ANTHRAQUINONE DERIVATIVES BEARING THIADIAZOL MOIETY, DESIGN, SYNTHESIS, CHARACTERIZATION, AND CYTOTOXIC EVALUATION
DOI:
https://doi.org/10.22159/ajpcr.2025v18i9.56543Keywords:
anthraquinone, anticancer, 1,3,4-Thiadiazole, cytotoxic evaluation., Heterocyclic CompoundsAbstract
Objectives: The primary goals were to study biological activity in vivo, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) cell viability assay, the synthesis of new anthraquinone derivatives MI(6–9) bearing heterocyclic scaffolds(1,3,4-thiadiazole), and molecular docking studies.
Methods: Molecular docking studies (using Ligand Designer from Glide [Schrodinger LLC]) for the proposed compounds against Vegfr2 and topoisomerase II receptors with sunitinib and doxorubicin as references, respectively. The synthesis of new anthraquinone derivatives MI(6-9) bearing heterocyclic scaffolds(1,3,4-thiadiazole), characterized through melting point, TLC, and spectral data acquisition (infrared [IR], attenuated total reflectance-Fourier transform IR, nuclear magnetic resonance), and evaluated in vivo using an MTT cytotoxicity assay with sunitinib and doxorubicin as a standard.
Results: The docking score of compound MI8 is (−7.403), which is higher than sunitinib (−7.086), while MI6 and MI7 are slightly lower than it. The docking scores of compounds MI8 (−5.194), MI6 (−4.887), and MI9 (−4.843) are higher than that of doxorubicin (−4.761). The results of the cytotoxicity study showed that the compound MI8 exhibited the most potent inhibitory activity, comparable to sunitinib and doxorubicin, since its inhibitory concentration (IC50) is 3.00 μg/mL, while sunitinib has 6.89 μg/mL and doxorubicin has 2.89 μg/mL in the breast cancer cell line, while in the lung cancer cell line, the compound MI8 has an IC50 of 4.10 μg/mL, but sunitinib has 3.00 μg/mL and doxorubicin has 2.83 μg/mL. GraphPad Prism 8.5 was used for data analysis and graphing software.
Conclusion: The molecules (MI6–MI9) that were designed were successfully synthesized, and MI8 demonstrated superior cell inhibition activity, which indicated a high potential for antiproliferative function.
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