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Antitumor Activity of Ionic Liquids Based on Ampicillin
Ricardo Ferraz1,2, João Costa-Rodrigues3, Maria H Fernandes4
1Departamento de Química, REQUIMTE-CQFB, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, 2829-516 Caparica (Portugal).
Chemmedchem
|July 21, 2015
Summary
Novel ampicillin-based ionic liquids (API-ILs) demonstrate significant antiproliferative effects against multiple cancer cell lines. The lead compound, [C2 OHMIM][Amp], shows potent antitumor activity with low toxicity to normal cells.
Area of Science:
- Medicinal Chemistry
- Drug Discovery
- Nanotechnology
Background:
- Ionic liquids (ILs) are salts that are liquid at room temperature, offering unique solvent properties.
- Active pharmaceutical ingredient ionic liquids (API-ILs) are a novel class of ILs where the active drug forms one of the ions.
- Ampicillin, a widely used antibiotic, has limited efficacy against cancer and can be susceptible to degradation.
Purpose of the Study:
- To synthesize and evaluate novel ampicillin-based ionic liquids (API-ILs) for their antiproliferative activity against various human cancer cell lines.
- To assess the cytotoxicity of these API-ILs against normal human cell lines to determine their safety profile.
- To identify the most promising API-IL candidate for further preclinical development.
Main Methods:
- Synthesis of ampicillin salts with various cations (ammonium, imidazolium, phosphonium, pyridinium).
- In vitro antiproliferative assays against T47D (breast), PC3 (prostate), HepG2 (liver), MG63 (osteosarcoma), and RKO (colon) cancer cell lines.
- Cytotoxicity assays against primary skin fibroblasts (SF) and gingival fibroblasts (GF).
Main Results:
- Several API-ILs exhibited potent antiproliferative activity, with IC50 values ranging from 5 to 42 nM against cancer cell lines.
- Ampicillin sodium salt showed negligible cytotoxic activity, highlighting the enhanced efficacy of API-ILs.
- The 1-hydroxyethyl-3-methylimidazolium-ampicillin ([C2 OHMIM][Amp]) API-IL demonstrated significant antitumor effects and low toxicity to normal fibroblasts.
- Most synthesized API-ILs displayed minimal toxicity towards normal human cell lines.
Conclusions:
- Novel ampicillin-based ionic liquids (API-ILs) represent a promising new class of anticancer agents.
- The [C2 OHMIM][Amp] API-IL exhibits a favorable balance of high antitumor efficacy and low general toxicity.
- This lead API-IL warrants further investigation for its potential in cancer therapy.