385
Views
72
CrossRef citations to date
0
Altmetric
Reviews

Recent development on naphthoquinone derivatives and their therapeutic applications as anticancer agents

&
Pages 1087-1108 | Published online: 08 May 2013

Bibliography

  • Kumagai Y, Shinkai Y, Miura T, et al. The chemical biology of naphthoquinones and its environmental implications. Annu Rev Pharmacol Toxicol 2012;52:221-47
  • Wu HQ, Huang Z, Bu XZ, et al. The molecular mechanism involved in the cytotoxicity of alkannin derivatives. Eur J Med Chem 2005;40:1341-5
  • Barkanova SV, Derkacheva VM, Dolotova OA, et al. Homogeneous oxidation of aromatics in nucleus with peracetic acid catalyzed by iron and manganese phthalocyanin complexes. Tetrahedron Lett 1996;37:1637-40
  • Tanoue Y, Sakata K, Hashimoto M, et al. Convenient synthesis of 1,4-naphthoquinones from polymethoxynaphthalenes. Oxidative demethylation with silver-catalyzed ammoniumperoxodisulfate. Bull Chem Soc Jpn 1994;67:2593-5
  • Menegazzo I, Sandona G, Moro S, et al. A versatile synthesis of the 1,4-dihydroxynaphthoquinone nucleus. Tetrahedron Lett 2000;41:6631-4
  • Lawrence H, Ge Y, Sebti SM, et al. Inventors. H Lee Moffitt Cancer and Research Institute, Inc., assignee. Proteasome inhibitors for selectively inducing apoptosis in cancer cells. WO005534; 2010
  • Richardson PG, Hideshima T, Anderson KC. Bortezomib (PS-341): A novel, first-in-class proteasome inhibitor for the treatment of multiple myeloma and other cancers. Cancer Control 2003;10:361-9
  • Wang H, Vath GM, Kawamura A, et al. Over-expression, purification and characterization of recombinant human arylamine N-acetyltransferase 1. Protein J 2005;24:65-77
  • Kawamura A, Westwood I, Wakefield L, et al. Mouse N-acetyltransferase type 2, the homologue of human N-acetyltransferase type 1. Biochem Pharmacol 2008;75:1550-60
  • Russel AJ, Sim E, Davies SG, et al. Inventors. Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, assignee. 1,4-quinones and their sulfur analogues useful as ligands of N-acetyltransferase. WO005142; 2011
  • Hernandez L, Bea S, et al. Cdc25A and the splicing variant Cdc25B2, but not Cdc25B1-B3 or C, are over-expressed in aggressive human non-Hodgkin's lymphomas. Int J Cancer 2000;89:148-52
  • Nishiyama S, Imoto M, Shinbashi A, et al. Inventors. Keio University, Japan, assignee. Preparation of naphthoquinone derivatives, and Cdc25 phosphatase inhibitors and antitumor agents containing them. JP220037; 2005
  • Kar S, Wang M, Ham SW, et al. Fluorinated Cpd5, a pure arylating K-vitamin derivative, inhibits human hepatoma cell growth by inhibiting Cdc25 and activating MAPK. Biochem Pharmacol 2006;72:1217-27
  • Nishiyama S, Imoto M, Shinbashi A, et al. Inventors. Keio University, Japan, assignee. Preparation of naphthoquinones, their use as tyrosine inhibitors, cell proliferation inhibitors and antibacterial agents and their medical compositions. JP316001; 2006
  • Kern SE, Kinzler KW, Bruskin K, et al. Identification of p53 as a sequence-specific DNA binding protein. Science 1991;252:1708-11
  • Lim S, Kim H, Jung G. p53 Inhibits tumor cell invasion via the degradation of snail protein in hepatocellular carcinoma. FEBS Lett 2010;584:2231-6
  • Park BJ, Ha NC, Lee SH, et al. Inventors. Pusan National University, Industry University Cooperation Foundation, the Industry and Academic Cooperation in Chungnam National University S. Korea, assignee. Preparation of naphthoquinone derivatives as inhibitors of p53 snail binding. WO059004; 2010
  • Schneider E, Hsiang YH, Liu LF. DNA topoisomerases as anticancer drug target. Adv Pharmacol 1990;1:149-83
  • Kongkathip N, Luangkamin S, Kongkathip B, et al. Synthesis of novel rhinacanthins and related anticancer naphthoquinone esters. J Med Chem 2004;47:4427-38
  • Choi JG, Jung YS, Lee HG; Inventors. Hankyong National University, Industry-Academy Cooperation Foundation, S. Korea, assignee. Naphthoquinone derivative as topoisomerase II inhibitor and process for the preparation thereof. KR118736; 2010
