메뉴 건너뛰기




Volumn 53, Issue 21, 2010, Pages 7647-7663

Targeting the polyamine transport system with benzazepine- and azepine-polyamine conjugates

Author keywords

[No Author keywords available]

Indexed keywords

3,3' DIAMINODIPROPYLAMINE; AMIDINE; AZEPINE DERIVATIVE; BENZAZEPINE DERIVATIVE; ETHER DERIVATIVE; IMINOETHER DERIVATIVE; LACTAM; N 1 (4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) 6,7 DIHYDROXYSPERMINE; N 1 (4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) NORSPERMINE; N 1 (4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) OCTANE 1,8 DIAMINE; N 1 (4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) PUTRESCINE; N 1 (4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) SPERMIDINE; N 1 (4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) SPERMINE; N 1 (4,5 DIHYDRO 3H AZEPIN 2 YL) AZANONANE 1,9 DIAMINE; N 1 (4,5 DIHYDRO 3H AZEPIN 2 YL) NORSPERMIDINE; N 1 (4,5 DIHYDRO 3H AZEPIN 2 YL) OCTANE 1,8 DIAMINE; N 1 (4,5 DIHYDRO 3H AZEPIN 2 YL) SPERMIDINE; N 1 (4,5 DIHYDRO 3H AZEPIN 2 YL) SPERMINE; N 1 (7 AMINO 4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) SPERMINE; N 1 (7 BROMO 4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) SPERMINE; N 1 (7 METHOXY 4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) SPERMINE; N 1 (7 NITRO 4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) SPERMINE; N 8 (4,5 DIHYDRO 3H AZEPIN 2 YL) SPERMIDINE; N1 (4,5 DIHYDRO 3H 1 BENZAZEPIN 2 YL) HOMOSPERMINE; NITROBENZAZEPINE; PUTRESCINE; SPERMIDINE; SPERMINE; THIOLACTAM; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 78149242572     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1007648     Document Type: Article
Times cited : (33)

References (81)
  • 1
    • 0035002972 scopus 로고    scopus 로고
    • Polyamine uptake systems in Escherichia coli
    • Igarashi, K.; Ito, K.; Kashiwagi, K. Polyamine uptake systems in Escherichia coli Res. Microbiol. 2001, 152, 271-278
    • (2001) Res. Microbiol. , vol.152 , pp. 271-278
    • Igarashi, K.1    Ito, K.2    Kashiwagi, K.3
  • 2
    • 0033572636 scopus 로고    scopus 로고
    • Polyamine transport in bacteria and yeast
    • Igarashi, K.; Kashiwagi, K. Polyamine transport in bacteria and yeast Biochem. J. 1999, 344, 633-642
    • (1999) Biochem. J. , vol.344 , pp. 633-642
    • Igarashi, K.1    Kashiwagi, K.2
  • 3
    • 17644403556 scopus 로고    scopus 로고
    • Identification and characterization of a polyamine permease from the protozoan parasite Leishmania major
    • Hasne, M. P.; Ullman, B. Identification and characterization of a polyamine permease from the protozoan parasite Leishmania major J. Biol. Chem. 2005, 280, 15188-15194
    • (2005) J. Biol. Chem. , vol.280 , pp. 15188-15194
    • Hasne, M.P.1    Ullman, B.2
  • 4
    • 77950255730 scopus 로고    scopus 로고
    • A high-affinity putrescine-cadaverine transporter from Trypanosoma cruzi
    • Hasne, M. P.; Coppens, I.; Soysa, R.; Ullman, B. A high-affinity putrescine-cadaverine transporter from Trypanosoma cruzi Mol. Microbiol. 2010, 76, 78-91
    • (2010) Mol. Microbiol. , vol.76 , pp. 78-91
    • Hasne, M.P.1    Coppens, I.2    Soysa, R.3    Ullman, B.4
  • 6
    • 0033104906 scopus 로고    scopus 로고
    • Proteoglycan involvement in polyamine uptake
    • Belting, M.; Persson, S.; Fransson, L. A. Proteoglycan involvement in polyamine uptake Biochem. J. 1999, 338, 317-323
    • (1999) Biochem. J. , vol.338 , pp. 317-323
    • Belting, M.1    Persson, S.2    Fransson, L.A.3
  • 7
    • 0037108939 scopus 로고    scopus 로고
    • Role of endocytosis in the internalization of spermidine-C(2)-BODIPY, a highly fluorescent probe of polyamine transport
