메뉴 건너뛰기




Volumn 53, Issue 22, 2010, Pages 7967-7978

Synthesis and biological evaluation of polyenylpyrrole derivatives as anticancer agents acting through caspases-dependent apoptosis

Author keywords

[No Author keywords available]

Indexed keywords

3 BUTYL 6 [9 (3 CHLORO PYRROL 2 YL) NONA 2,4,6,8 TETRAEN 2 YL) 4 METHOXY PYRAN 2 ONE; ANTINEOPLASTIC AGENT; AUXARCONJUGATIN B; CASPASE; CYTOCHROME C; POLYENYLPYRROLE DERIVATIVE; PROTEIN BAX; PROTEIN BCL 2; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 78649528654     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100619x     Document Type: Article
Times cited : (56)

References (50)
  • 1
    • 0034630167 scopus 로고    scopus 로고
    • Induction of apoptosis by cancer chemotherapy
    • Kaufmann, S. H.; Earnshaw, W. C. Induction of apoptosis by cancer chemotherapy Exp. Cell Res. 2000, 256, 42-49
    • (2000) Exp. Cell Res. , vol.256 , pp. 42-49
    • Kaufmann, S.H.1    Earnshaw, W.C.2
  • 2
    • 33746886979 scopus 로고    scopus 로고
    • Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy
    • Fulda, S.; Debatin, K. M. Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy Oncogene 2006, 25, 4798-4811
    • (2006) Oncogene , vol.25 , pp. 4798-4811
    • Fulda, S.1    Debatin, K.M.2
  • 3
    • 0242656497 scopus 로고    scopus 로고
    • Death receptor-induced cell killing
    • Thorburn, A. Death receptor-induced cell killing Cell. Signalling 2004, 16, 139-144
    • (2004) Cell. Signalling , vol.16 , pp. 139-144
    • Thorburn, A.1
  • 4
    • 0345276414 scopus 로고    scopus 로고
    • Bcl-2-family proteins and the role of mitochondria in apoptosis
    • Kuwana, T.; Newmeyer, D. D. Bcl-2-family proteins and the role of mitochondria in apoptosis Curr. Opin. Cell Biol. 2003, 15, 691-699
    • (2003) Curr. Opin. Cell Biol. , vol.15 , pp. 691-699
    • Kuwana, T.1    Newmeyer, D.D.2
  • 5
    • 3943071150 scopus 로고    scopus 로고
    • Cytochrome C-mediated apoptosis
    • Jiang, X.; Wang, X. Cytochrome C-mediated apoptosis Annu. Rev. Biochem. 2004, 73, 87-106
    • (2004) Annu. Rev. Biochem. , vol.73 , pp. 87-106
    • Jiang, X.1    Wang, X.2
  • 6
    • 66249095944 scopus 로고    scopus 로고
    • A dihydrobenzofuran lignan induces cell death by modulating mitochondrial pathway and G2/M cell cycle arrest
    • Bose, J. S.; Gangan, V.; Prakash, R.; Jain, S. K.; Manna, S. K. A dihydrobenzofuran lignan induces cell death by modulating mitochondrial pathway and G2/M cell cycle arrest J. Med. Chem. 2009, 52, 3184-3190
    • (2009) J. Med. Chem. , vol.52 , pp. 3184-3190
    • Bose, J.S.1    Gangan, V.2    Prakash, R.3    Jain, S.K.4    Manna, S.K.5
  • 8
    • 0026030568 scopus 로고
    • Chemistry and biology of the immunophilins and their immunosuppressive ligands
    • Schreiber, S. L. Chemistry and biology of the immunophilins and their immunosuppressive ligands Science 1991, 251, 283-287
    • (1991) Science , vol.251 , pp. 283-287
    • Schreiber, S.L.1
  • 9
    • 0026575583 scopus 로고
    • Natural products as probes in the study of cellular functions. Investigation of immunophilins
