Phosphanegold(I) thiolates, Ph3PAu[SC(OR)=NC6H4Me-4] for R = Me, Et and iPr, induce apoptosis, cell cycle arrest and inhibit cell invasion of HT-29 colon cancer cells through modulation of the nuclear factor-κB activation pathway and ubiquitination

Journal of Biological Inorganic Chemistry

Volumn 20, Issue 5, 2015, Pages 855-873

  Ooi, Kah Kooi ^a   Yeo, Chien Ing ^b   Ang, Kok Pian ^a   Akim, Abdah Md ^a   Cheah, Yoke Kqueen ^a   Halim, Siti Nadiah Abdul ^b   Seng, Hoi Ling ^a,c   Tiekink, Edward R T ^a,b  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b UNIVERSITY OF MALAYA   (Malaysia)

^c SUNWAY UNIVERSITY   (Malaysia)

Author keywords

Apoptosis; Carbonimidothioates; Gold(I) compounds; Nuclear factor B activation pathway; Phosphanegold thiolates

Indexed keywords

ANTINEOPLASTIC AGENT; CASPASE 10; CASPASE 3; CASPASE 7; CASPASE 8; CASPASE 9; CISPLATIN; CYTOCHROME C; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; PACLITAXEL; PHOSPHANEGOLD CARBONIMIDOTHIOATE DERIVATIVE; PROTEIN P53; PROTEIN P73; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; ORGANOGOLD COMPOUND; PHOSPHINE; PHOSPHINE DERIVATIVE; THIOL DERIVATIVE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL LINE; CELL GROWTH; CELL INVASION; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; CELL VIABILITY; COLON ADENOCARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DNA FRAGMENTATION; DOWN REGULATION; DRUG POTENCY; DRUG STABILITY; DRUG STRUCTURE; ENZYME ACTIVITY; G1 PHASE CELL CYCLE CHECKPOINT; G2 PHASE CELL CYCLE CHECKPOINT; GENE EXPRESSION REGULATION; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; UBIQUITINATION; UPREGULATION; CELL CYCLE CHECKPOINT; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; COLONIC NEOPLASMS; DRUG EFFECTS; HT 29 CELL LINE; METABOLISM; PATHOLOGY; PREVENTION AND CONTROL; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR INVASION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE CHECKPOINTS; CELL PROLIFERATION; CELL SURVIVAL; COLONIC NEOPLASMS; HT29 CELLS; HUMANS; MOLECULAR STRUCTURE; NEOPLASM INVASIVENESS; NF-KAPPA B; ORGANOGOLD COMPOUNDS; PHOSPHINES; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; UBIQUITINATION;

EID: 84932192272     PISSN: 09498257     EISSN: 14321327     Source Type: Journal    
DOI: 10.1007/s00775-015-1271-5     Document Type: Article

References (107)