    • Soulet, D.; Covassin, L.; Kaouass, M.; Charest-Gaudreault, R.; Audette, M.; Poulin, R. Role of endocytosis in the internalization of spermidine-C(2)-BODIPY, a highly fluorescent probe of polyamine transport Biochem. J. 2002, 367, 347-357
    • (2002) Biochem. J. , vol.367 , pp. 347-357
    • Soulet, D.1    Covassin, L.2    Kaouass, M.3    Charest-Gaudreault, R.4    Audette, M.5    Poulin, R.6
  • 8
    • 77953072049 scopus 로고    scopus 로고
    • The polyamine transport system as a target for anticancer drug development
    • Palmer, A. J.; Wallace, H. M. The polyamine transport system as a target for anticancer drug development Amino Acids 2010, 38, 415-422
    • (2010) Amino Acids , vol.38 , pp. 415-422
    • Palmer, A.J.1    Wallace, H.M.2
  • 9
    • 0141633535 scopus 로고    scopus 로고
    • Thirty years of polyamine-related approaches to cancer therapy. Retrospect and prospect. Part 1. Selective enzyme inhibitors
    • DOI 10.2174/1389450033490885
    • Seiler, N. Thirty years of polyamine-related approaches to cancer therapy. Retrospect and prospect. Part 1. Selective enzyme inhibitors Curr. Drug Targets 2003, 4, 537-564 (Pubitemid 37139049)
    • (2003) Current Drug Targets , vol.4 , Issue.7 , pp. 537-564
    • Seiler, N.1
  • 10
    • 0141761500 scopus 로고    scopus 로고
    • Thirty years of polyamine-related approaches to cancer therapy. Retrospect and prospect. Part 2. Structural analogues and derivatives
    • DOI 10.2174/1389450033490876
    • Seiler, N. Thirty years of polyamine-related approaches to cancer therapy. Retrospect and prospect. Part 2. Structural analogues and derivatives Curr. Drug Targets 2003, 4, 565-585 (Pubitemid 37139050)
    • (2003) Current Drug Targets , vol.4 , Issue.7 , pp. 565-585
    • Seiler, N.1
  • 12
    • 0025298549 scopus 로고
    • Polyamine transport in mammalian cells
    • Seiler, N.; Dezeure, F. Polyamine transport in mammalian cells Int. J. Biochem. 1990, 22, 211-218
    • (1990) Int. J. Biochem. , vol.22 , pp. 211-218
    • Seiler, N.1    Dezeure, F.2
  • 13
    • 0026596554 scopus 로고
    • Uptake and cytotoxicity of novel nitroimidazole-polyamine conjugates in Ehrlich ascites tumour cells
    • Holley, J.; Mather, A.; Cullis, P.; Symons, M. R.; Wardman, P.; Watt, R. A.; Cohen, G. M. Uptake and cytotoxicity of novel nitroimidazole-polyamine conjugates in Ehrlich ascites tumour cells Biochem. Pharmacol. 1992, 43, 763-769
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 763-769
    • Holley, J.1    Mather, A.2    Cullis, P.3    Symons, M.R.4    Wardman, P.5    Watt, R.A.6    Cohen, G.M.7
  • 15
    • 0032211359 scopus 로고    scopus 로고
    • Tumor-targeted apoptosis by a novel spermine analogue, 1,12-diaziridinyl-4,9-diazadodecane, results in therapeutic efficacy and enhanced radiosensitivity of human prostate cancer
    • Eiseman, J. L.; Rogers, F. A.; Guo, Y.; Kauffman, J.; Sentz, D. L.; Klinger, M. F.; Callery, P. S.; Kyprianou, N. Tumor-targeted apoptosis by a novel spermine analogue, 1,12-diaziridinyl-4,9-diazadodecane, results in therapeutic efficacy and enhanced radiosensitivity of human prostate cancer Cancer Res. 1998, 58, 4864-4870
    • (1998) Cancer Res. , vol.58 , pp. 4864-4870
    • Eiseman, J.L.1    Rogers, F.A.2    Guo, Y.3    Kauffman, J.4    Sentz, D.L.5    Klinger, M.F.6    Callery, P.S.7    Kyprianou, N.8
  • 17
    • 1242338910 scopus 로고    scopus 로고
    • Synthesis and DNA damaging ability of enediyne-polyamine conjugates
    • Suzuki, I.; Shigenaga, A.; Nemoto, H.; Shibuya, M. Synthesis and DNA damaging ability of enediyne-polyamine conjugates Tetrahedron Lett. 2004, 45, 1955-1959
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1955-1959
    • Suzuki, I.1    Shigenaga, A.2    Nemoto, H.3    Shibuya, M.4
  • 20
