Development of novel 9-O-substituted-13-octylberberine derivatives as potential anti-hepatocellular carcinoma agents

References

• Sung H, Ferlay J, Siegel RL, et al. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin 2021;71:209–49.
   PubMed Web of Science ®Google Scholar
• Llovet JM, Kelley RK, Villanueva A, et al. Hepatocellular carcinoma. Nat Rev Dis Primers 2021;7:6.
   PubMed Web of Science ®Google Scholar
• Hartke J, Johnson M, Ghabril M. The diagnosis and treatment of hepatocellular carcinoma. Semin Diagn Pathol 2017;34:153–9.
   PubMed Web of Science ®Google Scholar
• Gosalia AJ, Martin P, Jones PD. Advances and future directions in the treatment of hepatocellular carcinoma. Gastroenterol Hepatol 2017;13:398–410.
   PubMedGoogle Scholar
• Heimbach JK, Kulik LM, Finn RS, et al. AASLD guidelines for the treatment of hepatocellular carcinoma. Hepatology 2018;67:358–80.
   PubMed Web of Science ®Google Scholar
• Shen XJ, Wu D, Tang M, et al. Liver computed tomographic perfusion for monitoring the early therapeutic response to sorafenib in advanced hepatocellular carcinoma patients. J Cancer Res Ther 2018;14:1556–62.
   PubMed Web of Science ®Google Scholar
• Finn RS, Merle P, Granito A, et al. Outcomes of sequential treatment with sorafenib followed by regorafenib for HCC: additional analyses from the phase III RESORCE trial. J Hepatol 2018;69:353–8.
   PubMed Web of Science ®Google Scholar
• Zhang SS, Long FY, Lin H, et al. Regulatory roles of phytochemicals on circular RNAs in cancer and other chronic diseases. Front Pharmacol 2021;12:105936.
   Google Scholar
• Newman DJ, Cragg GM. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod 2020;83:770–803.
   PubMed Web of Science ®Google Scholar
• Och A, Podgorski R, Nowak R. Biological activity of berberine-A summary update. Toxins 2020;12:713.
   PubMed Web of Science ®Google Scholar
• Song DY, Hao JY, Fan DM. Biological properties and clinical applications of berberine. Front Med -Prc 2020;14:564–82.
   PubMed Web of Science ®Google Scholar
• Xu JH, Long YM, Ni LW, et al. Anticancer effect of berberine based on experimental animal models of various cancers: a systematic review and meta-analysis. BMC Cancer 2019;19:589.
   PubMed Web of Science ®Google Scholar
• Liu D, Meng X, Wu DL, et al. A natural isoquinoline alkaloid with antitumor activity: studies of the biological activities of berberine. Front Pharmacol 2019;10:9.
   PubMed Web of Science ®Google Scholar
• Zhou MT, Deng Y, Liu MC, et al. The pharmacological activity of berberine, a review for liver protection. Eur J Pharmacol 2021;890:173655.
   PubMed Web of Science ®Google Scholar
• Liu B, Wang GS, Yang J, et al. Berberine inhibits human hepatoma cell invasion without cytotoxicity in healthy hepatocytes. PLoS One 2011;6:e21416.
   PubMed Web of Science ®Google Scholar
• Yang XL, Huang N. Berberine induces selective apoptosis through the AMPK-mediated mitochondrial/caspase pathway in hepatocellular carcinoma. Mol Med Rep 2013;8:505–10.
   PubMed Web of Science ®Google Scholar
• Huang Y, Wang K, Gu C, et al. Berberine, a natural plant alkaloid, synergistically sensitizes human liver cancer cells to sorafenib. Oncol Rep 2018;40:1525–32.
   PubMed Web of Science ®Google Scholar
• Wang KY, Yu GX, Lin JE, et al. Berberine sensitizes human hepatoma cells to regorafenib via modulating expression of circular RNAs. Front Pharmacol 2021;12:632201.
   PubMed Web of Science ®Google Scholar
• Devarajan N, Jayaraman S, Mahendra J, et al. Berberine-a potent chemosensitizer and chemoprotector to conventional cancer therapies. Phytother Res 2021;35:3059–77.
   PubMed Web of Science ®Google Scholar
• Liu CS, Zheng YR, Zhang YF, et al. Research progress on berberine with a special focus on its oral bioavailability. Fitoterapia 2016;109:274–82.
   PubMed Web of Science ®Google Scholar
• Cui HM, Zhang QY, Wang JL, et al. Poor permeability and absorption affect the activity of four alkaloids from Coptis. Mol Med Rep 2015;12:7160–8.
   PubMed Web of Science ®Google Scholar
• Habtemariam S. Recent advances in berberine inspired anticancer approaches: from drug combination to novel formulation technology and derivatization. Molecules 2020;25:1426.
   PubMed Web of Science ®Google Scholar
• Chen JC, Wang TY, Xu ST, et al. Design, synthesis and biological evaluation of novel nitric oxide-donating protoberberine derivatives as antitumor agents. Eur J Med Chem 2017;132:173–83.
   PubMed Web of Science ®Google Scholar
• Buolamwini J. Cell cycle molecular targets in novel anticancer drug discovery. Curr Pharm Des 2000;6:379–92.
   PubMed Web of Science ®Google Scholar
• Murat P, Balasubramanian S. Existence and consequences of G-quadruplex structures in DNA. Curr Opin Genet Dev 2014;25:22–9.
   PubMed Web of Science ®Google Scholar
• Savva L, Georgiades SN. Recent developments in small-molecule ligands of medicinal relevance for harnessing the anticancer potential of G-quadruplexes. Molecules 2021;26:841.
   PubMed Web of Science ®Google Scholar
• Maiti M, Kumar GS. Polymorphic nucleic acid binding of bioactive isoquinoline alkaloids and their role in cancer. J Nucleic Acids 2010;2010:1–23.
   Google Scholar
• Jeong SY, Seol DW. The role of mitochondria in apoptosis. BMB Rep 2008;41:11–22.
   PubMed Web of Science ®Google Scholar
• Jiang X, Wang X. Cytochrome C-mediated apoptosis. Annu Rev Biochem 2004;73:87–106.
   PubMed Web of Science ®Google Scholar
• Thornberry NA, Lazebnik Y. Caspases: enemies within. Science 1998;281:1312–6.
   PubMed Web of Science ®Google Scholar
• Festjens N, van Gurp M, van Loo G, et al. Bcl-2 family members as sentinels of cellular integrity and role of mitochondrial intermembrane space proteins in apoptotic cell death. Acta Haematol 2004;111:7–27.
   PubMed Web of Science ®Google Scholar
• Stopher D, Mcclean S. An improved method for the determination of distribution coefficients. J Pharm Pharmacol 1990;42:144.
   PubMed Web of Science ®Google Scholar
• Vogel GH, Determination of solubility by hyphenated HPLC methods. Drug discovery and evaluation: safety and pharmacokinetics assay. New York: Springer; 2006. p. 400–402.
   Google Scholar