Vitamin K3 thio-derivative: a novel specific apoptotic inducer in the doxorubicin-sensitive and -resistant cancer cells

Investigational New Drugs - Tập 38 Số 3 - Trang 650-661 - 2020
Mohamed‐Elamir F. Hegazy1, Masashi Fukaya2, Mona Dawood1, Ge Yan1, Anette Klinger3, Edmond Fleischer3, Asmaa W. Zaglool4
1Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, Johannes Gutenberg-University, Staudingerweg 5, 55128 Mainz, Germany
2Institute of Biological Chemistry, Washington State University, Pullman, WA 99164-6340 USA
3MicroCombiChem GmbH, Wiesbaden, Germany
4Department of Animal Wealth Development, Faculty of Veterinary Medicine, Zagazig University, El-Zeraa str. 114, Zagazig 44511, Egypt.

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Nikolaou M, Pavlopoulou A, Georgakilas AG, Kyrodimos E (2018) The challenge of drug resistance in cancer treatment: a current overview. Clin Exp Metastasis 35(4):309–318

Barbuti AM, Zhang G-N, Gupta P, Narayanan S, Chen Z-S (2019) EGFR and HER2 inhibitors as sensitizing agents for Cancer chemotherapy. In: Protein kinase inhibitors as sensitizing agents for chemotherapy. Academic Press, Cambridge, pp 1–11

Gillet J-P, Efferth T, Remacle J (2007) Chemotherapy-induced resistance by ATP-binding cassette transporter genes. BBA-REV CANCER 1775(2):237–262

Robey RW, Pluchino KM, Hall MD, Fojo AT, Bates SE, Gottesman MM (2018) Revisiting the role of ABC transporters in multidrug-resistant cancer. Nat Rev Cancer:18(7)452–464

DiNicolantonio JJ, Bhutani J, O'Keefe JH (2015) The health benefits of vitamin K. Open Heart 2(1):e000300. https://doi.org/10.1136/openhrt-2015-000300

Josey BJ, Inks ES, Wen X, Chou CJ (2013) Structure-activity relationship study of vitamin k derivatives yields highly potent neuroprotective agents. J Med Chem 56(3):1007–1022. https://doi.org/10.1021/jm301485d

Koyano H, Someya A, Nagaoka I, Yamashita T (1988) Effect of vitamin K3 on macrophage functions and intracellular calcium. Comp Biochem Physiol A Comp Physiol 91(1):115–121

Schwalfenberg GK (2017) Vitamins K1 and K2: the emerging Group of Vitamins Required for human health. J Nutr Metab 2017:6254836. https://doi.org/10.1155/2017/6254836

Akbari S, Rasouli-Ghahroudi AA (2018) Vitamin K and bone metabolism: a review of the latest evidence in preclinical studies. Biomed Res Int 2018:4629383. https://doi.org/10.1155/2018/4629383

van Ballegooijen AJ, Beulens JW (2017) The role of vitamin K status in cardiovascular health: evidence from observational and clinical studies. Curr Nutr Rep 6(3):197–205. https://doi.org/10.1007/s13668-017-0208-8

Anwar F, Khan R, Sachan R, Kazmi I, Rawat A, Sabih A, Singh R, Afzal M, Ahmad A, Al-Orab AS (2018) Therapeutic role of calcium and vitamin K3 in chemically induced hepatocarcinogenesis–new tools for cancer treatment. Arch Physiol Biochem:1–6

Bonilla-Porras AR, Jimenez-Del-Rio M, Velez-Pardo C (2011) Vitamin K3 and vitamin C alone or in combination induced apoptosis in leukemia cells by a similar oxidative stress signalling mechanism. Cancer Cell Int 11:19. https://doi.org/10.1186/1475-2867-11-19

Chen J, Hu X, Cui J (2018) Shikonin, vitamin K3 and vitamin K5 inhibit multiple glycolytic enzymes in MCF-7 cells. Oncol Lett 15(5):7423–7432. https://doi.org/10.3892/ol.2018.8251

