Apoptosis of human breast carcinoma cells in the presence of cis-platin and L-/D-PPMP: IV. Modulation of replication complexes and glycolipid: Glycosyltransferases

Glycoconjugate Journal

Volumn 23, Issue 3-4, 2006, Pages 175-187

  Boyle, Patrick J ^a   Ma, Rui ^a   Tuteja, Narendra ^b   Banerjee, Sipra ^c   Basu, Subhash ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b INTERNATIONAL CENTRE FOR GENETIC ENGINEERING AND BIOTECHNOLOGY ICGEB   (India)

^c LERNER RESEARCH INSTITUTE   (United States)

Author keywords

Anti cancer drugs; Apoptosis; Carcinoma cells; Caspase 3; Caspase 9; cis platin; D PPMP; DNA polymerase ; GD1a ganglioside; GD3 ganglioside; Helicase III; L PPMP; SAT 2; SAT 3; SAT 4

Indexed keywords

1 PHENYL 2 HEXADECANOYLAMINO 3 MORPHOLINO 1 PROPANOL; ANTINEOPLASTIC AGENT; APHIDICOLIN; CASPASE 3; CASPASE 8; CASPASE 9; CISPLATIN; DNA DIRECTED DNA POLYMERASE ALPHA; FLUORESCENT DYE; GENOMIC DNA; GLYCOLIPID; GLYCOSPHINGOLIPID; GLYCOSYLTRANSFERASE; HELICASE; HELICASE 3; MORPHOLINE DERIVATIVE; PHOSPHATIDYLSERINE; PROPANOL; PSS 380; SIALYLTRANSFERASE; SIALYLTRANSFERASE 2; SIALYLTRANSFERASE 4; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CONTROLLED STUDY; DNA DEGRADATION; DNA RECOMBINATION; DNA REPAIR; DNA REPLICATION; DOSE RESPONSE; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME MECHANISM; HUMAN; HUMAN CELL; PHENOTYPE; PRIORITY JOURNAL;

ACETYLTRANSFERASES; ANTINEOPLASTIC AGENTS; APOPTOSIS; BREAST NEOPLASMS; CARBOHYDRATE SEQUENCE; CASPASES; CELL LINE, TUMOR; CISPLATIN; DNA HELICASES; DNA POLYMERASE I; DNA REPLICATION; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; GLYCOLIPIDS; GLYCOSYLTRANSFERASES; HUMANS; MOLECULAR SEQUENCE DATA; MORPHOLINES; PHOSPHATIDYLSERINES; SIALYLTRANSFERASES; SPHINGOLIPIDS;

EID: 33646578513     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-006-7923-5     Document Type: Article

References (88)

