Is the Aromatic Fragment of Piano‐Stool Ruthenium Compounds an Essential Feature for Anticancer Activity? The Development of New Ru<sup>II</sup>‐[9]aneS<sub>3</sub> Analogues

Serli, Barbara; Zangrando, Ennio; Gianferrara, Teresa; Scolaro, Claudine; Dyson, Paul J.; Bergamo, Alberta; Alessio, Enzo

doi:10.1002/ejic.200500210

Cited by 118 publications

(123 citation statements)

References 44 publications

(56 reference statements)

Supporting

Mentioning

115

Contrasting

Order By: Relevance

“…After 20 min of irradiation at 420 nm (Fig. 2B) [15] and by the appearance of free pyridine peaks in the 1 H spectrum. These results are in agreement with the reported observations for analogue piano-stool ruthenium complexes [5].…”

Section: Dark Stability and Photochemical Behavior Of 1-3 In Aqueous mentioning

confidence: 95%

“…S4). 6 ], which gave the same aqua species 2a upon release of the Cl ligand [15,16]. Interestingly, resonances for coordinated py in 2 could still be seen after 60 min of irradiation, indicating that the photo-induced ligand release was not complete (92% from NMR signal integration).…”

Section: Dark Stability and Photochemical Behavior Of 1-3 In Aqueous mentioning

confidence: 97%

“…The procedure for obtaining the precursor complex [Ru( [9]aneS 3 )(bpy)Cl][PF 6 ] is similar to that previously described for the corresponding CF 3 SO 3 compound [ 15 ]. To [Ru( [9]aneS 3 )(dmso-S) 2 Cl][PF 6 ] (100 mg, 0.16 mmol) suspended in methanol (10 mL), 2,2'-bipyridine (25.6 mg, 0.16 mmol) was added and the mixture was heated under reflux for 1 h. During this time the colour of the solution changed from yellow to orange and the formation of the product as deep yellow solid was observed.…”

Section: Synthesis and Characterization Of Compoundsmentioning

confidence: 99%

See 2 more Smart Citations

Design of photoactivatable metallodrugs: Selective and rapid light-induced ligand dissociation from half-sandwich [Ru([9]aneS3)(N–N′)(py)]2+ complexes

Ragazzon

Bratsos

Alessio

et al. 2012

Inorganica Chimica Acta

Self Cite

View full text Add to dashboard Cite

Copyright and reuse:The Warwick Research Archive Portal (WRAP) makes the work of researchers of the University of Warwick available open access under the following conditions. Copyright © and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable the material made available in WRAP has been checked for eligibility before being made available.Copies of full items can be used for personal research or study, educational, or not-forprofit purposes without prior permission or charge. Provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. Publisher's statement:"NOTICE: this is the author's version of a work that was accepted for publication in Inorganica Chimica Acta .Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Inorganica Chimica Acta, Vol. (3, [9]aneN 3 = 1,4,7-triazacyclononane), is reported along with the X-ray crystal structure of 1. We investigated whether these complexes have photochemical properties which might make them suitable for use as pro-drugs in photochemotherapy. Complexes 1 and 2 underwent rapid (minutes) aquation with dissociation of the pyridine ligand in aqueous solution when irradiated with blue light (λ = 420 or 467 nm). The photodecompostion of 3 was much slower. All complexes readily formed adducts with 9-ethylguanine (9-EtG) when this model nucleobase was present in the photolysis solution. Similarly, complex 1 formed adducts with the tripeptide glutathione (GSH), but only when photoactivated. HPLC-MS studies of 1 showed that irradiation promoted rapid formation of 1:1 (major) and 1:2 (minor) adducts of the oligonucleotide d(ATACATGCTACATA) with the fragment {Ru([9]aneS 3 )(bpy)} 2+ . Density functional theory (DFT) calculations and time-dependent DFT reproduced the major features of the absorption spectra and suggested that the lowest-lying triplet state with 3 MLCT character, which is readily accessible via intersystem crossing, might be responsible for the 2 observed dissociative behaviour of the excited states. These complexes are promising for further study as potential photochemotherapeutic agents.

show abstract

Section: Dark Stability and Photochemical Behavior Of 1-3 In Aqueous mentioning

confidence: 95%

Section: Dark Stability and Photochemical Behavior Of 1-3 In Aqueous mentioning

confidence: 97%

Section: Synthesis and Characterization Of Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

Design of photoactivatable metallodrugs: Selective and rapid light-induced ligand dissociation from half-sandwich [Ru([9]aneS3)(N–N′)(py)]2+ complexes