Huang J, Lu Z, Xiao Y, He B, Pan C, Zhou X, Xu N, Liu X (2018) Inhibition of Siah2 ubiquitin ligase by vitamin K3 attenuates chronic myeloid leukemia chemo-resistance in hypoxic microenvironment. Med Sci Monit 24:727–735

Ivanova D, Zhelev Z, Getsov P, Nikolova B, Aoki I, Higashi T, Bakalova R (2018) Vitamin K: redox-modulation, prevention of mitochondrial dysfunction and anticancer effect. Redox Biol 16:352–358. https://doi.org/10.1016/j.redox.2018.03.013

Nakaoka E, Tanaka S, Onda K, Sugiyama K, Hirano T (2015) Effects of vitamin K3 and K5 on Daunorubicin-resistant human T Lymphoblastoid leukemia cells. Anticancer Res 35(11):6041–6048

Scott GK, Atsriku C, Kaminker P, Held J, Gibson B, Baldwin MA, Benz CC (2005) Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Mol Pharmacol 68(3):606–615. https://doi.org/10.1124/mol.105.013474

Teixeira J, Amorim R, Santos K, Soares P, Datta S, Cortopassi GA, Serafim TL, Sardão VA, Garrido J, Borges F (2018) Disruption of mitochondrial function as mechanism for anti-cancer activity of a novel mitochondriotropic menadione derivative. Toxicology 393:123–139

Fukaya M, Nakamura S, Hegazy MEF, Sugimoto Y, Hayashi N, Nakashima S, Yoshikawa M, Efferth T, Matsuda H (2018) Cytotoxicity of sesquiterpene alkaloids from Nuphar plants toward sensitive and drug-resistant cell lines. Food Funct 9(12):6279–6286

Hegazy M-EF, Hamed AR, El-Halawany AM, Hussien TA, Abdelfatah S, Ohta S, Paré PW, Abdel-Sattar E, Efferth T (2018) Cytotoxicity of abietane diterpenoids from Salvia multicaulis towards multidrug-resistant cancer cells. Fitoterapia 130:54–60

Mbaveng AT, Ndontsa BL, Kuete V, Nguekeu YM, Çelik İ, Mbouangouere R, Tane P, Efferth T (2018) A naturally occuring triterpene saponin ardisiacrispin B displayed cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death. Phytomedicine 43:78–85

Seo E-J, Sugimoto Y, Greten HJ, Efferth T (2018) Repurposing of bromocriptine for cancer therapy. Front Pharmacol 9

Gfeller D, Grosdidier A, Wirth M, Daina A, Michielin O, Zoete V (2014) SwissTargetPrediction: a web server for target prediction of bioactive small molecules. Nucleic Acids Res 42(W1):W32–W38

Seo E-J, Wu C-F, Ali Z, Wang Y-H, Khan SI, Walker LA, Khan IA, Efferth T (2016) Both phenolic and non-phenolic green tea fractions inhibit migration of cancer cells. Front Pharmacol 7:398

Ivanova D, Zhelev Z, Lazarova D, Getsov P, Bakalova R, Aoki I (2018) Vitamins C and K3: a powerful redox system for sensitizing leukemia lymphocytes to Everolimus and Barasertib. Anticancer Res 38(3):1407–1414. https://doi.org/10.21873/anticanres.12364

Jinghe X, Mizuta T, Ozaki I (2015) Vitamin K and hepatocellular carcinoma: the basic and clinic. World J Clin Cases 3(9):757–764. https://doi.org/10.12998/wjcc.v3.i9.757

Lamson DW, Plaza SM (2003) The anticancer effects of vitamin K. Altern Med Rev 8(3):303–318

Fujii S, Kagechika H (2017) Medicinal chemistry of vitamin K derivatives and metabolites. In: vitamin K2-vital for health and wellbeing. IntechOpen

Yang H, Ganguly A, Cabral F (2010) Inhibition of cell migration and cell division correlates with distinct effects of microtubule inhibiting drugs. J Biol Chem 285(42):32242–32250