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Volumn 64, Issue 6, 2009, Pages 1235-1251

Pyrrolotetrazinones deazaanalogues of temozolomide induce apoptosis in Jurkat cell line: Involvement of tubulin polymerization inhibition

Author keywords

Antimitotic; Apoptosis; G2 M block; Mitochondrial depolarization; Pyrrolotetrazinones; Tubulin

Indexed keywords

ANTIMITOTIC AGENT; BETA ACTIN; CASPASE 3; DOXORUBICIN; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PACLITAXEL; PROTEIN BAX; PROTEIN BCL 2; PYRROLE DERIVATIVE; PYRROLOTETRAZINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; TEMOZOLOMIDE; UNCLASSIFIED DRUG; VINBLASTINE;

EID: 69049093766     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-009-0994-9     Document Type: Article
Times cited : (9)

References (47)
  • 1
    • 0028944359 scopus 로고
    • Cancer research campaign phase II trial of temozolomide in metastatic melanoma
    • NM Bleehen ES Newlands SM Lee, et al. 1995 Cancer research campaign phase II trial of temozolomide in metastatic melanoma J Clin Oncol 13 910 913
    • (1995) J Clin Oncol , vol.13 , pp. 910-913
    • Bleehen, N.M.1    Newlands, E.S.2    Lee, S.M.3
  • 2
    • 0027172819 scopus 로고
    • Temozolomide: A new oral cytotoxic chemotherapeutic agent with promising activity against primary brain tumors
    • SM O'Reilly ES Newlands MG Glaser, et al. 1993 Temozolomide: a new oral cytotoxic chemotherapeutic agent with promising activity against primary brain tumors Eur J Cancer 29A 940 942
    • (1993) Eur J Cancer , vol.29 , pp. 940-942
    • O'Reilly, S.M.1    Newlands, E.S.2    Glaser, M.G.3
  • 3
    • 0026513077 scopus 로고
    • Phase I trial of temozolomide (CCRG 81045: M&B 39831: NSC 362856)
    • ES Newlands GRP Blackledge JA Slack, et al. 1992 Phase I trial of temozolomide (CCRG 81045: M&B 39831: NSC 362856) Br J Cancer 65 287 291
    • (1992) Br J Cancer , vol.65 , pp. 287-291
    • Newlands, E.S.1    Blackledge, G.R.P.2    Slack, J.A.3
  • 4
    • 0030993717 scopus 로고    scopus 로고
    • Temozolomide: A review of its discovery, chemical properties, pre-clinical development and clinical trials
    • ES Newlands MFG Stevens SR Wedge, et al. 1997 Temozolomide: a review of its discovery, chemical properties, pre-clinical development and clinical trials Cancer Treat Rep 23 35 61
    • (1997) Cancer Treat Rep , vol.23 , pp. 35-61
    • Newlands, E.S.1    Stevens, M.F.G.2    Wedge, S.R.3
  • 5
    • 0023617794 scopus 로고
    • In vitro and in vivo Methazolastone-induced DNA damage and repair in L-1210 leukemia sensitive and resistano to chloroethylnitrosoureas
    • CV Catapano M Broggini E Erba, et al. 1987 In vitro and in vivo Methazolastone-induced DNA damage and repair in L-1210 leukemia sensitive and resistano to chloroethylnitrosoureas Cancer Res 47 4884 4889
    • (1987) Cancer Res , vol.47 , pp. 4884-4889
    • Catapano, C.V.1    Broggini, M.2    Erba, E.3
  • 6
    • 0028133013 scopus 로고
    • NMR and molecular modeling investigation of the mechanism of activation of the antitumor drug temozolomide and its interaction with DNA
    • BJ Denny RT Wheelhouse MFG Stevens, et al. 1994 NMR and molecular modeling investigation of the mechanism of activation of the antitumor drug temozolomide and its interaction with DNA Biochemistry 33 9045 9051
