Cell cycle arrest in cultured neuroblastoma cells exposed to a bis(thiosemicarbazonato) metal complex

BioMetals

Volumn 24, Issue 1, 2011, Pages 117-133

  Bica, Laura ^a,b   Meyerowitz, Jodi ^a,b   Parker, Sarah J ^a,b   Caragounis, Aphrodite ^a,b   Du, Tai ^a,b   Paterson, Brett M ^a,c   Barnham, Kevin J ^a,b,c   Crouch, Peter J ^a,b   White, Anthony R ^a,b   Donnelly, Paul S ^a,c  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b FLOREY INSTITUTE OF NEUROSCIENCE AND MENTAL HEALTH   (Australia)

^c UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Bis(thiosemicarbazone); Cell cycle; Copper; Protein microarray

Indexed keywords

ANTINEOPLASTIC METAL COMPLEX; CASPASE 3; CASPASE 8; CHECKPOINT KINASE 2; CYCLIN D1; CYCLIN DEPENDENT KINASE 7; GLYOXAL BIS(4 METHYLTHIOSEMICARBAZONATO)COPPER; PROTEIN P53; PROTEIN P57; SOMATOMEDIN RECEPTOR; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL GROWTH; CONTROLLED STUDY; DRUG EXPOSURE; FLUORESCENCE ACTIVATED CELL SORTING; HUMAN; HUMAN CELL; IN VITRO STUDY; NEUROBLASTOMA CELL; PROTEIN EXPRESSION; PROTEIN MICROARRAY; PROTEIN PHOSPHORYLATION;

ANTINEOPLASTIC AGENTS; BRAIN NEOPLASMS; CELL CYCLE; CELL PROLIFERATION; COPPER; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; HUMANS; MOLECULAR STRUCTURE; NEUROBLASTOMA; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; THIOSEMICARBAZONES; TUMOR CELLS, CULTURED;

ANIMALIA;

EID: 79951725943     PISSN: 09660844     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10534-010-9380-7     Document Type: Article

References (56)