1. Díaz-Rubio E, Tabernero J, Gómez-España A, Massutí B, Sastre J, Chaves M, Abad A, Carrato A, Queralt B, Reina JJ, Maurel J, Gonzalez-Flores E, Aparicio J, Rivera F, Losa F, Aranda E (2007) J Clin Oncol 25:4224-4230. doi: 10.1200/JCO.2006.09.8467
2. Tredan O, Galmarini CM, Patel K, Tannock IF (2007) J Natl Cancer Inst 99:1441-1454. doi: 10.1093/jnci/djm135
3. Schulenburg A, Bramswig K, Herrmann H, Karlic H, Mirkina I, Hubmann R, Laffer S, Marian B, Shehata M, Krepler C, Pehamberger H, Grunt T, Jager U, Zielinski CC, Valent P (2010) Crit Rev Oncol Hematol 76:79-98. doi: 10.1016/j.critrevonc.2010.01.001
4. Karin M, Greten FR (2005) Nat Rev Immunol 5:749-759. doi: 10.1038/nri1703
5. Naugler WE, Karin M (2008) Curr Opin Genet Dev 18:19-26. doi: 10.1016/j.gde.2008.01.020
6. Escarcega RO, Fuentes-Alexandro S, Garcia-Carrasco M, Gatica A, Zamora A (2007) Clin Oncol 19:154-161. doi: 10.1016/J.Clon.2006.11.013
7. Reddy KB, Nabha SM, Atanaskova N (2003) Cancer Metastasis Rev 22:395-403. doi: 10.1023/A:1023781114568
8. Testa JR, Bellacosa A (2001) Proc Natl Acad Sci USA 98:10983-10985. doi: 10.1073/pnas.211430998
9. Lee R, Collins T (2001) Circ Res 88:262-264. doi: 10.1161/01.RES.88.3.262
10. Rayet B, Gélinas C (1999) Oncogene 18:6938-6947. doi: 10.1038/sj.onc.1203221
11. Richmond A (2002) Nat Rev Immunol 2:664-674. doi: 10.1038/nri887
12. Nakanishi C, Toi M (2005) Nat Rev Cancer 5:297-309. doi: 10.1038/nrc1588
13. Mathas S, Lietz A, Janz M, Hinz M, Jundt F, Scheidereit C, Bommert K, Dorken B (2003) Blood 102:1028-1034. doi: 10.1182/blood-2002-04-1154
14. Teicher BA, Herman TS, Holden SA, Wang YY, Pfeffer MR, Crawford JW, Frei E III (1990) Science 247:1457-1461. doi: 10.1126/science.2108497
15. Desoize B, Jardillier J (2000) Crit Rev Oncol Hematol 36:193-207. doi: 10.1016/S1040-8428(00)00086-X
16. Kang HG, Jenabi JM, Zhang J, Keshelava N, Shimada H, May WA, Ng T, Reynolds CP, Triche TJ, Sorensen PH (2007) Cancer Res 67:3094-3105. doi: 10.1158/0008-5472.CAN-06-3259
17. Oktem G, Bilir A, Selvi N, Yurtseven ME, Vatansever S, Ates U, Uysal A, Omay SB (2006) Oncol Res 16:195-203. doi: 10.3727/000000006783981107
18. Reyes-Zurita FJ, Pachon-Pena G, Lizarraga D, Rufino-Palomares EE, Cascante M, Lupianez JA (2011) BMC Cancer 11:154. doi: 10.1186/1471-2407-11-154
19. Berners-Price SJ, Filipovska A (2011) Metallomics 3:863-873. doi: 10.1039/C1MT00062D
20. Ott I (2009) Coord Chem Rev 253:1670-1681. doi: 10.1016/j.ccr.2009.02.019
21. Nardon C, Schmitt SM, Yang HJ, Zuo J, Fregona D, Dou QP (2014) PLoS One 9:e84248. doi: 10.1371/journal.pone.0084248
22. Yeo CI, Ooi KK, Md Akim A, Ang KP, Fairuz ZA, Halim SNA, Ng SW, Seng HL, Tiekink ERT (2013) J Inorg Biochem 127:24-38. doi: 10.1016/j.jinorgbio.2013.05.011
23. Yeo CI, Sim JH, Khoo CH, Goh ZJ, Ang KP, Cheah YK, Fairuz ZA, Halim SNA, Ng SW, Seng HL, Tiekink ERT (2013) Gold Bull 46:145-152. doi: 10.1007/s13404-013-0091-z
24. X'Pert HighScore Plus (2009) PANalytical B.V., Almelo, The Netherlands
