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Volumn 46, Issue 24, 2003, Pages 5129-5138

Defining the Molecular Requirements for the Selective Delivery of Polyamine Conjugates into Cells Containing Active Polyamine Transporters

Author keywords

[No Author keywords available]

Indexed keywords

EFLORNITHINE; N (ANTHRACEN 9 YLMETHYL)BUTANEDIAMINE; N (ANTHRACEN 9 YLMETHYL)BUTYLAMINE; POLYAMINE; PUTRESCINE; SPERMIDINE; SPERMINE; UNCLASSIFIED DRUG;

EID: 0242691701     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030223a     Document Type: Article
Times cited : (98)

References (62)
  • 1
    • 0033832989 scopus 로고    scopus 로고
    • The Effect of Polyamine Homologation on the Transport and Cytotoxicity Properties of Polyamine-(DNA-Intercalator) Conjugates
    • Phanstiel, O., IV; Price, H. L.; Wang, L.; Juusola, J.; Kline, M.; Shah, S. M. The Effect of Polyamine Homologation on the Transport and Cytotoxicity Properties of Polyamine-(DNA-Intercalator) Conjugates. J. Org. Chem. 2000, 65, 5590-5599.
    • (2000) J. Org. Chem. , vol.65 , pp. 5590-5599
    • Phanstiel IV, O.1    Price, H.L.2    Wang, L.3    Juusola, J.4    Kline, M.5    Shah, S.M.6
  • 2
    • 0035950080 scopus 로고    scopus 로고
    • The Influence of Polyamine Architecture on the Transport and Topoisomerase II Inhibitory Properties of Polyamine DNA-Intercalator Conjugates
    • Wang, L.; Price, H. L.; Juusola, J.; Kline, M.; Phanstiel, IV, O. The Influence of Polyamine Architecture on the Transport and Topoisomerase II Inhibitory Properties of Polyamine DNA-Intercalator Conjugates. J. Med. Chem. 2001, 44, 3682-3691.
    • (2001) J. Med. Chem. , vol.44 , pp. 3682-3691
    • Wang, L.1    Price, H.L.2    Juusola, J.3    Kline, M.4    Phanstiel IV, O.5
  • 3
    • 0038240603 scopus 로고    scopus 로고
    • Synthesis Biological Evaluation of N′ -(anthracen-9-ylmethyl)-triamines as Molecular Recognition Elements for the Polyamine Transporter
    • Wang, C.; Delcros, J.-G.; Biggerstaff, J.; Phanstiel IV, O. Synthesis and Biological Evaluation of N′-(anthracen-9-ylmethyl)-triamines as Molecular Recognition Elements for the Polyamine Transporter. J. Med. Chem. 2003, 46, 2663-2671.
    • (2003) J. Med. Chem. , vol.46 , pp. 2663-2671
    • Wang, C.1    Delcros, J.-G.2    Biggerstaff, J.3    Phanstiel IV, O.4
  • 4
    • 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 IV, O. 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
  • 6
    • 0033214643 scopus 로고    scopus 로고
    • Probing the mechanism of transport and compartmentalisation of polyamines in mammalian cells
    • and refs therein
    • (a) 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 and refs therein.
    • (1999) Chem. Biol. , vol.6 , pp. 717-729
    • Cullis, P.M.1    Green, R.E.2    Merson-Davies, L.3    Travis, N.4
  • 7
    • 0025298549 scopus 로고
    • Polyamine transport in mammalian cells
    • (b) 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
  • 10
    • 0029658872 scopus 로고    scopus 로고
    • The 1.8-A X-ray structure of the Escherichia coli PotD protein complexed with spermidine and the mechanism of polyamine binding
    • Sugiyama, S.; Matsuo, Y.; Maenaka, K.; Vassylyev, D. G.; Matsushima, M.; Kashiwagi, K.; Igarashi, K.; Morikawa, K. The 1.8-A X-ray structure of the Escherichia coli PotD protein complexed with spermidine and the mechanism of polyamine binding. Protein Sci. 1996, 5, 1984-1990.