1. S Banudevi K Senthilkumar G Sharmila R Arunkumar MR Vijayababu J Arunakaran 2010 Effect of zinc on regulation of insulin-like growth factor signaling in human androgen-independent prostate cancer cells Clin Chim Acta 411 172 178 1:CAS:528:DC%2BD1MXhs1WgtLrL 10.1016/j.cca.2009.10.023 19913001
2. H Beraldo LP Boyd DX West 1998 Copper(II) and nickel(II) complexes of glyoxaldehyde bis((N3)-substituted thiosemicarbazones) Trans Met Chem 23 67 71 1:CAS:528:DyaK1cXks1SrtA%3D%3D 10.1023/A:1006958018049
3. PJ Blower TC Castle AR Cowley JR Dilworth PS Donnelly E Labisbal FE Sowrey SJ Teat MJ Went 2003 Structural trends in copper(II) bis(thiosemicarbazone) radiopharmaceuticals Dalton Trans 7 4416 4425 10.1039/b307499d
4. BA Booth AC Sartorelli 1966 Synergistic interaction of kethoxal bis(thiosemicarbazone) and cupric ions in sarcoma 180 Nature 210 104 105 1:CAS:528:DyaF28XhtVygurY%3D 10.1038/210104b0 5956340
5. BA Booth AC Sartorelli 1967 Metabolic effects of copper in intact cells: comparitive activity of cupric chloride and the cupric chelate of kethoxal bis(thiosemicarbazone) Mol Pharmacol 1967 290 302
6. WJ Chen CY Chang JK Lin 2003 Induction of G1 phase arrest in MCF human breast cancer cells by pentagalloylglucose through the down-regulation of CDK4 and CDK2 activities and up-regulation of the CDK inhibitors p27(Kip) and p21(Cip) Biochem Pharmacol 65 1777 1785 1:CAS:528:DC%2BD3sXktVOrsrg%3D 12781329
7. D Chen F Peng QC Cui KG Daniel S Orlu J Liu QP Dou 2005 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 1:CAS:528: DC%2BD2MXntFGitr0%3D 10.2741/1749 15970547 (Pubitemid 40910532)
8. DW Coulter J Blatt AJ D'Ercole BM Moats-Staats 2008 IGF-I receptor inhibition combined with rapamycin or temsirolimus inhibits neuroblastoma cell growth Anticancer Res 28 1509 1516 1:CAS:528:DC%2BD1cXos1WktL4%3D 18630505 (Pubitemid 351892923)
9. AR Cowley JR Dilworth PS Donnelly E Labisbal A Sousa 2002 An unusual dimeric structure of a Cu(I) bis(thiosemicarbazone) complex: implications for the mechanism of hypoxic selectivity of the Cu(II) derivatives J Am Chem Soc 124 5270 5271 1:CAS:528:DC%2BD38XivVOls7g%3D 10.1021/ja012668z 11996559 (Pubitemid 34506915)
10. AR Cowley J Davis JR Dilworth PS Donnelly R Dobson A Nightingale JM Peach B Shore D Kerr L Seymour 2005 Fluorescence studies of the intra-cellular distribution of zinc bis(thiosemicarbazone) complexes in human cancer cells Chem Commun (Camb) 7 845 847 10.1039/b417206j (Pubitemid 40313250)
11. JAP Crim G Harold 1967 The Antitumor activity of Cu(II)KTS, the copper(II) chelate of 3-ethoxy-2-oxobutyraldehyde bis(thiosemicarbazone) Cancer Res 27 1278 1285 1:STN:280:DyaK3c3htlCmuw%3D%3D 4952520
12. PJ Crouch LW Hung PA Adlard M Cortes V Lal G Filiz KA Perez M Nurjono A Caragounis T Du K Laughton I Volitakis AI Bush QX Li CL Masters R Cappai RA Cherny PS Donnelly AR White KJ Barnham 2009 Increasing Cu bioavailability inhibits a beta oligomers and tau phosphorylation Proc Natl Acad Sci USA 106 381 386 1:CAS:528:DC%2BD1MXhtVels7Y%3D 10.1073/pnas.0809057106 19122148
13. KG Daniel D Chen S Orlu QC Cui FR Miller QP Dou 2005 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 1:CAS:528:DC%2BD2MXht1WmsrvJ 10.1186/bcr1322 16280039
14. JLJ Dearling JS Lewis DW McCarthy MJ Welch PJ Blower 1998 Redox-active metal complexes for imaging hypoxic tisssues: structure-activity relationships in Cu(II) bis(thiosemicarbazone) complexes J Chem Soc Chem Commun 21 2531 2533
15. JL Dearling JS Lewis GE Mullen MT Rae J Zweit PJ Blower 1998 Design of hypoxia-targeting radiopharmaceuticals: selective uptake of copper-64 complexes in hypoxic cells in vitro Eur J Nucl Med 25 788 792 1:CAS:528:DyaK1cXktlyisr8%3D 10.1007/s002590050283 9662602 (Pubitemid 28377043)
