NDLI: d- Versus l-Glucose Conjugation: Mitochondrial Targeting of a Light-Activated Dual-Mode-of-Action Ruthenium-Based Anticancer Prodrug

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d- Versus l-Glucose Conjugation: Mitochondrial Targeting of a Light-Activated Dual-Mode-of-Action Ruthenium-Based Anticancer Prodrug

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d- Versus l-Glucose Conjugation: Mitochondrial Targeting of a Light-Activated Dual-Mode-of-Action Ruthenium-Based Anticancer Prodrug

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Lameijer, Lucien N. Hopkins, Samantha L. Askes, Sven H. C. Brevé, Tobias G. Bonnet, Sylvestre
Description	Author Affiliation: Lameijer LN ( Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA, Leiden, The Netherlands.); Hopkins SL ( Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA, Leiden, The Netherlands.); Brevé TG ( Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA, Leiden, The Netherlands.); Askes SH ( Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA, Leiden, The Netherlands.); Bonnet S ( Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA, Leiden, The Netherlands.)
Abstract	Light-activated ruthenium polypyridyl anticancer prodrugs often suffer from poor water solubility, poor selectivity, and/or ill-defined intracellular targets. Coordination of the d- or l-glucose thioether ligand 3 (2-(2-(2-(methylthio)ethoxy)ethoxy)ethyl-β-glucopyranoside) to the highly lipophilic ruthenium complex $[Ru(tpy)(dppn)(H_{2}O)]^{2+}$ $([1]^{2+};$ dppn=benzo[i]dipyrido-[3,2-a:2′,3′-c]phenazine, tpy=2,2′:6′,2′′-terpyridine) solved all these problems at once. The two enantiomers of $[Ru(tpy)(dppn)(3)][PF_{6}]_{2},$ $[d-2][PF_{6}]_{2}$ and $[l-2][PF_{6}]_{2},$ were soluble in water, which allowed the influence of the chirality of the glucose moiety on uptake, toxicity, and intracellular localization of the prodrug to be probed without changing any other physicochemical properties. Both compounds showed mild, but different, cytotoxicity in A549 (human lung carcinoma) and MCF-7 (human breast adenocarcinoma) cancer cells in the dark, whereas following low doses of visible light irradiation $(3.1 J cm^{−2}$ at λ = 454 nm), a similar, but high cytotoxicity $(EC_{50}$ < 1 μm), was observed. Irrespective of the chirality, both slightly emissive Ru complexes were found in the mitochondria, and two modes of action may contribute to light-induced cell death: 1) the glucose thioether ligand is photosubstituted by water, thus $[1]^{2+},$ which interacts with DNA at an exceptionally high 400:1 base pair/Ru ratio, is released; 2) both $[1]^{2+}$ and $[2]^{2+}$ produce massive amounts of singlet oxygen, which leads to very efficient photodynamic DNA cleavage.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	51
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-12-19
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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