    • (1994) Biochemistry , vol.33 , pp. 9045-9051
    • Denny, B.J.1    Wheelhouse, R.T.2    Stevens, M.F.G.3
  • 7
    • 10744233628 scopus 로고    scopus 로고
    • Novel poly(ADP-ribose) polymerase-1 inhibitor, AG14361, restores sensitivity to temozolomide in mismatch repair-deficient cells
    • NJ Curtin LZ Wang A Yiakouvaki 2004 Novel poly(ADP-ribose) polymerase-1 inhibitor, AG14361, restores sensitivity to temozolomide in mismatch repair-deficient cells Clin Cancer Res 10 881 889
    • (2004) Clin Cancer Res , vol.10 , pp. 881-889
    • Curtin, N.J.1    Wang, L.Z.2    Yiakouvaki, A.3
  • 8
    • 2542590281 scopus 로고    scopus 로고
    • Plasma and cerebrospinal fluid population pharmacokinetics of temozolomide in malignant glioma patients
    • S Ostermann C Csajka T Buclin 2004 Plasma and cerebrospinal fluid population pharmacokinetics of temozolomide in malignant glioma patients Clin Cancer Res 10 3728 3736
    • (2004) Clin Cancer Res , vol.10 , pp. 3728-3736
    • Ostermann, S.1    Csajka, C.2    Buclin, T.3
  • 9
    • 0037298870 scopus 로고    scopus 로고
    • Plasma and cerebrospinal fluid pharmacokinetics of intravenous temozolomide in non-human primates
    • M Patel C McCully K Godwin, et al. 2003 Plasma and cerebrospinal fluid pharmacokinetics of intravenous temozolomide in non-human primates J Neurooncol 61 203 207
    • (2003) J Neurooncol , vol.61 , pp. 203-207
    • Patel, M.1    McCully, C.2    Godwin, K.3
  • 10
    • 0038300305 scopus 로고    scopus 로고
    • Pyrrolo[2, 1-d][1,2,3,5]tetrazin-4(3H)-ones, a new class of azolotetrazines with potent antitumor activity
    • P Diana P Barraja A Lauria, et al. 2003 Pyrrolo[2, 1-d][1,2,3,5]tetrazin- 4(3H)-ones, a new class of azolotetrazines with potent antitumor activity Bioorg Med Chem 11 2371 2380
    • (2003) Bioorg Med Chem , vol.11 , pp. 2371-2380
    • Diana, P.1    Barraja, P.2    Lauria, A.3
  • 11
    • 33749011163 scopus 로고    scopus 로고
    • The NCI60 human tumor cell line anticancer drug screen
    • RH Shoemaker 2006 The NCI60 human tumor cell line anticancer drug screen Nat Rev Cancer 6 813 823
    • (2006) Nat Rev Cancer , vol.6 , pp. 813-823
    • Shoemaker, R.H.1
  • 12
    • 0037075063 scopus 로고    scopus 로고
    • Mining the National cancer Institute's tumor-screening data base: Identification of compounds with similar cellular activities
    • AA Rabow RH Shoemaker EA Sausville, et al. 2002 Mining the National cancer Institute's tumor-screening data base: identification of compounds with similar cellular activities J Med Chem 45 818 840
    • (2002) J Med Chem , vol.45 , pp. 818-840
    • Rabow, A.A.1    Shoemaker, R.H.2    Sausville, E.A.3
  • 13
    • 0026012758 scopus 로고
    • Pleiotropic-resistant phenotype is a multifactorial phenomenon in human colon carcinoma cell lines
    • G Toffoli A Viel I Tuimoto, et al. 1991 Pleiotropic-resistant phenotype is a multifactorial phenomenon in human colon carcinoma cell lines Br J Cancer 63 51 56
    • (1991) Br J Cancer , vol.63 , pp. 51-56
    • Toffoli, G.1    Viel, A.2    Tuimoto, I.3
  • 15
    • 0037444386 scopus 로고    scopus 로고
