A Fluorescent Silver(I) Carbene Complex with Anticancer Properties: Synthesis, Characterization, and Biological Studies

Fabbrini, Maria Giulia; Cirri, Damiano; Pratesi, Alessandro; Ciofi, Lorenzo; Marzo, Tiziano; Guerri, Annalisa; Nistri, Silvia; Dell'Accio, Alfonso; Gamberi, Tania; Bencini, Andrea; Messori, Luigi

doi:10.1002/cmdc.201800672

Cited by 41 publications

(34 citation statements)

References 30 publications

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“…Sample preparation. Cytochrome c (Cyt c) was commercially available and used as received; the TrxR dodecapeptide ( TrxR-pept ) was synthesized as reported in the literature [ 63 , 64 ]. The stock solutions of the selected iron-based complexes were prepared in DMSO up to a final concentration of 10 −2 M. The stock solution of TrxR-pept was prepared in LC-MS grade water by dissolving the required amount of lyophilized peptide to reach a final concentration of 10 −3 M. The stock solution of Cyt c 10 −3 M was prepared by dissolving the required amount of protein in 2 mM ammonium acetate solution at pH 6.8.…”

Section: Methodsmentioning

confidence: 99%

Anticancer Diiron Vinyliminium Complexes: A Structure–Activity Relationship Study

et al. 2021

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A series of 16 novel diiron complexes of general formula [Fe2Cp2(CO)(μ-CO){μ-η1:η3-C(R′)C(R″)CN(R)(Y)}]CF3SO3 (2–7), bearing different substituents on the bridging vinyliminium ligand, was synthesized in 69–95% yields from the reactions of diiron μ-aminocarbyne precursors with various alkynes. The products were characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy; moreover the X-ray structures of 2c (R = Y = CH2Ph, R′ = R″ = Me) and 3a (R = CH2CH=CH2, Y = R′ = Me, R″ = H) were ascertained by single-crystal X-ray diffraction studies. NMR and UV–Vis methods were used to assess the D2O solubility, the stability in aqueous solution at 37 °C and the octanol–water partition coefficients of the complexes. A screening study evidenced a potent cytotoxicity of 2–7 against the A2780 cancer cell line, with a remarkable selectivity compared to the nontumoral Balb/3T3 cell line; complex 4c (R = Cy, Y = R′ = R″ = Me) revealed as the most performant of the series. The antiproliferative activity of a selection of complexes was also assessed on the cisplatin-resistant A2780cisR cancer cell line, and these complexes were capable of inducing a significant ROS production. Moreover, ESI-MS experiments indicated the absence of interaction of selected complexes with cytochrome c and the potentiality to inhibit the thioredoxin reductase enzyme (TrxR).

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Section: Methodsmentioning

confidence: 99%

Anticancer Diiron Vinyliminium Complexes: A Structure–Activity Relationship Study

et al. 2021

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“…In particular, it is a strong inhibitor of the TrxR system [ 26 ]. This inhibition likely occurs through selective coordination of the gold(I) center at the level of the –Cys-Sec– redox-active motif of the enzyme [ 25 , 27 , 28 , 29 ]. Due to these features, it has been recently repurposed as an antiviral, antiparasitic, antibacterial, and anticancer agent [ 21 ].…”

Section: The Strategiesmentioning

confidence: 99%

Strategies for the Improvement of Metal-Based Chemotherapeutic Treatments

Cirri¹,

Bartoli²,

Pratesi³

et al. 2021

Biomedicines

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This article provides an overview of the various research approaches we have explored in recent years to improve metal-based agents for cancer or infection treatments. Although cisplatin, carboplatin, and oxaliplatin remain the cornerstones in tumor chemotherapy, the discovery and approval of novel inorganic anticancer drugs is a very slow process. Analogously, although a few promising inorganic drugs have found clinical application against parasitic or bacterial infections, their use remains relatively limited. Moreover, the discovery process is often affected by small therapeutic enhancements that are not attractive for the pharmaceutical industry. However, the availability of increasing mechanistic information for the modes of action of established inorganic drugs is fueling the exploration of various approaches for developing effective inorganic chemotherapy agents. Through a series of examples, some from our own research experience, we focus our attention on a number of promising strategies, including (1) drug repurposing, (2) the simple modification of the chemical structures of approved metal-based drugs, (3) testing novel drug combinations, and (4) newly synthesized complexes coupling different anticancer drugs. Accordingly, we aim to suggest and summarize a series of reliable approaches that are exploitable for the development of improved and innovative treatments.

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“…Fabbrini et al synthesized the silver(I) NHC complex, bis(1‐[anthracen‐9‐ylmethyl]‐3‐ethylimidazol‐2‐ylidene) silver chloride ([Ag[EIA] 2 ]Cl) ( 12 ), bearing two anthracenyl fluorescent probes (Figure 5) (Fabbrini et al, 2019). The cytotoxic effect of the fluorescent complex 12 was investigated against human SH‐SY5Y neuroblastoma cells and compared with cisplatin.…”

Section: Silver (Ag)mentioning

confidence: 99%

Silver(I)‐N‐heterocyclic carbene complexes challenge cancer; evaluation of their anticancer properties and in silico studies

Şahin‐Bölükbaşı

Cantürk-Kılıçkaya

Kılıçkaya

2021

Drug Development Research

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Because of the continuous need for efficient therapeutic agents against various kinds of cancers and infectious diseases, the pharmaceutical industry has to find new candidates and strategies to develop novel and efficient drugs. They increasingly use computational tools in R&D stages for screening extensive sets of drug candidates before starting pre‐clinical and clinical trials. N‐Heterocyclic carbenes (NHCs) can be evaluated as good drug candidates because they offer both anti‐cancer and anti‐inflammatory features with their general low‐toxicity profiles. To date, different kinds of NHCs (Cu, Co, Ni, Au, Ag, Ru, etc.) have been synthesized and their therapeutic uses has been shown. Here, we have reviewed the recent studies focused on Ag(I)‐NHC complexes and their anti‐cancer activities. Also, existing examples of the usage of density functional theory and structure–activity relationship have been evaluated.

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A Fluorescent Silver(I) Carbene Complex with Anticancer Properties: Synthesis, Characterization, and Biological Studies

Cited by 41 publications

References 30 publications

Anticancer Diiron Vinyliminium Complexes: A Structure–Activity Relationship Study

Anticancer Diiron Vinyliminium Complexes: A Structure–Activity Relationship Study

Strategies for the Improvement of Metal-Based Chemotherapeutic Treatments

Silver(I)‐N‐heterocyclic carbene complexes challenge cancer; evaluation of their anticancer properties and in silico studies

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