1. Wyllie, A.H.: Apoptosis: cell death in tissue regulation. J. Pathol. 153, 313-316 (1987)
2. Arends, M.J., Wyllie, A.H.: Apoptosis: mechanisms and roles in pathology. Int. Rev. Exp. Pathol. 32, 223-254 (1991)
3. Wajant, H.: The Fassignaling pathway: more than a paradigm. Science, 296, 1635-6 (2002)
4. Strasser, A., O'Connor, L., Dixit, V.M.: Apoptosis signaling. Annu. Rev. Biochem. 69, 217-245 (2000)
5. Couldwell, W.T., Hinton, D.R., He, S., Chen, T.C., Sebat, I., Weiss, M.H., Law, R.E.: Protein kinaseC inhibitors induce apoptosis in human malignant glioma cell lines. FEBS Lett. 345, 43-46 (1994)
6. Issandou, M., Faucher, C., Bayard, F., Darbon, J.M.: Opposite effects of tamoxifen on in vitro protein kinase C activity and endogenous protein phosphorylation in intact MCF-7 cells. Cancer Res. 50, 5845-5850 (1990)
7. Pisha, E., Chai, H., Lee, I.S., Chagwedera, T.E., Farnsworth, N.R., Cordell, G.A., Beecher, C.W., Fong, H.H., Kinghorn, A.D., Brown, D.M., et al.: Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis. Nat. Med. 1, 1046-51 (1995)
8. Ritke, M.K., Rusnak, J.M., Lazo, J.S., Allan, W.P., Dive, C., Heer, S., Yalowich, J.C.: Differential inductionof etoposide-mediated apoptosis in human leukemia HL-60 and K562 cells. Mol. Pharmacol. 46, 605-611 (1994)
9. Schmidt, M.L., Kuzmanoff, K.L., Ling-Indeck, L., Pezzuto, J.M.: Betulinic acid induces apoptosis in human neuroblastoma cell lines. Eur. J. Cancer 33, 2007-2010 (1997)
10. Cifone, M.G., Roncaioli, P., DeMaria, R., Camarda, G., Santoni, A., Ruberti, G., Testi, R.: Multiple pathwaysoriginate at the Fas/APO-1 (CD95) receptor: sequential involvement of phosphatidylcholine-specific phospholipase C and acidic sphingomyelinase in the propagation of the apoptotic signal. Embo. J. 14, 5859-5868 (1995)
11. Bharti, A.C., Singh, S.M.: Induction ofapoptosis in bone marrow cells by gangliosides produced by a T cell lymphoma. Immunol. Lett. 72, 39-48 (2000)
12. Colell, A., Morales, A., Fernandez-Checa, J.C., Garcia-Ruiz, C.: Ceramide generatedby acidic sphingomyelinase contributes to tumor necrosis factor-alpha-mediated apoptosis in human colon HT-29 cells through glycosphingolipids formation. Possible role of ganglioside GD3. FEBS Lett. 526, 135-141 (2002)
13. Malisan, F., Testi, R.: GD3 in cellular ageing and apoptosis. Exp. Gerontol. 37, 1273-1282 (2002)
14. Paris, R., Morales, A., Coll, O., Sanchez-Reyes, A., Garcia-Ruiz, C., Fernandez-Checa, J.C.: Ganglioside GD3 sensitizes human hepatoma cells to cancer therapy. J. Biol. Chem. 277, 49870-49876 (2002)
15. Watanabe, R., Ohyama, C., Aoki, H., Takahashi, T., Satoh, M., Saito, S., Hoshi, S., Ishii, A., Saito, M., Arai, Y.: Ganglioside G(M3) overexpression induces apoptosis and reduces malignant potential in murine bladder cancer. Cancer Res. 62, 3850-3854 (2002)
16. Simon, B.M., Malisan, F., Testi, R., Nicotera, P., Leist, M.: Disialoganglioside GD3 is released by microglia and induces oligodendrocyte apoptosis. Cell. Death. Differ. 9, 758-767 (2002)
17. Copani, A., Melchiorri, D., Caricasole, A., Martini, F., Sale, P., Carnevale, R., Gradini, R., Sortino, M.A., Lenti, L., De Maria, R., Nicoletti, F.: Beta-amyloid-induced synthesis of the ganglioside GD3 is a requisite for cell cycle reactivation and apoptosis in neurons. J. Neurosci. 22, 3963-3968 (2002)
