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Volumn 45, Issue 26, 2002, Pages 5776-5785

Design, synthesis, and physicochemical and biological characterization of a new iron chelator of the family of hydroxychromenes

Author keywords

[No Author keywords available]

Indexed keywords

CHROMENE DERIVATIVE; HYDROXYCHROMENE; IRON CHELATING AGENT; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

EID: 0037137604     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm021022u     Document Type: Article
Times cited : (11)

References (44)
  • 1
    • 0022529172 scopus 로고
    • Oxygen free radicals and iron in relation to biology and medicine: Some problems and concepts
    • Halliwell, B.; Gutteridge, J. M. C. Oxygen free radicals and iron in relation to biology and medicine: Some problems and concepts. Arch. Biochem. Biophys. 1986, 246, 501-514.
    • (1986) Arch. Biochem. Biophys. , vol.246 , pp. 501-514
    • Halliwell, B.1    Gutteridge, J.M.C.2
  • 2
    • 0026710009 scopus 로고
    • The role of iron in oxygen-mediated toxicities
    • Ryan, T. P.; Aust, S. D. The Role of Iron in Oxygen-Mediated Toxicities. Crit. Rev. Toxicol. 1992, 22, 119-141.
    • (1992) Crit. Rev. Toxicol. , vol.22 , pp. 119-141
    • Ryan, T.P.1    Aust, S.D.2
  • 3
    • 0026597915 scopus 로고
    • Redox cycling of iron and lipid peroxidation
    • Minotti, G.; Aust, S. D. Redox Cycling of Iron and Lipid Peroxidation. Lipids 1992, 27, 219-226.
    • (1992) Lipids , vol.27 , pp. 219-226
    • Minotti, G.1    Aust, S.D.2
  • 4
    • 0030988742 scopus 로고    scopus 로고
    • Biochemistry and pathology of radical-mediated protein oxidation
    • Dean, R. T.; Fu, S.; Stocker, R.; Davies, M. J. Biochemistry and pathology of radical-mediated protein oxidation. Biochem. J. 1997, 324, 1-18.
    • (1997) Biochem. J. , vol.324 , pp. 1-18
    • Dean, R.T.1    Fu, S.2    Stocker, R.3    Davies, M.J.4
  • 5
    • 0031859464 scopus 로고    scopus 로고
    • DNA damage by iron hydrogen peroxide in vitro and in vivo
    • Linn, S. DNA damage by iron and hydrogen peroxide in vitro and in vivo. Drug Metab. Rev. 1998, 30, 313-326.
    • (1998) Drug Metab. Rev. , vol.30 , pp. 313-326
    • Linn, S.1
  • 6
    • 0029922315 scopus 로고    scopus 로고
    • Metals, oxidative stress, and hepatic fibrogenesis
    • Pietrangelo, A. Metals, oxidative stress, and hepatic fibrogenesis. Semin. Liver Dis. 1996, 16, 13-30.
    • (1996) Semin. Liver Dis. , vol.16 , pp. 13-30
    • Pietrangelo, A.1
  • 7
    • 0018164919 scopus 로고
    • Non-specific serum iron in thalassemia: An abnormal serum fraction of potential toxicity
    • Hershko, C.; Graham, G.; Bates, G. W.; Rachmilewitz, E. A. Non-specific serum iron in thalassemia: An abnormal serum fraction of potential toxicity. Brit. J. Haematol. 1978, 40, 255-263.
    • (1978) Brit. J. Haematol. , vol.40 , pp. 255-263
    • Hershko, C.1    Graham, G.2    Bates, G.W.3    Rachmilewitz, E.A.4
  • 8
    • 0012076430 scopus 로고    scopus 로고
    • Alterations in iron in neurodegenerative disorders: Implications and possible therapeutic agents
    • Yasui, M. et al., Eds.; CRC Press: Boca Raton
    • Dexter, D. T.; Jenner, P. Alterations in iron in neurodegenerative disorders: Implications and possible therapeutic agents. In Mineral and Metal Neurotoxicology; Yasui, M. et al., Eds.; CRC Press: Boca Raton, 1997; pp 365-378.
    • (1997) Mineral and Metal Neurotoxicology , pp. 365-378
    • Dexter, D.T.1    Jenner, P.2
  • 9
    • 0032867670 scopus 로고    scopus 로고
    • Development of clinical methods of iron deprivation for suppression of neoplastic and infectious diseases
