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Updated: Apr 29, 2026
Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Synthesis, characterization and antitumor activity of new ferrocene incorporated N,N'-disubstituted thioureas
Bhajan Lal1, Amin Badshah, Ataf Ali Altaf
1Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan.
Abstract:
We report herein the synthesis, structural characterization and activity against human ovarian tumour models: A2780 (parent), A2780(cisR) (resistant to cisplatin) and A2780(ZD0473R) (resistant to the cisplatin analogue denoted as ZD0473) of two ferrocene incorporated N,N'-disubstituted thioureas {1-benzoyl-3-(4-ferrocenylphenyl)thiourea, B16, and 1-acetyl-3-(4-ferrocenylphenyl)thiourea, B3}. Structural characterization has been based on FT-IR, multinuclear ((1)H and (13)C) NMR, elemental analysis and single crystal X-ray diffractometry. Ferrocene-incorporated thioureas may present themselves as a new class of metal-based tumour active compounds. The cyclic voltammetric measurements indicate that B16 undergoes partial intercalation with the CT-DNA whereas B3 undergoes only electrostatic interaction with the same. Partial prevention of BamH1 digestion of pBR322 plasmid DNA that has been interacted with high concentrations of both B16 and B3 indicates that even non-covalent interactions can induce significant conformational changes in the DNA.
Insights
Two novel ferrocene-containing thioureas show potential as metal-based anticancer agents. These compounds exhibit activity against ovarian tumor models and interact with DNA, suggesting a new class of anti-tumor compounds.
Area of Science:
- Medicinal Chemistry
- Organometallic Chemistry
- Biochemistry
Background:
- Ovarian cancer remains a significant health challenge, with drug resistance limiting treatment efficacy.
- Metal-based compounds, particularly those incorporating ferrocene, offer unique mechanisms for anti-cancer activity.
- Thiourea derivatives are known for their diverse biological properties.
Purpose of the Study:
- To synthesize and characterize novel ferrocene-incorporated N,N'-disubstituted thioureas.
- To evaluate the anti-tumor activity of these compounds against human ovarian cancer models, including cisplatin-resistant cell lines.
- To investigate the DNA interaction mechanisms of the synthesized compounds.
Main Methods:
- Synthesis of 1-benzoyl-3-(4-ferrocenylphenyl)thiourea (B16) and 1-acetyl-3-(4-ferrocenylphenyl)thiourea (B3).
- Structural characterization using FT-IR, NMR (1H and 13C), elemental analysis, and X-ray crystallography.
- In vitro anti-tumor activity testing against A2780, A2780(cisR), and A2780(ZD0473R) ovarian cancer cell lines.
- Cyclic voltammetry and DNA interaction studies (CT-DNA binding and plasmid DNA digestion assays).
Main Results:
- Successful synthesis and full structural elucidation of B16 and B3.
- Both compounds demonstrated anti-tumor activity against parent and resistant ovarian cancer cell lines.
- B16 showed partial intercalation with CT-DNA, while B3 exhibited electrostatic interaction.
- High concentrations of B16 and B3 partially prevented DNA digestion, indicating DNA conformational changes.
Conclusions:
- Ferrocene-incorporated thioureas represent a promising new class of metal-based anti-tumor agents.
- The observed DNA interactions contribute to their anti-cancer mechanisms.
- These compounds warrant further investigation for ovarian cancer therapy.
