Antimicrobial and antiproliferative activity studies of some new quinoline-3-carbaldehyde hydrazone derivatives

PÜSKÜLLÜ M. O., ÇELİK İ., EROL M., FATULLAYEV H., UZUNHİSARCIKLI E., Kuyucuklu G.

Bioorganic Chemistry, cilt.101, 2020 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 101
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.bioorg.2020.104014
  • Dergi Adı: Bioorganic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chimica, EMBASE, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: Quinoline, Hydrazone, Antimicrobial activity, Cytotoxicity, Molecular docking, SPECTROSCOPIC INVESTIGATIONS, THERMAL-PROPERTIES, COMPLEXES, BINDING
  • Erciyes Üniversitesi Adresli: Evet

Özet

© 2020 Elsevier Inc.In this study, a total of 22 piece quinoline-3-carbaldehyde hydrazone derivative compounds were designed and synthesized, 2 of which were not original, their antimicrobial activities were determined with microdilution method and their in vitro cytotoxic effect was investigated in MCF-7 and A549 cells by MTT assay. When the activity results are examined, although the antimicrobial effects of quinoline derivatives, in general, are weaker than standard drugs; 3q5 and 3q6 against MRSA showed promising activity with MIC:16 µg/ml compared to reference drugs. Compounds generally showed weaker cytotoxic activity on the A549 and MCF-7 cell line. 3q12, 3q17 and 3q22 at 100 µM reduced cell viability to 59.28%, 76.24% and 72.92% on A549 cells, respectively. Compound 3q6, one of the most effective compounds against MRSA, formed a 2.10 Å long hydrogen bond between the quinoline nitrogen and ARG132 in the DNA topoisomerase IV active site (PDB: 3FV5). Theoretical ADME profiles of all compounds comply with Lipinski and other limiting rules. In addition, MEP analysis of 3q6, geometric optimization and molecular reactivity analysis were calculated with the 6-311G (d,p) base set DFT/B3LYP theory, and ΔE = ELUMO-EHOMO, which is a measure of the stable structure of the molecule, was calculated as 0.13377 for 3q6 and had the most stable electronic structure among all compounds.