    • Weinberg, E. D. Development of clinical methods of iron deprivation for suppression of neoplastic and infectious diseases. Cancer Invest. 1999, 17, 507-513.
    • (1999) Cancer Invest. , vol.17 , pp. 507-513
    • Weinberg, E.D.1
  • 10
    • 0006348848 scopus 로고    scopus 로고
    • Potential use of iron chelators against oxidative damage
    • Galey, J. B. Potential use of iron chelators against oxidative damage. Adv. Pharmacol. 1997, 38, 1167-203.
    • (1997) Adv. Pharmacol. , vol.38 , pp. 1167-1203
    • Galey, J.B.1
  • 12
    • 0033606807 scopus 로고    scopus 로고
    • Iron, atherosclerosis, and ischemic heart disease
    • de Valk, B.; Marx, J. J. M. Iron, atherosclerosis, and ischemic heart disease. Arch. Int. Med. 1999, 26, 1542-1548.
    • (1999) Arch. Int. Med. , vol.26 , pp. 1542-1548
    • De Valk, B.1    Marx, J.J.M.2
  • 13
    • 0028861997 scopus 로고
    • Chelation therapy in β-thalassemia: The benefits and limitations of desferrioxamine
    • Giardina, P. J.; Grady, R. W. Chelation therapy in β-thalassemia: The benefits and limitations of desferrioxamine. Semin. Hematol. 1995, 32, 304-312.
    • (1995) Semin. Hematol. , vol.32 , pp. 304-312
    • Giardina, P.J.1    Grady, R.W.2
  • 14
    • 0031001278 scopus 로고    scopus 로고
    • Iron-chelating therapy and the treatment of thalassemia
    • Olivieri, N. F.; Brittenham, G. M. Iron-chelating therapy and the treatment of thalassemia. Blood 1997, 89, 739-761.
    • (1997) Blood , vol.89 , pp. 739-761
    • Olivieri, N.F.1    Brittenham, G.M.2
  • 15
    • 0031612367 scopus 로고    scopus 로고
    • Iron chelators for clinical use
    • Sigel, A.;. Sigel, H., Eds.; Marcel Dekker: New York
    • Tilbrook, G. S.; Hider, R. C. Iron Chelators for Clinical Use. In Metal Ions in Biological Systems; Sigel, A.;. Sigel, H., Eds.; Marcel Dekker: New York, 1998; Vol. 35, pp 691-730.
    • (1998) Metal Ions in Biological Systems , vol.35 , pp. 691-730
    • Tilbrook, G.S.1    Hider, R.C.2
  • 16
    • 0032055861 scopus 로고    scopus 로고
    • Pyridoxal isonicotinoyl hydrazone and its analogues: Potential orally effective iron-chelating agents for the treatment of iron overload disease
    • Richardson, D. R.; Ponka, P. Pyridoxal isonicotinoyl hydrazone and its analogues: Potential orally effective iron-chelating agents for the treatment of iron overload disease. J. Lab. Clin. Med. 1998, 131, 306-315.
    • (1998) J. Lab. Clin. Med. , vol.131 , pp. 306-315
    • Richardson, D.R.1    Ponka, P.2
  • 18
    • 0032528402 scopus 로고    scopus 로고
    • The iron chelator L1 potentiates oxidative DNA damage in iron-loaded liver cells
    • Cregg, L.; Hebbel, R. P.; Miller, W.; Solovey, A.; Selby, S.; Enright, H. The iron chelator L1 potentiates oxidative DNA damage in iron-loaded liver Cells. Blood 1998, 32, 632-638.
    • (1998) Blood , vol.32 , pp. 632-638
    • Cregg, L.1    Hebbel, R.P.2    Miller, W.3    Solovey, A.4    Selby, S.5    Enright, H.6
  • 19
    • 0032055192 scopus 로고    scopus 로고
    • Iron chelation therapy: The need for orally active drugs
    • Hoffbrand, A. V. Iron chelation therapy: The need for orally active drugs. J. Lab. Clin. Med. 1998, 131, 290-291.
    • (1998) J. Lab. Clin. Med. , vol.131 , pp. 290-291
    • Hoffbrand, A.V.1
  • 23
    • 0004179163 scopus 로고
    • Electron paramagnetic resonance spectra of transition metal ion complexes
    • Saunders College Publishing: New York
    • Drago, S. Electron Paramagnetic Resonance Spectra of Transition Metal ion Complexes. Physical Methods for Chemists; Saunders College Publishing: New York, 1992; pp 559-603.
    • (1992) Physical Methods for Chemists , pp. 559-603
    • Drago, S.1
  • 25
    • 0000590373 scopus 로고    scopus 로고
    • PM3 analysis of transition-metal complexes
