Novel copper complexes as potential proteasome inhibitors for cancer treatment (Review)
- Authors:
- Zhen Zhang
- Huiyun Wang
- Maocai Yan
- Huannan Wang
- Chunyan Zhang
-
Affiliations: Institute of Antitumor Drug Research, School of Pharmacy, Jining Medical University, Rizhao, Shandong 276826, P.R. China, Neurobiology Institute, Jining Medical University, Jining, Shandong 272100, P.R. China - Published online on: December 9, 2016 https://doi.org/10.3892/mmr.2016.6022
- Pages: 3-11
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Guo Z and Sadler PJ: Metals in medicine. Angew Chem Int Edit. 38:1512–1531. 1999. View Article : Google Scholar | |
|
Schmitt SM, Frezza M and Dou QP: New applications of old metal-binding drugs in the treatment of human cancer. Front Biosci (Schol Ed.). 4:375–391. 2012.PubMed/NCBI | |
|
Verani CN: Metal complexes as inhibitors of the 26S proteasome in tumor cells. J Inorg Biochem. 106:59–67. 2012. View Article : Google Scholar : PubMed/NCBI | |
|
Chen D, Milacic V, Frezza M and Dou QP: Metal Complexes, their cellular targets and potential for cancer therapy. Curr Pharm Des. 15:777–791. 2009. View Article : Google Scholar : PubMed/NCBI | |
|
Zhang CX and Lippard SJ: New metal complexes as potential therapeutics. Curr Opin Chem Biol. 7:481–499. 2003. View Article : Google Scholar : PubMed/NCBI | |
|
Skrott Z and Cvek B: Diethyldithiocarbamate complex with copper: The mechanism of action in cancer cells. Mini Rev Med Chem. 12:1184–1192. 2012. View Article : Google Scholar : PubMed/NCBI | |
|
Berners-Price SJ and Filipovska A: Gold compounds as therapeutic agents for human diseases. Metallomics. 3:863–873. 2011. View Article : Google Scholar : PubMed/NCBI | |
|
Fregona D, Giovagnini L, Ronconi L, Marzano C, Trevisan A, Sitran S, Biondi B and Bordin F: Pt(II) and Pd(II) derivatives of ter-butylsarcosinedithiocarbamate. Synthesis, chemical and biological characterization and in vitro nephrotoxicity. J Inorg Biochem. 93:181–189. 2003. View Article : Google Scholar : PubMed/NCBI | |
|
Chen D, Frezza M, Shakya R, Cui QC, Milacic V, Verani CN and Dou QP: Inhibition of the proteasome activity by gallium(III) complexes contributes to their anti prostate tumor effects. Cancer Res. 67:9258–9265. 2007. View Article : Google Scholar : PubMed/NCBI | |
|
Chen D, Cui QC, Yang H and Dou QP: Disulfiram, a clinically used anti-alcoholism drug and copper-binding agent, induces apoptotic cell death in breast cancer cultures and xenografts via inhibition of the proteasome activity. Cancer Res. 66:10425–10433. 2006. View Article : Google Scholar : PubMed/NCBI | |
|
Chen D, Cui QC, Yang H, Barrea RA, Sarkar FH, Sheng S, Yan B, Reddy GP and Dou QP: Clioquinol, a therapeutic agent for Alzheimer's disease, has proteasome-inhibitory, androgen receptor-suppressing, apoptosis-inducing, and antitumor activities in human prostate cancer cells and xenografts. Cancer Res. 67:1636–1644. 2007. View Article : Google Scholar : PubMed/NCBI | |
|
Zhai S, Yang L, Cui QC, Sun Y, Dou QP and Yan B: Tumor cellular proteasome inhibition and growth suppression by 8-hydroxyquinoline and clioquinol requires their capabilities to bind copper and transport copper into cells. J Biol Inorg Chem. 15:259–269. 2010. View Article : Google Scholar : PubMed/NCBI | |
|