    • 33846597027 scopus 로고    scopus 로고
    • Amplification of DNA-binding affinities of protoberberine alkaloids by appended polyamines
    • Pang, J. Y.; Long, Y. H.; Chen, W. H.; Jiang, Z. H. Amplification of DNA-binding affinities of protoberberine alkaloids by appended polyamines Bioorg. Med. Chem. Lett. 2007, 17, 1018-1021
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 1018-1021
    • Pang, J.Y.1    Long, Y.H.2    Chen, W.H.3    Jiang, Z.H.4
  • 21
    • 0028142339 scopus 로고
    • The comparative toxicity of chlorambucil and chlorambucil-spermidine conjugate to BALB/c mice
    • Verschoyle, R. D.; Carthew, P.; Holley, J. L.; Cullis, P.; Cohen, G. M. The comparative toxicity of chlorambucil and chlorambucil-spermidine conjugate to BALB/c mice Cancer Lett. 1994, 85, 217-222
    • (1994) Cancer Lett. , vol.85 , pp. 217-222
    • Verschoyle, R.D.1    Carthew, P.2    Holley, J.L.3    Cullis, P.4    Cohen, G.M.5
  • 22
    • 0033214643 scopus 로고    scopus 로고
    • Probing the mechanism of transport and compartmentalisation of polyamines in mammalian cells
    • Cullis, P. M.; Green, R. E.; Merson-Davies, L.; Travis, N. Probing the mechanism of transport and compartmentalisation of polyamines in mammalian cells Chem. Biol. 1999, 6, 717-729
    • (1999) Chem. Biol. , vol.6 , pp. 717-729
    • Cullis, P.M.1    Green, R.E.2    Merson-Davies, L.3    Travis, N.4
  • 23
    • 0242691701 scopus 로고    scopus 로고
    • Defining the molecular requirements for the selective delivery of polyamine conjugates into cells containing active polyamine transporters
    • Wang, C.; Delcros, J. G.; Cannon, L.; Konate, F.; Carias, H.; Biggerstaff, J.; Gardner, R. A.; Phanstiel, O., 4th Defining the molecular requirements for the selective delivery of polyamine conjugates into cells containing active polyamine transporters J. Med. Chem. 2003, 46, 5129-5138
    • (2003) J. Med. Chem. , vol.46 , pp. 5129-5138
    • Wang, C.1    Delcros, J.G.2    Cannon, L.3    Konate, F.4    Carias, H.5    Biggerstaff, J.6    Gardner, R.A.7    Phanstiel IV, O.8
  • 25
    • 64249139629 scopus 로고    scopus 로고
    • Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system
    • Guminski, Y.; Grousseaud, M.; Cugnasse, S.; Brel, V.; Annereau, J. P.; Vispe, S.; Guilbaud, N.; Barret, J. M.; Bailly, C.; Imbert, T. Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system Bioorg. Med. Chem. Lett. 2009, 19, 2474-2477
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 2474-2477
    • Guminski, Y.1    Grousseaud, M.2    Cugnasse, S.3    Brel, V.4    Annereau, J.P.5    Vispe, S.6    Guilbaud, N.7    Barret, J.M.8    Bailly, C.9    Imbert, T.10
  • 27
    • 0023220612 scopus 로고
    • Chain-fluorinated polyamines as tumor markers-I. in vivo transformation of 2,2-difluoroputrescine into 6,6-difluorospermidine and 6,6-difluorospermine
    • Sarhan, S.; Knödgen, B.; Gerhart, F.; Seiler, N. Chain-fluorinated polyamines as tumor markers-I. In vivo transformation of 2,2-difluoroputrescine into 6,6-difluorospermidine and 6,6-difluorospermine Int. J. Biochem. 1987, 19, 843-852
    • (1987) Int. J. Biochem. , vol.19 , pp. 843-852
    • Sarhan, S.1    Knödgen, B.2    Gerhart, F.3    Seiler, N.4
  • 28
    • 0023953239 scopus 로고
    • Chain-fluorinated polyamines as tumour markers. III. Determination of geminal difluoropolyamines and their precursor 2,2-difluoroputrescine in normal tissues and experimental tumours by in vitro and in vivo 19F NMR spectroscopy
    • Hull, W. E.; Kunz, W.; Port, R. E.; Seiler, N. Chain-fluorinated polyamines as tumour markers. III. Determination of geminal difluoropolyamines and their precursor 2,2-difluoroputrescine in normal tissues and experimental tumours by in vitro and in vivo 19F NMR spectroscopy NMR Biomed. 1988, 1, 11-19