    • Elevated level of microtubule destabilizing factors in a taxol-resistant/dependent A549 cell line with α-tubulin mutation
    • LA Martello P Verdier-Pinard HJ Shen, et al. 2003 Elevated level of microtubule destabilizing factors in a taxol-resistant/dependent A549 cell line with α-tubulin mutation Cancer Res 63 448 454
    • (2003) Cancer Res , vol.63 , pp. 448-454
    • Martello, L.A.1    Verdier-Pinard, P.2    Shen, H.J.3
  • 16
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and citotoxic assay
    • T Mosmann 1983 Rapid colorimetric assay for cellular growth and survival: application to proliferation and citotoxic assay J Immunol Meth 65 55 63
    • (1983) J Immunol Meth , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 17
    • 0030612749 scopus 로고    scopus 로고
    • JC-1 but not DiOC6(3) or rhodamine 123 is a reliable fluorescent probe to asses ΔΨ changes in intact cells: Implications for studies on mitochondrial functionality during apoptosis
    • S Salvioli A Ardizzoni C Franceschi, et al. 1997 JC-1 but not DiOC6(3) or rhodamine 123 is a reliable fluorescent probe to asses ΔΨ changes in intact cells: implications for studies on mitochondrial functionality during apoptosis FEBS Lett 411 77 82
    • (1997) FEBS Lett , vol.411 , pp. 77-82
    • Salvioli, S.1    Ardizzoni, A.2    Franceschi, C.3
  • 18
    • 0032211437 scopus 로고    scopus 로고
    • Critical evaluation of the use of hydroethidine as a measure of superoxide anion radical
    • L Benov L Sztejnberg I Fridovich 1998 Critical evaluation of the use of hydroethidine as a measure of superoxide anion radical Free Radical Biol Med 25 826 831
    • (1998) Free Radical Biol Med , vol.25 , pp. 826-831
    • Benov, L.1    Sztejnberg, L.2    Fridovich, I.3
  • 19
    • 0028985120 scopus 로고
    • Direct cardiolipin assay in yeast using the red fluorescence emission of 10-N-nonyl acridine orange
    • PF Gallet A Maftah JM Petit, et al. 1995 Direct cardiolipin assay in yeast using the red fluorescence emission of 10-N-nonyl acridine orange Eur J Biochem 228 113 119
    • (1995) Eur J Biochem , vol.228 , pp. 113-119
    • Gallet, P.F.1    Maftah, A.2    Petit, J.M.3
  • 20
    • 38749151548 scopus 로고    scopus 로고
    • Central role of p53 and mitochondrial damage in PUVA-induced apoptosis in human keratinocytes
    • G Viola E Fortunato L Cecconet, et al. 2008 Central role of p53 and mitochondrial damage in PUVA-induced apoptosis in human keratinocytes Tox Appl Pharm 227 84 96
    • (2008) Tox Appl Pharm , vol.227 , pp. 84-96
    • Viola, G.1    Fortunato, E.2    Cecconet, L.3
  • 21
    • 33645380372 scopus 로고    scopus 로고
    • Synthesis and biological activity of 7-phenyl-6, 9-dihydro-3H-pyrrolo[3, 2-f]quinoline-9-ones: A new class of antimitotic agents devoid of aromatase activity
    • V Gasparotto I Castagliuolo G Chiarellotto, et al. 2006 Synthesis and biological activity of 7-phenyl-6, 9-dihydro-3H-pyrrolo[3, 2-f]quinoline-9-ones: a new class of antimitotic agents devoid of aromatase activity J Med Chem 49 1910 1915
    • (2006) J Med Chem , vol.49 , pp. 1910-1915
    • Gasparotto, V.1    Castagliuolo, I.2    Chiarellotto, G.3
  • 22
    • 0021950830 scopus 로고
