Heterobimetallic Complexes for Theranostic Applications

Fernández‐Moreira, Vanesa; Gimeno, M. Concepción

doi:10.1002/chem.201705335

Cited by 50 publications

(55 citation statements)

References 97 publications

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“…Surprisingly, although (diimine)Re I tris‐carbonyl complexes are known to be emissive and are often used as luminescent probes, as reported, for instance, for Au I /Re I heterobimetallic systems, all Pt II /Re I heterobimetallic complexes appear to be nonemissive. This quenching may be explained by the heavy‐atom effect, due to the proximity of the Pt II center to the {(

\overset{N N}{true}

)Re(CO) 3 } fragment.…”

Section: Resultsmentioning

confidence: 99%

A Bis‐Chelating / Ligand for the Synthesis of Heterobimetallic Platinum(II)/Rhenium(I) Complexes: Tools for the Optimization of a New Class of Platinum(II) Anticancer Agents

Bertrand

Botuha

Forté

et al. 2020

Chemistry A European J

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The two independent O _ N _ Oa nd N _ Nc oordination sites of an ewly synthesized bis[2-(hydroxyphenyl)-1,2,4-triazole] platform have been exploited to prepare fourm onometallic neutral (O _ N _ O)Pt II complexes carryingD MSO, pyridine, triphenylphosphine, or N-heterocyclic carbene as the fourth ligand.T hen, the second N _ Nc oordination site was used to introduce an IR-active rhenium tricarbonyl entity,a ffording the four correspondingh eterobimetallic neutral Pt II / Re I complexes,a sw ell as ac ationic Pt II /Re I derivative.X-ray crystallographic studiess howed that distortiono ft he organic platform occurred to accommodate the coordination geometry of both metal centers. No ligand exchange or transchelation occurred upon incubation of the Pt II complexes in aqueouse nvironment or in the presence of Fe III ,r espectively. The antiproliferativea ctivity of the ligand and complexes was first screened on the triple-negative breast cancerc ell line MDA-MB-231. Then, the IC 50 values of the most active candidates were determined on aw ider panel of human cancerc ells (MDA-MB-231, MCF-7, and A2780), as well as on anontumorigenic cell line (MCF-10A). Low micromolar activities were reached for the complexes carrying aD MSO ligand, making them the first examples of highly active, but hydrolytically stable, Pt II complexes. Finally,t he characteristic mid-IRs ignature of the {Re(CO) 3 }f ragment in the Pt/Re heterobimetallic complexes wasu sed to quantify their uptake in breast cancer cells.

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\overset{N N}{true}

)Re(CO) 3 } fragment.…”

Section: Resultsmentioning

confidence: 99%

A Bis‐Chelating / Ligand for the Synthesis of Heterobimetallic Platinum(II)/Rhenium(I) Complexes: Tools for the Optimization of a New Class of Platinum(II) Anticancer Agents

Bertrand

Botuha

Forté

et al. 2020

Chemistry A European J

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“…Furthermore, aurophilic interactions might be beneficial for cell imaging studies due to their often observed fluorescence [11] . In addition, functionalization of the bridge between both NHC moieties of the ligand enables potential sites for bioconjugation and the synthesis of theranostic agents [12] . Recently, Au(I) bridge‐functionalized NHC complexes (e. g. allyl, [13] hydroxyl [8] or carboxylate [9] ) have been reported.…”

Section: Figurementioning

confidence: 99%

Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification

Jakob

Dominelli

Schlagintweit

et al. 2020

Chemistry An Asian Journal

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A straightforward modification route to obtain mono‐ and di‐substituted anthroyl ester bridge functionalized dinuclear Au(I) bis‐N‐heterocyclic carbene complexes is presented. The functionalization can be achieved starting from a hydroxyl‐functionalized ligand precursor followed by transmetallation of the corresponding Ag complex or via esterification of the hydroxyl‐functionalized gold complex. The compounds are characterized by NMR‐spectroscopy, ESI‐MS, elemental analysis and SC‐XRD. The mono‐ester Au complex shows quantum yields around 18%. In contrast, the corresponding syn‐di‐ester Au complex, exhibits significantly lower quantum yields of around 8%. Due to insufficient water solubility of the di‐ester, only the mono‐ester complex has been tested regarding its antiproliferative activity against HeLa‐ (cervix) and MCF‐7‐ (breast) cancer cell lines and a healthy fibroblast cell line (V79). IC50 values of 7.26 μM in the HeLa cell line and 7.92 μM in the MCF‐7 cell line along with selectivity indices of 8.8 (HeLa) and 8.0 (MCF‐7) are obtained. These selectivity indices are significantly higher than those obtained for the reference drugs cisplatin or auranofin.