  • Min J, Du Y, Thepchatin P, et al. Inventors. Emory University, USA, assignee. Heat shock protein 90 inhibitors, methods of preparing same and methods for their use. WO042500; 2010
  • Chang J, Xie W, Wang L; Inventors. Xinxiang Medical College, Peop. Rep. China, assignee. Preparation of naphthoquinone derivatives as PI3 kinase inhibitors for treatment of cancer. CN1587255; 2005
  • Bonnet D. Normal and Leukaemic stem cells. Br J Haematol 2005;130:469-79
  • Ailles LE, Weissman IL. Cancer stem cells in solid tumors. Curr Opin Biotechnol 2007;18:460-6
  • Li CJ, Jiang Z, Rogoff H, et al. Inventors. Boston Biomedical, Inc. USA. Assignee. A novel group of STAT3 pathway inhibitors and cancer stem cell pathway inhibitors. WO036099; 2009
  • Borgstrom P; Inventors. Pellficure Pharmaceuticals, Inc. USA. Assignee. Novel treatment of prostrate carcinoma. WO018948; 2012
  • Tareen B, Summers JL, Jamison J, et al. A 12 week open label, phase I/IIa study using Apatone® for the treatment of prostate cancer patients who have failed standard therapy. Int J Med Sci 2008;5:62-7
  • Lu QB; Inventors. 414 Woodrow Drive, Waterloo, Ontario, Canada. Assignee. Combination therapy for cancer comprising a platinum based antineoplastic agent and a biocompatible electron donor. WO026219; 2011
  • Lu QB, Kalantari S, Wang CR. Electron transfer reaction mechanism of cisplatin with DNA at the molecular level. Mol Pharm 2007;4:624-8
  • Lu QB. Molecular mechanism of combination treatments of low dose cisplatin with radiotherapy and photodynamic therapy. J Med Chem 2007;50:2601-4
  • Brown DM; Inventors. ChemGenex Therapeutics, Inc. USA. Assignee. Naphthoquinone compositions and uses thereof treatment of cellular proliferative disease. WO91740; 2001
  • Bringmann G, Rudenauer S, Brun R, et al. Inventors. Julius-Maximilians-Universitat Wurzburg, Germany. Assignee. Anti-infective and antitumoral compounds isolated from tropical lianas. WO098082; 2009
  • Tang W, Chan F; Inventors. Guizhou University, Peop. Rep. China. Preparation of antitumor agent from Juglans regia. CN101185671; 2007
  • Linardi MDF, de Oliveira MM, Sampaio MRP. A lapachol derivative active against mouse lymphocytic leukemia P-388. J Med Chem 1975;18:1159-61
  • Vargas MD, Pinto ADC, Camara CDA, et al. Inventors. Braz. Pedido PI, Brazil. Natural naphthoquinones and semisynthetic partially hydrogenated derivatives of lapachol with cytotoxic and antitumor activity. BR002766; 2005
  • Konoshima T, Kozuka M, Koyama J, et al. Studies on inhibitors of skin tumor promotion VI. Inhibitory effects of quinones on Epstein-Barr virus activation. J Nat Prod 1989;52:987-95
  • Ueda S, Umemura T, Dohguchi K, et al. Production of antitumor-promoting furano-naphthoquinones in Tabebuia avellanedae cell cultures. Phytochemistry 1994;36:323-5
  • Fujiwara A, Mori T, Iida A, et al. Antitumor-promoting naphthoquinones from Catapa ovate. J Nat Prod 1998;61:629-32
  • Kapadia GJ, Balasubramanian V, Tokuda H, et al. Antitumor promoting effects of naphthoquinone derivatives on short term Epstein-Barr early antigen activation assay and in mouse skin carcinogenesis. Cancer Lett 1997;113:47-53
  • Itoigawa M, Ito C, Tan HTW, et al. Cancer chemopreventive activity of naphthoquinones and their analogs from Avicennia plants. Cancer Lett 2011;174:135-9
  • Sacau EP, Estvez-Braun A, Ravelo AG, et al. Inhibitory effects of lapachol derivatives on Epstein-Barr virus activation. Bioorg Med Chem 2003;11:483-8
  • Kim YS, Park SY, Lee HJ, et al. Synthesis and cytotoxicity of 6,11-dihydropyrido- and 6,11-dihydrobenzo[2,3-b]phenazine-6,11-dione derivatives. Bioorg Med Chem 2003;11:1709-14
  • Shaikh IA, Johnson F, Grollman AP. Streptonigrin-1. Structure-activity relationships among simple bicyclic analogues. Rate dependence of DNA degradation on quinone reduction potential. J Med Chem 1986;29:1329-40