    • 4′, 6-Diamidino-2-phenylindole, a fluorescent probe for tubulin and microtubule
    • D Bonne C Heusele C Simon, et al. 1985 4′, 6-Diamidino-2- phenylindole, a fluorescent probe for tubulin and microtubule J Biol Chem 260 2819 2825
    • (1985) J Biol Chem , vol.260 , pp. 2819-2825
    • Bonne, D.1    Heusele, C.2    Simon, C.3
  • 23
    • 0029043888 scopus 로고
    • A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled Annexin V
    • I Vermes C Haanen H Steffens-Nakken, et al. 1995 A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled Annexin V J Immun Method 184 39 51
    • (1995) J Immun Method , vol.184 , pp. 39-51
    • Vermes, I.1    Haanen, C.2    Steffens-Nakken, H.3
  • 24
    • 0028800947 scopus 로고
    • Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: Inhibition by overexpression of Bcl-2 and Abl
    • SJ Martin CP Reutelingsperger AJ McGahon, et al. 1995 Early redistribution of 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) J Exp Med , vol.182 , pp. 1545-1556
    • Martin, S.J.1    Reutelingsperger, C.P.2    McGahon, A.J.3
  • 25
    • 3442886811 scopus 로고    scopus 로고
    • The pathophysiology of mitochondrial cell death
    • DR Green G Kroemer 2005 The pathophysiology of mitochondrial cell death Science 305 626 629
    • (2005) Science , vol.305 , pp. 626-629
    • Green, D.R.1    Kroemer, G.2
  • 27
    • 0029101644 scopus 로고
    • Sequential reduction of mitochondrial transmembrane potential and generation of reactive oxygen species in early programmed cell death
    • N Zamzami P Marchetti M Castedo, et al. 1995 Sequential reduction of mitochondrial transmembrane potential and generation of reactive oxygen species in early programmed cell death J Exp Med 182 367 377
    • (1995) J Exp Med , vol.182 , pp. 367-377
    • Zamzami, N.1    Marchetti, P.2    Castedo, M.3
  • 28
    • 0032496143 scopus 로고    scopus 로고
    • Superoxide in apoptosis. Mitochondrial generation triggered by cytochrome c loss
    • J Cai DP Jones 1998 Superoxide in apoptosis. Mitochondrial generation triggered by cytochrome c loss J Biol Chem 273 11401 11404
    • (1998) J Biol Chem , vol.273 , pp. 11401-11404
    • Cai, J.1    Jones, D.P.2
  • 29
    • 13844262622 scopus 로고    scopus 로고
    • Intracellular generation of reactive oxygen species by mitochondria
    • H Nohl L Gille K Staniek 2005 Intracellular generation of reactive oxygen species by mitochondria Biochem Pharmacol 69 719 723
    • (2005) Biochem Pharmacol , vol.69 , pp. 719-723
    • Nohl, H.1    Gille, L.2    Staniek, K.3
  • 30
    • 33845480548 scopus 로고    scopus 로고
    • Caspase function in programmed cell death
    • S Kumar 2007 Caspase function in programmed cell death Cell Death Differ 14 32 43
    • (2007) Cell Death Differ , vol.14 , pp. 32-43
    • Kumar, S.1
  • 31
    • 0344142396 scopus 로고    scopus 로고
    • Emerging role of caspase-3 in apoptosis
    • AG Porter RU Janicke 1999 Emerging role of caspase-3 in apoptosis Cell Death Differ 6 99 104
    • (1999) Cell Death Differ , vol.6 , pp. 99-104
    • Porter, A.G.1    Janicke, R.U.2
  • 32
    • 0032509239 scopus 로고    scopus 로고
    • Importance of poly(ADP-ribose) polymerase and its cleavage in apoptosis. Lesson from an uncleavable mutant
