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

• Published in: Bioorganic chemistry Vol. 101; p. 104014
• Main Authors: Puskullu, Mustafa Orhan, Celik, Ismail, Erol, Meryem, Fatullayev, Hanifa, Uzunhisarcikli, Ebru, Kuyucuklu, Gulcan
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.08.2020; Elsevier
• Subjects: A549 Cells; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antimicrobial activity; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biochemistry & Molecular Biology; Cell Proliferation - drug effects; Chemistry; Chemistry, Organic; Cytotoxicity; Humans; Hydrazone; Hydrazones - chemistry; Hydrazones - pharmacology; Life Sciences & Biomedicine; MCF-7 Cells; Microbial Sensitivity Tests; Molecular docking; Molecular Docking Simulation; Physical Sciences; Quinoline; Science & Technology; Structure-Activity Relationship; Quinoline; Cytotoxicity; Antimicrobial activity; Hydrazone; Molecular docking; SPECTROSCOPIC INVESTIGATIONS; THERMAL-PROPERTIES; COMPLEXES; BINDING
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2020.104014

[Display omitted] •22 piece quinoline-3-carbaldehyde hydrazone derivatives were synthesized.•Antimicrobial effects were evaluated against some bacteria and fungus.•Antiproliferatif activity studies performed on A549 and MCF- cell line.•Molecular docking studies of all compounds were performed.•DFT/B3LYP theory study of compounds were carried out with 6-311G (d,p) base set. 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.