Photostable NIR emitting ruthenium(II) conjugates; uptake and biological activity in live cells

Cullinane, David; Gkika, Karmel S.; Byrne, Aisling; Keyes, Tia E.

doi:10.1016/j.jinorgbio.2020.111032

Cited by 17 publications

(18 citation statements)

References 65 publications

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“…25). 138,[156][157][158][159][160][161] Notably, in our hands, the parent complexes all failed to permeate the cell membrane under the same conditions. Nona-arginine appears to be similarly effective for vectorisation of metal complexes as reported by the Policar group who studied Re(I) derivatives including [ReCl(CO) 3 (phen-(Arg) 9 )] 9+ and [Re(CO) 3 (Py)(phen-(Arg) 9 )] 10+ for membrane labelling.…”

Section: View Article Onlinesupporting

confidence: 52%

“… 167 Interestingly, we also found that conjugation to the more lipophilic [Ru(biq) 2 (trzbenz)] + complex also resulted in higher dark toxicity than expected. 161 Combined, these recent examples of probes bearing higher charge (Os( ii ) case) and higher lipophilicity (Ru-biq case) indicates that there is a limit to the robustness of MPP vectorisation, but it is nonetheless a powerful method to target the mitochondria with metal complex imaging probes where the balance is met.…”

Section: Cell Penetrating Peptides Enhance Uptake Mediate Toxicity and Are Capable Of Discrete Subcellular Targetingmentioning

confidence: 99%

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Strategies to promote permeation and vectorization, and reduce cytotoxicity of metal complex luminophores for bioimaging and intracellular sensing

et al. 2021

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Section: View Article Onlinesupporting

confidence: 52%

Section: Cell Penetrating Peptides Enhance Uptake Mediate Toxicity and Are Capable Of Discrete Subcellular Targetingmentioning

confidence: 99%

Strategies to promote permeation and vectorization, and reduce cytotoxicity of metal complex luminophores for bioimaging and intracellular sensing

et al. 2021

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“…Several Ru(II)-polypyridyl complexes have been derivatized with CPPs, MPP, ERD, or NLS for targeted PDT of cancer [ 62 , 123 , 124 , 125 , 126 , 127 , 128 , 129 ]. Gold(I)-MPP conjugates with cytotoxic activity against multi-drug resistant breast cancer cells have been reported as well [ 130 ].…”

Section: Other Emerging Targetsmentioning

confidence: 99%

Emerging Molecular Receptors for the Specific-Target Delivery of Ruthenium and Gold Complexes into Cancer Cells

2021

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Cisplatin and derivatives are highly effective in the treatment of a wide range of cancer types; however, these metallodrugs display low selectivity, leading to severe side effects. Additionally, their administration often results in the development of chemoresistance, which ultimately results in therapeutic failure. This scenario triggered the study of other transition metals with innovative pharmacological profiles as alternatives to platinum, ruthenium- (e.g., KP1339 and NAMI-A) and gold-based (e.g., Auranofin) complexes being among the most advanced in terms of clinical evaluation. Concerning the importance of improving the in vivo selectivity of metal complexes and the current relevance of ruthenium and gold metals, this review article aims to survey the main research efforts made in the past few years toward the design and biological evaluation of target-specific ruthenium and gold complexes. Herein, we give an overview of the inorganic and organometallic molecules conjugated to different biomolecules for targeting membrane proteins, namely cell adhesion molecules, G-protein coupled receptors, and growth factor receptors. Complexes that recognize the progesterone receptors or other targets involved in metabolic pathways such as glucose transporters are discussed as well. Finally, we describe some complexes aimed at recognizing cell organelles or compartments, mitochondria being the most explored. The few complexes addressing targeted gene therapy are also presented and discussed.

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“… 3 − 6 While the emission maxima of complexes of Ir(III) and Ru(II) can be tuned toward the NIR, it can be synthetically challenging and such tuning may compromise photostability, exacerbated in the physiological conditions of temperature and buffered media, as well as emission quantum yield. 7 − 9 Conversely, osmium (II) polypyridyl complexes exhibit similar advantages to Ru(II) for imaging but with the additional benefits of outstanding photostability and deep-red to NIR emission in the 700–850 nm spectral region, making them attractive candidates, in particular for tissue imaging (although still prone to the impact of the energy gap law). Although Os(II) polypyridyl complexes have to date, been much less explored for imaging applications than Ir or Ru, they are gaining increasing focus.…”

Section: Introductionmentioning

confidence: 99%

Os(II)-Bridged Polyarginine Conjugates: The Additive Effects of Peptides in Promoting or Preventing Permeation in Cells and Multicellular Tumor Spheroids

et al. 2021

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The preparation of two polyarginine conjugates of the complex Os(II) [bis-(4′-(4-carboxyphenyl)-2,2′:6′,2″-terpyridine)] [Os-(R n ) 2 ] x + ( n = 4 and 8; x = 10 and 18) is reported, to explore whether the R8 peptide sequence that promotes cell uptake requires a contiguous amino acid sequence for membrane permeation or if this can be accomplished in a linearly bridged structure with the additive effect of shorter peptide sequences. The conjugates exhibit NIR emission centered at 754 nm and essentially oxygen-insensitive emission with a lifetime of 89 ns in phosphate-buffered saline. The uptake, distribution, and cytotoxicity of the parent complex and peptide derivatives were compared in 2D cell monolayers and a three-dimensional (3D) multicellular tumor spheroid (MCTS) model. Whereas, the bis-octaarginine sequences were impermeable to cells and spheroids, and the bis-tetraarginine conjugate showed excellent cellular uptake and accumulation in two 2D monolayer cell lines and remarkable in-depth penetration of 3D MCTSs of pancreatic cancer cells. Overall, the data indicates that cell permeability can be promoted via non-contiguous sequences of arginine residues bridged across the metal centre.

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Photostable NIR emitting ruthenium(II) conjugates; uptake and biological activity in live cells

Cited by 17 publications

References 65 publications

Strategies to promote permeation and vectorization, and reduce cytotoxicity of metal complex luminophores for bioimaging and intracellular sensing

Strategies to promote permeation and vectorization, and reduce cytotoxicity of metal complex luminophores for bioimaging and intracellular sensing

Emerging Molecular Receptors for the Specific-Target Delivery of Ruthenium and Gold Complexes into Cancer Cells

Os(II)-Bridged Polyarginine Conjugates: The Additive Effects of Peptides in Promoting or Preventing Permeation in Cells and Multicellular Tumor Spheroids

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