18. Kristal, B.S., Brown, A.M.: Apoptogenic gangliosideGD3 directly induces the mitochondrial permeability transition. JBiol. Chem. 274, 23169-23175 (1999)
19. Scorrano, L., Petronilli, V., Di Lisa, F., Bernardi, P.: Commitment toapoptosis by GD3 ganglioside depends on opening of the mitochondrial permeability transition pore. J. Biol. Chem. 274, 22581-22585 (1999)
20. Rippo, M.R., Malisan, F., Ravagnan, L., Tomassini, B., Condo, I., Costantini, P., Susin, S.A., Rufini, A., Todaro, M., Kroemer, G., Testi, R.: GD3 ganglioside directly targets mitochondria in a bcl-2-controlled fashion. Faseb. J. 14, 2047-2054 (2000)
21. Kristal, B.S., Brown, A.M.: Ganglioside GD3, the mitochondrial permeability transition, and apoptosis. Ann. N. Y. Acad. Sci. 893, 321-324 (1999)
22. Morales, A., Colell, A., Mari, M., Garcia-Ruiz, C., Fernandez-Checa, J.C.: Glycosphingolipids andmitochondria: role in apoptosis and disease. Glycoconj. J. 20, 579-588 (2004)
23. Ma, R., Koulov, A., Moulton, C., Basu, M., Banerjee, S., Goodson, H., Basu, S.: Apoptosis ofhuman breast carcinoma cells in the presence of disialosyl gangliosides: II. Treatment of SKBR3 cells with GD3 and GD1b gangliosides. Glycoconj. J. 20, 319-330 (2004)
24. Hannun, Y.A., Luberto, C., Argraves, K.M.: Enzymes ofsphingolipid metabolism: from modular to integrative signaling. Biochemistry 40, 4893-4903 (2001)
25. Pettus, B.J., Chalfant, C.E., Hannun, Y.A.: Ceramide inapoptosis: an overview and current perspectives. Biochim. Biophys. Acta. 1585, 114-125 (2002)
26. Tilly, J.L., Kolesnick, R.N.: Sphingolipids, apoptosis, cancer treatments and the ovary: investigating a crime against female fertility. Biochim. Biophys. Acta. 1585, 135-138 (2002)
27. Cuvillier, O.: Sphingosine inapoptosis signaling. Biochim. Biophys. Acta. 1585, 153-162 (2002)
28. Radin, N.S.: Killing tumoursby ceramide-induced apoptosis: a critique of available drugs. Biochem. J. 371, 243-256 (2003)
29. Bieberich, E., Hu, B., Silva, J., MacKinnon, S., Yu, R.K., Fillmore, H., Broaddus, W.C., Ottenbrite, R.M.: Synthesis andcharacterization of novel ceramide analogs for induction of apoptosis in human cancer cells. Cancer Lett. 181, 55-64 (2002)
30. Okazaki, T., Bell, R.M., Hannun, Y.A.: Sphingomyelin turnoverinduced by vitamin D3 in HL-60 cells. Role in cell differentiation. J. Biol. Chem. 264, 19076-19080 (1989)
31. Okazaki, T., Bielawska, A., Bell, R.M., Hannun, Y.A.: Role ofceramide as a lipid mediator of 1 alpha, 25-dihydroxyvitamin D3-induced HL-60 cell differentiation. J. Biol. Chem. 265, 15823-15831 (1990)
32. Basu, S., Ma, R., Mikulla, B., Bradley, M., Moulton, C., Basu, M., Banerjee, S., Inokuchi, J.: Apoptosis ofhuman carcinoma cells in the presence of inhibitors of glycosphingolipid biosynthesis: I. Treatment of Colo-205 and SKBR3 cells with isomers of PDMP and PPMP. Glycoconj. J. 20, 157-168 (2004)
33. Kolesnick, R.N.: Sphingomyelin andderivatives as cellular signals. Prog. Lipid. Res. 30, 1-38 (1991)
34. Basu, M., Kelly, P., Girzadas, M., Li, Z., Basu, S.: Properties ofanimal ceramide glycanases. Methods. Enzymol. 311, 287-297 (2000)
35. Dastgheib, S., Basu, S.S., Li, Z., Basu, M., Basu, S.: Analyses ofglycosphingolipids using clam, Mercenaria mercenaria, ceramide glycanase. Methods. Enzymol. 312, 196-205 (2000)
