Semisynthesis and anti-cancer properties of novel honokiol derivatives in human nasopharyngeal carcinoma CNE-2Z cells

References

• Sung H, Ferlay J, Siegel RL, Laversanne M, Soerjomataram I, Jemal A, Bray F. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 2021;71(3):209–249.
   PubMed Web of Science ®Google Scholar
• Cao SM, Xu YJ, Lin GZ, Huang QH, Wei KR, Xie SH, Liu Q. Estimation of cancer burden in Guangdong Province, China in 2009. Chin J Cancer. 2015; 34 (12):594–601.
   PubMedGoogle Scholar
• Chen YP, Chan ATC, Le QT, Blanchard P, Sun Y, Ma J. Nasopharyngeal carcinoma. Lancet. 2019;394(10192):64–80.
   PubMed Web of Science ®Google Scholar
• Lee AW, Ma BB, Ng WT, Chan AT. Management of nasopharyngeal carcinoma: current practice and future perspective. J Clin Oncol. 2015;33(29):3356–3364.
   PubMed Web of Science ®Google Scholar
• Peng H, Chen L, Zhang Y, Li WF, Mao YP, Liu X, Zhang F, Guo R, Liu LZ, Tian L, et al. The tumor response to induction chemotherapy has prognostic value for long-term survival outcomes after intensity-modulated radiation therapy in nasopharyngeal carcinoma. Sci Rep. 2016;6:24835.
   PubMed Web of Science ®Google Scholar
• Hong B, Lui VW, Hashiguchi M, Hui EP, Chan AT. Targeting tumor hypoxia in nasopharyngeal carcinoma. Head Neck. 2013;35(1):133–145.
   PubMed Web of Science ®Google Scholar
• Semenza GL. Targeting HIF-1 for cancer therapy. Nat Rev Cancer. 2003;3(10):721–732.
   PubMed Web of Science ®Google Scholar
• Masoud GN, Li W. HIF-1α pathway: role, regulation and intervention for cancer therapy. Acta Pharm Sin B. 2015;5(5):378–389.
   PubMed Web of Science ®Google Scholar
• Xu L, Huan L, Guo T, Wu Y, Liu Y, Wang Q, Huang S, Xu Y, Liang L, He X. LncRNA SNHG11 facilitates tumor metastasis by interacting with and stabilizing HIF-1α. Oncogene. 2020;39(46):7005–7018.
   PubMed Web of Science ®Google Scholar
• Al-Ostoot FH, Sherapura A, Vigneshwaran V, Basappa G, Vivek HK, Prabhakar BT, Khanum SA. Targeting HIF-1α by newly synthesized indolephenoxyacet- amide (IPA) analogs to induce anti-angiogenesis-mediated solid tumor suppression. Pharmacol Rep. 2021;73(5):1328–1343.
   PubMed Web of Science ®Google Scholar
• Huang ZY, Zhang LH, Zhao C, Liu R, Tong H, Gan C, Lan T, Tang CW, Gao JH. High HIF-1α expression predicts poor prognosis of patients with colon adenocarcinoma. Int J Clin Exp Pathol. 2018;11(12):5635–5646.
   PubMed Web of Science ®Google Scholar
• Wei T-T, Lin Y-T, Tang S-P, Luo C-K, Tsai C-T, Shun C-T, Chen C-C. Metabolic targeting of HIF-1α potentiates the therapeutic efficacy of oxaliplatin in colorectal cancer. Oncogene. 2020;39(2):414–427.
   PubMed Web of Science ®Google Scholar
• Xie W, Liu L, He H, Yang K. Prognostic value of hypoxia-inducible factor-1 alpha in nasopharyngeal carcinoma: a meta-analysis. Int J Biol Markers. 2018; 33(4):1724600818778756.
   Web of Science ®Google Scholar
• Zhang L, Song J, Kong L, Yuan T, Li W, Zhang W, Hou B, Lu Y, Du G. The strategies and techniques of drug discovery from natural products. Pharmacol Ther. 2020;216:107686.
   PubMed Web of Science ®Google Scholar
• Min HY, Jang HJ, Park KH, Hyun SY, Park SJ, Kim JH, Son J, Kang SS, Lee HY. The natural compound gracillin exerts potent antitumor activity by targeting mitochondrial complex II. Cell Death Dis. 2019;10(11):810.
   PubMedGoogle 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(3):770–803.
   PubMed Web of Science ®Google Scholar
• Fujita M, Itokawa H, Sashida Y. Honokiol, a new phenolic compound isolated from the bark of Magnolia obovata Thunb. Chem Pharm Bull. 1972;20(1):212–213.