Yang Y, Kitagaki J, Wang H, Hou DX and Perantoni AO: Targeting the ubiquitin-proteasome system for cancer therapy. Cancer Sci. 100:24–28. 2009. View Article : Google Scholar : PubMed/NCBI | |
|
Ciehanover A, Hod Y and Hershko A: A heat-stable polypeptide component of an ATP-dependent proteolytic system from reticulocytes. Biochem Biophys Res Commun. 81:1100–1105. 1978. View Article : Google Scholar : PubMed/NCBI | |
|
Hershko A, Ciechanover A, Heller H, Haas AL and Rose IA: Proposed role of ATP in protein breakdown: Conjugation of protein with multiple chains of the polypeptide of ATP-dependent proteolysis. Proc Natl Acad Sci USA. 77:1783–1786. 1980. View Article : Google Scholar : PubMed/NCBI | |
|
Nalepa G, Rolfe M and Harper JW: Drug discovery in the ubiquitin-proteasome system. Nat. Rev Drug Discov. 5:596–613. 2006. View Article : Google Scholar : PubMed/NCBI | |
|
Adams J: The proteasome: A suitable antineoplastic target. Nat Rev Cancer. 4:349–60. 2004. View Article : Google Scholar : PubMed/NCBI | |
|
Frezza M, Schmitt S and Dou QP: Targeting the ubiquitin-proteasome pathway: An emerging concept in cancer therapy. Curr Top Med Chem. 11:2888–2905. 2011. View Article : Google Scholar : PubMed/NCBI | |
|
Wójcik C and DeMartino GN: Intracellular localization of proteasomes. Int J Biochem Cell Biol. 35:579–2589. 2003. View Article : Google Scholar : PubMed/NCBI | |
|
Nandi D, Tahiliani P, Kumar A and Chandu D: The ubiquitin-proteasome system. J Biosci. 31:137–155. 2006. View Article : Google Scholar : PubMed/NCBI | |
|
Groll M, Heinemeyer W, Jäger S, Ullrich T, Bochtler M, Wolf DH and Huber R: The catalytic sites of 20S proteasomes and their role in subunit maturation: A mutational and crystallographic study. Proc Natl Acad Sci USA. 96:10976–10983. 1999. View Article : Google Scholar : PubMed/NCBI | |
|
Via L Dalla, Nardon C and Fregona D: Targeting the ubiquitin-proteasome pathway with inorganic compounds to fight cancer: A challenge for the future. Future Med Chem. 4:525–543. 2012. View Article : Google Scholar : PubMed/NCBI | |
|
An B, Goldfarb RH, Siman R and Dou QP: Novel dipeptidyl proteasome inhibitors overcome Bcl-2 protective function and selectively accumulate the cyclin-dependent kinase inhibitor p27 and induce apoptosis in transformed, but not normal, human fibroblasts. Cell Death Differ. 5:1062–1075. 1998. View Article : Google Scholar : PubMed/NCBI | |
|
Rajkumar SV, Richardson PG, Hideshima T and Anderson KC: Proteasome inhibition as a novel therapeutic target in human cancer. J Clin Oncol. 23:630–639. 2005.PubMed/NCBI | |
|
Orlowski RZ and Kuhn DJ: Proteasome inhibitors in cancer therapy: Lessons from the first decade. Clin Cancer Res. 14:1649–1657. 2008. View Article : Google Scholar : PubMed/NCBI | |
|
Kane RC, Bross PF, Farrell AT and Pazdur R: Velcade: U.S. FDA approval for the treatment of multiple myeloma progressing on prior therapy. Oncologist. 8:508–513. 2003. View Article : Google Scholar : PubMed/NCBI | |
|
Potts BC, Albitar MX, Anderson KC, Baritaki S, Berkers C, Bonavida B, Chandra J, Chauhan D, Cusack JC Jr, Fenical W, et al: Marizomib, a proteasome inhibitor for all seasons: Preclinical profile and a framework for clinical trials. Curr Cancer Drug Tar. 11:254–284. 2011. View Article : Google Scholar | |
|
Kane RC, Dagher R, Farrell A, Ko CW, Sridhara R, Justice R and Pazdur R: Bortezomib for the treatment of mantle cell lymphoma. Clin Cancer Res. 13:5291–5294. 2007. View Article : Google Scholar : PubMed/NCBI | |