    • (1988) NMR Biomed. , vol.1 , pp. 11-19
    • Hull, W.E.1    Kunz, W.2    Port, R.E.3    Seiler, N.4
  • 29
    • 0024474541 scopus 로고
    • N -3-[18F]fluoropropylputrescine as potential PET imaging agent for prostate and prostate derived tumors
    • Hwang, D. R.; Lang, L. X.; Mathias, C. J.; Kadmon, D.; Welch, M. J. N -3-[18F]fluoropropylputrescine as potential PET imaging agent for prostate and prostate derived tumors J. Nucl. Med. 1989, 30, 1205-1210
    • (1989) J. Nucl. Med. , vol.30 , pp. 1205-1210
    • Hwang, D.R.1    Lang, L.X.2    Mathias, C.J.3    Kadmon, D.4    Welch, M.J.5
  • 30
    • 0030778447 scopus 로고    scopus 로고
    • Boron-containing polyamines as DNA targeting agents for neutron capture therapy of brain tumors: Synthesis and biological evaluation
    • Cai, J. P.; Soloway, A. H.; Barth, R. F.; Adams, D. M.; Hariharan, J. R.; Wyzlic, I. M.; Radcliffe, K. Boron-containing polyamines as DNA targeting agents for neutron capture therapy of brain tumors: synthesis and biological evaluation J. Med. Chem. 1997, 40, 3887-3896
    • (1997) J. Med. Chem. , vol.40 , pp. 3887-3896
    • Cai, J.P.1    Soloway, A.H.2    Barth, R.F.3    Adams, D.M.4    Hariharan, J.R.5    Wyzlic, I.M.6    Radcliffe, K.7
  • 31
    • 0033535562 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of boron-containing polyamines as potential agents for neutron capture therapy of brain tumors
    • Zhuo, J. C.; Cai, J. P.; Soloway, A. H.; Barth, R. F.; Adams, D. M.; Ji, W. H.; Tjarks, W. Synthesis and biological evaluation of boron-containing polyamines as potential agents for neutron capture therapy of brain tumors J. Med. Chem. 1999, 42, 1282-1292
    • (1999) J. Med. Chem. , vol.42 , pp. 1282-1292
    • Zhuo, J.C.1    Cai, J.P.2    Soloway, A.H.3    Barth, R.F.4    Adams, D.M.5    Ji, W.H.6    Tjarks, W.7
  • 32
    • 0035950083 scopus 로고    scopus 로고
    • N -Benzylpolyamines as vectors of boron and fluorine for cancer therapy and imaging: Synthesis and biological evaluation
    • Martin, B.; Posseme, F.; Le Barbier, C.; Carreaux, F.; Carboni, B.; Seiler, N.; Moulinoux, J. P.; Delcros, J. G. N -Benzylpolyamines as vectors of boron and fluorine for cancer therapy and imaging: synthesis and biological evaluation J. Med. Chem. 2001, 44, 3653-3664
    • (2001) J. Med. Chem. , vol.44 , pp. 3653-3664
    • Martin, B.1    Posseme, F.2    Le Barbier, C.3    Carreaux, F.4    Carboni, B.5    Seiler, N.6    Moulinoux, J.P.7    Delcros, J.G.8
  • 33
    • 0036315183 scopus 로고    scopus 로고
    • (Z)-1,4-Diamino-2-butene as a vector of boron, fluorine, or iodine for cancer therapy and imaging: Synthesis and biological evaluation
    • Martin, B.; Posseme, F.; Le Barbier, C.; Carreaux, F.; Carboni, B.; Seiler, N.; Moulinoux, J. P.; Delcros, J. G. (Z)-1,4-Diamino-2-butene as a vector of boron, fluorine, or iodine for cancer therapy and imaging: synthesis and biological evaluation Bioorg. Med. Chem. 2002, 10, 2863-2871
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 2863-2871
    • Martin, B.1    Posseme, F.2    Le Barbier, C.3    Carreaux, F.4    Carboni, B.5    Seiler, N.6    Moulinoux, J.P.7    Delcros, J.G.8
  • 37
    • 0042832967 scopus 로고    scopus 로고
    • Xylylated dimers of putrescine and polyamines: Influence of the polyamine backbone on spermidine transport inhibition
    • Covassin, L.; Desjardins, M.; Soulet, D.; Charest-Gaudreault, R.; Audette, M.; Poulin, R. Xylylated dimers of putrescine and polyamines: influence of the polyamine backbone on spermidine transport inhibition Bioorg. Med. Chem. Lett. 2003, 13, 3267-3271
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 3267-3271
