Silver(I) complexes based on novel tripodal thioglycosides: synthesis, structure and antimicrobial activity

Gottschaldt, Michael; Pfeifer, Annett; Koth, Daniel; Görls, Helmar; Dahse, Hans‐Martin; Möllmann, Ute; Obata, Makoto; Yano, Shigenobu

doi:10.1016/j.tet.2006.09.038

Cited by 30 publications

(23 citation statements)

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“…Additional advantages of the use of silver complexes as new metallodrugs are their relative low toxicity to humans and selectivity against some types of tumor cells . Some examples of silver(I) complexes selective towards cancer cells are those with tripodal NS 3 ligands, which have selectivity against leukemia K‐562 cell line and two complexes with 2‐mercapto‐3,4,5,6‐tetrahydropyrimidine that show selectivity against the cell line L1210 of murine leukemia, with IC 50 values of 3.4 ± 0.1 and 3.5 ± 0.1 mg⋅mL −1 . This kind of selectivity towards cancer cells exhibited by Ag(I) complexes might be related to hydrophilic–lipophilic balance and due to the stability of the complexes provided by the ligands …”

Section: Introductionmentioning

confidence: 74%

A Silver Complex with Cycloserine: Synthesis, Spectroscopic Characterization, Crystal Structure and In Vitro Biological Studies

et al. 2018

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Synthesis, characterization and biological activities of a silver(I) complex with cycloserine (AgCIC) are presented. Elemental, thermal and mass spectrometric analyses permitted proposing the minimal formula AgC3H5N2O2. The structure of the AgCIC complex was solved by powder X‐ray diffraction (XRD) studies. Coordination of the ligand to silver was shown to occur by the nitrogen atom of the heterocyclic ring and by the nitrogen and oxygen atoms of the amino and carbonyl groups, leading to a polymeric arrangement. Infrared (IR) and nuclear magnetic resonance (NMR) spectroscopic analyses confirmed the coordination sites. Antibacterial assays revealed the activity of the AgCIC complex against Mycobacterium tuberculosis, with minimal inhibitory concentration (MIC90) of 79.1 μmol⋅L−1, and against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa bacterial strains. Antiproliferative assays over a panel of tumoral and non‐tumoral cells showed that the AgCIC complex is more active and selective than doxorubicin against breast and leukemia cancer cells, considering the total growth inhibition (TGI) values. The interaction of the complex with biomolecules and its mutagenicity were also investigated.

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Section: Introductionmentioning

confidence: 74%

A Silver Complex with Cycloserine: Synthesis, Spectroscopic Characterization, Crystal Structure and In Vitro Biological Studies

et al. 2018

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“…This biological and/or pharmaceutical relevance of Ag(I)–NHC complexes has promoted the synthesis of model silver compounds containing functionalized NHC ligands. The stability of the central bioactive benzimidazole core has inspired medicinal chemists to synthesize new potential Ag(I)–NHC complexes to explore their anticancer potential . Furthermore, their high stability and ease of derivatization make them suitable compounds for drug discovery and development.…”

Section: Introductionmentioning

confidence: 99%

Nitrile‐functionalized Hg(II)‐ and Ag(I)‐N‐heterocyclic carbene complexes: synthesis, crystal structures, nuclease and DNA binding activities

Haque

Budagumpi

Choo

et al. 2012

Applied Organom Chemis

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Various nitrile‐functionalized benzimidazol‐2‐ylidene carbene complexes of Hg(II) and Ag(I) were synthesized by the interaction of 1‐benzyl/1‐butyl‐3‐(cyano‐benzyl)‐3 H‐benzimidazol‐1‐ium mono/dihexafluorophosphate with Hg(OAc)2/Ag2O in acetonitrile. Two of the benzimidazolium salts were structurally characterized by single crystal X‐ray diffraction technique. Structures of reported compounds were characterized by 1 H, 13C NMR, FT‐IR, UV–visible spectroscopic techniques, and molar conductivity and elemental analyses. For bis‐benzimidazolium salt, dinuclear Hg(II)– and Ag(I)–carbene complexes were obtained. Nuclease activity and binding interactions of the synthesized benzimidazolium salts and their Ag(I)–carbene complexes with DNA were studied using agarose gel electrophoresis and, absorption spectroscopy and viscosity measurements, respectively. Ag(I)–carbene complexes showed higher DNA binding activity compared to their respective benzimidazolium salts. However, a benzimidazolium salt and two of the Ag(I) complexes showed remarkably higher nuclease activity both, in the presence and absence of an oxidizing agent. Copyright © 2012 John Wiley & Sons, Ltd.

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“…Deacetylation of 3a-c was performed in methanol/water at 60°C by stirring the mixtures with OH --loaded Dowex resin. [46] After filtration through silica gel, the pure products 4a-c could be obtained. Although we did not observe any problems with these substances so far, with an azide nitrogen content of up to 34 % (for 4a) the compounds should be handled with circumspection to avoid accidents.…”

Section: Ligand Synthesismentioning

confidence: 99%

In^III and Ga^III Complexes of Sugar‐Substituted Tripodal Trisalicylidene Imines: The First ⁶⁸Ga‐Labelled Sugar Derivative

et al. 2009

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Gallium and indium complexes derived from salicylaldimines of 1,1,1-tris(aminomethyl)ethane (TAME) with pendant xylose, glucose and galactose units have been synthesised as model compounds for potential application as radiotracers. The formed neutral complexes have been characterised by NMR spectroscopy, elemental analysis, mass spectrometry and, in the case of the galactose-bearing In III complex, by single-crystal X-ray structure analysis. Octahedral coordination was observed with the appearance of an equilibrium of

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Silver(I) complexes based on novel tripodal thioglycosides: synthesis, structure and antimicrobial activity

Cited by 30 publications

References 31 publications

A Silver Complex with Cycloserine: Synthesis, Spectroscopic Characterization, Crystal Structure and In Vitro Biological Studies

A Silver Complex with Cycloserine: Synthesis, Spectroscopic Characterization, Crystal Structure and In Vitro Biological Studies

Nitrile‐functionalized Hg(II)‐ and Ag(I)‐N‐heterocyclic carbene complexes: synthesis, crystal structures, nuclease and DNA binding activities

In^III and Ga^III Complexes of Sugar‐Substituted Tripodal Trisalicylidene Imines: The First ⁶⁸Ga‐Labelled Sugar Derivative

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Silver(I) complexes based on novel tripodal thioglycosides: synthesis, structure and antimicrobial activity

Cited by 30 publications

References 31 publications

A Silver Complex with Cycloserine: Synthesis, Spectroscopic Characterization, Crystal Structure and In Vitro Biological Studies

A Silver Complex with Cycloserine: Synthesis, Spectroscopic Characterization, Crystal Structure and In Vitro Biological Studies

Nitrile‐functionalized Hg(II)‐ and Ag(I)‐N‐heterocyclic carbene complexes: synthesis, crystal structures, nuclease and DNA binding activities

InIII and GaIII Complexes of Sugar‐Substituted Tripodal Trisalicylidene Imines: The First 68Ga‐Labelled Sugar Derivative

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In^III and Ga^III Complexes of Sugar‐Substituted Tripodal Trisalicylidene Imines: The First ⁶⁸Ga‐Labelled Sugar Derivative