|
Kuhn DJ, Orlowski RZ and Bjorklund C: Second generation proteasome inhibitors: Carfilzomib and immunoproteasome-specific inhibitors (IPSIs). Curr Cancer Drug Targets. 11:285–295. 2011. View Article : Google Scholar : PubMed/NCBI | |
|
Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shenk KD, Sun CM, Demo SD, Bennett MK, Leeuwen FW, Chanan-Khan AA and Orlowski RZ: Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood. 110:3281–3290. 2007. View Article : Google Scholar : PubMed/NCBI | |
|
Kupperman E, Lee EC, Cao Y, Bannerman B, Fitzgerald M, Berger A, Yu J, Yang Y, Hales P, Bruzzese F, et al: Evaluation of the proteasome inhibitor MLN9708 in preclinical models of human cancer. Cancer Res. 70:1970–1980. 2010. View Article : Google Scholar : PubMed/NCBI | |
|
Lee EC, Fitzgerald M, Bannerman B, Donelan J, Bano K, Terkelsen J, Bradley DP, Subakan O, Silva MD, Liu R, et al: Antitumor activity of the investigational proteasome inhibitor MLN9708 in mouse models of B-cell and plasma cell malignancies. Clin Cancer Res. 17:7313–7323. 2011. View Article : Google Scholar : PubMed/NCBI | |
|
Sanchez E, Li M, Steinberg JA, Wang C, Shen J, Bonavida B, Li ZW, Chen H and Berenson JR: The proteasome inhibitor CEP-18770 enhances the anti-myeloma activity of bortezomib and melphalan. Br J Haematol. 148:569–581. 2010. View Article : Google Scholar : PubMed/NCBI | |
|
Labbe S and Thiele DJ: Pipes and wiring: The regulation of copper uptake and distribution in yeast. Trends Microbiol. 7:500–505. 1999. View Article : Google Scholar : PubMed/NCBI | |
|
Tapiero H, Townsend DM and Tew KD: Trace elements in human physiology and pathology. Copper. Biomed Pharmacother. 57:386–398. 2003. View Article : Google Scholar | |
|
Kuo HW, Chen SF, Wu CC, Chen DR and Lee JH: Serum and tissue trace elements in patients with breast cancer in Taiwan. Biol Trace Elem Res. 89:1–11. 2002. View Article : Google Scholar : PubMed/NCBI | |
|
Nayak SB, Bhat VR, Upadhyay D and Udupa SL: Copper and ceruloplasmin status in serum of prostate and colon cancer patients. Indian J Physiol Pharmacol. 47:108–110. 2003.PubMed/NCBI | |
|
Diez M, Arroyo M, Cerdàn FJ, Muñoz M, Martin MA and Balibrea JL: Serum and tissue trace metal levels in lung cancer. Oncology. 46:230–234. 1989.PubMed/NCBI | |
|
Turecký L, Kalina P, Uhlíková E, Námerová S and Krizko J: Serum ceruloplasmin and copper levels in patients with primary brain tumors. Klin Wochenschr. 62:187–189. 1984. View Article : Google Scholar : PubMed/NCBI | |
|
Finney L, Vogt S, Fukai T and Glesne D: Copper and angiogenesis: Unravelling a relationship key to cancer progression. Clin Exp Pharmacol Physiol. 36:88–94. 2009. View Article : Google Scholar : PubMed/NCBI | |
|
Fox SB, Gasparini G and Harris AL: Angiogenesis: Pathological, prognostic, and growth-factor pathways and their link to trial design and anticancer drugs. Lancet Oncol. 2:278–289. 2001. View Article : Google Scholar : PubMed/NCBI | |
|
Rau KM, Huang CC, Chiu TJ, Chen YY, Lu CC, Liu CT, Pei SN and Wei YC: Neovascularization evaluated by CD105 correlates well with prognostic factors in breast cancers. Exp Ther Med. 4:231–236. 2012.PubMed/NCBI | |
|
Daniel KG, Harbach RH, Guida WC and Dou QP: Copper storage diseases: Menkes, Wilson's, and cancer. Front Biosci. 9:2652–2662. 2004. View Article : Google Scholar : PubMed/NCBI | |