36. Basu, M., Kelly, P., O'Donnell, P., Miguel, M., Bradley, M., Sonnino, S., Banerjee, S., Basu, S.: Ceramide glycanaseactivities in human cancer cells. Biosci. Rep. 19, 449-460 (1999)
37. Spiegel, S., Milstien, S.: Functions ofa new family of sphingosine-1-phosphate receptors. Biochim. Biophys. Acta. 1484, 107-116 (2000)
38. Igarashi, Y.: Functional rolesof sphingosine, sphingosine 1-phosphate, and methylsphingosines: in regard to membrane sphingolipid signaling pathways. J. Biochem. (Tokyo) 122, 1080-1087 (1997)
39. Kerr, J.F., Wyllie, A.H., Currie, A.R., Apoptosis: a basic biological phenomenon with wide-ranging implications in tissue kinetics. Br. J. Cancer. 26, 239-257 (1972)
40. Cohen, G., Sun, X., Fearnhead, H., MacFarlane, M., Brown, D., Snowden, R., Dinsale, D.: Formation oflarge molecular weight fragments of DNA is a key committed step of apoptosis in thymocytes. J. Immunol., 153, 507-516 (1994)
41. Martin, S., Reutelingsperger, C., McGahon, A., Rader, J., Schie, R.v., LaFace, D., Green, D.: Early redistributionof plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl. J. Exp. Med. 182, 1545-1556 (1995)
42. Martin, S., Green, D.: Protease activationduring apoptosis: death by a thousand cuts? Cell. 82, 349-352 (1995)
43. Wyllie, A.: Glucocorticoid-induced thymocyte apoptosis is associated with endogenous endonuclease activation. Nature 284, 555-556 (1980)
44. Liu, X., Zou, H., Slaughter, C., Wang, X.: DFF, a heterodimeric protein that functions downstream of Caspase-3 to trigger DNA fragmentation during apoptosis. Cell 89, 175-184 (1997)
45. Enari, M., Sakahira, H., Yokoyama, H., Okawa, K., Iwamatsu, A., Nagata, S., A caspase-activated DNase that degrades DNA during apoptosis, and its inhibitor ICAD. Nature 391, 43-50 (1998)
46. Halenbeck, R., MacDonald, H., Roulston, A., Chen, T., Conroy, L., Williams, L., CPAN, a human nuclease regulated by the caspase-sensitive inhibitor DFF45. Curr. Biol. 8, 537-540 (1998)
47. Seki, K., Yoshikawa, H., Shiiki, K., Hamada, Y., Akamatsu, N., Tasaka, K.: Cis-platin (CDDP) specifically induces apoptosis via sequential activation of Caspase-8, -3 and -6 in osteosarcoma. Cancer Chemother Pharmacol. 45, 199-206 (2000)
48. Henkels, K.M., Turchi, J.J., Cis-platin-induced apoptosis proceeds by Caspase-3-dependent and - independent pathways in cis-platin-resistant and -sensitive human ovarian cancer cell lines. Cancer Res. 59, 3077-3083 (1999)
49. Tavassoli, M., Soltaninia, J., Rudnicka, J., Mashanyare, D., Johnson, N., Gaken, J.: Tamoxifen inhibits the growth of head and neck cancer cells and sensitizes these cells to cis-platin induced-apoptosis: role of TGF-beta1. Carcinogenesis 23, 1569-1575 (2002)
50. Rahmouni, A., Leng, M.: Reaction ofnucleic acids with cis-diamminedichloroplatinum (II): interstrand cross-links. Biochemistry 26, 7229-7234 (1987)
51. Kelley, T.J., Moghaddas, S., Bose, R., Basu, S.: Inhibition ofimmunopurified DNA polymerase-alpha from PA-3 prostate tumor cells by platinum (II) antitumor drugs. Cancer Biochem. Biophys. 13, 135-146 (1993)
52. Bose, R., Li, D., Kennedy, M., Basu, S.: Facile Formationof cis-Platin Nonapeptide Complex of Human DNA Polymerase-alpha Origin. J. Chem. Soc. Commun. Royal Soc. Chem. 1731-1732 (1995)
53. Bose, R.N., Li, D., Yang, W.W., Basu, S.: NMR structuresof a nonapeptide from DNA binding domain of human polymerase-alpha determined by iterative complete-relaxation-matrix approach. J. Biomol. Struct. Dyn. 16, 1075-1085 (1999)