    • FJ Oliver G de la Rubia V Rolli, et al. 1998 Importance of poly(ADP-ribose) polymerase and its cleavage in apoptosis. Lesson from an uncleavable mutant J Biol Chem 273 33533 33539
    • (1998) J Biol Chem , vol.273 , pp. 33533-33539
    • Oliver, F.J.1    De La Rubia, G.2    Rolli, V.3
  • 33
    • 0036022402 scopus 로고    scopus 로고
    • Poly(ADP-ribose) polymerase-1 cleavage during apoptosis: An update
    • C Soldani AI Scovassi 2002 Poly(ADP-ribose) polymerase-1 cleavage during apoptosis: an update Apoptosis 7 321 328
    • (2002) Apoptosis , vol.7 , pp. 321-328
    • Soldani, C.1    Scovassi, A.I.2
  • 34
    • 0031037897 scopus 로고    scopus 로고
    • The release of cytochrome c from mitochondria: A primary site for Bcl-2 regulation of apoptosis
    • RM Kluck E Bossy-Wetzel DR Green, et al. 1997 The release of cytochrome c from mitochondria: a primary site for Bcl-2 regulation of apoptosis Science 275 1132 1136
    • (1997) Science , vol.275 , pp. 1132-1136
    • Kluck, R.M.1    Bossy-Wetzel, E.2    Green, D.R.3
  • 35
    • 0030861571 scopus 로고    scopus 로고
    • Bcl-2 and Bax function independently to regulate cell death
    • CM Knudson SJ Korsmeyer 1997 Bcl-2 and Bax function independently to regulate cell death Nature Genet 16 358 363
    • (1997) Nature Genet , vol.16 , pp. 358-363
    • Knudson, C.M.1    Korsmeyer, S.J.2
  • 36
    • 0032880829 scopus 로고    scopus 로고
    • The effect of antimicrotubule agents on signal transduction pathway of apoptosis: A review
    • LG Wang XM Liu W Kreis, et al. 1999 The effect of antimicrotubule agents on signal transduction pathway of apoptosis: a review Cancer Chemother Pharmacol 44 355 361
    • (1999) Cancer Chemother Pharmacol , vol.44 , pp. 355-361
    • Wang, L.G.1    Liu, X.M.2    Kreis, W.3
  • 37
    • 0141774441 scopus 로고    scopus 로고
    • Tubulin and microtubules as targets for anticancer drugs
    • JA Hadfield S Ducki N Hirst, et al. 2003 Tubulin and microtubules as targets for anticancer drugs Prog Cell Cyc Res 5 309 325
    • (2003) Prog Cell Cyc Res , vol.5 , pp. 309-325
    • Hadfield, J.A.1    Ducki, S.2    Hirst, N.3
  • 38
    • 1942438028 scopus 로고    scopus 로고
    • Microtubule as a target for anticancer drugs
    • MA Jordan L Wilson 2004 Microtubule as a target for anticancer drugs Nature Rev Cancer 4 253 265
    • (2004) Nature Rev Cancer , vol.4 , pp. 253-265
    • Jordan, M.A.1    Wilson, L.2
  • 39
    • 0027360552 scopus 로고
    • Mechanism of mitotic block and inhibition of cell proliferation by taxol at low concentrations
    • MA Jordan RJ Toso D Thrower, et al. 1993 Mechanism of mitotic block and inhibition of cell proliferation by taxol at low concentrations Proc Natl Acad Sci USA 90 9552 9556
    • (1993) Proc Natl Acad Sci USA , vol.90 , pp. 9552-9556
    • Jordan, M.A.1    Toso, R.J.2    Thrower, D.3
  • 40
    • 0032191054 scopus 로고    scopus 로고
    • Microtubule tread milling: What goes around comes around
    • RL Margolis R Wilson 1998 Microtubule tread milling: what goes around comes around Bioessay 20 830 836
    • (1998) Bioessay , vol.20 , pp. 830-836
    • Margolis, R.L.1    Wilson, R.2
  • 41
    • 0141996464 scopus 로고    scopus 로고