    • Rosen, M. K.; Schreiber, S. L. Natural products as probes in the study of cellular functions. Investigation of immunophilins Angew. Chem., Int. Ed. Engl. 1992, 31, 384-400
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 384-400
    • Rosen, M.K.1    Schreiber, S.L.2
  • 10
    • 0002782054 scopus 로고
    • Control of nosema disease of honeybees with fumagillin
    • Katznelson, H.; Jamieson, C. A. Control of nosema disease of honeybees with fumagillin Science 1952, 115, 70-71
    • (1952) Science , vol.115 , pp. 70-71
    • Katznelson, H.1    Jamieson, C.A.2
  • 11
    • 0001404141 scopus 로고
    • Fumagillin (H-3), a new antibiotic with amebicidal properties
    • McCowen, M. C.; Callender, M. E.; Lawlis, J. F., Jr. Fumagillin (H-3), a new antibiotic with amebicidal properties Science 1951, 113, 202-203
    • (1951) Science , vol.113 , pp. 202-203
    • McCowen, M.C.1    Callender, M.E.2    Lawlis, Jr.J.F.3
  • 12
    • 33644760244 scopus 로고    scopus 로고
    • Polyenylpyrroles and polyenylfurans from an Australian isolate of the soil ascomycete Gymnoascus reessii
    • Clark, B. R.; Capon, R. J.; Lacey, E.; Tennant, S.; Gill, J. H. Polyenylpyrroles and polyenylfurans from an Australian isolate of the soil ascomycete Gymnoascus reessii Org. Lett. 2006, 8, 701-704
    • (2006) Org. Lett. , vol.8 , pp. 701-704
    • Clark, B.R.1    Capon, R.J.2    Lacey, E.3    Tennant, S.4    Gill, J.H.5
  • 13
    • 0027293455 scopus 로고
    • Rumbrin, a new cytoprotective substance produced by Auxarthron umbrinum: I - Taxonomy, production, isolation and biological activities
    • Yamagishi, Y.; Matsuoka, M.; Odagawa, A.; Kato, S.; Shindo, K.; Mochizuki, J. Rumbrin, a new cytoprotective substance produced by Auxarthron umbrinum. I. Taxonomy, production, isolation and biological activities J. Antibiot. 1993, 46, 884-887 (Pubitemid 23235535)
    • (1993) Journal of Antibiotics , vol.46 , Issue.6 , pp. 884-887
    • Yamagishi, Y.1    Matsuoka, M.2    Odagawa, A.3    Kato, S.4    Shindo, K.5    Mochizuki, J.6
  • 14
    • 0027181571 scopus 로고
    • Rumbrin, a new cytoprotective substance produced by Auxarthron umbrinum: II - Physico-chemical properties and structure determination
    • Yamagishi, Y.; Shindo, K.; Kawai, H. Rumbrin, a new cytoprotective substance produced by Auxarthron umbrinum. II. Physico-chemical properties and structure determination J. Antibiot. 1993, 46, 888-891 (Pubitemid 23235536)
    • (1993) Journal of Antibiotics , vol.46 , Issue.6 , pp. 888-891
    • Yamagishi, Y.1    Shindo, K.2    Kawai, H.3
  • 15
    • 0032831613 scopus 로고    scopus 로고
    • Three pyrrolyloctatetraenyl-alpha-pyrones from Auxarthron conjugatum
    • Hosoe, T.; Fukushima, K.; Takizawa, K.; Miyaji, M.; Kawai, K.-I. Three pyrrolyloctatetraenyl-alpha-pyrones from Auxarthron conjugatum Phytochemistry 1999, 52, 459-463
    • (1999) Phytochemistry , vol.52 , pp. 459-463
    • Hosoe, T.1    Fukushima, K.2    Takizawa, K.3    Miyaji, M.4    Kawai, K.-I.5
  • 16
    • 34249069183 scopus 로고    scopus 로고
    • The effect of halide salts on the production of Gymnoascus reessii polyenylpyrroles
