Design, synthesis and biological evaluation of novel podophyllotoxin derivatives as tubulin-targeting anticancer agents

References

• Abd Emoniem N, Mukhtar RM, Ghaboosh H, Elshamly EM, Mohamed MA, Elsaman T, Alzain AA. 2023. Turning down PI3K/AKT/mTOR signalling pathway by natural products: an in silico multi-target approach. SAR QSAR Environ Res. 34(2):163–182. doi: 10.1080/1062936X.2023.2181392.
   PubMed Web of Science ®Google Scholar
• Aggarwal C, Somaiah N, Simon G. 2012. Antiangiogenic agents in the management of non-small cell lung cancer: where do we stand now and where are we headed? Cancer Biol Ther. 13(5):247–263. doi: 10.4161/cbt.19594.
   PubMed Web of Science ®Google Scholar
• Bai G, Zhao D, Ran X, Zhang L, Zhao D. 2020. Novel hybrids of podophyllotoxin and coumarin inhibit the growth and migration of human oral squamous carcinoma cells. Front Chem. 8:626075–626087. doi: 10.3389/fchem.2020.626075.
   PubMed Web of Science ®Google Scholar
• Bromberg KD, Burgin AB, Osheroff N. 2003. A two-drug model for etoposide action against human topoisomerase II alpha. J Biol Chem. 278(9):7406–7412. doi: 10.1074/jbc.M212056200.
   PubMed Web of Science ®Google Scholar
• Chang TH, Szabo E. 2002. Enhanced growth inhibition by combination differentiation therapy with ligands of peroxisome proliferator-activated receptor-gamma and inhibitors of histone deacetylase in adenocarcinoma of the lung. Clin Cancer Res. 8(4):1206–1212.
   PubMed Web of Science ®Google Scholar
• Cui YJ, Liu C, Ma CC, Ji YT, Yao YL, Tang LQ, Zhang CM, Wu JD, Liu ZP. 2020. SAR investigation and discovery of water-soluble 1-methyl-1,4-dihydroindeno[1,2-c]pyrazoles as potent tubulin polymerization inhibitors. J Med Chem. 63(23):14840–14866. doi: 10.1021/acs.jmedchem.0c01345.
   PubMed Web of Science ®Google Scholar
• Ferlay J, Colombet M, Soerjomataram I, Parkin DM, Piñeros M, Znaor A, Bray F. 2021. Cancer statistics for the year 2020: an overview. Int J Cancer. 149(4):778–789. doi: 10.1002/ijc.33588.
   Web of Science ®Google Scholar
• Gordaliza M, Castro MA, del Corral JM, Feliciano AS. 2000. Antitumor properties of podophyllotoxin and related compounds. Curr Pharm Des. 6(18):1811–1839. doi: 10.2174/1381612003398582.
   PubMed Web of Science ®Google Scholar
• Gudimchuk NB, Ulyanov EV, O’Toole E, Page CL, Vinogradov DS, Morgan G, Li G, Moore JK, Szczesna E, Roll-Mecak A, et al. 2020. Mechanisms of microtubule dynamics and force generation examined with computational modeling and electron cryotomography. Nat Commun. 11(1):3765–3779. doi: 10.1038/s41467-020-17553-2.
   PubMed Web of Science ®Google Scholar
• Guo JX, Zhou YH, Huang YQ, Liu GJ, Pan JX. 2017. Synergistic effects of chlorambucil and TRAIL on apoptosis and proliferation of Raji cells. Eur Rev Med Pharmacol Sci. 21(20):4703–4710.
   PubMed Web of Science ®Google Scholar
• Jiang N, Dai Q, Su X, Fu J, Feng X, Peng J. 2020. Role of PI3k/Akt pathway in cancer: the framework of malignant behavior. Mol Biol Rep. 47(6):4587–4629. doi: 10.1007/s11033-020-05435-1.
   PubMed Web of Science ®Google Scholar
• Khwaja S, Kumar K, Das R, Negi AS. 2021. Microtubule associated proteins as targets for anticancer drug development. Bioorg Chem. 116:105320–105335. doi: 10.1016/j.bioorg.2021.105320.
   PubMed Web of Science ®Google Scholar
• Ma Y, Yang X, Han H, Wen Z, Yang M, Zhang Y, Fu J, Wang X, Yin T, Lu G, et al. 2021. Design, synthesis and biological evaluation of anilide (dicarboxylic acid) shikonin esters as antitumor agents through targeting PI3k/Akt/mTor signaling pathway. Bioorg Chem. 111:104872–104883. doi: 10.1016/j.bioorg.2021.104872.