  • Lin AJ, Lillis BJ, Sartorelli AC. Potential bioreductive alkylating agents. 5. Antineoplastic activity of quinone-5,8-diones, naphthazarins and naphthoquinones. J Med Chem 1975;18:917-21
  • Yamashita Y, Kawada S, Fujii N, et al. Induction of mammalian DNA topoisomerase II dependent DNA cleavage by antitumor antibiotic Streptonigrin. Cancer Res 1990;50:5841-4
  • Beall HD, Siegel D, Liu Y, et al. Role of NAD(P)H: quinone oxidoreductase (DT-diaphorase) in cytotoxicity and induction of DNA damage by Streptonigrin. Biochem Biopharmacol 1996;51:645-52
  • Noto V, Taper HS, Jiang YH, et al. Effects of sodium ascorbate (vitamin C) and 2-methyl-1,4-naphthoquinone (vitamin K3) treatment on human tumor cell growth in vitro. Cancer 1989;63:901-6
  • Ngo EO, Sun TP, Chang JY. Menadione-induced DNA damage in a human tumor cell line. Biochem Pharmacol 1991;42:1961-8
  • Juan CC, Wu FYH. Vitamin K3 inhibits growth of human hepatoma HepG2 cells by decreasing activities of both p34CDC2 kinase and phosphatase. Biochem Biophys Res Commun 1993;190:907-13
  • McKonkey DJ, Hartzell P, Nicotera P. Stimulation of endogenous endonuclease activity in hepatocytes exposed to oxidative stress. Toxicol Lett 1998;42:123-30
  • Hockenbery DM, Oltvai ZN, Yin XM. Bcl-2 functions in an antioxidant pathway to prevent apoptosis. Cell 1993;75:241-51
  • Wu FYH, Liao WC, Chang HM. Comparison of antitumor activity of vitamin K1-, K2 and K-3 on human tumor cells by two (MTT and SRB) cell viability assays. Life Sci 1993;52:1797-804
  • Chen C, Liu YZ, Shia KS, et al. Synthesis and anticancer evaluation of Vitamin K3 analogues. Bioorg Med Chem Lett 2002;12:2729-32
  • Yuan X, Yuan P; Inventors. Wuhan Botanical garden, Chinese Academy of Sciences, Peop. Rep. China. Method for separating naphthoquinones from Arnebia euchroma. CN102228499; 2011
  • Wu HQ, Huang ZS, Bu XZ, et al. The molecular mechanism involved in the cytotoxicity of alkannin derivatives. Eur J Med Chem 2005;40:1341-5
  • Wang Y, Su Y, Xie J, et al. Inventors. Zhejiang University, Peop. Rep. China, assignee. Naphthoquinone cycloalkoxy substituted alkannin derivatives useful in the treatment of cancer. CN101654406; 2010
  • Li S, Zhao L, Xie T, et al. Inventors. Shanghai Jiao Tong University, Peop. Rep. China. Assignee. Sulfur containing shikonin and naphthoquinone derivatives for anti-tumorigenesis. CN101239936; 2008
  • Kim SH, Lee HJ; Inventors. Industry Academic Cooperation Foundation of Kyunghee University, S. Korea. Assignee. 6-(1-Oxopropyl)-5,8-dimethoxy-1,4-naphthoquinone compound for inhibiting induction of angiogenesis caused by hypoxia induced in malignant tumor and pharmaceutical composition containing the same. KR007967; 2006
  • Kim SH, Lee HJ, Lee EO, et al. Inventors. Kyunghee University, S Korea. Assignee. 6-[1,4-{bis(2-chloroethyl)amino}aminophenyl]butanoyloxy]pentyl-5,8-dimethoxy-1,4-naphthoquinone having anticancer activity, a method for preparing same compound and pharmaceutical compositions containing it. KR000241; 2006
  • Li S, Xie T, Xu D, et al. Inventors. (Shanghai) Jiao Tong University, Peop Rep. China; Shanghai Tianjia Biomedicine Co. Ltd. Assignee. Preparation of naphthoquinone carboxylic acid derivatives as antitumor agents. CN1827578; 2006
  • Nevinskii GA, Zakharoa OD, Goryunov LI, et al. Inventors. Uchrezhdemie RANIkhBFM RAN, Russia; NIOK him. N.N.Vorozhtsova SO RAN. Assignee. Fluorinated 1,4-naphthoquinone derivatives having cytotoxic effect on human cancer cells in culture. RU2443678; 2012
  • Wu L, Yang C, Ma S, et al. Inventors. Faming Zhuunli Shenquing, Peop. Rep. China. Assignee. 14-(4-Flourophenyl)-14H-dibenzo[a,i]xanth-8,13-dione and its synthesis method and medical application as antitumor agent. CN102060834; 2011
  • Ding K, Pei D, Zhou J, et al. Inventors. Guanzhou Institute of Biomedicine and Health, Chinese academy of Sciences, Peop. Rep. China. Faming Zhuanli Shenqing, assignee. Preparation of 1,4-naphthoquinone compounds as antitumor agents. CN101838248; 2010