    • Clark, B. R.; Lacey, E.; Gill, J. H.; Capon, R. J. The effect of halide salts on the production of Gymnoascus reessii polyenylpyrroles J. Nat. Prod. 2007, 70, 665-667
    • (2007) J. Nat. Prod. , vol.70 , pp. 665-667
    • Clark, B.R.1    Lacey, E.2    Gill, J.H.3    Capon, R.J.4
  • 17
    • 70350509072 scopus 로고    scopus 로고
    • Discovery of new natural products by intact-cell mass spectrometry and LC-SPE-NMR: Malbranpyrroles, novel polyketides from thermophilic fungus Malbranchea sulfurea
    • Yang, Y.-L.; Liao, W.-Y.; Liu, W.-Y.; Liaw, C. C.; Shen, C.-N.; Huang, Z.-Y.; Wu., S.-H. Discovery of new natural products by intact-cell mass spectrometry and LC-SPE-NMR: malbranpyrroles, novel polyketides from thermophilic fungus Malbranchea sulfurea Chem.-Eur. J. 2009, 15, 11573-11580
    • (2009) Chem.-Eur. J. , vol.15 , pp. 11573-11580
    • Yang, Y.-L.1    Liao, W.-Y.2    Liu, W.-Y.3    Liaw, C.C.4    Shen, C.-N.5    Huang, Z.-Y.6    Wu, S.-H.7
  • 18
    • 33845939119 scopus 로고    scopus 로고
    • Total synthesis of gymnoconjugatins A and B
    • Coleman, R. S.; Walczak, M. C. Total synthesis of gymnoconjugatins A and B J. Org. Chem. 2006, 71, 9841-9844
    • (2006) J. Org. Chem. , vol.71 , pp. 9841-9844
    • Coleman, R.S.1    Walczak, M.C.2
  • 19
    • 20444484806 scopus 로고    scopus 로고
    • Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. rapid, one-pot assembly of polyene systems
    • Coleman, R. S.; Walczak, M. C. Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. rapid, one-pot assembly of polyene systems Org. Lett. 2005, 7, 2289-2291
    • (2005) Org. Lett. , vol.7 , pp. 2289-2291
    • Coleman, R.S.1    Walczak, M.C.2
  • 20
    • 30444433269 scopus 로고
    • Copper and cobalt mediated regioselective alkylation of polyketide models: Methyl 3,5-dioxohexanoate and triacetic acid lactone
    • Cervello, J.; Marquet, J.; Moreno-Mañas, M. Copper and cobalt mediated regioselective alkylation of polyketide models: methyl 3,5-dioxohexanoate and triacetic acid lactone Tetrahedron 1990, 46, 2035-2046
    • (1990) Tetrahedron , vol.46 , pp. 2035-2046
    • Cervello, J.1    Marquet, J.2    Moreno-Mañas, M.3
  • 21
    • 27744559331 scopus 로고    scopus 로고
    • Synthesis of new series of 1-aryl-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic acid as potential antibacterial agents
    • Nagawade, R. R.; Khanna, V. V.; Bhagwat, S. S.; Shinde, D. B. Synthesis of new series of 1-aryl-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic acid as potential antibacterial agents Eur. J. Med. Chem. 2005, 40, 1325-1330
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 1325-1330
    • Nagawade, R.R.1    Khanna, V.V.2    Bhagwat, S.S.3    Shinde, D.B.4
  • 22
    • 0034701604 scopus 로고    scopus 로고
    • The "hirao reduction" revisited: A procedure for the synthesis of terminal vinyl bromides by the reduction of 1,1-dibromoalkenes
    • Abbas, S.; Hayes, C. J.; Worden, S. The "Hirao reduction" revisited: a procedure for the synthesis of terminal vinyl bromides by the reduction of 1,1-dibromoalkenes Tetrahedron Lett. 2000, 41, 3215-3219
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3215-3219
    • Abbas, S.1    Hayes, C.J.2    Worden, S.3
  • 23