|
Daniel KG, Gupta P, Harbach RH, Guida WC and Dou QP: Organic copper complexes as a new class of proteasome inhibitors and apoptosis inducers in human cancer cells. Biochem Pharmacol. 67:1139–1151. 2004. View Article : Google Scholar : PubMed/NCBI | |
|
Daniel KG, Chen D, Orlu S, Cui QC, Miller FR and Dou QP: Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells. Breast Cancer Res. 7:R897–R908. 2005. View Article : Google Scholar : PubMed/NCBI | |
|
Daniel KG, Chen D, Yan B and Dou QP: Copper-binding compounds as proteasome inhibitors and apoptosis inducers in human cancer. Front Biosci. 12:135–144. 2007. View Article : Google Scholar : PubMed/NCBI | |
|
Barrea RA, Chen D, Irving TC and Dou QP: Synchrotron X-ray imaging reveals a correlation of tumor copper speciation with clioquinol's anticancer activity. J Cell Biochem. 108:96–105. 2009. View Article : Google Scholar : PubMed/NCBI | |
|
Ritchie CW, Bush AI and Masters CL: Metal-protein attenuating compounds and Alzheimer's disease. Expert Opin Investig Drugs. 13:1585–1592. 2004. View Article : Google Scholar : PubMed/NCBI | |
|
Ritchie CW, Bush AI, Mackinnon A, Macfarlane S, Mastwyk M, MacGregor L, Kiers L, Cherny R, Li QX, Tammer A, et al: Metal-protein attenuation with iodochlorhydroxyquin (clioquinol) targeting Abeta amyloid deposition and toxicity in Alzheimer disease: A pilot phase 2 clinical trial. Arch Neurol. 60:1685–1691. 2003. View Article : Google Scholar : PubMed/NCBI | |
|
Barcia E, Salama A, Fernández-Carballido A and Negro S: Protective effects of clioquinol on human neuronal-like cells: A new formulation of clioquinol-loaded PLGA microspheres for Alzheimer's disease. J Drug Target. 19:637–646. 2011. View Article : Google Scholar : PubMed/NCBI | |
|
Mao F, Yan J, Li J, Jia X, Miao H, Sun Y, Huang L and Li X: New multi-target-directed small molecules against Alzheimer's disease: A combination of resveratrol and clioquinol. Org Biomol Chem. 12:5936–5944. 2014. View Article : Google Scholar : PubMed/NCBI | |
|
Chen D, Peng FY, Cui QC, Daniel KG, Orlu S, Liu JG and Dou QP: Inhibition of prostate cancer cellular proteasome activity by a pyrrolidine dithiocarbamate-copper complex is associated with suppression of proliferation and induction of apoptosis. Front Biosci. 10:2932–2939. 2005. View Article : Google Scholar : PubMed/NCBI | |
|
Yu Z, Wang F, Milacic V, Li X, Cui QC, Zhang B, Yan B and Dou QP: Evaluation of copper-dependent proteasome-inhibitory and apoptosis-inducing activities of novel pyrrolidine dithiocarbamate analogues. Int J Mol Med. 20:919–925. 2007.PubMed/NCBI | |
|
Wang F, Zhai S, Liu X, Li L, Wu S, Dou QP and Yan B: A novel dithiocarbamate analogue with potentially decreased ALDH inhibition has copper-dependent proteasome-inhibitory and apoptosis-inducing activity in human breast cancer cells. Cancer Lett. 300:87–95. 2011. View Article : Google Scholar : PubMed/NCBI | |
|
Meyer RE: Prospects for a rational pharmacotherapy of alcoholism. J Clin Psychiatry. 50:403–412. 1989.PubMed/NCBI | |
|
Reisinger EC, Kern P, Ernst M, Bock P, Flad HD and Dietrich M: Inhibition of HIV progression by dithiocarb. German DTC Study Group. Lancet. 335:679–682. 1990. View Article : Google Scholar : PubMed/NCBI | |
|