    • Microtubules, microtubule-interfering agents and apoptosis
    • F Mollinedo C Gajate 2003 Microtubules, microtubule-interfering agents and apoptosis Apoptosis 8 413 450
    • (2003) Apoptosis , vol.8 , pp. 413-450
    • Mollinedo, F.1    Gajate, C.2
  • 42
    • 0034307316 scopus 로고    scopus 로고
    • Paclitaxel induces release of cytochrome c from mitochondria isolated from human neuroblastoma cells
    • N Andre M Braguer G Brasseur, et al. 2000 Paclitaxel induces release of cytochrome c from mitochondria isolated from human neuroblastoma cells Cancer Res 60 5349 5353
    • (2000) Cancer Res , vol.60 , pp. 5349-5353
    • Andre, N.1    Braguer, M.2    Brasseur, G.3
  • 43
    • 0037021417 scopus 로고    scopus 로고
    • Paclitaxel targets mitochondria upstream of caspase activation in intact human neuroblastoma cells
    • N Andre M Carre G Brasseur, et al. 2003 Paclitaxel targets mitochondria upstream of caspase activation in intact human neuroblastoma cells FEBS lett 532 256 260
    • (2003) FEBS Lett , vol.532 , pp. 256-260
    • Andre, N.1    Carre, M.2    Brasseur, G.3
  • 44
    • 0032563202 scopus 로고    scopus 로고
    • Phosphorylation of Bcl-2 is a marker of M phase events and not a determinant of apoptosis
    • YH Lyng C Tornos R Perez Soler 1998 Phosphorylation of Bcl-2 is a marker of M phase events and not a determinant of apoptosis J Biol Chem 273 18984 18991
    • (1998) J Biol Chem , vol.273 , pp. 18984-18991
    • Lyng, Y.H.1    Tornos, C.2    Perez Soler, R.3
  • 45
    • 0033499801 scopus 로고    scopus 로고
    • Bcl-2 is phosphorylated and inactivated by an ASK1/Jun N terminal protein kinase pathway normally activated at G2/M phase
    • K Yamamomoto H Ichijo SJ Korsmeyer 1999 Bcl-2 is phosphorylated and inactivated by an ASK1/Jun N terminal protein kinase pathway normally activated at G2/M phase Mol Cell Biol 19 8469 8478
    • (1999) Mol Cell Biol , vol.19 , pp. 8469-8478
    • Yamamomoto, K.1    Ichijo, H.2    Korsmeyer, S.J.3
  • 46
    • 0032776120 scopus 로고    scopus 로고
    • Mitogen-activated protein kinase pathway is dispensable for microtubule-active drug-induced Raf-1/Bcl-2 phosphorylation and apoptosis in leukemia cells
    • MV Blagosklonny Y Chuman RC Bergan 1999 Mitogen-activated protein kinase pathway is dispensable for microtubule-active drug-induced Raf-1/Bcl-2 phosphorylation and apoptosis in leukemia cells Leukemia 13 1028 1036
    • (1999) Leukemia , vol.13 , pp. 1028-1036
    • Blagosklonny, M.V.1    Chuman, Y.2    Bergan, R.C.3
  • 47
    • 0032877433 scopus 로고    scopus 로고
    • Bax:Bcl-2 ratio modulation by Bryostatin1 and novel antitubulin agents is important for susceptibility to drug induced apoptosis in the human early pre-B acute lymphoblastic leukaemia cell line Reh
    • NR Wall RM Mohammad AM Al-Katib 1999 Bax:Bcl-2 ratio modulation by Bryostatin1 and novel antitubulin agents is important for susceptibility to drug induced apoptosis in the human early pre-B acute lymphoblastic leukaemia cell line Reh Leukemia Res 23 881 888
    • (1999) Leukemia Res , vol.23 , pp. 881-888
    • Wall, N.R.1    Mohammad, R.M.2    Al-Katib, A.M.3


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