    • 0033605767 scopus 로고    scopus 로고
    • Synthesis of 2-acyl-3-chloropyrroles: Application to the synthesis of the trail pheromone of the ant Atta texana
    • Abbaspour Tehrani, K.; Borremans, D.; De Kimpe, N. Synthesis of 2-acyl-3-chloropyrroles: application to the synthesis of the trail pheromone of the ant Atta texana Tetrahedron 1999, 55, 4133-4152
    • (1999) Tetrahedron , vol.55 , pp. 4133-4152
    • Abbaspour Tehrani, K.1    Borremans, D.2    De Kimpe, N.3
  • 25
    • 0037019541 scopus 로고    scopus 로고
    • Callipeltoside A: Total synthesis, assignment of the absolute and relative configuration, and evaluation of synthetic analogues
    • Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. Callipeltoside A: total synthesis, assignment of the absolute and relative configuration, and evaluation of synthetic analogues J. Am. Chem. Soc. 2002, 124, 10396-10415
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10396-10415
    • Trost, B.M.1    Gunzner, J.L.2    Dirat, O.3    Rhee, Y.H.4
  • 26
    • 0035844707 scopus 로고    scopus 로고
    • An olefination approach to the enantioselective syntheses of several styryllactones
    • Harris, J. M.; O'Doherty, G. A. An olefination approach to the enantioselective syntheses of several styryllactones Tetrahedron 2001, 57, 5161-5171
    • (2001) Tetrahedron , vol.57 , pp. 5161-5171
    • Harris, J.M.1    O'Doherty, G.A.2
  • 27
    • 0028288470 scopus 로고
    • Synthesis of a photoactivatable 9- Z -oleic acid for protein kinase C labeling
    • Rühmann, A.; Wentrup, C. Synthesis of a photoactivatable 9- Z -oleic acid for protein kinase C labeling Tetrahedron 1994, 50, 3785-3796
    • (1994) Tetrahedron , vol.50 , pp. 3785-3796
    • Rühmann, A.1    Wentrup, C.2
  • 28
    • 0035971917 scopus 로고    scopus 로고
    • Synthesis of the novel 1,7,9-trioxadispiro[4.1.5.2]-tetradecane ring system present in the spirolides
    • Caprio, V.; Brimble, M. A.; Furkert, D. P. Synthesis of the novel 1,7,9-trioxadispiro[4.1.5.2]-tetradecane ring system present in the spirolides Tetrahedron 2001, 57, 4023-4034
    • (2001) Tetrahedron , vol.57 , pp. 4023-4034
    • Caprio, V.1    Brimble, M.A.2    Furkert, D.P.3
  • 29
    • 34249069183 scopus 로고    scopus 로고
    • The effect of halide salts on the production of Gymnoascus reessii polyenylpyrroles
    • Clark, B. R.; Lacey, E.; Gill, J. H.; Capon, R. J. The effect of halide salts on the production of Gymnoascus reessii polyenylpyrroles J. Nat. Prod. 2007, 70, 665-667
    • (2007) J. Nat. Prod. , vol.70 , pp. 665-667
    • Clark, B.R.1    Lacey, E.2    Gill, J.H.3    Capon, R.J.4
  • 30
    • 58149278881 scopus 로고    scopus 로고
    • Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions
    • Yin, G.; Gao, M.; Wang, Z.; Wu, Y.; Wu, A. Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions Bull. Chem. Soc. Jpn. 2008, 81, 369-372
    • (2008) Bull. Chem. Soc. Jpn. , vol.81 , pp. 369-372
    • Yin, G.1    Gao, M.2    Wang, Z.3    Wu, Y.4    Wu, A.5
  • 31
    • 0001221639 scopus 로고
    • Preparation of halomethaneboronates
    • Wuts, P. G. M.; Thompson, P. A. Preparation of halomethaneboronates J. Organomet. Chem. 1982, 234, 137-141