   Web of Science ®Google Scholar
• Rauf A, Olatunde A, Imran M, Alhumaydhi FA, Aljohani ASM, Khan SA, Uddin MS, Mitra S, Emran TB, Khayrullin M, et al. Honokiol: A review of its pharmacological potential and therapeutic insights. Phytomedicine. 2021;90:153647.
   PubMed Web of Science ®Google Scholar
• Luo LX, Li Y, Liu ZQ, Fan XX, Duan FG, Li RZ, Yao XJ, Leung EL, Liu L. Honokiol induces apoptosis, G1 arrest, and autophagy in KRAS mutant lung cancer cells. Front Pharmacol. 2017;8:199.
   PubMed Web of Science ®Google Scholar
• Tian W, Xu D, Deng YC. Honokiol, a multifunctional tumor cell death inducer. Pharmazie. 2012;67(10):811–816.
   PubMed Web of Science ®Google Scholar
• Wang WD, Shang Y, Li Y, Chen SZ. Honokiol inhibits breast cancer cell metastasis by blocking EMT through modulation of Snail/Slug protein translation. Acta Pharmacol Sin. 2019; 40(9):1219–1227.
   PubMed Web of Science ®Google Scholar
• Bai X, Cerimele F, Ushio-Fukai M, Waqas M, Campbell PM, Govindarajan B, Der CJ, Battle T, Frank DA, Ye K, et al. Honokiol, a small molecular weight natural product, inhibits angiogenesis in vitro and tumor growth in vivo. J Biol Chem. 2003;278(37):35501–35507.
   PubMed Web of Science ®Google Scholar
• Chio CC, Tai YT, Mohanraj M, Liu SH, Yang ST, Chen RM. Honokiol enhances temozolomide-induced apoptotic insults to malignant glioma cells via an intrinsic mitochondrion-dependent pathway. Phytomedicine. 2018;49:41–51.
   PubMed Web of Science ®Google Scholar
• Sabarwal A, Wedel J, Liu K, Zurakowski D, Chakraborty S, Flynn E, Briscoe DM, Balan M, Pal S. A combination therapy using an mTOR inhibitor and honokiol effectively induces autophagy through the modulation of AXL and rubicon in renal cancer cells and restricts renal tumor growth following organ transplantation. Carcinogenesis. 2022;43(4):360–370.
   PubMed Web of Science ®Google Scholar
• Ponnurangam S, Mammen JM, Ramalingam S, He Z, Zhang Y, Umar S, Subramaniam D, Anant S. Honokiol in combination with radiation targets notch signaling to inhibit colon cancer stem cells. Mol Cancer Ther. 2012;11(4):963–972.
   PubMed Web of Science ®Google Scholar
• Lin D, Yan Z, Chen A, Ye J, Hu A, Liu J, Peng J, Wu X. Anti-proliferative activity and structure-activity relationship of honokiol derivatives. Bioorg Med Chem. 2019;27(16):3729–3734.
   PubMed Web of Science ®Google Scholar
• Ma L, Chen J, Wang X, Liang X, Luo Y, Zhu W, Wang T, Peng M, Li S, Jie S, et al. Structural modification of honokiol, a biphenyl occurring in Magnolia officinalis: the evaluation of honokiol analogues as inhibitors of angiogenesis and for their cytotoxicity and structure-activity relationship. J Med Chem. 2011;54(19):6469–6481.
   PubMed Web of Science ®Google Scholar
• Xu T, Tian W, Zhang Q, Liu J, Liu Z, Jin J, Guo Y, Bai LP. Novel 1,3,4-thiadia- zole/oxadiazole-linked honokiol derivatives suppress cancer via inducing PI3K/Akt/mTOR-dependent autophagy. Bioorg Chem. 2021;115:105257.
   PubMed Web of Science ®Google Scholar
• Shi X, Zhang T, Lou H, Song H, Li C, Fan P. Anticancer effects of honokiol via mitochondrial dysfunction are strongly enhanced by the mitochondria-targeting carrier berberine. J Med Chem. 2020;63(20):11786–11800.
   PubMed Web of Science ®Google Scholar
• Zhu M, Li B, Ma H, Huang X, Wang H, Dai Y, Li Y, Li HM, Wu CZ. Synthesis and in vitro antitumor evaluation of honokiol derivatives. Bioorg Med Chem Lett. 2020;30(2):126849.
   PubMed Web of Science ®Google Scholar
• Nilsson BO. Biological effects of aminoguanidine: an update. Inflamm Res. 1999;48 (10):509–515.
