New 4,5-Diarylimidazol-2-ylidene-iodidogold(I) Complexes with High Activity against Esophageal Adenocarcinoma Cells.
Sebastian W SchleserHindole GhoshGerald HörnerJonathan SeibSangita BhattacharyyaBirgit WeberRainer SchobertPrasad DandawateBernhard BiersackPublished in: International journal of molecular sciences (2023)
Inspired by the vascular-disrupting agent combretastatin A-4 and recently published anticancer active N -heterocyclic carbene (NHC) complexes of Au(I), a series of new iodidogold(I)-NHC complexes was synthesized and characterized. The iodidogold(I) complexes were synthesized by a route involving van Leusen imidazole formation and N -alkylation, followed by complexation with Ag 2 O, transmetalation with chloro(dimethylsulfide)gold(I) [Au(DMS)Cl], and anion exchange with KI. The target complexes were characterized by IR spectroscopy, 1 H and 13 C NMR spectroscopy, and mass spectrometry. The structure of 6c was validated via single-crystal X-ray diffraction. A preliminary anticancer screening of the complexes using two esophageal adenocarcinoma cell lines showed promising nanomolar activities for certain iodidogold(I) complexes accompanied with apoptosis induction, as well as c -Myc and cyclin D1 suppression in esophageal adenocarcinoma cells treated with the most promising derivative 6b .
Keyphrases
- cell cycle arrest
- mass spectrometry
- induced apoptosis
- squamous cell carcinoma
- high resolution
- cell death
- endoplasmic reticulum stress
- oxidative stress
- liquid chromatography
- systematic review
- magnetic resonance imaging
- randomized controlled trial
- neoadjuvant chemotherapy
- signaling pathway
- sensitive detection
- gold nanoparticles
- locally advanced
- reduced graphene oxide
- capillary electrophoresis
- ionic liquid
- radiation therapy
- pi k akt
- quantum dots
- gas chromatography
- lymph node
- cell proliferation
- crystal structure
- high performance liquid chromatography