    • (1982) J. Organomet. Chem. , vol.234 , pp. 137-141
    • Wuts, P.G.M.1    Thompson, P.A.2
  • 32
    • 0141799739 scopus 로고    scopus 로고
    • Gleevec (STI-571) inhibits lung cancer call growth (A549) and potentiates the cisplatin effect in vitro
    • Zhang, W.; Gao, W. Y.; Turner, S.; Ducatman, B. S. Gleevec (STI-571) inhibits lung cancer call growth (A549) and potentiates the cisplatin effect in vitro Mol. Cancer 2003, 2, 1-9
    • (2003) Mol. Cancer , vol.2 , pp. 1-9
    • Zhang, W.1    Gao, W.Y.2    Turner, S.3    Ducatman, B.S.4
  • 33
    • 0037564046 scopus 로고    scopus 로고
    • Vitamin C inhibits FAS-induced apoptosis in monocytes and U937 cells
    • Perez-Cruz, I.; Carcamo, J. M.; Golde, D. W. Vitamin C inhibits FAS-induced apoptosis in monocytes and U937 cells Blood 2003, 102, 336-343
    • (2003) Blood , vol.102 , pp. 336-343
    • Perez-Cruz, I.1    Carcamo, J.M.2    Golde, D.W.3
  • 34
    • 4544250814 scopus 로고    scopus 로고
    • Reactive oxygen species produced by NAD(P)H oxidase inhibit apopotosis in pancreatic cancer cells
    • Vaquero, E. C.; Edderkaoui, M.; Pandol, S. J.; Gukovsky, I.; Gukovskaya, A. S. Reactive oxygen species produced by NAD(P)H oxidase inhibit apopotosis in pancreatic cancer cells J. Biol. Chem. 2004, 279, 34643-34654
    • (2004) J. Biol. Chem. , vol.279 , pp. 34643-34654
    • Vaquero, E.C.1    Edderkaoui, M.2    Pandol, S.J.3    Gukovsky, I.4    Gukovskaya, A.S.5
  • 35
    • 66249095944 scopus 로고    scopus 로고
    • A dihydrobenzofuran lignan induces cell death by modulating mitochondrial pathway and G2/M cell cycle arrest
    • Bose, J. S.; Gangan, V.; Prakash, R.; Jain, S. K.; Manna, S. K. A dihydrobenzofuran lignan induces cell death by modulating mitochondrial pathway and G2/M cell cycle arrest J. Med. Chem. 2009, 52, 3184-3190
    • (2009) J. Med. Chem. , vol.52 , pp. 3184-3190
    • Bose, J.S.1    Gangan, V.2    Prakash, R.3    Jain, S.K.4    Manna, S.K.5
  • 36
    • 0042577026 scopus 로고    scopus 로고
    • Vincristine induced apoptosis in acute lymphoblastic leukemia cells: A mitochondrial pathway regulated by reactive oxygen species
    • Croninge, E.; Meeuwsen-De Boer, G. J.; De Graaf, S. S. N.; Kamps, W. A.; De Bont, E. S. J. M. Vincristine induced apoptosis in acute lymphoblastic leukemia cells: a mitochondrial pathway regulated by reactive oxygen species Int. J. Oncol. 2002, 21, 1339-1345
    • (2002) Int. J. Oncol. , vol.21 , pp. 1339-1345
    • Croninge, E.1    Meeuwsen-De Boer, G.J.2    De Graaf, S.S.N.3    Kamps, W.A.4    De Bont, E.S.J.M.5
  • 37
    • 0036899079 scopus 로고    scopus 로고
    • Apoptosomes: Engines for caspase activation
    • Adams, J. M.; Cory, S. Apoptosomes: engines for caspase activation Curr. Opin. Cell Biol. 2002, 14, 715-720
    • (2002) Curr. Opin. Cell Biol. , vol.14 , pp. 715-720
    • Adams, J.M.1    Cory, S.2
  • 38
    • 0034058683 scopus 로고    scopus 로고
    • Distinct stages of cytochrome c release from mitochondria: Evidence for a feedback amplification loop linking caspase activation to mitochondrial dysfunction in genotoxic stress induced apoptosis