16. JL Dearling JS Lewis GE Mullen MJ Welch PJ Blower 2002 Copper bis(thiosemicarbazone) complexes as hypoxia imaging agents: structure-activity relationships J Biol Inorg Chem 7 249 259 1:CAS:528:DC%2BD38Xit1KitLk%3D 10.1007/s007750100291 11935349 (Pubitemid 36056377)
17. WQ Ding B Liu JL Vaught H Yamauchi SE Lind 2005 Anticancer activity of the antibiotic clioquinol Cancer Res 65 3389 3395 1:CAS:528:DC%2BD2MXjt1yrsLs%3D 10.1158/0008-5472.CAN-04-4385 15833873 (Pubitemid 41060687)
18. WQ Ding HJ Yu SE Lind 2008 Zinc-binding compounds induce cancer cell death via distinct modes of action Cancer Lett 271 251 259 1:CAS:528: DC%2BD1cXht1entLnI 10.1016/j.canlet.2008.06.011 18639975
19. PS Donnelly A Caragounis T Du KM Laughton I Volitakis RA Cherny RA Sharples AF Hill QX Li CL Masters KJ Barnham AR White 2008 Selective intracellular release of copper and zinc ions from bis(thiosemicarbazonato) complexes reduces levels of Alzheimer disease amyloid-{beta} peptide J Biol Chem 283 4568 4577 1:CAS:528:DC%2BD1cXhvFelur0%3D 10.1074/jbc.M705957200 18086681
20. T Du G Filiz A Caragounis PJ Crouch AR White 2008 Clioquinol promotes cancer cell toxicity through tumor necrosis factor alpha release from macrophages J Pharmacol Exp Ther 324 360 367 1:CAS:528:DC%2BD1cXhsF2ntg%3D%3D 10.1124/jpet.107.130377 17940196 (Pubitemid 350294161)
21. T Du S La Fontaine M Abdo S Bellingham M Greenough I Volitakis R Cherny AI Bush P Hudson J Camakaris JF Mercer P Crouch CL Masters VM Perreau AR White 2008 Investigating copper-regulated protein expression in Menkes fibroblasts using antibody microarrays Proteomics 8 1819 1831 1:CAS:528:DC%2BD1cXlvFeltLc%3D 10.1002/pmic.200700895 18384105 (Pubitemid 351678282)
22. MT Fodero-Tavoletti VL Villemagne BM Paterson AR White QX Li J Camakaris G O'Keefe R Cappai KJ Barnham PS Donnelly 2010 Bis(thiosemicarbazonato) Cu-64 complexes for positron emission tomography imaging of Alzheimer's disease J Alzheimer's Dis 20 49 55 1:CAS:528:DC%2BC3cXksV2ms7Y%3D
23. FA French BL Freelander 1958 Carcinostatic action of polycarbonyl compounds and their derivatives I. 3-ethoxy-2-ketobutyraldehyde and related compounds Cancer Res 18 172 175 1:CAS:528:DyaG1cXhtFKgtrY%3D 13511372
24. FA French BL Freelander 1958 Carcinostatic action of polycarbonyl compounds and their derivatives. IV. Glyoxal bis (thiosemicarbazone) and derivatives Cancer Res 18 1290 1300 1:CAS:528:DyaG1MXisVCqtQ%3D%3D 13608436
25. Y Fujibayashi H Taniuchi Y Yonekura H Ohtani J Konishi A Yokoyama 1997 Copper-62-ATSM: a new hypoxia imaging agent with high membrane permeability and low redox potential J Nucl Med 38 1155 1160 1:CAS:528:DyaK2sXltFChsL8%3D 9225812 (Pubitemid 27339632)
26. BA Gingras T Suprunchuk CH Bayley 1962 The preparation of some thiosemicarbazones and their copper complexes Can J Chem 40 1053 1:CAS:528:DyaF38XksFChtL4%3D 10.1139/v62-161
27. AB Gladden JA Diehl 2005 Location, location, location: the role of cyclin D1 nuclear localization in cancer J Cell Biochem 96 906 913 1:CAS:528:DC%2BD2MXht1Kgur7J 10.1002/jcb.20613 16163738 (Pubitemid 41688717)
28. A Herman-Antosiewicz H Xiao KL Lew SV Singh S Kaulfuss P Burfeind J Gaedcke JG Scharf 2007 Induction of p21 protein protects against sulforaphane-induced mitotic arrest in LNCaP human prostate cancer cell line Mol Cancer Ther 26 1673 1681 10.1158/1535-7163.MCT-06-0807 (Pubitemid 46954034)
29. S Kaulfuss P Burfeind J Gaedcke JG Scharf 2009 Dual silencing of insulin-like growth factor-I receptor and epidermal growth factor receptor in colorectal cancer cells is associated with decreased proliferation and enhanced apoptosis Mol Cancer Ther 8 821 833 1:CAS:528:DC%2BD1MXks1amtr4%3D 10.1158/1535-7163.MCT-09-0058 19372555