54. Hiraishi, K., Suzuki, K., Hakomori, S., Adachi, M., Le (y) antigen expression is correlated with apoptosis (programmed cell death). Glycobiology 3, 381-390 (1993)
55. Basu, S., Ma, R., Boyle, P.J., Mikulla, B., Bradley, M., Smith, B., Basu, M., Banerjee, S.: Apoptosis ofhuman carcinoma cells in the presence of potential anti-cancer drugs: III. Treatment of Colo-205 and SKBR3 cells with: cis-platin, Tamoxifen, Melphalan, Betulinic acid, L-PDMP, L-PPMP, and GD3 ganglioside. Glycoconj. J. 20, 563-577 (2004)
56. Boubelik, M., Floryk, D., Bohata, J., Draberova, L., Macak, J., Smid F, Draber, P.: Lex glycosphingolipids-mediated cell aggregation. Glycobiology 8, 139-146 (1998)
57. Koulov, A.V., Stucker, K.A., Lakshmi, C., Robinson, J.P., Smith, B.D.: Detection ofapoptotic cells using a synthetic fluorescent sensor for membrane surfaces that contain phosphatidylserine. Cell. Death. Differ. 10, 1357-1359 (2003)
58. Basu, M., De, T., Das, K.K., Kyle, J.W., Chon, H.C., Schaeper, R.J., Basu, S.: Glycolipids. Methods. Enzymol. 138, 575-607 (1987)
59. Boyle, P.J.: Characterization of DNA Helicase-III in Replication Complexes Isolated from Embryonic Chicken Brain and Breast Carcinoma Cells, in Department of Chemistry and Biochemistry. 2005, University of Notre Dame: Notre Dame, IN
60. Mullen, O.L., Dodd, M.C., Minton, J.P.: Evaluation ofdye exclusion and colony inhibition techniques for detection of polyoma-specific, cell-mediated immunity. J. Natl. Cancer Inst. 54, 229-231 (1975)
61. Porter, A.G., Janicke, R.U.: Emerging rolesof Caspase-3 in apoptosis. Cell. Death. Differ. 6, 99-104 (1999)
62. Kumar, S.: Mechanisms mediatingcaspase activation in cell death. Cell. Death. Differ. 6, 1060-1066 (1999)
63. Nunez, G., Benedict, M.A., Hu, Y., Inohara, N., Caspases: the proteases of the apoptotic pathway. Oncogene 17, 3237-3245 (1998)
64. Hearps, A.C., Burrows, J., Connor, C.E., Woods, G.M., Lowenthal, R.M., Ragg, S.J.: Mitochondrial cytochromec release precedes transmembrane depolarisation and Caspase-3 activation during ceramide-induced apoptosis of Jurkat T cells. Apoptosis 7, 387-394 (2002)
65. Chandra, J., Kaufmann, S.H.: Apoptotic pathways in cancer progression and treatment in Signal Transduction and Human Disease, 143-170 (2003); John Wiley and Sons, New Jersey
66. Stennicke, H.R., Salvesen, G.S.: Catalytic propertiesof the caspases. Cell. Death. Differ. 6, 1054-1059 (1999)
67. Thornberry, N.A., Lazebnik, Y.: Caspases: enemies within. Science 281, 1312-1316 (1998)
68. Volckova, E., Dudones, L.P., Bose, R.N.: HPLC determinationof binding of cis-platin to DNA in the presence of biological thiols: implications of dominant platinum-thiol binding to its anticancer action. Pharm. Res. 19, 124-131 (2002)
69. Tuteja, N., Rahma, K., Tuteja, R., Ochem, A., Skopac, D., Falaschi, A.: DNA helicase III from HeLa cells: an enzyme that acts preferentially on partially unwound DNA duplexes. Nucleic Acids Res. 20, 5329-5337 (1992)
70. Peyrone, M.: Ueber dieEinWirkung des Ammoniaks auf Platinchlorur. Ann. Chem. Pharm. 51, 1-29 (1844)
71. Rosenberg, B., Vancamp, L., Krigas, T.: Inhibition Of Cell Division In Escherichia Coli By Electrolysis Products From A Platinum Electrode. Nature 205, 698-699 (1965)