25. Kuan FS, Ho SY, Tadbuppa PP, Tiekink ERT (2008) CrystEngComm 10:548-564. doi: 10.1039/b717198f
26. Tadbuppa PP, Tiekink ERT (2009) Acta Crystallogr E65:m1587. doi: 10.1107/S1600536809047618
27. Elmore S (2007) Toxicol Pathol 35:495-516. doi: 10.1080/01926230701320337
28. Enari M, Sakahira H, Yokoyama H, Okawa K, Iwamatsu A, Nagata S (1998) Nature 391:43-50. doi: 10.1038/34112
29. Jackson SP, Bartek J (2009) Nature 461:1071-1078. doi: 10.1038/nature08467
30. Abraham RT (2001) Genes Dev 15:2177-2196. doi: 10.1101/gad.914401
31. Gouvea LR, Garcia LS, Lachter DR, Nunes PR, de Castro Pereira F, Silveira-Lacerda EP, Louro SR, Barbeira PJ, Teixeira LR (2012) Eur J Med 55:67-73. doi: 10.1016/j.ejmech.2012.07.004
32. Oh HL, Lee DK, Lim H, Lee CH (2010) J Ethnopharmacol 129:135-139. doi: 10.1016/j.jep.2010.02.010
33. Cheng CC, Yang SM, Huang CY, Chen JC, Chang WM, Hsu SL (2005) Cancer Chemother Pharmacol 55:531-540. doi: 10.1007/s00280-004-0919-6
34. Nigg EA (1995) BioEssays 17:471-480. doi: 10.1002/bies.950170603
35. King RW, Jackson PK, Kirschner MW (1994) Cell 79:563-571. doi: 10.1016/0092-8674(94)90542-8
36. Krek W, Nigg EA (1991) EMBO J 10:305-316
37. Jin P, Gu Y, Morgan DO (1996) J Cell Biol 134:963-970. doi: 10.1083/jcb.134.4.963
38. Grana X, Reddy EP (1995) Oncogene 11:211-219
39. Harper JW, Adami GR, Wei N, Keyomarsi K, Elledge SJ (1993) Cell 75:805-816. doi: 10.1016/0092-8674(93)90499-G
40. Xiong Y, Hannon GJ, Zhang H, Casso D, Kobayashi R, Beach D (1993) Nature 366:701-704. doi: 10.1038/366701a0
41. Cho JH, Lee JG, Yang YI, Kim JH, Ahn JH, Baek NI, Lee KT, Choi JH (2011) Food Chem Toxicol 49:1737-1744. doi: 10.1016/j.fct.2011.04.019
42. Zhao R, Xiang N, Domann FE, Zhong W (2009) Nutr Cancer 61:397-407. doi: 10.1080/01635580802582751
43. Baus F, Gire V, Fisher D, Piette J, Dulić V (2003) EMBO J22:3992-4002. doi: 10.1093/emboj/cdg387
44. Hsu YL, Kuo PL, Lin LT, Lin CC (2005) J Pharmacol Exp Ther 313:333-344. doi: 10.1124/jpet.104.078808
45. Abbas T, Dutta A (2009) Nat Rev Cancer 9:400-414. doi: 10.1038/nrc2657
46. Ting NS, Lee WH (2004) DNA Repair 3:935-944. doi: 10.1016/j.dnarep.2004.03.026
47. Yarden RI, Pardo-Reoyo S, Sgagias M, Cowan KH, Brody LC (2002) Nat Genet 30:285-289. doi: 10.1038/ng837
48. Sorensen CS, Syljuasen RG (2012) Nucleic Acids Res 40:477-486. doi: 10.1093/nar/gkr697
49. Takisawa H, Mimura S, Kubota Y (2000) Curr Opin Cell Biol 12:690-696. doi: 10.1016/S0955-0674(00)00153-8
50. Maiorano D, Lemaitre JM, Mechali M (2000) J Biol Chem 12:8426-8431. doi: 10.1074/Jbc.275.12.8426
51. Williams GH, Romanowski P, Morris LS, Madine M, Mills AD, Stoeber K, Marr J, Laskey RA, Coleman N (1998) Proc Natl Acad Sci USA 95:14932-14937. doi: 10.1073/Pnas.95.25.14932
52. Stoeber K, Tlsty TD, Happerfield L, Thomas GA, Romanov S, Bobrow L, Williams ED, Williams GH (2001) J Cell Sci 114:2027-2041
53. Stoeber K, Halsall I, Freeman A, Swinn R, Doble A, Morris L, Coleman N, Bullock N, Laskey RA, Hales CN, Williams GH (1999) Lancet 354:1524-1525. doi: 10.1016/S0140-6736(99)04265-8