    • Chen, Q.; Gong, B.; Almasan, A. Distinct stages of cytochrome c release from mitochondria: evidence for a feedback amplification loop linking caspase activation to mitochondrial dysfunction in genotoxic stress induced apoptosis Cell Death Differ. 2000, 7, 227-233
    • (2000) Cell Death Differ. , vol.7 , pp. 227-233
    • Chen, Q.1    Gong, B.2    Almasan, A.3
  • 39
    • 0032800354 scopus 로고    scopus 로고
    • Early release and subsequent c aspase-mediated degradation of cytochrome c in apoptotic cerebellar granule cells
    • Bobba, A.; Atlante, A.; Giannattasio, S.; Sgaramella, P.; Calissano, P.; Marra, E. Early release and subsequent c aspase-mediated degradation of cytochrome c in apoptotic cerebellar granule cells FEBS Lett. 1999, 457, 126-130
    • (1999) FEBS Lett. , vol.457 , pp. 126-130
    • Bobba, A.1    Atlante, A.2    Giannattasio, S.3    Sgaramella, P.4    Calissano, P.5    Marra, E.6
  • 40
    • 0344009736 scopus 로고    scopus 로고
    • N -Caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3
    • Park, J. B.; Schonen, N. N -Caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3 Cancer Lett. 2003, 202, 161-171
    • (2003) Cancer Lett. , vol.202 , pp. 161-171
    • Park, J.B.1    Schonen, N.2
  • 41
    • 0030752756 scopus 로고    scopus 로고
    • 2/Bax ratios in chronic lymphocytic leukaemia and their correlation with in vitro apoptosis and clinical resistance
    • 2/Bax ratios in chronic lymphocytic leukaemia and their correlation with in vitro apoptosis and clinical resistance Br. J. Cancer 1997, 76, 935-938
    • (1997) Br. J. Cancer , vol.76 , pp. 935-938
    • Pepper, C.1    Hoy, T.2    Bently, D.P.3
  • 46
    • 0033591217 scopus 로고    scopus 로고
    • P53 suppresses the activation of the Bcl-2 promoter by the Brn-3a POU family transcription factor
    • Budhram-Mahadeo, V.; Morris, P. J.; Smith, M. D.; Midgley, C. A.; Boxer, L. M.; Latchman, D. S. p53 suppresses the activation of the Bcl-2 promoter by the Brn-3a POU family transcription factor J. Biol. Chem. 1999, 274, 15237-15244
    • (1999) J. Biol. Chem. , vol.274 , pp. 15237-15244
    • Budhram-Mahadeo, V.1    Morris, P.J.2    Smith, M.D.3    Midgley, C.A.4    Boxer, L.M.5    Latchman, D.S.6
  • 48
    • 0028883179 scopus 로고
    • Tumor suppressor p53 is a direct transcriptional activator of the human bax gene
    • Miyashita, T.; Reed, J. C. Tumor suppressor p53 is a direct transcriptional activator of the human bax gene Cell 1995, 80, 293-299
    • (1995) Cell , vol.80 , pp. 293-299
    • Miyashita, T.1    Reed, J.C.2
  • 49
    • 0346873049 scopus 로고    scopus 로고
    • Anticancer therapy targeting the apoptotic pathway
    • Hu, W.; Kavanagh, J. J. Anticancer therapy targeting the apoptotic pathway Lancet Oncol. 2003, 4, 921-729
    • (2003) Lancet Oncol. , vol.4 , pp. 921-729
    • Hu, W.1    Kavanagh, J.J.2
  • 50
    • 0028943734 scopus 로고
    • Apoptosis in the pathogenesis and treatment of disease
    • Thompson, C. B. Apoptosis in the pathogenesis and treatment of disease Science 1995, 267, 1456-1462
    • (1995) Science , vol.267 , pp. 1456-1462
    • Thompson, C.B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.