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“…In recent years heterometallic species have been identified as emerging tools for theranosis . Typically, such compounds are formed by two distinct metallic fragments connected through a linker, where each of the fragments is specifically designed for either cell imaging or therapeutic applications.…”

Section: Introductionmentioning

confidence: 99%

Luminescent Bimetallic Ir^III/Au^I Peptide Bioconjugates as Potential Theranostic Agents

Luengo

Marzo

Reback

et al. 2020

Chemistry A European J

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Diverse iridium peptide bioconjugates and the corresponding iridium/gold bimetallic complexes have been synthesized starting from a cyclometallated carboxylic acid substituted IrIII complex [Ir(ppy)2(Phen‐5‐COO)] by solid phase peptide synthesis (SPPS). The selected peptide sequences were an enkephalin derivative Tyr‐Gly‐Gly‐Phe‐Leu together with the propargyl‐substituted species Tyr‐Gly‐Pgl‐Phe‐Leu to allow gold coordination (Pgl: propyrgyl‐glycine, HC≡C‐Gly), and a specific short peptide, Ala‐Cys‐Ala‐Phen, containing a cysteine residue. Introduction of the gold center has been achieved via a click reaction with the alkynyl group leading to an organometallic Au−C(triazole) species, or by direct coordination to the sulfur atom of the cysteine. The photophysical properties of these species revealed predominantly an emission originating from the Ir complex, using mixed metal‐to‐ligand and ligand‐to‐ligand charge transfer excited states of triplet multiplicity. The formation of the peptide bioconjugates caused a systematic redshift of the emission profiles. Lysosomal accumulation was observed for all the complexes, in contrast to the expected mitochondrial accumulation triggered by the gold complexes. Only the cysteine‐containing Ir/Au bioconjugate displayed cytotoxic activity. The absence of activity may be related to the lack of endosomal/lysosomal escape for the cationic peptide conjugates. Interestingly, the different coordination sphere of the gold atom may play a crucial role, as the Au−S(cysteine) bond may be more readily cleaved in a biological environment than the Au−C(triazole) bond, and thus the Au fragment could be released from or trapped in the lysosomes, respectively. This work represents a starting point in the development of bimetallic peptide bioconjugates as theranostics and in the knowledge of factors that contribute to anti‐proliferative activity.

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Heterobimetallic Complexes for Theranostic Applications

Cited by 50 publications

References 97 publications

A Bis‐Chelating / Ligand for the Synthesis of Heterobimetallic Platinum(II)/Rhenium(I) Complexes: Tools for the Optimization of a New Class of Platinum(II) Anticancer Agents

A Bis‐Chelating / Ligand for the Synthesis of Heterobimetallic Platinum(II)/Rhenium(I) Complexes: Tools for the Optimization of a New Class of Platinum(II) Anticancer Agents

Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification

Luminescent Bimetallic Ir^III/Au^I Peptide Bioconjugates as Potential Theranostic Agents

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Heterobimetallic Complexes for Theranostic Applications

Cited by 50 publications

References 97 publications

A Bis‐Chelating / Ligand for the Synthesis of Heterobimetallic Platinum(II)/Rhenium(I) Complexes: Tools for the Optimization of a New Class of Platinum(II) Anticancer Agents

A Bis‐Chelating / Ligand for the Synthesis of Heterobimetallic Platinum(II)/Rhenium(I) Complexes: Tools for the Optimization of a New Class of Platinum(II) Anticancer Agents

Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification

Luminescent Bimetallic IrIII/AuI Peptide Bioconjugates as Potential Theranostic Agents

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Luminescent Bimetallic Ir^III/Au^I Peptide Bioconjugates as Potential Theranostic Agents