54. Rowinsky EK (2005) J Clin Oncol 23:9394-9407. doi: 10.1200/Jco.2005.02.2889
55. Fulda S, Debatin KM (2006) Oncogene 25:4798-4811. doi: 10.1038/Sj.Onc.1209518
56. Slee EA, O'Connor DJ, Lu X (2004) Oncogene 23:2809-2818. doi: 10.1038/Sj.Onc.1207516
57. Leung AW, Halestrap AP (2008) Biochim Biophys Acta 1777:946-952. doi: 10.1016/j.bbabio.2008.03.009
58. Ricchelli F, Sileikyté J, Bernardi P (2011) Biochim Biophys Acta 1807:482-490. doi: 10.1016/j.bbabio.2011.02.012
59. Skulachev VP (1996) FEBS Lett 397:7-10. doi: 10.1016/0014-5793(96)00989-1
60. Le Bras M, Clément MV, Pervaiz S, Brenner C (2005) Histo Histopathol 20:205-219. doi: 10.1096/fj.05-5603rev
61. Chen F, Vallyathan V, Castranova V, Shi X (2001) Mol Cell Biochem 222:183-188. doi: 10.1023/A:1017970330982
62. LeBel CP, Ischiropoulos H, Bondy SC (1992) Chem Res Toxicol 5:227-231. doi: 10.1021/tx00026a012
63. Gomes A, Fernandes E, Lima JLFC (2005) J Biochem Biophys Meth 65:45-80. doi: 10.1016/j.jbbm.2005.10.003
64. Krammer PH (1999) Adv Immunol 71:163-210. doi: 10.1016/S0065-2776(08)60402-2
65. Hockenbery DM, Giedt CD, O'Neill JW, Manion MK, Banker DE (2002) Adv Cancer Res 85:203-242. doi: 10.1016/S0065-230X(02)85007-2
66. Henry-Mowatt J, Dive C, Martinou JC, James D (2004) Oncogene 23:2850-2860. doi: 10.1038/sj.onc.1207534
67. Yuan S, Yu X, Topf M, Ludtke SJ, Wang X, Akey CW (2010) Structure 18:571-583. doi: 10.1016/j.str.2010.04.001
68. Lupidi G, Avenali L, Bramucci M, Quassinti L, Pettinari R, Khalife HK, Gali-Muhtasib H, Marchetti F, Pettinari C (2013) J Inorg Biochem 124:78-87. doi: 10.1016/j.jinorgbio.2013.03.014
69. Lakin ND, Jackson SP (1999) Oncogene 18:7644-7655. doi: 10.1038/sj.onc.1203015
70. Oda E, Ohki R, Murasawa H, Nemoto J, Shibue T, Yamashita T, Tokino T, Taniguchi T, Tanaka N (2000) Science 288:1053-1058. doi: 10.1126/science.288.5468.1053
71. Miyashita T, Reed JC (1995) Cell 80:293-299. doi: 10.1016/0092-8674(95)90412-3
72. Sax JK, Fei P, Murphy ME, Bernhard E, Korsmeyer SJ, El-Deiry WS (2002) Nat Cell Biol 4:842-849. doi: 10.1038/ncb866
73. Nakano K, Vousden KH (2001) Mol Cell 7:683-694. doi: 10.1016/S1097-2765(01)00214-3
74. Moll UM, Wolff S, Speidel D, Deppert W (2005) Curr Opin Cell Biol 17:631-636. doi: 10.1016/j.ceb.2005.09.007
75. Haupt S, Berger M, Goldberg Z, Haupt Y (2003) J Cell Sci 116:4077-4085. doi: 10.1242/jcs.00739
76. Milhas D, Cuvillier O, Therville N, Clave P, Thomsen M, Levade T, Benoist H, Segui B (2005) J Biol Chem 280:19836-19842. doi: 10.1074/jbc.M414358200
77. Abd El-Ghany RM, Sharaf NM, Kassem LA, Mahran LG, Heikal OA (2009) Drug Discov Ther 3:296-306. doi: 10.1016/j.toxlet.2009.06.686
78. Fulda S (2009) Cancer Lett 281:128-133. doi: 10.1016/j.canlet.2008.11.023
79. Yin XM (2006) Gene 369:7-19. doi: 10.1016/j.gene.2005.10.038
80. Dobbelstein M, Strano S, Roth J, Blandino G (2005) Biochem Biophys Res Commun 331:688-693. doi: 10.1016/j.bbrc.2005.03.155
81. Zhu J, Jiang J, Zhou W, Chen X (1998) Cancer Res 58:5061-5065