Hersh EM, Brewton G, Abrams D, Bartlett J, Galpin J, Gill P, Gorter R, Gottlieb M, Jonikas JJ and Landesman S: Ditiocarb sodium (diethyldithiocarbamate) therapy in patients with symptomatic HIV infection and AIDS. A randomized, double-blind, placebo-controlled, multicenter study. JAMA. 265:1538–1544. 1991. View Article : Google Scholar : PubMed/NCBI | |
|
Pang H, Chen D, Cui QC and Dou QP: Sodium diethyldithiocarbamate, an AIDS progression inhibitor and a copper-binding compound, has proteasome-inhibitory and apoptosis-inducing activities in cancer cells. Int J Mol Med. 19:809–816. 2007.PubMed/NCBI | |
|
Han J, Li L, Yue X, Chang J, Shi W and Hua Y: A binuclear complex constituted by diethyldithiocarbamate and copper(I) functions as a proteasome activity inhibitor in pancreatic cancer cultures and xenografts. Toxicol Appl Pharmacol. 273:477–483. 2013. View Article : Google Scholar : PubMed/NCBI | |
|
Cerchiaro G, Aquilano K, Filomeni G, Rotilio G, Ciriolo MR and Ferreira AM: Isatin-Schiff base copper(II) complexes and their influence on cellular viability. J Inorg Biochem. 99:1433–1440. 2005. View Article : Google Scholar : PubMed/NCBI | |
|
Adsule S, Barve V, Chen D, Ahmed F, Dou QP, Padhye S and Sarkar FH: Novel Schiff base copper complexes of quinoline-2 carboxyaldehyde as proteasome inhibitors in human prostate cancer cells. J Med Chem. 49:7242–7246. 2006. View Article : Google Scholar : PubMed/NCBI | |
|
Xiao Y, Bi C, Fan Y, Cui C, Zhang X and Dou QP: L-glutamine Schiff base copper complex as a proteasome inhibitor and an apoptosis inducer in human cancer cells. Int J Oncol. 33:1073–1079. 2008.PubMed/NCBI | |
|
Zhong X, Yi J, Sun J, Wei HL, Liu WS and Yu KB: Synthesis and crystal structure of some transition metal complexes with a novel bis-Schiff base ligand and their antitumor activities. Eur J Med Chem. 41:1090–1092. 2006. View Article : Google Scholar : PubMed/NCBI | |
|
Creaven BS, Devereux M, Karcz D, Kellett A, McCann M, Noble A and Walsh M: Copper(II) complexes of coumarin-derived Schiff bases and their anti-Candida activity. J Inorg Biochem. 103:1196–1203. 2009. View Article : Google Scholar : PubMed/NCBI | |
|
Creaven BS, Czeglédi E, Devereux M, Enyedy ÉA, Foltyn-Arfa Kia A, Karcz D, Kellett A, McClean S, Nagy NV, Noble A, et al: Biological activity and coordination modes of copper(II) complexes of Schiff base-derived coumarin ligands. Dalton Trans. 39:10854–10865. 2010. View Article : Google Scholar : PubMed/NCBI | |
|
Duff B, Thangella VR, Creaven BS, Walsh M and Egan DA: Anti-cancer activity and mutagenic potential of novel copper(II) quinolinone Schiff base complexes in hepatocarcinoma cells. Eur J Pharmacol. 689:45–55. 2012. View Article : Google Scholar : PubMed/NCBI | |
|
Zhang X, Bi CF, Fan Y, Cui Q, Chen D, Xiao Y and Dou QP: Induction of tumor cell apoptosis by taurine Schiff base copper complex is associated with the inhibition of proteasomal activity. Int J Mol Med. 22:677–682. 2008.PubMed/NCBI | |
|
Zuo J, Bi C, Fan Y, Buac D, Nardon C, Daniel KG and Dou QP: Cellular and computational studies of proteasome inhibition and apoptosis induction in human cancer cells by amino acid Schiff base-copper complexes. J Inorg Biochem. 118:83–93. 2013. View Article : Google Scholar : PubMed/NCBI | |
|
Zhang Z, Bi CF, Fan YH, Zhang N, Deshmukh R, Yan X, Lv X, Zhang P, Zhang X and Dou QP: L-Ornithine Schiff base-copper and -cadmium complexes as new proteasome inhibitors and apoptosis inducers in human cancer cells. J Biol Inorg Chem. 20:109–121. 2015. View Article : Google Scholar : PubMed/NCBI | |
