The Effect of Fatty Alkanolamide Structure on Cytotoxic and Antimicrobial Activity | ||
| Egyptian Journal of Chemistry | ||
| Volume 67, Issue 9, September 2024, Pages 289-295 PDF (498.06 K) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/ejchem.2023.212786.8007 | ||
| Authors | ||
| Tuti Wukirsari* 1; Nadiroh Nadiroh1; Tiara F Kembara1; Muhamad Irsyad A. Gunawan2; Bambang Pontjo Priosoeryanto3; Sri Handayani1; Sumi Hudiyono1 | ||
| 1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia | ||
| 2Department of Chemistry, Faculty of Matematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia | ||
| 3School of Veterinary Medicine and Biomedicine, IPB University, Bogor, Indonesia | ||
| Abstract | ||
| This research was conducted to explore the prospect of fatty acid derivatives as candidates for anticancer and antimicrobial drugs. Synthesis of fatty alkanolamides was carried out by direct amidation of fatty acids with alkanolamines. Several fatty acids and alkanolamines were used as starting materials to investigate the effect of the chain length, the presence of C=C bond, and the number of hydroxyl group of alkanolamides on the cytotoxic activity against HeLa cell line and also antimicrobial activity against Escherichia coli and Staphylococcus aureus. The structure of synthesized alkanolamides was characterized using FTIR and 1H-NMR spectroscopy, the cytotoxic activity was evaluated using a standard MTT assay, and the antimicrobial activity was determined using the disc diffusion method. The data showed that all alkanolamides exhibited cytotoxic and antimicrobial activity. A long-saturated alkyl chain was advantageous for the activities. Alkanolamide stearate-monoethanolamine showed the highest cytotoxic activity (IC50 = 37.5 M) and antimicrobial activity. The presence of C=C bond decreased the activities. However, the polyunsaturated alkyl chain expressed greater activities than the monounsaturated alkyl chain. The number of hydroxyl groups on alkanolamines residue indicated a small contribution to the activity. Therefore, fatty alkanolamide is promising to be developed as an anti-cancer and antimicrobial drug. | ||
| Keywords | ||
| Fatty alkanolamide; direct amidation; cytotoxic activity; antimicrobial activity; lipoamide | ||
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