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Triethylammonium Salts of Dicoumarol: Synthesis, Characterization, Human Antiglioblastoma, Antimicrobial and
Sadia Rehman1, Muhammad Ikram2, Afzal Khan2,3,4
1Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan. sadia@awkum.edu.pk.
Abstract:
The most typical primary brain tumor, glioblastoma multiforme (GBM), has a dismal prognosis. They are removed through arduous, potentially fatal operations. The primary cause of tumor recurrence following surgery is glioblastoma stem cells (GSCs). In order to combat the recurrent glioblastoma malignant cells, medications have been developed. Chemotherapies now in use are expensive and encounter resistance. To combat inherent and developed resistance, new and powerful chemotherapeutics are being synthesized. In this regard, dicoumarols were deprotonated by triethylamine to produce corresponding salts which are reported and used for the first time for human antiglioblastoma activity. Spectroscopic characterizations like 1H and 13C-NMR were carried out. The cytotoxicity of normal human astrocytes (NHA) and human glioblastoma cells (A172 and LN229) were both examined in terms of dose and time dependence. The range of the IC50 value for all the deprotonated derivatives against A172 was found to be 2.81-0.24 µM, whereas the range against LN229 was found to be 2.50-0.85 µM. According to cytotoxicity results, malignant cell death was seen in GBM cells treated with triethylamine salts of dicoumarols compared to the control group, which suggested that salts may cause apoptosis in GBM cells. Antimicrobial and antifungal activities were also investigated for all the triethylamine salts of dicoumarols suggesting that salt formation enhances antimicrobial potentials manyfolds compared to the standard drug used. Free radical activities were also investigated using DPPH free radicals.
Insights
New dicoumarol salts show potent anti-glioblastoma activity, offering a promising alternative to current therapies for glioblastoma multiforme (GBM). These compounds also exhibit enhanced antimicrobial and free radical scavenging properties.
Area of Science:
- Medicinal Chemistry
- Oncology
- Pharmacology
Background:
- Glioblastoma multiforme (GBM) is an aggressive brain tumor with poor prognosis.
- Glioblastoma stem cells (GSCs) drive tumor recurrence after surgery.
- Existing chemotherapy for GBM is costly and faces resistance.
Purpose of the Study:
- To synthesize and evaluate novel dicoumarol derivatives for antiglioblastoma activity.
- To investigate the cytotoxicity of these compounds against human glioblastoma cells.
- To explore their antimicrobial, antifungal, and free radical scavenging properties.
Main Methods:
- Dicoumarols were deprotonated using triethylamine to form salts.
- Spectroscopic characterization (¹H and ¹³C-NMR) was performed.
- Cytotoxicity assays were conducted on normal human astrocytes (NHA) and glioblastoma cell lines (A172, LN229).
- Antimicrobial, antifungal, and DPPH free radical assays were performed.
Main Results:
- The synthesized triethylamine salts of dicoumarols demonstrated significant cytotoxicity against A172 (IC₅₀: 2.81–0.24 µM) and LN229 (IC₅₀: 2.50–0.85 µM) glioblastoma cells.
- Treated GBM cells showed evidence of malignant cell death, suggesting apoptosis induction.
- Salt formation significantly enhanced antimicrobial and antifungal activities compared to the standard drug.
- Free radical scavenging activity was also observed.
Conclusions:
- Triethylamine salts of dicoumarols represent a novel therapeutic strategy against glioblastoma.
- These compounds exhibit potent cytotoxic effects on glioblastoma cells, potentially via apoptosis.
- Dicoumarol salt formation enhances their antimicrobial and free radical scavenging capabilities, suggesting broader therapeutic potential.
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