Abstract:Caffeine based N‐heterocyclic carbene (NHC)‐silver complex anchored on magnetic nanoparticles (MNP‐Caff‐NHC@Ag complex) has been prepared by covalent grafting of caffeine on the surface of chloro‐functionalized Fe3O4 magnetic nanoparticles followed by complexation with silver (I) acetate. The MNP‐Caff‐NHC@Ag complex has been characterized by Fourier transform infrared (FT‐IR) spectroscopy, energy‐dispersive X‐ray (EDX) spectroscopy, transmission electron microscopy (TEM), X‐ray diffraction (XRD), thermogravime… Show more
“…Possessing an imidazole-type substructure, caffeine has already experienced some use as an NHC ligand but the overall number of publications referring to this is still minor . For example, the antimicrobial and anticancer properties of caffeine-derived NHC complexes have been studied thoroughly [17,20,25,[30][31][32][33]. It has to emphasized that caffeine represents a promising starting point for the design of NHC-type ligands, due to its availability, low price and, most notably, green footprint compared to others.…”
N-Heterocyclic carbenes (NHCs) have seen more and more use over the years. The go-to systems that are usually considered are derivatives of benzimidazole or imidazole. Caffeine possesses an imidazole unit and was already utilized as a carbene-type ligand; however, its use within a tridentate bis-NHC system has—to the best of our knowledge—not been reported so far. The synthesis of the ligand is straightforward and metal complexes are readily available via silver-salt metathesis. A platinum(II) and a palladium(II) complex were isolated and a crystal structure of the former was examined. For the Pt(II) complex, luminescence is observed in solid state as well as in solution.
“…Possessing an imidazole-type substructure, caffeine has already experienced some use as an NHC ligand but the overall number of publications referring to this is still minor . For example, the antimicrobial and anticancer properties of caffeine-derived NHC complexes have been studied thoroughly [17,20,25,[30][31][32][33]. It has to emphasized that caffeine represents a promising starting point for the design of NHC-type ligands, due to its availability, low price and, most notably, green footprint compared to others.…”
N-Heterocyclic carbenes (NHCs) have seen more and more use over the years. The go-to systems that are usually considered are derivatives of benzimidazole or imidazole. Caffeine possesses an imidazole unit and was already utilized as a carbene-type ligand; however, its use within a tridentate bis-NHC system has—to the best of our knowledge—not been reported so far. The synthesis of the ligand is straightforward and metal complexes are readily available via silver-salt metathesis. A platinum(II) and a palladium(II) complex were isolated and a crystal structure of the former was examined. For the Pt(II) complex, luminescence is observed in solid state as well as in solution.
“…Willans et al, Pellei et al, Jin et al, Rashinkar et al, Kühn et al, Razali et al, and our group reported the synthesis of the different Ag-NHC complexes and their anticancer activities against to different cancer cell lines. [21][22][23][24][25][26][27] Studies showed that NHC complexes have unique structural scaffolds for target-specific biomolecules relevant to cancer. Barnard et al, [28] Hindi et al, [29] Teyssot et al, [30] Lin et al, [31] Bernard and Berners-Price, [32] Dada et al, [33] Hackenberg et al, [33] Veenboer et al, [11] Budagumpi and Endud, [35] and our group [36][37][38][39] have been investigated anticancer properties of NHC complexes in various types of cancer.…”
New seven Au-N-heterocyclic carbene (NHC) complexes have been synthesized via transmetalation from Ag-NHC complexes. NHC salts, Ag-NHC, and Au-NHC complexes were fully characterized by widely used spectroscopic techniques. The molecular and crystal structures of 3b and 3f Au-NHC complexes were clarified through the single-crystal X-ray diffraction method.According to X-ray diffraction analysis results, the coordination geometry around Au(I) atoms in the complexes are revealed to be almost linear with C-Au-Cl angle. Anticancer activity, DNA binding, xanthine oxidase (XO) inhibitory activity studies, and molecular docking studies were evaluated for all Au-NHC complexes to explore the binding mechanism at the active site. The IC 50 value of Au-NHC complexes against human colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines was defined by MTT assay. The IC 50 values for MCF-7 in the range of 5.2 ± 2 to 152.4 ± 1 μM and Caco-2 5.2 ± 1 to 152.7 ± 2 μM showed that 3a, 3b, 3c, 3d, and 3g have better anticancer activity than Cisplatin incredibly complex 3a against both cancer cell line. All Au-NHC complexes showed excellent antimicrobial activity against different bacteria and fungi. 3a was the complex that exhibited the best antimicrobial activity here as well. The XO inhibitory activity experimental results indicated that all gold complexes showed remarkable inhibition activity against XO compared to the generally used standard, allopurinol. The range of IC 50 value was determined from 0.407 to 2.681 μM. 3d complex showed the lowest IC50 value at 0.407 μM. DNA binding experiments were performed using agarose gel electrophoresis to observe the ability of synthesized Au-NHC complexes to interact with the supercoiled pUC19 plasmid DNA. Molecular docking studies were performed to determine the binding mode of all active compounds against the XO enzyme, antibacterial, antifungal, and MCF-7 cell lines.
“…The anticancer potential of Ag–NHC complexes and their synthesis have been the attention of various research teams. Ag–NHC complexes have been reported to show good to excellent anticancer potential against many cell lines [ 23 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ]. Scheme 1 Structure of cytotoxic properties studied Ag–NHC complexes against different cancer cells.…”
Section: Introductionmentioning
confidence: 99%
“…The anticancer potential of Ag-NHC complexes and their synthesis have been the attention of various research teams. Ag-NHC complexes have been reported to show good to excellent anticancer potential against many cell lines [23,36,37,38,39,40,41,42].…”
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