82. Takahashi H, Ichimiya S, Nimura Y, Watanabe M, Furusato M, Wakui S, Yatani R, Aizawa S, Nakagawara A (1998) Cancer Res 58:2076-2077. doi: 10.1186/1471-2121-12-8
83. Kovalev S, Marchenko N, Swendeman S, LaQuaglia M, Moll UM (1998) Cell Growth Differ 9:897-903
84. Irwin, Kondo K, Marin MC, Cheng LS, Hahn WC, Kaelin WG Jr (2003) Cancer Cell. doi: 10.1016/S1535-6108(03)00078-3
85. Wertz IE, Dixit VM (2008) Cytokine Growth Factor Rev 19:313-324. doi: 10.1016/j.cytogfr.2008.04.014
86. Karin M (2006) Nature 441:431-436. doi: 10.1038/nature04870
87. Song HY, Regnier CH, Kirschning CJ, Goeddel DV, Rothe M (1997) Proc Natl Acad Sci USA 94:9792-9796. doi: 10.1073/pnas.94.18.9792
88. Ea CK, Deng L, Xia ZP, Pineda G, Chen ZJ (2006) Mol Cell 22:245-257. doi: 10.1016/j.molcel.2006.03.026
89. Deng L, Wang C, Spencer E, Yang L, Braun A, You J, Slaughter C, Pickart C, Chen ZJ (2000) Cell 103:351-361. doi: 10.1016/S0092-8674(00)00126-4
90. Hayden MS, Ghosh S (2004) Genes Dev 18:2195-2224. doi: 10.1101/gad.1228704
91. Shi Y, Xu P, Qin J (2011) Mol Cell Proteomics 10(R110):006882. doi: 10.1074/mcp.R110.006882
92. Fan Y, Shi Y, Liu S, Mao R, An L, Zhao Y, Zhang H, Zhang F, Xu G, Qin J, Yang J (2012) Cell Signal 24:1381-1389. doi: 10.1016/j.cellsig.2012.02.017
93. Wertz IE, O'Rourke KM, Zhou H, Eby M, Aravind L, Seshagiri S, Wu P, Wiesmann C, Baker R, Boone DL, Ma A, Koonin EV, Dixit VM (2004) Nature 430:694-699. doi: 10.1038/nature02794
94. Kuo JC, Wang WJ, Yao CC, Wu PR, Chen RH (2006) J Cell Biol 172:619-631. doi: 10.1083/jcb.200505138
95. Harrison B, Kraus M, Burch L, Stevens C, Craig A, Gordon-Weeks P, Hupp TR (2008) J Biol Chem 283:9999-10014. doi: 10.1074/jbc.M706040200
96. Yoo HJ, Byun HJ, Kim BR, Lee KH, Park SY, Rho SB (2012) Cell Signal 24:1471-1477. doi: 10.1016/j.cellsig.2012.03.010
97. Kodama N, Asakawa A, Inui A, Masuda Y, Nanba H (2005) Oncol Rep 13:497-502
98. Yang L, Cao Z, Yan H, Wood WC (2003) Cancer Res 63:6815-6824
99. LaCasse EC (2013) Cancer Lett 332:215-224. doi: 10.1016/j.canlet.2012.06.015
100. Nguyen DX, Massague J (2007) Nat Rev Genet 8:341-352. doi: 10.1038/nrg2101
101. Madani I, De Neve W, Mareel M (2008) Bull Cancer 95:292-300. doi: 10.1684/bdc.2008.0598
102. Tanei T, Morimoto K, Shimazu K, Kim SJ, Tanji Y, Taguchi T, Tamaki Y, Noguchi S (2009) Clin Cancer Res 15:4234-4241. doi: 10.1158/1078-0432.CCR-08-1479
103. Mehrotra S, Languino LR, Raskett CM, Mercurio AM, Dohi T, Altieri DC (2010) Cancer Cell 17:53-64. doi: 10.1016/j.ccr.2009.11.021
104. Tan W, Zhang W, Strasner A, Grivennikov S, Cheng JQ, Hoffman RM, Karin M (2011) Nature 470:548-553. doi: 10.1038/nature09707
105. Pikarsky E, Porat RM, Stein I, Abramovitch R, Amit S, Kasem S, Gutkovich-Pyest E, Urieli-Shoval S, Galun E, Ben-Neriah Y (2004) Nature 431:461-466. doi: 10.1038/nature02924
106. Wu Y, Deng J, Rychahou PG, Qiu S, Evers BM, Zhou BP (2009) Cancer Cell 15:416-428. doi: 10.1016/j.ccr.2009.03.016
107. Park BK, Zhang H, Zeng Q, Dai J, Keller ET, Giordano T, Gu K, Shah V, Pei L, Zarbo RJ, McCauley L, Shi S, Chen S, Wang CY (2007) Nat Med 13:62-69. doi: 10.1038/nm1519