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Quinoline-sulfamoyl carbamates/sulfamide derivatives: Synthesis, cytotoxicity, carbonic anhydrase activity, and

Elmas Begum Cakmak1, Belma Zengin Kurt2, Dilek Ozturk Civelek3

  • 1Sakarya University, Institute of Natural Sciences, 54050 Sakarya, Turkey.

Bioorganic Chemistry
|March 8, 2021
PubMed

Insights

Novel quinoline derivatives were synthesized and tested as carbonic anhydrase inhibitors. Compound 2m showed potent inhibition of carbonic anhydrase IX, a key cancer target, while other compounds displayed significant cytotoxicity against cancer cell lines.

Area of Science:

  • Medicinal Chemistry
  • Biochemistry
  • Oncology

Background:

  • Carbonic anhydrase (CA) IX and XII are highly expressed in human cancers.
  • CA IX overexpression in hypoxic tumors correlates with poor prognosis, making it a significant cancer target.

Purpose of the Study:

  • To synthesize and characterize novel quinoline-based compounds.
  • To evaluate the inhibitory activity of these compounds against carbonic anhydrase isoforms (CA I, II, IX, and XII).
  • To assess the cytotoxic effects of the synthesized compounds on various human cancer cell lines.

Main Methods:

  • Synthesis of 27 novel compounds in two series: sulfamoylcarbamate-based quinoline (2a-2o) and sulfamide-based quinoline (3a-3l).
  • Characterization using IR, NMR, and mass spectrometry.
  • Enzyme inhibition assays against CA I, II, IX, and XII.
  • Cytotoxicity assays on human colorectal (HT-29), breast (MCF7), prostate (PC3) adenocarcinoma, and healthy skin fibroblast (CCD-986Sk) cell lines.

Main Results:

  • Compound 2m (2-Phenylpropyl (N-(quinolin-8-yl)sulfamoyl)carbamate) demonstrated the highest inhibition of human carbonic anhydrase IX (hCA IX) with a Ki of 0.5 µM.
  • Compounds 2j, 3a, 3e, and 3f exhibited the most significant cytotoxic activity across all tested cancer and healthy cell lines.

Conclusions:

  • The synthesized quinoline derivatives show potential as carbonic anhydrase inhibitors, particularly for CA IX.
  • Specific compounds possess promising cytotoxic effects against multiple cancer cell lines, warranting further investigation for cancer therapy.
Keywords:
CA inhibitionCytotoxicityMolecular dockingMolecular dynamics simulationsQuinolineSulfamideSulfamoyl carbamate

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