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Exploring etofenamate hydrazide-hydrazone/copper(II) complexes: Synthesis, anticancer activity, carbonic anhydrase IX inhibition and docking studies

Cakmak, Sude Saral; Erdogan, Omer; Basoglu, Faika; Coruh, Ufuk; Cevik, Ozge; Karakus, Sevgi


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{
  "DOI": "10.1016/j.molstruc.2024.138555", 
  "abstract": "<p>Hydrazide-hydrazone derivatives have garnered significant interest from researchers globally due to their wide range of biological activities, including antiviral, anticancer, and anti-inflammatory properties. In this study, a novel series of etofenamate hydrazide-hydrazone compounds (2a-2s) and their Cu(II) complexes (3a-3s) were designed and synthesized. The compounds were characterized using various analytical techniques such as FT-IR, 1H NMR, 13C NMR, MS, and elemental analysis. Additionally, the compound 2c and Cu(II) hydrazone complex 3a were further characterized using single X-ray crystallography. The anti-proliferative activity of the compounds was evaluated against Ishikawa human endometrial cancer cell line and non-tumour L929 cells using MTT assay. Additionally, the apoptotic potential of the compounds was investigated through caspase-3 activity, Bax and Bcl2 gene expression analysis, and annexin-V binding. Furthermore, carbonic anhydrase IX activity and in silico studies were conducted to elucidate the mechanism of action. Overall, compound 3s demonstrated significant antiproliferative effects with an IC50 value of 0.27 +/- 0.01 mu M against Ishikawa cells.</p>", 
  "author": [
    {
      "family": "Cakmak", 
      "given": " Sude Saral"
    }, 
    {
      "family": "Erdogan", 
      "given": " Omer"
    }, 
    {
      "family": "Basoglu", 
      "given": " Faika"
    }, 
    {
      "family": "Coruh", 
      "given": " Ufuk"
    }, 
    {
      "family": "Cevik", 
      "given": " Ozge"
    }, 
    {
      "family": "Karakus", 
      "given": " Sevgi"
    }
  ], 
  "container_title": "JOURNAL OF MOLECULAR STRUCTURE", 
  "id": "283851", 
  "issued": {
    "date-parts": [
      [
        2024, 
        1, 
        1
      ]
    ]
  }, 
  "page": "19", 
  "title": "Exploring etofenamate hydrazide-hydrazone/copper(II) complexes: Synthesis, anticancer activity, carbonic anhydrase IX inhibition and docking studies", 
  "type": "article-journal", 
  "volume": "1312"
}
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