A Bis(dipyridophenazine)(2‐(2‐pyridyl)pyrimidine‐4‐carboxylic acid)ruthenium(II) Complex with Anticancer Action upon Photodeprotection

Joshi, Tanmaya; Pierroz, Vanessa; Mari, Cristina; Gemperle, Lea; Ferrari, Stefano; Gasser, Gilles

doi:10.1002/ange.201309576

Cited by 44 publications

(14 citation statements)

References 52 publications

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“…In cells, they took advantage of the IR modality of the probe to quantify the internalization of the conjugates. They could also show that apparent discrepancies with fluorescence quantification were due to a variable fluorescence enhancement of the probes in membrane environment, which hampered rigorous quantification [13,[103][104][105][106]. In skin biopsies, the IR modality also enabled them to quantify the penetration of the peptide conjugate into skin, while the fluorescence modality could be used to compare its localization with those of nuclei, using common fluorescence stain like DAPI.…”

Section: N-terminal Labelling Of Peptidementioning

confidence: 99%

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

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

112

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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: N-terminal Labelling Of Peptidementioning

confidence: 99%

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

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

112

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“…[6a, 25] Using a calibration curve, it is thus possible to estimate an intracellular quantity of the compound. [6a] This is a major advantage of IR spectroscopy over luminescence [12] for which the quantum yield is highly dependent on the environment [8] (see an example above).…”

Section: Quantification Of the Cellular Uptake By Ftirmentioning

confidence: 99%

“…[11] In this article, the FTIR signature of the M(CO) core, known to be appropriate for titration, [4c] was used for a direct quantification within a collection of cells. [6a] Generally speaking, luminescence cannot be directly implemented for intracellular quantification [12] since the quantum yield is highly dependent on the environment. [8] But, in the particular case of this series, we show that luminescence of the [Re(CO) 3 (pyta)] core can be relevantly used for quantification.…”

Section: Introductionmentioning

confidence: 99%

Influence of the Side‐Chain Length on the Cellular Uptake and the Cytotoxicity of Rhenium Triscarbonyl Derivatives: A Bimodal Infrared and Luminescence Quantitative Study

Clède

Lambert

Saint-Fort

et al. 2014

Chemistry A European J

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Rhenium triscarbonyl complexes fac-[Re(CO)3 (N^N)] with appropriate ancillary N^N ligands are relevant for fluorescent bio-imaging. Recently, we have shown that [Re(CO)3 ] cores can also be efficiently mapped inside cells using their IR signature and that they can thus be used in a bimodal approach. To describe them we have coined the term SCoMPIs for single-core multimodal probes for imaging. In the context of the use of these SCoMPIs in bio-imaging, the questions of their cellular uptake and cytotoxicity are critical. We report here a series of compounds derived from the [Re(CO)3 Cl(pyta)] core (pyta=4-(2-pyridyl)-1,2,3-triazole). The pyta ligand is of interest because it can be easily functionalized. Aliphatic side chains (C4 , C8 , and C12 ) were appended to this core. A correlative study involving IR and luminescence was performed to monitor and quantify their cellular internalization. We studied the relationship between lipophilicity (log P(o/w)), cytotoxicity (IC50 ), and cellular uptake, and we showed that both uptake and cytotoxicity increase with the length of the side chain, with a higher uptake for the C12 derivative. This study stresses the distinction that has to be made between apparent toxicity, determined as an incubation concentration IC50 , and intrinsic toxicity. Indeed, the intrinsic toxicity of a compound can remain hidden if it is not cell permeable. Therefore it must be kept in mind that IC50 values are composite values, reflecting both cellular uptake and intrinsic toxicity.

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“…Recently, several examples of transition metal complexes as either oxygen dependent or independent photosensitizers in PDT have been reported, including Ru(II), Re(I) and Pt(IV) 9 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 . Here, we demonstrate the potential of a small, low-weight Pt(II) complex for PDT.…”

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confidence: 99%

Photodynamic killing of cancer cells by a Platinum(II) complex with cyclometallating ligand

Doherty

Sazanovich

McKenzie

et al. 2016

Sci Rep

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Photodynamic therapy that uses photosensitizers which only become toxic upon light-irradiation provides a strong alternative to conventional cancer treatment due to its ability to selectively target tumour material without affecting healthy tissue. Transition metal complexes are highly promising PDT agents due to intense visible light absorption, yet the majority are toxic even without light. This study introduces a small, photostable, charge-neutral platinum-based compound, Pt(II) 2,6-dipyrido-4-methyl-benzenechloride, complex 1, as a photosensitizer, which works under visible light. Activation of the new photosensitizer at low concentrations (0.1–1 μM) by comparatively low dose of 405 nm light (3.6 J cm−2) causes significant cell death of cervical, colorectal and bladder cancer cell lines, and, importantly, a cisplatin resistant cell line EJ-R. The photo-index of the complex is 8. We demonstrate that complex 1 induces irreversible DNA single strand breaks following irradiation, and that oxygen is essential for the photoinduced action. Neither light, nor compound alone led to cell death. The key advantages of the new drug include a remarkably fast accumulation time (diffusion-controlled, minutes), and photostability. This study demonstrates a highly promising new agent for photodynamic therapy, and attracts attention to photostable metal complexes as viable alternatives to conventional chemotherapeutics, such as cisplatin.

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A Bis(dipyridophenazine)(2‐(2‐pyridyl)pyrimidine‐4‐carboxylic acid)ruthenium(II) Complex with Anticancer Action upon Photodeprotection

Cited by 44 publications

References 52 publications

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

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

Influence of the Side‐Chain Length on the Cellular Uptake and the Cytotoxicity of Rhenium Triscarbonyl Derivatives: A Bimodal Infrared and Luminescence Quantitative Study

Photodynamic killing of cancer cells by a Platinum(II) complex with cyclometallating ligand

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