72. Rosenberg, B., VanCamp, L., Trosko, J.E., Mansour, V.H., Platinum compounds: a new class of potent antitumour agents. Nature 222, 385-386 (1969)
73. Pinto, A.L., Lippard, S.J.: Binding ofthe antitumor drug cis-diamminedichloroplatinum (II) (cis-platin) to DNA. Biochim. Biophys. Acta. 780, 167-180 (1985)
74. Bose, R.N., Li, D., Kennedy, M., Basu, S.: Facile Formationof cis-platin Nonapeptide Complex of Human DNA Polymerase-a Origin. J. Chem. Soc. Commun. Royal Soc. Chem. 1731-1732 (1995)
75. Volckova, E., Evanics, F., Yang, W.W., Bose, R.N.: Unwinding of DNA polymerases by the antitumor drug, cis-diamminedichloroplatinum (II). Chem. Commun. (Camb), 1128-1129 (2003)
76. Rossi, D., Gaidano, G.: Messengers ofcell death: apoptotic signaling in health and disease. Haematologica 88, 212-218 (2003)
77. Fredman, P., Nilsson, O., Svennerholm, L., Myrvold, H., Persson, B., Pettersson, S., Holmgren, J., Lindholm, L.: Colorectal carcinomashave a characteristic ganglioside pattern. Med. Biol. 61, 45-48 (1983)
78. Wikstrand, C.J., Fredman, P., McLendon, R.R., Svennerholm, L., Bigner, D.D.: Altered expressionof ganglioside phenotypes of human gliomas in vivo and in vitro. Mol. Chem. Neuropathol. 21, 129-138 (1994)
79. Thomas, C.P., Buronfosse, A., Fertil, B., Portoukalian, J.: Surface expressionof GD3 disialogangliosides in human melanoma cells is correlated to both metastatic potential in vivo and radiosensitivity in vitro. C. R. Acad. Sci. III, 318, 1233-1238 (1995)
80. Marquina, G., Waki, H., Fernandez, L.E., Kon, K., Carr, A., Valiente, O., Perez, R., Ando, S.: Gangliosides expressedin human breast cancer. Cancer Res. 56, 5165-5171 (1996)
81. Magnani, J.L., Nilsson, B., Brockhaus, M., Zopf, D., Steplewski, Z., Koprowski, H., Ginsburg, V.: A monoclonalantibody-defined antigen associated with gastrointestinal cancer is a ganglioside containing sialylated lacto-N-fucopentaose II. J. Biol. Chem. 257, 14365-14369 (1982)
82. Kannagi, R., Izawa, M., Koike, T., Miyazaki, K., Kimura, N.: Carbohydrate-mediated cell adhesion in cancer metastasis and angiogenesis. Cancer Sci. 95, 377-384 (2004)
83. Zeisig, R., Stahn, R., Wenzel, K., Behrens, D., Fichtner, I.: Effect ofsialyl Lewis X-glycoliposomes on the inhibition of E-selectin-mediated tumour cell adhesion in vitro. Biochim. Biophys. Acta. 1660, 31-40 (2004)
84. Magnani, J.L.: The discovery, biology, and drug development of sialyl Lea and sialyl Lex. Arch. Biochem. Biophys. 426, 122-131 (2004)
85. Basu S.: The serendipity of ganglioside biosynthesis: pathways to CARS and HY-CARS glycosyltrnsferases. Glycobiology 1, 469-475 (1991)
86. Basu, M., Hawes, J., Li, Z., Ghosh, S., Khan, F.A., Zhang, B.J., Basu, S., Basu, M.: Biosynthesis in vitro of SA-LeX and SA-diLeX by al-3 fucosyltransferases from colon carcinoma and embryonic brain tissues. Glycobiology 1, 527-535 (1991)
87. Basu, S., Basu, M., Dastgheib, S., Hawes, J.W.: Biosynthesis andregulation of glycosphingolipids in "Comprehensive Natural Products Chemistry" (eds. D. Barton, K. Nakanishi, O. Meth-Cohen, and B.M. Pinto), Vol-3. Pergamon Press, New York 107-128 (1999)
88. Basu, S., Kaufman, B., Roseman, S.: Conversion ofTay-Sachs ganglioside to monosialoganglioside by brain uridine diphosphoate D-galactose:glycolipid galactosyltransferase. J. Biol. Chem. 240, 4114-4117 (1965)