Lamotrigine derivatives-synthesis, anti-cancer, and anti-MDR-bacterial activities
Journal of Molecular Structure, cilt.1264, 2022 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1264
- Basım Tarihi: 2022
- Doi Numarası: 10.1016/j.molstruc.2022.133277
- Dergi Adı: Journal of Molecular Structure
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
- Anahtar Kelimeler: Lamotrigine, Quaternary ammonium salts, Anti-bacterial activity, Staphylococcus aureus, Cancer cell lines, Cytotoxicity, HeLa, Breast cancer, MCF-7, MDA-MB
- İstanbul Medipol Üniversitesi Adresli: Evet
Özet
A new series of quaternary ammonium salts 3–21 of lamotrigine (6-(2, 3-dichlorophenyl)-1, 2, 4-triazine-3, 5-diamine) was synthesized via N-alkylation of lamotrigine using different benzyl bromides. The new analogues were characterized by using FT-IR, NMR, and mass spectrometric techniques. Single-crystal X-ray diffraction analysis of compound 10 was also carried out to confirm the position of substitution and salt formation. All the compounds 3-21 were tested for various biological activities, including anti-bacterial, and anti-cancer properties. All compounds, except 20, exhibited a potent growth inhibition of Staphylococcus aureus strains as compared to the ofloxacin, the standard drug. Compounds 4, 7, 10, and 13 showed a significant toxicity towards HeLa cell line (derived from cervical carcinoma), whereas compounds 3, and 5 showed a significant activity towards HeLa, MCF-7 (estrogen and progesterone positive breast cancer cell line), and MDA-MB cell lines (epithelial, human breast cancer cell line), as compared to the standard drug doxorubicin. To the best of our knowledge all analogues of 6-(2, 3-dichlorophenyl)-1, 2, 4-triazine-3, 5-diamine, and their activity against MDR, and anti-cancer is reported here for the first time.