    • (1996) Protein Sci. , vol.5 , pp. 1984-1990
    • Sugiyama, S.1    Matsuo, Y.2    Maenaka, K.3    Vassylyev, D.G.4    Matsushima, M.5    Kashiwagi, K.6    Igarashi, K.7    Morikawa, K.8
  • 11
    • 0032504154 scopus 로고    scopus 로고
    • Crystal structure and mutational analysis of the Escherichia coli putrescine receptor. Structural basis for substrate specificity
    • Vassylyev, D. G.; Tomitori, H.; Kashiwagi, K.; Morikawa, K.; Igarashi, K. Crystal structure and mutational analysis of the Escherichia coli putrescine receptor. Structural basis for substrate specificity. J. Biol. Chem. 1998, 273, 17604-17609.
    • (1998) J. Biol. Chem. , vol.273 , pp. 17604-17609
    • Vassylyev, D.G.1    Tomitori, H.2    Kashiwagi, K.3    Morikawa, K.4    Igarashi, K.5
  • 12
    • 0028863669 scopus 로고
    • Spermidine-preferential uptake system in Escherichia coli. ATP hydrolysis by PotA protein and its association with membrane
    • Kashiwagi, K.; Endo, H.; Kobayashi, H.; Takio, K.; Igarashi, K. Spermidine-preferential uptake system in Escherichia coli. ATP hydrolysis by PotA protein and its association with membrane. J. Biol. Chem. 1995, 270, 25377-25382.
    • (1995) J. Biol. Chem. , vol.270 , pp. 25377-25382
    • Kashiwagi, K.1    Endo, H.2    Kobayashi, H.3    Takio, K.4    Igarashi, K.5
  • 13
    • 0027250513 scopus 로고
    • Functions of potA and potD proteins in spermidine-preferential uptake system in Escherichia coli
    • Kashiwagi, K.; Miyamoto, S.; Nukui, E.; Kobayashi, H.; Igarashi, K. Functions of potA and potD proteins in spermidine-preferential uptake system in Escherichia coli. J. Biol. Chem. 1993, 268, 19358-19363.
    • (1993) J. Biol. Chem. , vol.268 , pp. 19358-19363
    • Kashiwagi, K.1    Miyamoto, S.2    Nukui, E.3    Kobayashi, H.4    Igarashi, K.5
  • 14
  • 18
    • 0035804314 scopus 로고    scopus 로고
    • Terminally Alkylated Polyamine Analogues as Chemotherapeutic Agents
    • and references therein
    • (d) Casero, R. A., Jr.; Woster, P. M. Terminally Alkylated Polyamine Analogues as Chemotherapeutic Agents. J. Med. Chem. 2001, 44, 1-26 and references therein.
    • (2001) J. Med. Chem. , vol.44 , pp. 1-26
    • Casero Jr., R.A.1    Woster, P.M.2
  • 21
    • 0026459981 scopus 로고
    • Synthesis and Evaluation of novel spermidine derivatives as targeted cancer chemotherapeutic agents
    • Stark, P. A.; Thrall, B. D. Meadows, G. G.; Abdul-Monem, M. M. Synthesis and Evaluation of novel spermidine derivatives as targeted cancer chemotherapeutic agents. J. Med. Chem. 1992, 35, 4264-4269.
    • (1992) J. Med. Chem. , vol.35 , pp. 4264-4269
    • Stark, P.A.1    Thrall, B.D.2    Meadows, G.G.3    Abdul-Monem, M.M.4
  • 23
    • 0030599662 scopus 로고    scopus 로고
    • Synthesis of Carboranyl Polyamines for DNA Targeting
    • Cai, J.; Soloway, A. H. Synthesis of Carboranyl Polyamines for DNA Targeting. Tetrahedron Lett. 1996, 37, 9283-9286.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9283-9286
    • Cai, J.1    Soloway, A.H.2
  • 24
    • 0032499119 scopus 로고    scopus 로고
    • Synthesis of Novel Boronated Acridines and Spermidines as Possible Agents for BNCT
    • Ghaneolhosseini, H.; Tjarks, W.; Sjoberg, S. Synthesis of Novel Boronated Acridines and Spermidines as Possible Agents for BNCT. Tetrahedron 1998, 54, 3877-3884.
    • (1998) Tetrahedron , vol.54 , pp. 3877-3884
    • Ghaneolhosseini, H.1    Tjarks, W.2    Sjoberg, S.3
  • 25
    • 0032576806 scopus 로고    scopus 로고
    • Homologation of Polyamines in the Synthesis of Lipo-Spermine Conjugates and Related Lipoplexes
    • Blagbrough, I. S.; Geall, A. J. Homologation of Polyamines in the Synthesis of Lipo-Spermine Conjugates and Related Lipoplexes. Tetrahedron Lett. 1998, 443-446.
