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Itaconic acid hybrids as potential anticancer agents.

Ivana Perković1, Maja Beus1, Dominique Schols2

  • 1Department of Medicinal Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, 10 000, Zagreb, Croatia.

Molecular Diversity
|October 12, 2020
PubMed
Summary
This summary is machine-generated.

Novel hybrids combining itaconic acid with various scaffolds show significant anticancer activity against solid tumors and some hematological cancer cell lines. Compound 15 also demonstrated antiviral effects against Zika virus and Coxsackievirus B4.

Keywords:
Anticancer activityAntiviral activityHybridItaconic acidMichael acceptor

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • Itaconic acid, a natural compound, possesses a Michael acceptor moiety crucial for covalent drug binding in anticancer and antiviral agents.
  • Existing anticancer and antiviral drugs often incorporate aromatic structures similar to those used in the synthesized hybrids.
  • The study leverages the known bioactivity of itaconic acid derivatives and aromatic scaffolds to create novel therapeutic candidates.

Purpose of the Study:

  • To synthesize novel hybrid compounds incorporating itaconic acid with fluoroaniline, pyridine, indole, and quinoline scaffolds.
  • To evaluate the in vitro anticancer and antiviral activities of the synthesized hybrids.
  • To identify specific compounds with high therapeutic potential against various cancer cell lines and viruses.

Main Methods:

  • Synthesis of amido-ester hybrids (2-13) using monomethyl itaconate or monomethyl itaconyl chloride and amines.
  • Preparation of dimeric hybrids (14, 15) from itaconic acid and amino derivatives via standard coupling reactions (HATU/DIEA).
  • In vitro screening of synthesized hybrids against a panel of human tumor cell lines (MCF-7, HCT 116, etc.) and viral assays.

Main Results:

  • All synthesized hybrids (2-14) exhibited anticancer effects across multiple tumor cell lines, with solid tumors being more responsive than hematological cancers.
  • The MCF-7 breast adenocarcinoma cell line was the most sensitive to the tested compounds.
  • Hybrid 12 (amido-ester with chloroquine core) and hybrid 15 (mefloquine homodimer) displayed the highest anticancer activity (GI50 values 0.7–8.6 µM).
  • Compound 15 also demonstrated significant antiviral activity against Zika virus and Coxsackievirus B4 at low micromolar concentrations.

Conclusions:

  • The novel itaconic acid-based hybrids possess broad-spectrum anticancer properties, particularly against solid tumors.
  • Compounds 12 and 15 are promising candidates for further development as anticancer agents.
  • Compound 15 shows dual therapeutic potential, exhibiting both anticancer and antiviral activities, warranting further investigation.