    • Cundari, T. R.; Deng, J. PM3 analysis of transition-metal complexes. J. Chem. Inf. Comput. Sci. 1999, 39, 376-381.
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 376-381
    • Cundari, T.R.1    Deng, J.2
  • 26
    • 0001569222 scopus 로고
    • Coordination chemistry of microbial iron transport compounds. 19. Stability constants and electrochemical behaviour of enterobactin and model complexes
    • Harris, W. R.; Carrano, C. J.; Cooper, S. R.; Sofen, S. R.; Avdeef, A. E.; McArdle, J. V.; Raymond, K. N. Coordination chemistry of microbial iron transport compounds. 19. Stability constants and electrochemical behaviour of enterobactin and model complexes. J. Am. Chem. Soc. 1979, 101, 6097-6104.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6097-6104
    • Harris, W.R.1    Carrano, C.J.2    Cooper, S.R.3    Sofen, S.R.4    Avdeef, A.E.5    McArdle, J.V.6    Raymond, K.N.7
  • 27
    • 0001295932 scopus 로고    scopus 로고
    • Models of the cytochromes. Redox properties and thermodynamic stabilities of complexes of hindered iron(III) and iron(II) tetraphenylporphyrinates with substituted pyridines and imidazoles
    • Nesset, M. J. M.; Shokhirev, N. V.; Enemark, P. D.; Jacobson, S. E.; Walker, F. A. Models of the cytochromes. Redox properties and thermodynamic stabilities of complexes of hindered iron(III) and iron(II) tetraphenylporphyrinates with substituted pyridines and imidazoles. Inorg. Chem. 1996, 35, 5188-5200.
    • (1996) Inorg. Chem. , vol.35 , pp. 5188-5200
    • Nesset, M.J.M.1    Shokhirev, N.V.2    Enemark, P.D.3    Jacobson, S.E.4    Walker, F.A.5
  • 28
    • 0001101307 scopus 로고    scopus 로고
    • Electrochemical behaviour of the Fe(III) complexes of cyclic hydroxamate siderophores alcaligin and desferrioxamine E
    • Spasojevæ, I.; Armstrong, S. K.; Brickman, T. J.; Crumbliss, A. L. Electrochemical behaviour of the Fe(III) complexes of cyclic hydroxamate siderophores alcaligin and desferrioxamine E. Inorg. Chem. 1999, 38, 449-454.
    • (1999) Inorg. Chem. , vol.38 , pp. 449-454
    • Spasojevæ, I.1    Armstrong, S.K.2    Brickman, T.J.3    Crumbliss, A.L.4
  • 29
    • 0035142740 scopus 로고    scopus 로고
    • Iron(III) complexation by new aminocarboxylate chelators. Thermodynamic and kinetic studies
    • Serratrice, G.; Galey, J.-B.; Aman, E. S.; Dumats, J. Iron(III) complexation by new aminocarboxylate chelators. Thermodynamic and kinetic studies. Eur. J. Inorg. Chem. 2001, 471-479.
    • (2001) Eur. J. Inorg. Chem. , pp. 471-479
    • Serratrice, G.1    Galey, J.-B.2    Aman, E.S.3    Dumats, J.4
  • 30
    • 0012079179 scopus 로고
    • Reversible processes controlled by diffusion of complex ions
    • Academic Press: New York
    • Heyrovsky, I.; Kuta, J. Reversible processes controlled by diffusion of complex ions. Principles of Polarography; Academic Press: New York, 1966; pp 147-160.
    • (1966) Principles of Polarography , pp. 147-160
    • Heyrovsky, I.1    Kuta, J.2
  • 31
    • 0002256438 scopus 로고
    • Iron, cobalt, nichel and platinum metals
    • Interscience Publishers: New York
    • Kolthoff, I. M.; Lingane J. J. Iron, cobalt, nichel and platinum metals. Polarography; Interscience Publishers: New York, 1952; pp 475-492.
    • (1952) Polarography , pp. 475-492
    • Kolthoff, I.M.1    Lingane, J.J.2
  • 32
    • 33845183120 scopus 로고
    • Complexation of Fe(III), Ga(III), In(III), Al(III), and other highly charged metal ions
    • Metal Ion Recognition in Ligands with Negatively Charged Oxygen Donor Groups
    • Evers, A.; Hancock, R. D.; Martell, A. E.; Motekaitis, R. J. Metal Ion Recognition in Ligands with Negatively Charged Oxygen Donor Groups. Complexation of Fe(III), Ga(III), In(III), Al(III), and other highly charged metal ions. Inorg. Chem. 1989, 28, 2189-2195.