    • (1998) Tetrahedron Lett. , pp. 443-446
    • Blagbrough, I.S.1    Geall, A.J.2
  • 26
    • 0029089920 scopus 로고
    • Conjugation of a polyamine to the bifunctional alkylating agent chlorambucil does not alter the preferred cross-linking site in duplex DNA
    • Cullis, P. M.; Merson-Davies, L.; Weaver, R. Conjugation of a polyamine to the bifunctional alkylating agent chlorambucil does not alter the preferred cross-linking site in duplex DNA. J. Am. Chem. Soc. 1995, 117, 8033-8034.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8033-8034
    • Cullis, P.M.1    Merson-Davies, L.2    Weaver, R.3
  • 27
    • 0032103371 scopus 로고    scopus 로고
    • A novel technique for visualising the intracellular localization and distribution of transported polyamines in cultured pulmonary artery smooth muscle cells
    • Aziz, S. M.; Yatin, M.; Worthen, D. R.; Lipke, D. W.; Crooks, P. A. A novel technique for visualising the intracellular localization and distribution of transported polyamines in cultured pulmonary artery smooth muscle cells. J. Pharm. Biomed. Anal. 1998, 17, 307-320.
    • (1998) J. Pharm. Biomed. Anal. , vol.17 , pp. 307-320
    • Aziz, S.M.1    Yatin, M.2    Worthen, D.R.3    Lipke, D.W.4    Crooks, P.A.5
  • 29
    • 0021893570 scopus 로고
    • Biological properties of N-4 and N-1, N-8-spermidine derivatives in cultured L1210 leukemia cells
    • Porter, C. W.; Cavanaugh, P. F.; Ganis, B.; Kelly, E.; Bergeron, R. J. Biological properties of N-4 and N-1, N-8-spermidine derivatives in cultured L1210 leukemia cells. Cancer Res. 1985, 45, 2050-2057.
    • (1985) Cancer Res. , vol.45 , pp. 2050-2057
    • Porter, C.W.1    Cavanaugh, P.F.2    Ganis, B.3    Kelly, E.4    Bergeron, R.J.5
  • 31
    • 0021325432 scopus 로고
    • Aliphatic chain-length specificity of the polyamine transport system in ascites L1210 leukemia cells
    • Porter, C.; Miller, J.; Bergeron, R. J. Aliphatic chain-length specificity of the polyamine transport system in ascites L1210 leukemia cells. Cancer Res. 1984, 44, 126-128.
    • (1984) Cancer Res. , vol.44 , pp. 126-128
    • Porter, C.1    Miller, J.2    Bergeron, R.J.3
  • 32
    • 0031796041 scopus 로고    scopus 로고
    • QSAR analysis of polyamine transport inhibitors in L1210 cells
    • Xia, C. Q.; Yang, J. J.; Ren, S.; Lien, E. J. QSAR analysis of polyamine transport inhibitors in L1210 cells. J. Drug Targ. 1998, 6, 65-77.
    • (1998) J. Drug Targ. , vol.6 , pp. 65-77
    • Xia, C.Q.1    Yang, J.J.2    Ren, S.3    Lien, E.J.4
  • 33
    • 0025844980 scopus 로고
    • Molecular features necessary for the uptake of diamines and related compounds by the polyamine receptor of rat lung slices
    • O'Sullivan, M. C.; Golding, B. T.; Smith, L. L. and Wyatt, I. Molecular features necessary for the uptake of diamines and related compounds by the polyamine receptor of rat lung slices. Biochem. Pharm. 1991, 41, 1839-1848.
    • (1991) Biochem. Pharm. , vol.41 , pp. 1839-1848
    • O'Sullivan, M.C.1    Golding, B.T.2    Smith, L.L.3    Wyatt, I.4
  • 35
    • 0037108939 scopus 로고    scopus 로고
    • Role of endocytosis in the internalisation of spermidine-C2-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 internalisation of spermidine-C2-BODIPY, a highly fluorescent probe of polyamine transport. Biochemical J. 2002, 367, 347-357.
    • (2002) Biochemical 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
  • 37
    • 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
  • 38
    • 0024449739 scopus 로고
    • Expression of a human gene for polyamine transport in chinese hamster ovary cells
    • Byers, T. L.; Wechter, R.; Nuttall, M. E.; Pegg, A. E. Expression of a human gene for polyamine transport in chinese hamster ovary cells. Biochem. J. 1989, 263, 745-752.