Ragazzon

Bratsos

Alessio

et al. 2012

Inorganica Chimica Acta

Self Cite

View full text Add to dashboard Cite

show abstract

“…Essentially, the availability of solvated ions in general and aqua ions in particular made this possible (Scheme 4). [47][48][49][50] Scheme 4. The prototypical behaviour of [(…”

Section: Hydrated Organometallic Compoundsmentioning

confidence: 99%

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Alberto

2008

Eur J Inorg Chem

View full text Add to dashboard Cite

The chemistry of technetium is essentially driven by radiopharmaceutical applications. These comprise the syntheses of novel complexes but, moreover, the combination of targeting biomolecules with metal complexes. Aqua ions are especially convenient for facilitatating the introduction of metal cations into biomolecules, but are nonexistent for Tc and Re in the Mn triad. This microreview will discuss the chemistry of those Tc complexes that contain H2O as ligands. Special attention will be payed to organometallic aqua ions, i.e. complexes that are typically organometallic with water as ligand. Of particular interest is the coordination chemistry of [M(OH2)3(CO)3]+ (M = Mn, Tc, Re) complexes in water since it is the origin of the widely applied radiopharmaceutical research with 99mTc and 188Re. The chemistry of organometallic aqua ions is not confined to Werner‐type ligands, hence, a further emphasis will be placed on pure organometallic chemistry in water.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

show abstract

“…It has been found that a structurally diverse range of compounds all exhibit interesting properties. For example, a wide range of arenes can be tolerated and the arene can even be replaced by cyclopentadienyl, pentamethylcyclopentadienyl [6] or the sulphur macrocycle 1,4,7-trithiacyclononane without affecting the in vitro activity significantly [7]. It has even been found that some rhodium and osmium analogues, evaluated in HT29 colon carcinoma, A549 lung carcinoma and T47D breast carcinoma cell lines in vitro, display activities that are not too dissimilar from the related ruthenium(II)-arene complexes [8].…”

Section: Introductionmentioning

confidence: 99%

Remarkable Anticancer Activity of Triruthenium-Arene Clusters Compared to Tetraruthenium-Arene Clusters

et al. 2007

Self Cite

View full text Add to dashboard Cite

International audienceThe in vitro activity of a series of ruthenium clusters, [(C6H6)(C6Me6)2 Ru3(H)3(O)][BF4], [(C6H6)(1,4-iPrC6H4Me)(C6Me6)Ru3(H)3( O)][BF4], [(C6H6)4Ru4(H)4][BF4]2, [(C6H5Me)4Ru4(H)4][BF4]2 and [(C6H6)4Ru4(H)3(OH)][Cl]2, has been evaluated against A2780 and A2780cisR ovarian carcinoma cell lines. Both triruthenium clusters are very active compared to ruthenium compounds in general, whereas the tetraruthenium clusters do not display significant cytotoxicities. Since the triruthenium clusters are known to form supramolecular interactions with arenes and other functions, it is possible that such interactions are also important with respect to their mode of biological activity. The X-ray structure analysis of [(C6H5Me)4Ru4 (H)4][PF6]2 is also reported

show abstract

Is the Aromatic Fragment of Piano‐Stool Ruthenium Compounds an Essential Feature for Anticancer Activity? The Development of New Ru^II‐[9]aneS₃ Analogues

Cited by 118 publications

References 44 publications

Design of photoactivatable metallodrugs: Selective and rapid light-induced ligand dissociation from half-sandwich [Ru([9]aneS3)(N–N′)(py)]2+ complexes

Design of photoactivatable metallodrugs: Selective and rapid light-induced ligand dissociation from half-sandwich [Ru([9]aneS3)(N–N′)(py)]2+ complexes

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Remarkable Anticancer Activity of Triruthenium-Arene Clusters Compared to Tetraruthenium-Arene Clusters

Contact Info

Product

Resources

About

Is the Aromatic Fragment of Piano‐Stool Ruthenium Compounds an Essential Feature for Anticancer Activity? The Development of New RuII‐[9]aneS3 Analogues

Cited by 118 publications

References 44 publications

Design of photoactivatable metallodrugs: Selective and rapid light-induced ligand dissociation from half-sandwich [Ru([9]aneS3)(N–N′)(py)]2+ complexes

Design of photoactivatable metallodrugs: Selective and rapid light-induced ligand dissociation from half-sandwich [Ru([9]aneS3)(N–N′)(py)]2+ complexes

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Remarkable Anticancer Activity of Triruthenium-Arene Clusters Compared to Tetraruthenium-Arene Clusters

Contact Info

Product

Resources

About

Is the Aromatic Fragment of Piano‐Stool Ruthenium Compounds an Essential Feature for Anticancer Activity? The Development of New Ru^II‐[9]aneS₃ Analogues