  • Kinachi T, Mastuno S, Okamura N, et al. Inventors. Mokogawa University, Japan; Mikumi Pharma Ind., Jpn. Kokai Tokyo Koho, Japan. Assignee. Naphthoquinone compounds as rhinacanthin C analogs and antitumor agents containing them. JP047556;2010
  • Depierre G, Dessolin J, Laguerre M, et al. Inventors. Fluoforma, Fr.; Universite Bordeaux 1, France. Assignee. Amino acid N-[(1,4-naphthoquinon-3-yl)amide derivatives, their preparation, pharmaceutical compositions containing them and their use for prevention or treatment of diseases associated with abnormal cellular proliferation such as neoplasm. WO125196; 2007
  • Duan W, Zhang J, Ding J, et al. Inventors. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Peop. Rep. China. Assignee. Preparation of 1,4-naphthoquinone derivatives as anticancer agents. CN1690044; 2005
  • Granot Y, Biter S; Inventors. Ben Gurion University of the Negev Research and Development authority, Israel. Novel naphthoquinone derivatives and their use for treating cardiovascular diseases and malignancies. WO011136; 2006
  • Tandon VK, Chhor RB, Singh RV, et al. Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorg Med Chem Lett 2004;14:1079-83
  • Tandon VK, Singh RV, Yadav DP. Synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antiviral, antifungal and anticancer agents. Bioorg Med Chem Lett 2004;14:2901-4
  • Corral JMMD, Castro MA, Gordaliza M, et al. Synthesis and cytotoxicity of new heterocyclic terpenylnaphthoquinones. Bioorg Med Chem 2006;14:2816-27
  • Tandon VK, Maurya HK, Tripathi A, et al. 2,3-disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: synthesis and biological evaluation as potential antiproliferative and antifungal agents. Eur J Med Chem 2009;44:1086-92
  • Gomez-Monterrey I, Santelli G, Campiglia P, et al. Synthesis and cytotoxic evaluation of novel spirohydantoin derivatives of the dihydrothien[2,3-b]naphtho-4,9-dione system. J Med Chem 2005;48:1152-7
  • Oda I, Takahashi H, Ueno T, et al. Inventors. Japan energy Corp. Japan, Jpn. Kokai Tokyo Koho. Assignee. DNA polymerase β-inhibitors containing naphthoquinone derivatives and drugs containing them. JP139470; 2001
  • Kimachi T, Matsuno S, Okamura N, et al. Inventors. Mukogawa University, Japan Mikumi Pharmaceutical Industries Co. Ltd. Jpn. Kokai Tokyo Koho. Assignee. 1,2-naphthoquinone compounds and antitumor drugs containing them. JP047557; 2010
  • Berman E, McBride M. Comparative cellular pharmacology of daunorubicin and idarubicin in human multidrug-resistant leukemia cells. Blood 1992;79:3267-73
  • Chiodini B, Bassan R, Barbui T. Apoptosis by anthracyclines at therapeutic concentrations in MDR1-human leukemic cells. Adv Exp Med Biol 1999;457:313-24
  • Schroder JK, Kasimir-Bauer S, Seeber S, et al. In vitro effect of multidrug resistance modifiers on idarubicinol efflux in blasts of acute myeloid leukemia. J Cancer Res Clin Oncol 2000;126:111-16
  • Roovers DJ, Vliet MV, Bloem AC, et al. Idarubicin overcomes P-glycoprotein-related multidrug resistance: comparison with doxorubicin and daunorbicin in human multiple myeloma cell lines. Leuk Res 1999;23:539-48
  • Nakatsu S, Kondo S, Kondo Y, et al. Induction of apoptosis in multi-drug resistance (MDR) human glioblastoma cells by SN-38, a metabolite of the camptothecin derivative CPT-11. Cancer Chemother Pharmacol 1997;39:417-23
  • Jansen WJ, Hulscher TM, Ark-Otte J, et al. CPT-11 sensitivity in relation to the expression of P170-glycoprotein and multidrug resistance-associated protein. Br J Cancer 1998;77:359-65
  • Pec MK, Hellan M, Moser-Thier K, et al. Inhibitory effects of a novel marine terpenoid on sensitive and multidrug resistant KB cell lines. Anticancer Res 1998;18:3027-32
  • Miao ZH, Tang T, Zhang YX, et al. Cytotoxicity, apoptosis induction and downregulation of MDR-1 expression by the anti-topoisomerase II agent, salvicine, in multidrug-resistant tumor cells. Int J Cancer 2003;106:108-15

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.