   PubMed Web of Science ®Google Scholar
• Mansoori B, Mohammadi A, Davudian S, Shirjang S, Baradaran B. 2017. The different mechanisms of cancer drug resistance: a brief review. Adv Pharm Bull. 7(3):339–348. doi: 10.15171/apb.2017.041.
   PubMed Web of Science ®Google Scholar
• Mouna R, Broisat A, Ahmed A, Debiossat M, Boumendjel A, Ghezzi C, Kabouche Z. 2022. Antiproliferative activity, cell-cycle arrest, apoptotic induction and LC-HRMS/MS analyses of extracts from two Linum species. Pharm Biol. 60(1):1491–1501. doi: 10.1080/13880209.2022.2102196.
   PubMed Web of Science ®Google Scholar
• Panda M, Biswal BK. 2019. Cell signaling and cancer: a mechanistic insight into drug resistance. Mol Biol Rep. 46(5):5645–5659. doi: 10.1007/s11033-019-04958-6.
   PubMed Web of Science ®Google Scholar
• Pitts SL, Jablonksy MJ, Duca M, Dauzonne D, Monneret C, Arimondo PB, Anklin C, Graves DE, Osheroff N. 2011. Contributions of the d-ring to the activity of etoposide against human topoisomerase II alpha: potential interactions with DNA in the ternary enzyme-drug-DNA complex. Biochem. 50(22):5058–5066. doi: 10.1021/bi200531q.
   PubMed Web of Science ®Google Scholar
• Salem FS, Badr MO, Neamat-Allah AN. 2011. Biochemical and pathological studies on the effects of levamisole and chlorambucil on Ehrlich ascites carcinoma-bearing mice. Vet Ital. 47(1):89–95.
   PubMed Web of Science ®Google Scholar
• Shah Z, Gohar UF, Jamshed I, Mushtaq A, Mukhtar H, Zia-Ui-Haq M, Toma SI, Manea R, Moga M, Popovici B. 2021. Podophyllotoxin: history, recent advances and future prospects. Biomol. 11(4):603–629. doi: 10.3390/biom11040603.
   Google Scholar
• Shtilbans V, Wu M, Burstein DE. 2008. Current overview of the role of Akt in cancer studies via applied immunohistochemistry. Ann Diagn Pathol. 12(2):153–160. doi: 10.1016/j.anndiagpath.2007.12.001.
   PubMed Web of Science ®Google Scholar
• Siegel RL, Miller KD, Fuchs HE, Jemal A. 2022. Cancer statistics, 2022. CA Cancer J Clin. 72(1):7–33. doi: 10.3322/caac.21708.
   PubMed Web of Science ®Google Scholar
• Sk UH, Dixit D, Sen E. 2013. Comparative study of microtubule inhibitors-estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation. Eur J Med Chem. 68:47–57. doi: 10.1016/j.ejmech.2013.07.007.
   PubMed Web of Science ®Google Scholar
• Tshering Vogel DW, Zbaeren P, Thoeny HC. 2010. Cancer of the oral cavity and oropharynx. Cancer Imaging. 10(1):62–72. doi: 10.1102/1470-7330.2010.0008.
   PubMed Web of Science ®Google Scholar
• Xiao J, Gao M, Sun Z, Diao Q, Wang P, Gao F. 2020. Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: an update (2010-2020). Eur J Med Chem. 208:112830–112853. doi: 10.1016/j.ejmech.2020.112830.
   PubMed Web of Science ®Google Scholar
• Zhao W, Cong Y, Li HM, Li S, Shen Y, Qi Q, Zhang Y, Li YZ, Tang YJ. 2021. Challenges and potential for improving the druggability of podophyllotoxin-derived drugs in cancer chemotherapy. Nat Prod Rep. 38(3):470–488. doi: 10.1039/d0np00041h.
   PubMed Web of Science ®Google Scholar
• Zi CT, Gao YS, Yang L, Feng SY, Huang Y, Sun L, Jin Y, Xu FQ, Dong FW, Li Y, et al. 2019. Design, synthesis, and biological evaluation of novel biotinylated podophyllotoxin derivatives as potential antitumor agents. Front Chem. 7:434–447. doi: 10.3389/fchem.2019.00434.
   PubMed Web of Science ®Google Scholar