30. JK Kim JA Diehl 2009 Nuclear cyclin D1: an oncogenic driver in human cancer J Cell Physiol 220 292 296 1:CAS:528:DC%2BD1MXotFagsr4%3D 10.1002/jcp.21791 19415697
31. JS Lewis DW McCarthy TJ McCarthy Y Fujibayashi MJ Welch 1999 Evaluation of 64Cu-ATSM in vitro and in vivo in a hypoxic tumor model J Nucl Med 40 177 183 1:CAS:528:DyaK1MXos1aisA%3D%3D 9935074 (Pubitemid 29044189)
32. JS Lewis R Laforest F Dehdashti PW Grigsby MJ Welch BA Siegel 2008 An imaging comparison of 64Cu-ATSM and 60Cu-ATSM in cancer of the uterine cervix J Nucl Med 49 1177 1182 10.2967/jnumed.108.051326 18552145 (Pubitemid 351948028)
33. J Ma H Sawai Y Matsuo N Ochi A Yasuda H Takahashi T Wakasugi H Funahashi M Sato H Takeyama 2010 IGF-1 mediates PTEN suppression and enhances cell invasion and proliferation via activation of the IGF-1/PI3K/Akt signaling pathway in pancreatic cancer cells J Surg Res 160 90 101 1:CAS:528: DC%2BC3cXktlGht7s%3D 10.1016/j.jss.2008.08.016 19560785
34. RI Maurer PJ Blower JR Dilworth CA Reynolds Y Zheng 2002 Mullen GED. Studeis on the mechanism of hypoxic selectivity in copper bis(thiosemicarbazone) radiopharmaceuticals J Med Chem 45 1420 1:CAS:528:DC%2BD38XitFWqsbw%3D 10.1021/jm0104217 11906283 (Pubitemid 34246105)
35. DT Minkel DH Petering 1978 Ethoxy-2-oxobutyraldehyde bis(thiosemicarbazonato) Cu(II) with ehrlich ascites tumour cells Cancer Res 38 117 1:CAS:528:DyaE1cXhtFGjtro%3D 201367
36. DT Minkel LA Saryan DH Petering 1978 Structure-function correlations in the reaction of bis(thiosemicarbazonato) copper(II) complexes with ehrlich ascites tumor cells Cancer Res 38 124 129 1:CAS:528:DyaE1cXhs1eru74%3D 563285 (Pubitemid 8253524)
37. SI Pascu PA Waghorn TD Conry B Lin HM Betts JR Dilworth RB Sim GC Churchill FI Aigbirhio JE Warren 2008 Cellular confocal fluorescence studies and cytotoxic activity of new Zn(II) bis(thiosemicarbazonato) complexes Dalton Trans. 16 2107 2110 10.1039/b802806k 18398535 (Pubitemid 351503475)
38. HG Petering HH Buskirk JA Crim GJ Van Giessen 1963 The effect of metal ions on the antitumour activity of kethoxal bis-thiosemicarbazone Pharmacologist 5 271
39. HG Petering HH Buskirk GE Underwood 1964 The anti-tumor activity of 2-keto-3-ethoxybutyraldehyde bis(thiosemicarbazone) and related compounds Cancer Res 24 367 372 1:CAS:528:DyaF28XjtVaksg%3D%3D 14147809
40. DH Petering HH Buskirk JA Crim 1967 The effect of dietary mineral supplements of the rat on the antitumor activity of 3-ethoxy-2-oxobutyraldehyde bis(thiosemicarbazone) Cancer Res 27 1115 1121 1:CAS:528:DyaF2sXksVahsL8%3D 6027202
41. KA Price G Filiz A Caragounis T Du KM Laughton CL Masters RA Sharples AF Hill QX Li PS Donnelly KJ Barnham PJ Crouch AR White 2008 Activation of epidermal growth factor receptor by metal-ligand complexes decreases levels of extracellular amyloid beta peptide Int J Biochem Cell Biol 40 1901 1917 1:CAS:528:DC%2BD1cXnsF2mt70%3D 10.1016/j.biocel.2008.01.033 18346929
42. KA Price A Caragounis BM Paterson G Filiz I Volitakis CL Masters KJ Barnham PS Donnelly PJ Crouch AR White 2009 Sustained activation of glial cell epidermal growth factor receptor by bis(thiosemicarbazonato) metal complexes is associated with inhibition of protein tyrosine phosphatase activity J Med Chem 52 6606 1:CAS:528:DC%2BD1MXht1artL7F 10.1021/jm9007938 19807095
43. D Ramljak RJ Calvert PW Wiesenfeld BA Diwan B Catipovic WF Marasas TC Victor LM Anderson WC Gelderblom 2000 A potential mechanism for fumonisin B(1)-mediated hepatocarcinogenesis: cyclin D1 stabilization associated with activation of Akt and inhibition of GSK-3beta activity Carcinogenesis 21 1537 1546 1:CAS:528:DC%2BD3cXlvVeqtrw%3D 10.1093/carcin/21.8.1537 10910956 (Pubitemid 30601646)
