Biological activities of pyrenyl-derived thiosemicarbazone half-sandwich complexes

Raja, Nandhagopal; Devika, Neelakandan; Gupta, Gajendra; Nayak, V. Lakshma; Kamal, Ähmed; Nagesh, Narayana; Therrien, Bruno

doi:10.1016/j.jorganchem.2015.06.036

Cited by 30 publications

(12 citation statements)

References 69 publications

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“…33 A similar inhibition of the cell cycle at the G2/M phase has been recently observed for comparable ruthenium thiosemicarbazone complexes. 34 The details of the cell cycle assay for the palladium complexes are shown in Table S4 (ESI †).…”

Section: Dna Interactionmentioning

confidence: 99%

Palladium(ii) complexes with thiosemicarbazones derived from pyrene as topoisomerase IB inhibitors

et al. 2019

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Section: Dna Interactionmentioning

confidence: 99%

Palladium(ii) complexes with thiosemicarbazones derived from pyrene as topoisomerase IB inhibitors

et al. 2019

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“…[61] Recently, examples of fluorescent thiosemicarbazonato complexes derived from pyrene and anthracene were also prepared and tested in vitro. [62,63] However, in both cases, the thiosemicarbazone acted as a bidentate ligand. The copper complexes derived from the anthracene ligand were studied as chemotherapeutic agents for cervical cancer, [62] while the rhodium and iridium pyrene derivatized half-sandwich complexes were found to interact with DNA and presented some interest against lung and breast cancer cell lines.…”

Section: Multimodal Imagingmentioning

confidence: 99%

“…The copper complexes derived from the anthracene ligand were studied as chemotherapeutic agents for cervical cancer, [62] while the rhodium and iridium pyrene derivatized half-sandwich complexes were found to interact with DNA and presented some interest against lung and breast cancer cell lines. [63] As mentioned above, the possibility of tagging the ATSM core with a chromophore suitable for fluorescence in vitro had drawn the attention of several research groups over the last few years. Dilworth, Pascu, and collaborators reported a novel approach to evaluate the stability of bis(thiosemicarbazonato) complexes in vitro.…”

Section: Multimodal Imagingmentioning

confidence: 99%

“…Therefore, its interaction with amyloid‐β plaques in human brain sections was studied by epifluorescence microscopy 61. Recently, examples of fluorescent thiosemicarbazonato complexes derived from pyrene and anthracene were also prepared and tested in vitro 62,63. However, in both cases, the thiosemicarbazone acted as a bidentate ligand.…”

Section: Multimodal Imagingmentioning

confidence: 99%

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Applications of “Hot” and “Cold” Bis(thiosemicarbazonato) Metal Complexes in Multimodal Imaging

Cortezon‐Tamarit

Sarpaki

Calatayud

et al. 2016

The Chemical Record

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The applications of coordination chemistry to molecular imaging has become a matter of intense research over the past 10 years. In particular, the applications of bis(thiosemicarbazonato) metal complexes in molecular imaging have mainly been focused on compounds with aliphatic backbones due to the in vivo imaging success of hypoxic tumors with PET (positron emission tomography) using (64) CuATSM [copper (diacetyl-bis(N4-methylthiosemicarbazone))]. This compound entered clinical trials in the US and the UK during the first decade of the 21(st) century for imaging hypoxia in head and neck tumors. The replacement of the ligand backbone to aromatic groups, coupled with the exocyclic N's functionalization during the synthesis of bis(thiosemicarbazones) opens the possibility to use the corresponding metal complexes as multimodal imaging agents of use, both in vitro for optical detection, and in vivo when radiolabeled with several different metallic species. The greater kinetic stability of acenaphthenequinone bis(thiosemicarbazonato) metal complexes, with respect to that of the corresponding aliphatic ATSM complexes, allows the stabilization of a number of imaging probes, with special interest in "cold" and "hot" Cu(II) and Ga(III) derivatives for PET applications and (111) In(III) derivatives for SPECT (single-photon emission computed tomography) applications, whilst Zn(II) derivatives display optical imaging properties in cells, with enhanced fluorescence emission and lifetime with respect to the free ligands. Preliminary studies have shown that gallium-based acenaphthenequinone bis(thiosemicarbazonato) complexes are also hypoxia selective in vitro, thus increasing the interest in them as new generation imaging agents for in vitro and in vivo applications.

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“…Moreover, additional targets have emerged from more recent studies, including topoisomerase II, the metalloenzymes xanthine oxidase and tyrosinase, and the mitochondria signaling pathway [ 5 ]. Again, Ru-thiosemicarbazone metal complexes and half-sandwich type organometallic complexes are of particular interest because of their peculiar biological activity [ 19 , 20 , 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

A New Photoactivatable Ruthenium(II) Complex with an Asymmetric Bis-Thiocarbohydrazone: Chemical and Biological Investigations

et al. 2021

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The synthesis, photoactivation and biological activity of a new piano-stool Ru(II) complex is herein reported. The peculiarity of this complex is that its monodentate ligand which undergoes the photodissociation is an asymmetric bis-thiocarbohydrazone ligand that possesses a pyridine moiety binding to Ru(II) and the other moiety contains a quinoline that endows the ligand with the capacity of chelating other metal ions. In this way, upon dissociation, the ligand can be released in the form of a metal complex. In this article, the double ability of this new Ru(II) complex to photorelease the ligand and to chelate copper and nickel is explored and confirmed. The biological activity of this compound is studied in cell line A549 revealing that, after irradiation, proliferation inhibition is reached at very low half maximal inhibitory concentration (IC50) values. Further, biological assays reveal that the dinuclear complex containing Ni is internalized in cells.

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Biological activities of pyrenyl-derived thiosemicarbazone half-sandwich complexes

Cited by 30 publications

References 69 publications

Palladium(ii) complexes with thiosemicarbazones derived from pyrene as topoisomerase IB inhibitors

Palladium(ii) complexes with thiosemicarbazones derived from pyrene as topoisomerase IB inhibitors

Applications of “Hot” and “Cold” Bis(thiosemicarbazonato) Metal Complexes in Multimodal Imaging

A New Photoactivatable Ruthenium(II) Complex with an Asymmetric Bis-Thiocarbohydrazone: Chemical and Biological Investigations

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