   PubMed Web of Science ®Google Scholar
• Deng X, Song M. Synthesis, antibacterial and anticancer activity, and docking study of aminoguanidines containing an alkynyl moiety. J Enzyme Inhib Med Chem. 2020;35(1):354–364.
   PubMed Web of Science ®Google Scholar
• Liu DC, Gao MJ, Huo Q, Ma T, Wang Y, Wu CZ. Design, synthesis, and apoptosis-promoting effect evaluation of novel pyrazole with benzo[d]thiazole derivatives containing aminoguanidine units. J Enzyme Inhib Med Chem. 2019; 34(1):829–837.
   PubMed Web of Science ®Google Scholar
• Song M, Wang S, Wang Z, Fu Z, Zhou S, Cheng H, Liang Z, Deng X. Synthesis, antimicrobial and cytotoxic activities, and molecular docking studies of N- arysulfonylindoles containing an aminoguanidine, a semicarbazide, and a thiosemicarbazide moiety. Eur J Med Chem. 2019;166:108–118.
   PubMed Web of Science ®Google Scholar
• Wei ZY, Chi KQ, Yu ZK, Liu HY, Sun LP, Zheng CJ, Piao HR. Synthesis and biological evaluation of chalcone derivatives containing aminoguanidine or acylhydrazone moieties. Bioorg Med Chem Lett. 2016;26(24):5920–5925.
   PubMed Web of Science ®Google Scholar
• Guan S, Wei J, Huang L, Wu L. Chemotherapy and chemo-resistance in nasopharyngeal carcinoma. Eur J Med Chem. 2020; 207:112758.
   PubMed Web of Science ®Google Scholar
• Li HM, Miao J, Zhu M, Gao M, Dai Y, Huo Q, Ma T, Wu CZ. Bishonokiol A inhibits breast cancer cell invasion and migration by suppressing hypoxia inducible factor-1α. J Bioenerg Biomembr. 2019;51(3):239–248.
   PubMed Web of Science ®Google Scholar
• Richardson P. Fluorination methods for drug discovery and development. Expert Opin Drug Discov. 2016;11(10):983–999.
   PubMed Web of Science ®Google Scholar
• Shah P, Westwell AD. The role of fluorine in medicinal chemistry. J Enzyme Inhib Med Chem. 2007;22(5):527–540.
   PubMed Web of Science ®Google Scholar
• Lin JM, Prakasha GA, Sharma AK, Amin S. In vitro growth inhibition of human cancer cells by novel honokiol analgos. Bioorg Med Chem. 2012;20(10):3202–3211.
   PubMed Web of Science ®Google Scholar
• Liu HL, Wang J, Lin DZ, Liu H. Lead compound optimization strategy (2)– structure optimization strategy for reducing toxicity risks in drug design. Yao Xue Xue Bao. 2014;49(1):1–15.
   PubMedGoogle Scholar
• Huang CC, Su CW, Wang PH, Lu YT, Ho YT, Yang SF, Hsin CH, Lin CW. Dihydromyricetin inhibits cancer cell migration and matrix metalloproteinases-2 expression in human nasopharyngeal carcinoma through extracellular signal-regulated kinase signaling pathway. Environ Toxicol. 2022;37(5):1244–1253.
   PubMed Web of Science ®Google Scholar
• Rashid M, Zadeh LR, Baradaran B, Molavi O, Ghesmati Z, Sabzichi M, Ramezani F. Up-down regulation of HIF-1α in cancer progression. Gene. 2021; 798:145796.
   PubMed Web of Science ®Google Scholar
• Sung WW, Chu YC, Chen PR, Liao MH, Lee JW. Positive regulation of HIF-1α expression by EBC oncoprotein LMP1 in nasopharyngeal carcinoma cells. Cancer Lett. 2016;382(1):21–31.
   PubMed Web of Science ®Google Scholar
• Tang W, Zhao G. Small molecules targeting HIF-1α pathway for cancer therapy in recent years. Bioorg Med Chem. 2020;28(2):115235.
   PubMed Web of Science ®Google Scholar
• Xu R, Wang F, Yang H, Wang Z. Action sites and clinical application of HIF-1α inhibitors. Molecules. 2022;27(11):3426.
   PubMed Web of Science ®Google Scholar
• McAleese CE, Choudhury C, Butcher NJ, Minchin RF. Hypoxia-mediated drug resistance in breast cancers. Cancer Lett. 2021;502:189–199.
   PubMed Web of Science ®Google Scholar