    • Covassin, L.1    Desjardins, M.2    Soulet, D.3    Charest-Gaudreault, R.4    Audette, M.5    Poulin, R.6
  • 38
    • 64549132099 scopus 로고    scopus 로고
    • Lipophilic lysine-spermine conjugates are potent polyamine transport inhibitors for use in combination with a polyamine biosynthesis inhibitor
    • Burns, M. R.; Graminski, G. F.; Weeks, R. S.; Chen, Y.; O'Brien, T. G. Lipophilic lysine-spermine conjugates are potent polyamine transport inhibitors for use in combination with a polyamine biosynthesis inhibitor J. Med. Chem. 2009, 52, 1983-1993
    • (2009) J. Med. Chem. , vol.52 , pp. 1983-1993
    • Burns, M.R.1    Graminski, G.F.2    Weeks, R.S.3    Chen, Y.4    O'Brien, T.G.5
  • 39
    • 33645682384 scopus 로고    scopus 로고
    • Combination therapy with 2-difluoromethylornithine and a polyamine transport inhibitor against murine squamous cell carcinoma
    • Chen, Y.; Weeks, R. S.; Burns, M. R.; Boorman, D. W.; Klein-Szanto, A.; O'Brien, T. G. Combination therapy with 2-difluoromethylornithine and a polyamine transport inhibitor against murine squamous cell carcinoma Int. J. Cancer 2006, 118, 2344-2349
    • (2006) Int. J. Cancer , vol.118 , pp. 2344-2349
    • Chen, Y.1    Weeks, R.S.2    Burns, M.R.3    Boorman, D.W.4    Klein-Szanto, A.5    O'Brien, T.G.6
  • 40
    • 0038792284 scopus 로고    scopus 로고
    • Molecular requirements for targeting the polyamine transport system. Synthesis and biological evaluation of polyamine-anthracene conjugates
    • Wang, C.; Delcros, J. G.; Biggerstaff, J.; Phanstiel, O., 4th Molecular requirements for targeting the polyamine transport system. Synthesis and biological evaluation of polyamine-anthracene conjugates J. Med. Chem. 2003, 46, 2672-2682
    • (2003) J. Med. Chem. , vol.46 , pp. 2672-2682
    • Wang, C.1    Delcros, J.G.2    Biggerstaff, J.3    Phanstiel IV, O.4
  • 41
    • 0038240603 scopus 로고    scopus 로고
    • 1-(anthracen-9- ylmethyl)triamines as molecular recognition elements for the polyamine transporter
    • DOI 10.1021/jm030028w
    • Wang, C.; Delcros, J. G.; Biggerstaff, J.; Phanstiel, O., 4th Synthesis and biological evaluation of N 1-(anthracen-9-ylmethyl)triamines as molecular recognition elements for the polyamine transporter J. Med. Chem. 2003, 46, 2663-2671 (Pubitemid 36702535)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.13 , pp. 2663-2671
    • Wang, C.1    Delcros, J.-G.2    Biggerstaff, J.3    Phanstiel IV, O.4
  • 42
    • 8644275508 scopus 로고    scopus 로고
    • N 1-substituent effects in the selective delivery of polyamine conjugates into cells containing active polyamine transporters
    • Gardner, R. A.; Delcros, J. G.; Konate, F.; Breitbeil, F., 3rd; Martin, B.; Sigman, M.; Huang, M.; Phanstiel, O. t. N 1-substituent effects in the selective delivery of polyamine conjugates into cells containing active polyamine transporters J. Med. Chem. 2004, 47, 6055-6069
    • (2004) J. Med. Chem. , vol.47 , pp. 6055-6069
    • Gardner, R.A.1    Delcros, J.G.2    Konate, F.3    Breitbeil III, F.4    Martin, B.5    Sigman, M.6    Huang, M.7    Phanstiel, O.T.8
  • 44
    • 34547678624 scopus 로고    scopus 로고
    • Structure-activity investigations of polyamine-anthracene conjugates and their uptake via the polyamine transporter
    • Phanstiel, O. t.; Kaur, N.; Delcros, J. G. Structure-activity investigations of polyamine-anthracene conjugates and their uptake via the polyamine transporter Amino Acids 2007, 33, 305-313
    • (2007) Amino Acids , vol.33 , pp. 305-313
    • Phanstiel, O.T.1    Kaur, N.2    Delcros, J.G.3
  • 49
    • 0032576806 scopus 로고    scopus 로고
    • Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes
    • Geall, A. J.; Blagbrough, I. S. Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes Tetrahedron Lett. 1998, 39, 443-446
    • (1998) Tetrahedron Lett. , vol.39 , pp. 443-446
    • Geall, A.J.1    Blagbrough, I.S.2
  • 50
    • 0037459864 scopus 로고    scopus 로고
    • Synthesis of dihydroxylated polyamines from an erythronolactone
    • Le Roch, M.; Renault, J.; Penlaë, K.; Uriac, P. Synthesis of dihydroxylated polyamines from an erythronolactone Tetrahedron Lett. 2003, 44, 3451-3453
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3451-3453
    • Le Roch, M.1    Renault, J.2    Penlaë, K.3    Uriac, P.4
  • 51
    • 0030474273 scopus 로고    scopus 로고
    • Polyamine analogue regulation of NMDA MK-801 binding: A structure-activity study
    • Bergeron, R. J.; Weimar, W. R.; Wu, Q.; Feng, Y.; McManis, J. S. Polyamine analogue regulation of NMDA MK-801 binding: a structure-activity study J. Med. Chem. 1996, 39, 5257-5266
    • (1996) J. Med. Chem. , vol.39 , pp. 5257-5266
    • Bergeron, R.J.1    Weimar, W.R.2    Wu, Q.3    Feng, Y.4    McManis, J.S.5
  • 52
    • 0000323257 scopus 로고
    • Beckmann rearrangements. An investigation of special cases
    • Horning, V. L.; Stromberg, E. C.; Loyd, H. A. Beckmann rearrangements. An investigation of special cases J. Am. Chem. Soc. 1952, 74, 5153-5155
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 5153-5155
    • Horning, V.L.1    Stromberg, E.C.2    Loyd, H.A.3
  • 54
    • 0021331996 scopus 로고
    • Synthesis and beta-adrenergic blocking activity of 2-(N -substituted amino)-1,2,3,4-tetrahydronaphtalen-1-ol derivatives
    • Itoh, K.; Miyake, A.; Tada, N.; Hirata, M.; Oka, Y. Synthesis and beta-adrenergic blocking activity of 2-(N -substituted amino)-1,2,3,4- tetrahydronaphtalen-1-ol derivatives Chem. Pharm. Bull. (Tokyo) 1984, 32, 130-151
    • (1984) Chem. Pharm. Bull. (Tokyo) , vol.32 , pp. 130-151
    • Itoh, K.1    Miyake, A.2    Tada, N.3    Hirata, M.4    Oka, Y.5
  • 55
    • 78149257209 scopus 로고
    • Synthesis of 7-mercapto-2,3,4,5-tetrahydro-1 H -1-benzazepin-2-one
    • Osadchii, S. A.; Kochubei, N. V. Synthesis of 7-mercapto-2,3,4,5- tetrahydro-1 H -1-benzazepin-2-one Russ. J. Appl. Chem. 1994, 67, 1674-1676
    • (1994) Russ. J. Appl. Chem. , vol.67 , pp. 1674-1676
    • Osadchii, S.A.1    Kochubei, N.V.2
  • 56
    • 0020569610 scopus 로고
    • Synthesis of 7-phenylpyrimido[5,4- d ][1]benzazepin-2-ones
    • Chen, W. Y.; Gilman, N. W. Synthesis of 7-phenylpyrimido[5,4- d ][1]benzazepin-2-ones J. Heterocycl. Chem. 1983, 20, 663-666
    • (1983) J. Heterocycl. Chem. , vol.20 , pp. 663-666
    • Chen, W.Y.1    Gilman, N.W.2
  • 58
    • 0343104969 scopus 로고
    • Chemical reactions of caprolactam
    • Benson, R. E.; Cairns, T. L. Chemical reactions of caprolactam J. Am. Chem. Soc. 1948, 70, 2115-2118
    • (1948) J. Am. Chem. Soc. , vol.70 , pp. 2115-2118
    • Benson, R.E.1    Cairns, T.L.2
  • 59
    • 0011973012 scopus 로고
    • A convenient general synthesis of amidines
    • Weintraub, L.; Oles, S. R.; Kalish, N. A. A convenient general synthesis of amidines J. Org. Chem. 1968, 33, 1679-1681
    • (1968) J. Org. Chem. , vol.33 , pp. 1679-1681
    • Weintraub, L.1    Oles, S.R.2    Kalish, N.A.3
  • 60
    • 0026696758 scopus 로고
    • Pyrrolo[2,1- c ][1,4]benzodiazepines: A mild conversion of thiolactam into amidine
    • Foloppe, M. P.; Rault, S.; Robba, M. Pyrrolo[2,1- c ][1,4] benzodiazepines: a mild conversion of thiolactam into amidine Tetrahedron Lett. 1992, 33, 2803-2804
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2803-2804
    • Foloppe, M.P.1    Rault, S.2    Robba, M.3
  • 61
    • 0019326479 scopus 로고
