3-Chloromethylpyridyl bipyridine fac-tricarbonyl rhenium: a thiol-reactive luminophore for fluorescence microscopy accumulates in mitochondria

Amoroso, Angelo J.; Arthur, R.J.; Coogan, Michael P.; Court, Jacquelyn; Fernández‐Moreira, Vanesa; Hayes, Anthony Joseph; Lloyd, David; Millet, Coralie; Pope, Simon J. A.

doi:10.1039/b802215a

Cited by 151 publications

(104 citation statements)

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“…A great attention has been paid to the development of Re(I) complexes targeting the different cell compartments, that can be used as organelles trackers. A thiolreactive chloromethyl group was, for instance, appended to a Re(I) tricarbonyl complex (1, R=Cl, Figure 3) in order to immobilized the complex into the mitochondria through its reaction with reduced thiols [39]. Indeed, compound 1 (R=Cl) was found to co-localize with TMRE (tetramethylrhodamine ethyl ester), a known marker of mitochondria, in MCF-7 human breast cancer cell line (Figure 4.1).…”

Section: Re(i) Tricarbonyl Complexes With Specific Cell Localizationmentioning

confidence: 99%

“…This is generally done by tuning the structure of the N^N ligand, since it is involved in the MLCT. Two families of ligand have been particularly explored: (i) polypyridyl ligands, mostly derived from 2,2'-bipyridine (bpy) and 1,10-phenanthroline (phen) [19][20][21][23][24][25][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] and (ii) bis-quinoline and its derivatives, e.g. bis(phenanthridinylmethyl)amine (bpm) [22,[43][44][45].…”

Section: Spectroscopic Properties Of Luminescent Re(i) Tricarbonyl Comentioning

confidence: 99%

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Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

109

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Bio-imaging, by enabling the visualization of biomolecules of interest, has proved to be highly informative in the study of biological processes. Although fluorescence microscopy is probably one of the most used techniques, alternative methods of imaging, providing complementary information, are emerging. In this context, metal complexes represent valuable platforms for multimodal imaging, since they may combine interesting spectroscopic features and biologically relevant functionalization on a single molecular core. In particular, d6 low-spin rhenium tri-carbonyl complexes display unique luminescence and vibrational properties, and can be readily functionalized. Here we review their applications and potential as probes or drugs relying on their photophysical properties, before focusing on their use as multimodal probes for the labelling and imaging of peptides and proteins.

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Section: Re(i) Tricarbonyl Complexes With Specific Cell Localizationmentioning

confidence: 99%

Section: Spectroscopic Properties Of Luminescent Re(i) Tricarbonyl Comentioning

confidence: 99%

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

109

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“…[25] The use of rhenium-based complexes offers the additional possibility to exchange the rhenium centre with the radioisotope 99m Tc and thus to obtain gemitting radiomarkers. Most luminescent rhenium complexes with potential imaging applications contain the fac-Re(CO) 3 core and are based on bisimine ligands such as bipyridine or phenanthroline [26][27][28][29][30] or on tridentate chelates such as bis(pyridylmethyl)amine or bis(quinolinylmethyl)amine. [31][32][33][34][35][36] Here we report on the synthesis, characterization and photophysical behaviour of a novel chelating tridentate ligand based on bis(phenanthridinylmethyl)amine (bpm), its rhenium complexes and peptide conjugates.…”

Section: Introductionmentioning

confidence: 99%

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

et al. 2011

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Organometallic complexes possess great potential for imaging applications in biology, due to their kinetic stability and often favourable intrinsic properties. In this work we present a new class of Re(I) -tricarbonyl complexes with a substituted bis(phenanthridinylmethyl)amine (bpm) ligand. The complex Re(CO)(3) (R-bpm) could be conveniently prepared by microwave synthesis from [Re(CO)(3)(H(2)O)(3) ]Br and a suitably substituted bis(phenanthridinylmethyl)amine (R-bpm). Complex 5, with R=CH(2)-CO(2)-CH(3) , was characterized by a single-crystal X-ray structure. Complex 6 (R=CH(2)-C(6)H(4)-CO(2)H) was used in solid-phase peptide synthesis (SPPS) to label the neurotensin(8-13) (NT) fragment N-terminally. The complexes show luminescence emission with large Stokes shifts (λ(ex) =350 nm, λ(em) =570 nm). Cellular uptake and intracellular localization studies in several cell lines demonstrate the utility of the new Re(CO)(3) (R-bpm) complexes for fluorescence imaging and reveal significant differences between the simple methyl ester 5 and the NT bioconjugate 7.

