Synthesis of a Novel Macrocyclic Derivatives Based on Glucopyranoside and Application as Anticancer Activity
Keywords:
methyl 4,6-benzylidene-2,3-di-O-benzyl-D-glucopyranoside, PC3, pyranoside, WRL68, cancer cell linesAbstract
Cyclic compounds have gained attention in a variety of fields for their unique properties. Crown ethers, cryptands, and calixarenes are cyclic compounds that have been used in a range of applications such as chemical sensors and drug delivery systems. Cyclic peptides have shown promise in treating various diseases due to their enhanced stability and bioavailability. This study focuses on the synthesis and characterization of a pyranoside compound, -methyl 4,6-benzylidene-2,3-di-O-benzyl-D-glucopyranoside, which was synthesized via a phase transfer catalysis method. The synthesized compound was analyzed using FT-IR, 1H NMR, and 13C NMR spectroscopy. Field-emission scanning electron microscopy and EDX analysis were also carried out to study the morphology and elemental composition of the compound. The results of this study contribute to the potential applications compounds -methyl 4,6-benzylidene-2,3-di-O-benzyl-D-glucopyranoside were evaluated for their anticancer potential against two cancer cell lines PC3 (prostate cancer cells) and WRL68 (normal liver cells) compound 12 appears to have a greater effect on prostate cancer cells (PC3) compared to compound 11. At the highest concentration tested (400 µM), compound 12 showed a mean percentage inhibition of 95.72% in PC3 cells, while compound 11 showed a mean percentage inhibition of 33.29% at the same concentration. Furthermore, the IC50 value for compound 12 in PC3 cells was 112.9 µM, while the IC50 value for compound 11 was 24.38 µM, indicating that compound 11 is less potent in inhibiting the growth of PC3 cells. These results suggest that compound 12 may have greater potential as a therapeutic agent for prostate cancer.
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