    • Intracellular putrescine and spermidine deprivation induces increased uptake of the natural polyamines and methylglyoxal bis(guanylhydrazone)
    • Alhonen-Hongisto, L.; Seppanen, P.; Janne, J. Intracellular putrescine and spermidine deprivation induces increased uptake of the natural polyamines and methylglyoxal bis(guanylhydrazone) Biochem. J. 1980, 192, 941-945
    • (1980) Biochem. J. , vol.192 , pp. 941-945
    • Alhonen-Hongisto, L.1    Seppanen, P.2    Janne, J.3
  • 62
    • 0018233850 scopus 로고
    • Isolation of mutant mammalian cells altered in polyamine transport
    • Mandel, J. L.; Flintoff, W. F. Isolation of mutant mammalian cells altered in polyamine transport J. Cell Physiol. 1978, 97, 335-344
    • (1978) J. Cell Physiol. , vol.97 , pp. 335-344
    • Mandel, J.L.1    Flintoff, W.F.2
  • 64
    • 0024215527 scopus 로고
    • Chain-fluorinated polyamines as tumor markers-IV. Comparison of 2-fluoroputrescine and 2,2-difluoroputrescine as substrates of spermidine synthase in vitro and in vivo
    • Dezeure, F.; Sarhan, S.; seiler, N. Chain-fluorinated polyamines as tumor markers-IV. Comparison of 2-fluoroputrescine and 2,2-difluoroputrescine as substrates of spermidine synthase in vitro and in vivo Int. J. Biochem. 1988, 20, 1299-1312
    • (1988) Int. J. Biochem. , vol.20 , pp. 1299-1312
    • Dezeure, F.1    Sarhan, S.2    Seiler, N.3
  • 66
    • 0026697676 scopus 로고
    • Increased survival of L1210 leukemic mice by prevention of the utilization of extracellular polyamines. Studies using a polyamine-uptake mutant, antibiotics and a polyamine-deficient diet
    • Ask, A.; Persson, L.; Heby, O. Increased survival of L1210 leukemic mice by prevention of the utilization of extracellular polyamines. Studies using a polyamine-uptake mutant, antibiotics and a polyamine-deficient diet Cancer Lett. 1992, 66, 29-34
    • (1992) Cancer Lett. , vol.66 , pp. 29-34
    • Ask, A.1    Persson, L.2    Heby, O.3
  • 67
    • 0024596627 scopus 로고
    • The gastrointestinal tract as polyamine source for tumor growth
    • Sarhan, S.; Knödgen, B.; Seiler, N. The gastrointestinal tract as polyamine source for tumor growth Anticancer Res. 1989, 9, 215-224
    • (1989) Anticancer Res. , vol.9 , pp. 215-224
    • Sarhan, S.1    Knödgen, B.2    Seiler, N.3
  • 69
    • 0016176960 scopus 로고
    • Elevation of putrescine and spermidine in sera of patients with solid tumors
    • Nishioka, K.; Romsdahl, M. M. Elevation of putrescine and spermidine in sera of patients with solid tumors Clin. Chim. Acta 1974, 57, 155-161
    • (1974) Clin. Chim. Acta , vol.57 , pp. 155-161
    • Nishioka, K.1    Romsdahl, M.M.2
  • 70
    • 0016277319 scopus 로고
    • Increased polyamine concentrations in the cerebrospinal fluid of patients with brain tumors
    • Marton, L. J.; Heby, O.; Wilson, C. B. Increased polyamine concentrations in the cerebrospinal fluid of patients with brain tumors Int. J. Cancer 1974, 14, 731-735
    • (1974) Int. J. Cancer , vol.14 , pp. 731-735
    • Marton, L.J.1    Heby, O.2    Wilson, C.B.3
  • 71
    • 0025191132 scopus 로고
    • Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer
    • Loser, C.; Folsch, U. R.; Paprotny, C.; Creutzfeldt, W. Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer Pancreas 1990, 5, 119-127
    • (1990) Pancreas , vol.5 , pp. 119-127
    • Loser, C.1    Folsch, U.R.2    Paprotny, C.3    Creutzfeldt, W.4
  • 72
    • 0025060872 scopus 로고
    • Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer
    • Loser, C.; Folsch, U. R.; Paprotny, C.; Creutzfeldt, W. Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer Cancer 1990, 65, 958-966
    • (1990) Cancer , vol.65 , pp. 958-966
    • Loser, C.1    Folsch, U.R.2    Paprotny, C.3    Creutzfeldt, W.4
