

Versteegen R, Rossin R, Ten Hoeve W, Janssen H, Robillard M . Click to release: instantaneous doxorubicin elimination upon tetrazine ligation. Angew Chem Int Ed Engl. 2013; 52(52):14112-6. DOI: 10.1002/anie.201305969. View

15.

Uson L, Sebastian V, Mayoral A, Hueso J, Eguizabal A, Arruebo M . Spontaneous formation of Au-Pt alloyed nanoparticles using pure nano-counterparts as starters: a ligand and size dependent process. Nanoscale. 2015; 7(22):10152-61. PMC: 4447060. DOI: 10.1039/c5nr01819f. View

16.

Unciti-Broceta A . Bioorthogonal catalysis: Rise of the nanobots. Nat Chem. 2015; 7(7):538-9. DOI: 10.1038/nchem.2291. View

17.

Dorel R, Echavarren A . Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity. Chem Rev. 2015; 115(17):9028-72. PMC: 4580024. DOI: 10.1021/cr500691k. View

18.

Streu C, Meggers E . Ruthenium-induced allylcarbamate cleavage in living cells. Angew Chem Int Ed Engl. 2006; 45(34):5645-8. DOI: 10.1002/anie.200601752. View

19.

Li N, Lim R, Edwardraja S, Lin Q . Copper-free Sonogashira cross-coupling for functionalization of alkyne-encoded proteins in aqueous medium and in bacterial cells. J Am Chem Soc. 2011; 133(39):15316-9. PMC: 3184007. DOI: 10.1021/ja2066913. View

20.

Corma A, Garcia H . Supported gold nanoparticles as catalysts for organic reactions. Chem Soc Rev. 2008; 37(9):2096-126. DOI: 10.1039/b707314n. View