    • (1989) Biochem. J. , vol.263 , pp. 745-752
    • Byers, T.L.1    Wechter, R.2    Nuttall, M.E.3    Pegg, A.E.4
  • 40
    • 0021365435 scopus 로고
    • 14C-labeled polyamines and methylglyoxal bis(guanylhydrazone) by a rat prostate-derived tumor
    • 14C-labeled polyamines and methylglyoxal bis(guanylhydrazone) by a rat prostate-derived tumor. Cancer Res. 1984, 44, 1034-1040.
    • (1984) Cancer Res. , vol.44 , pp. 1034-1040
    • Heston, W.D.W.1    Kadmon, D.2    Covey, D.F.3    Fair, W.R.4
  • 41
    • 0031127323 scopus 로고    scopus 로고
    • Difluoromethylornithine enhanced uptake of tritiated putrescine in 9L rat brain tumors
    • (c) Redgate, E. S.; Grudziak, A. G.; Deutsch, M.; Boggs, S. S. Difluoromethylornithine enhanced uptake of tritiated putrescine in 9L rat brain tumors. Int. J. Radiat. Oncol. Biol. Phys. 1997, 38, 169-174.
    • (1997) Int. J. Radiat. Oncol. Biol. Phys. , vol.38 , pp. 169-174
    • Redgate, E.S.1    Grudziak, A.G.2    Deutsch, M.3    Boggs, S.S.4
  • 42
    • 0022850208 scopus 로고
    • Comparison and characterization of growth inhibition in L1210 cells by alpha-difluoromethylornithine, an inhibitor of ornithine decarboxylase, and N1, N8-bis(ethyl)-spermidine, an apparent regulator of the enzyme
    • Porter, C. W.; Ganis, B.; Vinson, T.; Marton, L. J.; Kramer, D. L.; Bergeron, R. J. Comparison and characterization of growth inhibition in L1210 cells by alpha-difluoromethylornithine, an inhibitor of ornithine decarboxylase, and N1, N8-bis(ethyl)-spermidine, an apparent regulator of the enzyme. Cancer Res. 1986, 46, 6279-6285.
    • (1986) Cancer Res. , vol.46 , pp. 6279-6285
    • Porter, C.W.1    Ganis, B.2    Vinson, T.3    Marton, L.J.4    Kramer, D.L.5    Bergeron, R.J.6
  • 43
    • 0038620773 scopus 로고
    • DNA Binding Studies Site Selective Fluorescence Sensitization of an Anthryl Probe
    • (a) Kumar, C. V.; Asuncion, E. H. DNA Binding Studies and Site Selective Fluorescence Sensitization of an Anthryl Probe. J. Am. Chem. Soc. 1993, 115, 8547-8553.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8547-8553
    • Kumar, C.V.1    Asuncion, E.H.2
  • 45
    • 0036827810 scopus 로고    scopus 로고
    • Synthesis and Characterization of N1-(4-toluenesulfonyl)-N1-(9-anthracenemethyl)triamines
    • Wang, C.; Abboud, K. A.; Phanstiel, O. IV Synthesis and Characterization of N1-(4-toluenesulfonyl)-N1-(9-anthracenemethyl)triamines. J. Org. Chem. 2002, 67, 7865-7868.
    • (2002) J. Org. Chem. , vol.67 , pp. 7865-7868
    • Wang, C.1    Abboud, K.A.2    Phanstiel IV, O.3
  • 46
    • 0032576850 scopus 로고    scopus 로고
    • Practical Synthesis of Unsymmetrical Polyamine Amides
    • Blagbrough, I. S.; Geall, A. J. Practical Synthesis of Unsymmetrical Polyamine Amides. Tetrahedron Lett. 1998, 439-442.
    • (1998) Tetrahedron Lett. , pp. 439-442
    • Blagbrough, I.S.1    Geall, A.J.2
  • 47
    • 0033870740 scopus 로고    scopus 로고
    • Synthesis of Polyamines, Their Derivatives, Analogues and Conjugates
    • Kuksa, V.; Buchan, R.; Lin, P. K. T. Synthesis of Polyamines, Their Derivatives, Analogues and Conjugates. Synthesis 2000, No. 9, 1189-1207.