44. AJ Ryan S Napoletano PA Fitzpatrick CA Currid NC O'Sullivan JH Harmey 2009 Expression of a protease-resistant insulin-like growth factor-binding protein-4 inhibits tumour growth in a murine model of breast cancer Br J Cancer 101 276 286 10.1038/sj.bjc.6605141
45. S Shukla S Gupta 2009 Apigenin suppresses insulin-like growth factor I receptor signaling in human prostate cancer: an in vitro and in vivo study Mol Carcinog 48 243 252 1:CAS:528:DC%2BD1MXjtFGqsbw%3D 10.1002/mc.20475 18726972
46. GK Smyth J Michaud HS Scott 2005 Use of within-array replicate spots for assessing differential expression in microarray experiments Bioinformatics 21 2067 2075 1:CAS:528:DC%2BD2MXjsl2nsLo%3D 10.1093/bioinformatics/bti270 15657102 (Pubitemid 40668046)
47. ML Teyssot AS Jarrousse A Chevry A De Haze C Beaudoin M Manin SP Nolan S Diez-Gonzalez L Morel A Gautier 2009 Toxicity of copper(I)-NHC complexes against human tumor cells: induction of cell cycle arrest, apoptosis, and DNA cleavage Chemistry 15 314 318 1:CAS:528:DC%2BD1MXpt12jsQ%3D%3D 10.1002/chem.200801992 19025730
48. GJ Van Giessen JA Crim DH Petering HG Petering 1973 Effect of heavy metals on the in vitro cytotoxicity of 3-ethoxy-2-oxobutyraldehyde bis (thiosemicarbazone) and related compounds J Natl Cancer Inst 51 139 146 4720869
49. AL Vavere JS Lewis 2007 A radiopharmaceutical for the PET imaging of hypoxia Dalton Trans 43 4893 4902 10.1039/b705989b 17992274 (Pubitemid 350015414)
50. J Wang XW Lv JP Shi XS Hu 2007 Mechanisms involved in ceramide-induced cell cycle arrest in human hepatocarcinoma cells World J Gastroenterol 13 1129 1134 1:CAS:528:DC%2BD2sXkvVaju74%3D 17373752 (Pubitemid 46511019)
51. L Wang J Wang BW Blaser AM Duchemin DF Kusewitt T Liu MA Caligiuri R Briesewitz 2007 Pharmacologic inhibition of CDK4/6: mechanistic evidence for selective activity or acquired resistance in acute myeloid leukemia Blood 110 2075 2083 1:CAS:528:DC%2BD2sXhtVGjtbbK 10.1182/blood-2007-02-071266 17537993 (Pubitemid 47443925)
52. JL Wilsbacher Q Zhang LA Tucker RD Hubbard GS Sheppard NY Bamaung SD Fidanze GT Wang X Hu SK Davidsen RL Bell J Wang 2008 Insulin-like growth factor-1 receptor and ErbB kinase inhibitor combinations block proliferation and induce apoptosis through cyclin D1 reduction and Bax activation J Biol Chem 283 23721 23730 1:CAS:528:DC%2BD1cXhtVWktr%2FL 10.1074/jbc.M708360200 18559346
53. HH Xia H He J De Wang Q Gu MC Lin B Zou LF Yu YW Sun AO Chan HF Kung BC Wong 2006 Induction of apoptosis and cell cycle arrest by a specific c-Jun NH2-terminal kinase (JNK) inhibitor, SP-600125, in gastrointestinal cancers Cancer Lett 241 268 274 1:CAS:528:DC%2BD28XotV2msb4%3D 10.1016/j.canlet.2005.10. 031 16337741 (Pubitemid 44163038)
54. Z Xiao PS Donnelly M Zimmermann AG Wedd 2008 Transfer of copper between bis(thiosemicarbazone) ligands and intracellular copper-binding proteins. insights into mechanisms of copper uptake and hypoxia selectivity Inorg Chem 47 4338 4347 1:CAS:528:DC%2BD1cXks1Ogu74%3D 10.1021/ic702440e 18412332
55. Z Yu F Wang V Milacic X Li QC Cui B Zhang B Yan QP Dou 2007 Evaluation of copper-dependent proteasome-inhibitory and apoptosis-inducing activities of novel pyrrolidine dithiocarbamate analogues Int J Mol Med 20 919 925 1:CAS:528:DC%2BD2sXhsVyjtb7J 17982703
56. H Zhang JS Wu F Peng 2008 Potent anticancer activity of pyrrolidine dithiocarbamate-copper complex against cisplatin-resistant neuroblastoma cells Anticancer Drugs 19 125 132 1:CAS:528:DC%2BD1cXitVSisQ%3D%3D 10.1097/CAD.0b013e3282f2bdff 18176108