Cytotoxic Ag(I) and Au(I) NHC-carbenes bind DNA and show TrxR inhibition

Guarra, Federica; Busto, Natalia; Guerri, Annalisa; Marchetti, Lorella; Marzo, Tiziano; Garcı́a, Begoña; Biver, Tarita; Gabbiani, Chiara

doi:10.1016/j.jinorgbio.2020.110998

Cited by 46 publications

(26 citation statements)

References 93 publications

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“…When comparing MCF-7 with L-929 (normal cells from the adipose tissue of mice) [ 20 ], cancer cell selectivity was observed, but there was no significant difference in their IC 50 values. Moreover, Guarra and coworkers evaluated the cell selectivity of the silver complex with a fluorescent anthracenyl-functionalized benzimidazole ligand in various human cancer cells and normal cells, and they reported that the cancer cell selectivity of the silver complex was as low as that of cisplatin [ 22 ]. In the present study, we performed cell viability assays using two types of normal human cells, i.e., HMSC and HMEC.…”

Section: Discussionmentioning

confidence: 99%

The selective cytotoxicity of silver thiosulfate, a silver complex, on MCF-7 breast cancer cells through ROS-induced cell death

et al. 2021

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Background Silver is a transition metal that is known to be less toxic than platinum. However, only few studies have reported the anticancer effects of some silver complexes and their possibility as an alternative to platinum complex. This study investigated the anticancer effects of the silver thiosulfate complex (STS), [Ag(S2O3)2]3−, consisting of silver and sodium thiosulfate. Methods In vitro cytotoxic activity of STS was investigated comparatively in human cancer cell lines (K562 and MCF-7) and normal human cells (mesenchymal stem cells and mammary epithelial cells). For its anticancer effects, cell cycle, mode of cell death, morphological changes, and accumulation of intracellular ROS and GSH were evaluated in MCF-7 to provide mechanistic insights. Results STS showed a concentration-dependent cytotoxicity in MCF-7 cell, which was abolished by pretreatment with N-acetylcysteine, suggesting ROS accumulation by STS. Moreover, STS caused cell cycle arrest at the G1 phase, decrease in the GSH levels, and morphological changes in MCF-7. Direct measurement of ROS demonstrated the elevation of intracellular ROS accumulation in cancer cells treated with STS; however, neither cytotoxicity nor ROS accumulation was observed in normal human cells. Conclusion The results obtained here are the first evidence to show that STS exhibited an anticancer activity through ROS-induced mechanisms, and that its cytotoxicity is highly selective to cancer cells. The results of the present study warrant further investigation on the detailed mechanism of STS actions, as well as its in vivo effectiveness and safety for clinical application.

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Section: Discussionmentioning

confidence: 99%

The selective cytotoxicity of silver thiosulfate, a silver complex, on MCF-7 breast cancer cells through ROS-induced cell death

et al. 2021

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“…The compound 299 showed IC 50 value in the range of 6±1 to 20±2 μM whereas the complex was less toxic to normal cell line (IC 50 =26±1 μM). The authors concluded that the act the highest activity of the silver complex is due to the strong binding ability of silver metal with the DNA [176] …”

Section: Medicinal Applicationsmentioning

confidence: 99%

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Nayak

Gaonkar

2021

ChemMedChem

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New weapons are constantly needed in the fight against cancer. The discovery of cisplatin as an anticancer drug prompted the search for new metal complexes. The successful history of cisplatin motivated chemists to develop a plethora of metal‐based molecules. Among them, metal‐N‐heterocyclic carbene (NHC) complexes have gained significant attention because of their suitable qualities for efficient drug design. The enhanced applications of coinage metal‐NHC complexes have encouraged a gradually increasing number of studies in the fields of medicinal chemistry that benefit from the fascinating chemical properties of these complexes. This review aims to present recent developments in synthetic strategies and medicinal applications of copper, silver and gold complexes supported by NHC ligands.

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“…Diğer pikler ve işaret ettikleri molekül kısımları ise şöyledir: (ppm) 9.65 (a / Asidik Hidrojen-karben), 8.06 (c aromatik/ benzimidazol kısmı) 7.82 (i aromatik/fitalimid grubu) 7.58 (j aromatik/fitalimid grubu), 7 13 C NMR kimyasal kayma değerleri kolaylık amacıyla molekül üzerinde de sunuldu (Şekil 5).…”

Section: şEkil 10 Befibr Için Deneysel(i) Ve Hesaplanan(ii) 1 H Nmr Spektrumlarıunclassified

“…Karbenlerin biyolojik etkinlikleri sadece antimikrobiyal etkinlikle sınırlı kalmamıştır. Özellikle altın ve platin kompleksleri antitumor etkinliğiyle auronofin ve cis-platinle karşılaştırılacak kadar olumlu sonuçlar almıştır [7,8]. Başlangıçtaki önyargıların aksine, 2007'den beri Peris ve Ghosh'un kataliz çalışmalarında da Ag(I)NHC bileşikleri beklenenden daha olumlu sonuçlar vermiş, bu konudaki daha ucuz, daha kolay elde edilen ve çevreci katalizör hedefleyen çalışmalara farklı bir yön kazandırmıştır.…”

Section: şEkil 1 Nhc Tuzlarının Yaygın Türleriunclassified

Synthesis, Investigation of Structural and Spectroscopic Properties of a Novel Symmetrical Benzimidazole Salt with Phthalimid Functional Groups

Kunduracıoğlu¹

2021

Academic Platform Journal of Engineering and Science

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Yeni bir N-Heterosiklik karben tuzu olan 1, 3-bis (N-(3-etil) fitalimid)-benzimidazol-3-yum bromür (BEFIBR) yüksek (%83) verimle sentezlenmiştir. Sentezlenen tuzun FT-IR ve 1 H ve 13 C NMR deneysel olarak ölçülmüştür. Bu ölçümlerde, karben C'u 169.35 ppm'de ve asidik karben H'i ise 9.65ppm'de gözlenmiştir. SPARTAN-14 kuantum kimya paket yazılımı kullanılarak kuantum mekaniksel hesaplamalar gerçekleştirilmiştir. Temel enerji ve spektroskopik değerlerin hesaplanmasında "Yoğunluk Fonksiyonel Kuramı" (DFT/EDF2) yöntemi ve 6-31G* temel seti kullanılmıştır. Bu hesaplamalar sonucunda bağ uzunlukları, bağ açıları FT-IR ve 1 H ve 13 C spektrumları hesaplanmıştır. Hesaplanan değerler, deneysel değerlere son derece yakındır. Ckarben 169.3ppm ve asidik H ise 9.62ppm olarak bulunmuştur. Böylece molekülün uzaysal duruşu da tahmin edilmiştir. Hesaplanan değerler ile deneysel yöntemle bulunan sonuçlar şekil ve tablolar üzerinde karşılaştırılmıştır. HOMO ve LUMO şekil ve enerji değerleri hesaplanarak tablo halinde aktarılmıştır.

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Cytotoxic Ag(I) and Au(I) NHC-carbenes bind DNA and show TrxR inhibition

Cited by 46 publications

References 93 publications

The selective cytotoxicity of silver thiosulfate, a silver complex, on MCF-7 breast cancer cells through ROS-induced cell death

The selective cytotoxicity of silver thiosulfate, a silver complex, on MCF-7 breast cancer cells through ROS-induced cell death

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Synthesis, Investigation of Structural and Spectroscopic Properties of a Novel Symmetrical Benzimidazole Salt with Phthalimid Functional Groups

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