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“…35 Meanwhile, Coogan and co-workers have developed rhenium complexes to stain mitochondria in which protein thiols react with a 3-chloromethylpyridyl group on the complex. 36 Thus, it seems likely that the emission detected in Figure 9b is due to thiolate adducts of the form PtL 1 SR. We note that Chan and co-workers have observed a diminution of the green luminescence from Pt(N^C^N)Cl units upon treatment with cysteine, interpreted in terms of displacement of the chloride ligand by a cysteine sulfur atom. 37 In their case, no red emission appeared, but this may be due to efficient quenching of the emission under the polar aqueous conditions employed.…”

Section: Relevance To Biological Thiols and Bioimaging Applicationsmentioning

confidence: 99%

Platinum(II) Complexes of N^∧C^∧N-Coordinating 1,3-Bis(2-pyridyl)benzene Ligands: Thiolate Coligands Lead to Strong Red Luminescence from Charge-Transfer States

et al. 2014

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A new family of platinum(II) complexes of the form PtL n SR have been prepared, where L n represents a cyclometalating, N ∧ C ∧ N-bound tridentate ligand and SR is a monodentate thiolate ligand. The complexes fall into two groups, those of PtL 1 SR where HL 1 = 1,3-bis(2-pyridyl)benzene, and those of PtL 2 SR, where HL 2 = methyl 3,5-bis(2pyridyl)benzoate. Each group consists of five complexes, where R = CH 3 , C 6 H 5 , p-C 6 H 4 -CH 3 , p-C 6 H 4 -OMe, p-C 6 H 4 -NO 2 . These compounds, which are bright red, orange, or yellow solids, are formed readily upon treatment of PtL n Cl with the corresponding potassium thiolate KSR in solution at room temperature. The replacement of the chloride by the thiolate ligand is accompanied by profound changes in the photophysical properties. A broad, structureless, low-energy band appears in the absorption spectra, not present in the spectra of PtL n Cl. In the photoluminescence spectra, the characteristic, highly structured phosphorescence bands of PtL n Cl in the green region are replaced by a broad, structureless emission band in the red region. These new bands are assigned to a π S /d Pt → π* N ∧ C ∧ N charge-transfer transition from the thiolate/platinum to the N ∧ C ∧ N ligand. This assignment is supported by electrochemical data and TD-DFT calculations and by the observation that the decreasing energies of the bands correlate with the electron-donating ability of the substituent, as do the increasing nonradiative decay rate constants, in line with the energy-gap law. However, the pair of nitro-substituted complexes do not fit the trends. Their properties, including much longer luminescence lifetimes, indicate that the lowest-energy excited state is localized predominantly on the arenethiolate ligand for these two complexes. Red-emitting thiolate adducts may be relevant to the use of PtL n Cl complexes in bioimaging, as revealed by the different distributions of emission intensity within live fibroplast cells doped with the parent complex, according to the region of the spectrum examined.

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3-Chloromethylpyridyl bipyridine fac-tricarbonyl rhenium: a thiol-reactive luminophore for fluorescence microscopy accumulates in mitochondria

Cited by 151 publications

References 23 publications

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

Platinum(II) Complexes of N^∧C^∧N-Coordinating 1,3-Bis(2-pyridyl)benzene Ligands: Thiolate Coligands Lead to Strong Red Luminescence from Charge-Transfer States

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3-Chloromethylpyridyl bipyridine fac-tricarbonyl rhenium: a thiol-reactive luminophore for fluorescence microscopy accumulates in mitochondria

Cited by 151 publications

References 23 publications

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

A Novel Organometallic ReI Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

Platinum(II) Complexes of N∧C∧N-Coordinating 1,3-Bis(2-pyridyl)benzene Ligands: Thiolate Coligands Lead to Strong Red Luminescence from Charge-Transfer States

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A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

Platinum(II) Complexes of N^∧C^∧N-Coordinating 1,3-Bis(2-pyridyl)benzene Ligands: Thiolate Coligands Lead to Strong Red Luminescence from Charge-Transfer States