Controlled masking and targeted release of redox-cycling ortho-quinones via a C-C bond-cleaving 1,6-elimination

Autor: Dunsmore, Lavinia, Navo, Claudio D., Becher, Julie, de Montes, Enrique Gil, Guerreiro, Ana, Hoyt, Emily, Brown, Libby, Zelenay, Viviane, Mikutis, Sigitas, Cooper, Jonathan, Barbieri, Isaia, Lawrinowitz, Stefanie, Siouve, Elise, Martin, Esther, Ruivo, Pedro R., Rodrigues, Tiago, da Cruz, Filipa P., Werz, Oliver, Vassiliou, George, Ravn, Peter, Jiménez-Osés, Gonzalo, Bernardes, Gonçalo J. L., 0000-0002-9125-6081, 0000-0003-0161-412X, 0000-0002-8417-4475, 0000-0001-6940-8803, 0000-0003-0064-639X, 0000-0003-3035-8970, 0000-0002-5064-4379, 0000-0003-4337-8022, 0000-0003-0105-4337, 0000-0001-6594-8917

Publikováno v: RIUR. Repositorio Institucional de la Universidad de La Rioja
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Natural products that contain ortho-quinones show great potential as anticancer agents but have been largely discarded from clinical development because their redox-cycling behaviour results in general systemic toxicity. Here we report conjugation of

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Controlled masking and targeted release of redox-cycling ortho-quinones via a C-C bond-cleaving 1,6-elimination.

Autor: Dunsmore L; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK., Navo CD; Center for Cooperative Research in Biosciences (CIC bioGUNE), Basque Research and Technology Alliance (BRTA), Derio-Bizkaia, Spain., Becher J; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK., de Montes EG; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK., Guerreiro A; Instituto de Medicina Molecular João Lobo Antunes, Faculdade de Medicina da Universidade de Lisboa, Lisbon, Portugal., Hoyt E; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK., Brown L; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK.; Biologics Engineering, R&D, AstraZeneca, Cambridge, UK., Zelenay V; Biologics Engineering, R&D, AstraZeneca, Cambridge, UK., Mikutis S; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK., Cooper J; Wellcome-MRC Cambridge Stem Cell Institute, Department of Haematology, University of Cambridge, Cambridge, UK., Barbieri I; Division of Cellular and Molecular Pathology, Department of Pathology, University of Cambridge, Cambridge, UK., Lawrinowitz S; Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich Schiller University Jena, Jena, Germany., Siouve E; Biologics Engineering, R&D, AstraZeneca, Cambridge, UK.; Department of Chemical Engineering and Biotechnology, University of Cambridge, Cambridge, UK., Martin E; Biologics Engineering, R&D, AstraZeneca, Cambridge, UK., Ruivo PR; Instituto de Medicina Molecular João Lobo Antunes, Faculdade de Medicina da Universidade de Lisboa, Lisbon, Portugal., Rodrigues T; Instituto de Medicina Molecular João Lobo Antunes, Faculdade de Medicina da Universidade de Lisboa, Lisbon, Portugal., da Cruz FP; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK., Werz O; Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich Schiller University Jena, Jena, Germany., Vassiliou G; Wellcome-MRC Cambridge Stem Cell Institute, Department of Haematology, University of Cambridge, Cambridge, UK., Ravn P; Biologics Engineering, R&D, AstraZeneca, Cambridge, UK.; Department of Biotherapeutic Discovery, H. Lundbeck A/S, Valby, Denmark., Jiménez-Osés G; Center for Cooperative Research in Biosciences (CIC bioGUNE), Basque Research and Technology Alliance (BRTA), Derio-Bizkaia, Spain. gjoses@cicbiogune.es.; Ikerbasque, Basque Foundation for Science, Bilbao, Spain. gjoses@cicbiogune.es., Bernardes GJL; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK. gb453@cam.ac.uk.; Instituto de Medicina Molecular João Lobo Antunes, Faculdade de Medicina da Universidade de Lisboa, Lisbon, Portugal. gb453@cam.ac.uk.

Publikováno v: Nature chemistry [Nat Chem] 2022 Jul; Vol. 14 (7), pp. 754-765. Date of Electronic Publication: 2022 Jun 27.