    • (2000) Synthesis , vol.9 , pp. 1189-1207
    • Kuksa, V.1    Buchan, R.2    Lin, P.K.T.3
  • 48
    • 0021715060 scopus 로고
    • The role of polyamine depletion and accumulation of decarboxylated S-adenosylmethionine in the inhibition of growth of SV-3T3 cells treated with alpha-difluoromethylornithine
    • (a) Pegg, A. E. The role of polyamine depletion and accumulation of decarboxylated S-adenosylmethionine in the inhibition of growth of SV-3T3 cells treated with alpha-difluoromethylornithine. Biochem. J. 1984, 224, No. 1, 29-38.
    • (1984) Biochem. J. , vol.224 , Issue.1 , pp. 29-38
    • Pegg, A.E.1
  • 49
    • 0021950649 scopus 로고
    • Determination of polyamines and related compounds by reversed-phase high-performance liquid chromatography: Improved separation systems
    • (b) Seiler, N.; Knödgen, B. Determination of polyamines and related compounds by reversed-phase high-performance liquid chromatography: Improved separation systems. J. Chromatography 1985, 339, 45-57.
    • (1985) J. Chromatography , vol.339 , pp. 45-57
    • Seiler, N.1    Knödgen, B.2
  • 50
    • 0038581602 scopus 로고    scopus 로고
    • Atmospheric pressure chemical ionization-mass spectrometry method to improve the determination of dansylated polyamines
    • (c) Gaboriau, F.; Havouis, R.; Moulinoux, J.-P.; Delcros, J.-G. Atmospheric pressure chemical ionization-mass spectrometry method to improve the determination of dansylated polyamines. Anal. Biochem. 2003, 318, 212-220.
    • (2003) Anal. Biochem. , vol.318 , pp. 212-220
    • Gaboriau, F.1    Havouis, R.2    Moulinoux, J.-P.3    Delcros, J.-G.4
  • 52
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50% inhibition (IC50) of an enzymatic reaction
    • Cheng, Y.-C.; Prusoff, W. H. Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50% inhibition (IC50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
    • (1973) Biochem. Pharmacol. , vol.22 , pp. 3099-3108
    • Cheng, Y.-C.1    Prusoff, W.H.2
  • 57
    • 0033104906 scopus 로고    scopus 로고
    • Proteoglycan involvement in polyamine uptake
    • (c) 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
  • 58
    • 0029981092 scopus 로고    scopus 로고
    • Evidence for the role of proteoglycans in cation-mediated gene transfer
    • Mislick, K. A.; Baldeschwieler, J. D. Evidence for the role of proteoglycans in cation-mediated gene transfer. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12349-12354.
    • (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 12349-12354
    • Mislick, K.A.1    Baldeschwieler, J.D.2
  • 59
    • 0032475867 scopus 로고    scopus 로고
    • Proteoglycans Mediate Cationic Liposome-DNA Complex-based Gene Delivery in Vitro and in Vivo
    • Mounkes, L. C.; Zhong, W.; Cipres-Palacin, G.; Heath, T. D.; Debs, R. J. Proteoglycans Mediate Cationic Liposome-DNA Complex-based Gene Delivery in Vitro and in Vivo. J. Biol. Chem. 1998, 273, 26164-26170.
    • (1998) J. Biol. Chem. , vol.273 , pp. 26164-26170
    • Mounkes, L.C.1    Zhong, W.2    Cipres-Palacin, G.3    Heath, T.D.4    Debs, R.J.5
  • 60
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 61
    • 0029590203 scopus 로고
    • Spermine uptake is necessary to induce haemoglobin synthesis in murine erythroleukemia cells
    • Clément, S.; Delcros, J. G.; Feuerstein, B. G. Spermine uptake is necessary to induce haemoglobin synthesis in murine erythroleukemia cells. Biochem. J. 1995, 312, 933-938.
    • (1995) Biochem. J. , vol.312 , pp. 933-938
    • Clément, S.1    Delcros, J.G.2    Feuerstein, B.G.3
  • 62
    • 0029827911 scopus 로고    scopus 로고
    • Substrate protection against inactivation of the mammalian polyamine transport system by 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide
    • Torossian, K.; Audette, M.; Poulin, R. Substrate protection against inactivation of the mammalian polyamine transport system by 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide. Biochem. J. 1996, 319, 21-26.
    • (1996) Biochem. J. , vol.319 , pp. 21-26
    • Torossian, K.1    Audette, M.2    Poulin, R.3


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