  • 73
    • 0028863744 scopus 로고
    • Determination of polyamines in serum by high-performance capillary zone electrophoresis with indirect ultraviolet detection
    • Zhou, G.; Yu, Q.; Ma, Y.; Xue, J.; Zhang, Y.; Lin, B. Determination of polyamines in serum by high-performance capillary zone electrophoresis with indirect ultraviolet detection J. Chromatogr., A 1995, 717, 345-349
    • (1995) J. Chromatogr., A , vol.717 , pp. 345-349
    • Zhou, G.1    Yu, Q.2    Ma, Y.3    Xue, J.4    Zhang, Y.5    Lin, B.6
  • 74
    • 38749095159 scopus 로고    scopus 로고
    • Analysis of polyamines as carbamoyl derivatives in urine and serum by liquid chromatography-tandem mass spectrometry
    • Byun, J. A.; Lee, S. H.; Jung, B. H.; Choi, M. H.; Moon, M. H.; Chung, B. C. Analysis of polyamines as carbamoyl derivatives in urine and serum by liquid chromatography-tandem mass spectrometry Biomed. Chromatogr. 2008, 22, 73-80
    • (2008) Biomed. Chromatogr. , vol.22 , pp. 73-80
    • Byun, J.A.1    Lee, S.H.2    Jung, B.H.3    Choi, M.H.4    Moon, M.H.5    Chung, B.C.6
  • 75
    • 0019131629 scopus 로고
    • High-performance liquid chromatographic procedure for the simultaneous determination of the natural polyamines and their monoacetyl derivatives
    • Seiler, N.; Knödgen, B. High-performance liquid chromatographic procedure for the simultaneous determination of the natural polyamines and their monoacetyl derivatives J. Chromatogr. 1980, 221, 227-235
    • (1980) J. Chromatogr. , vol.221 , pp. 227-235
    • Seiler, N.1    Knödgen, B.2
  • 76
    • 0022619688 scopus 로고
    • Variations in the response of salt stressed rhizobium strains to betaines
    • Bernard, T.; Pocard, J. A.; Perroud, B.; Le Rudulier, D. Variations in the response of salt stressed rhizobium strains to betaines Arch. Microbiol. 1986, 143, 359-364
    • (1986) Arch. Microbiol. , vol.143 , pp. 359-364
    • Bernard, T.1    Pocard, J.A.2    Perroud, B.3    Le Rudulier, D.4
  • 77
    • 0020079659 scopus 로고
    • Polyamine degradation in foetal and adult bovine serum
    • Gahl, W. A.; Pitot, H. C. Polyamine degradation in foetal and adult bovine serum Biochem. J. 1982, 202, 603-611
    • (1982) Biochem. J. , vol.202 , pp. 603-611
    • Gahl, W.A.1    Pitot, H.C.2
  • 78
    • 0023158779 scopus 로고
    • Evaluation of a tetrazolium-based semiautomated colorimetric assay: Assessment of radiosensitivity
    • Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Mitchell, J. B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of radiosensitivity Cancer Res. 1987, 47, 943-946 (Pubitemid 17027906)
    • (1987) Cancer Research , vol.47 , Issue.4 , pp. 943-946
    • Carmichael, J.1    DeGraff, W.G.2    Gazdar, A.F.3
  • 79
    • 0029590203 scopus 로고
    • Spermine uptake is necessary to induce haemoglobin synthesis in murine erythroleukaemia cells
    • Clement, S.; Delcros, J. G.; Feuerstein, B. G. Spermine uptake is necessary to induce haemoglobin synthesis in murine erythroleukaemia cells Biochem. J. 1995, 312, 933-938
    • (1995) Biochem. J. , vol.312 , pp. 933-938
    • Clement, S.1    Delcros, J.G.2    Feuerstein, B.G.3
  • 81
    • 0029827911 scopus 로고    scopus 로고
    • Substrate protection against inactivation of the mammalian polyamine-transport system by 1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide
    • Torossian, K.; Audette, M.; Poulin, R. Substrate protection against inactivation of the mammalian polyamine-transport system by 1-ethyl-3-(3- dimethylaminopropyl)carbodi-imide Biochem. J. 1996, 319, 21-26
    • (1996) Biochem. J. , vol.319 , pp. 21-26
    • Torossian, K.1    Audette, M.2    Poulin, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.