|
Hindo SS, Frezza M, Tomco D, Heeg MJ, Hryhorczuk L, McGarvey BR, Dou QP and Verani CN: Metals in anticancer therapy: Copper(II) complexes as inhibitors of the 20S proteasome. Eur J Med Chem. 44:4353–4361. 2009. View Article : Google Scholar : PubMed/NCBI | |
|
Zhang Z, Bi C, Schmitt SM, Fan Y, Dong L, Zuo J and Dou QP: 1,10-Phenanthroline promotes copper complexes into tumor cells and induces apoptosis by inhibiting the proteasome activity. J Biol Inorg Chem. 17:1257–1267. 2012. View Article : Google Scholar : PubMed/NCBI | |
|
Zhang S and Zhou J: Ternary copper(II) complex of 1,10-phenanthroline and glycine: Crystal structure and interaction with DNA. J Coord Chem. 61:2488–2498. 2008. View Article : Google Scholar | |
|
Seng HL, Wang WS, Kong SM, Ong HK Alan, Win YF, Abd Rahman RN Raja, Chikira M, Leong WK, Ahmad M, Khoo AS and Ng CH: Biological and cytoselective anticancer properties of copper(II)-polypyridyl complexes modulated by auxiliary methylated glycine ligand. Biometals. 125:1061–1681. 2012. | |
|
Ng CH, Kong SM, Tiong YL, Maah MJ, Sukram N, Ahmade M and Khoo AB: Selective anticancer copper(II)-mixed ligand complexes: Targeting of ROS and proteasomes. Metallomics. 6:892–906. 2014. View Article : Google Scholar : PubMed/NCBI | |
|
Dallavalle F, Gaccioli F, Franchi-Gazzola R, Lanfranchi M, Marchiò L, Pellinghelli MA and Tegoni M: Synthesis, molecular structure, solution equilibrium, and antiproliferative activity of thioxotriazoline and thioxotriazole complexes of copper II and palladium II. J Inorg Biochem. 92:95–104. 2002. View Article : Google Scholar : PubMed/NCBI | |
|
Tardito S, Isella C, Medico E, Marchiò L, Bevilacqua E, Hatzoglou M, Bussolati O and Franchi-Gazzola R: The thioxotriazole copper(II) complex A0 induces endoplasmic reticulum stress and paraptotic death in human cancer cells. J Biol Chem. 284:24306–24319. 2009. View Article : Google Scholar : PubMed/NCBI | |
|
Gandin V, Pellei M, Tisato F, Porchia M, Santini C and Marzano C: A novel copper complex induces paraptosis in colon cancer cells via the activation of ER stress signaling. J Cell Mol Med. 16:142–151. 2012. View Article : Google Scholar : PubMed/NCBI | |
|
Marzano C, Gandin V, Pellei M, Colavito D, Papini G, Lobbia GG, Del Giudice E, Porchia M, Tisato F and Santini C: In vitro antitumor activity of the water soluble copper(I) complexes bearing the tris(hydroxymethyl)phosphine ligand. J Med Chem. 51:798–808. 2008. View Article : Google Scholar : PubMed/NCBI | |
|
Bortolozzi R, Viola G, Porcù E, Consolaro F, Marzano C, Pellei M, Gandin V and Basso G: A novel copper(I) complex induces ER-stress-mediated apoptosis and sensitizes B-acute lymphoblastic leukemia cells to chemotherapeutic agents. Oncotarget. 5:5978–5991. 2014. View Article : Google Scholar : PubMed/NCBI | |
|
Liu N, Liu C, Li X, Liao S, Song W, Yang C, Zhao C, Huang H, Guan L, Zhang P, et al: A novel proteasome inhibitor suppresses tumor growth via targeting both 19S proteasome deubiquitinases and 20S proteolytic peptidases. Sci Rep. 4:52402014.PubMed/NCBI | |
|
Gourley M and Williamson JS: Angiogenesis: New targets for the development of anticancer chemotherapies. Curr Pharm Des. 6:417–439. 2000. View Article : Google Scholar : PubMed/NCBI |