    • (1989) Inorg. Chem. , vol.28 , pp. 2189-2195
    • Evers, A.1    Hancock, R.D.2    Martell, A.E.3    Motekaitis, R.J.4
  • 33
    • 0015715404 scopus 로고
    • Evidence that peroxidation of lysosomal membranes is initiated by hydroxyl free radicals produced during flavin enzyme activity
    • Fong, K. L.; McCay, P. B.; Poyer, J. L. Evidence that peroxidation of lysosomal membranes is initiated by hydroxyl free radicals produced during flavin enzyme activity. J. Biol. Chem. 1973, 248, 7792-7797.
    • (1973) J. Biol. Chem. , vol.248 , pp. 7792-7797
    • Fong, K.L.1    McCay, P.B.2    Poyer, J.L.3
  • 34
    • 0000166165 scopus 로고
    • 18-Crown-6 complexes of n-butylammonium and pyridinium chlorochromates. Mild and selective oxidizing agents for alcohols
    • Kasmai, H. S.; Mischke, S. G.; Blake, T. J. 18-Crown-6 Complexes of n-butylammonium and pyridinium chlorochromates. Mild and selective oxidizing agents for alcohols. J. Org. Chem. 1995, 60, 2267-2270.
    • (1995) J. Org. Chem. , vol.60 , pp. 2267-2270
    • Kasmai, H.S.1    Mischke, S.G.2    Blake, T.J.3
  • 35
  • 36
    • 33947469501 scopus 로고
    • The rearrangement of 2-acethyland 2-benzoylcoumarone oxime p-toluenesulfonates
    • Geissman, T. A.; Armen, A. The rearrangement of 2-acethyland 2-benzoylcoumarone oxime p-toluenesulfonates. J. Am. Chem. Soc. 1955, 77, 1623-1627.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 1623-1627
    • Geissman, T.A.1    Armen, A.2
  • 39
    • 33748729189 scopus 로고    scopus 로고
    • Amphoteric poly(amidoamine) polymers containing the ethylendiamine-N,n′-diacetic acid moiety. Stability of copper(II) and calcium(II) chelates
    • Casolaro, M.; Bignotti, F.; Ferruti, P. Amphoteric poly(amidoamine) polymers containing the ethylendiamine-N,n′-diacetic acid moiety. Stability of copper(II) and calcium(II) chelates. J. Chem. Soc., Faraday Trans. 1997, 3663-3668.
    • (1997) J. Chem. Soc., Faraday Trans. , pp. 3663-3668
    • Casolaro, M.1    Bignotti, F.2    Ferruti, P.3
  • 40
    • 0013566107 scopus 로고
    • Superquad: An improved general program for computation of formation constants from potentiometric data
    • Gans, P.; Sabatini, A.; Vacca, A. Superquad: An improved general program for computation of formation constants from potentiometric data. J. Chem. Soc., Dalton Trans. 1985, 1195-1200.
    • (1985) J. Chem. Soc., Dalton Trans. , pp. 1195-1200
    • Gans, P.1    Sabatini, A.2    Vacca, A.3
  • 41
    • 84988129057 scopus 로고
    • Optimisation of parameters for semiempirical methods. I. Method
    • Stewart, J. J. P. Optimisation of parameters for semiempirical methods. I. Method. J. Comput. Chem. 1989, 10, 209-220.
    • (1989) J. Comput. Chem. , vol.10 , pp. 209-220
    • Stewart, J.J.P.1
  • 42
    • 0004074379 scopus 로고    scopus 로고
    • Hypercube Inc., Gainesville, FL
    • Hyperchem 7.0, Hypercube Inc., Gainesville, FL.
    • Hyperchem 7.0
  • 43
    • 0008247296 scopus 로고
    • The fluorimetric analysis of ultramicro quantities of hydrogen peroxide
    • Keston, A. S.; Brandt, R. The fluorimetric analysis of ultramicro quantities of hydrogen peroxide. Anal. Biochem. 1965, 11, 1-5.
    • (1965) Anal. Biochem. , vol.11 , pp. 1-5
    • Keston, A.S.1    Brandt, R.2
  • 44
    • 0014075150 scopus 로고
    • Effects of in vivo and in vitro Ethanol Administration on Liver Lipid Peroxidation
    • Comporti, M.; Hartman, A.; Di Luzio, N. R. Effects of in vivo and in vitro Ethanol Administration on Liver Lipid Peroxidation. Lab. Invest. 1967, 16, 616-624.
    • (1967) Lab. Invest. , vol.16 , pp. 616-624
    • Comporti, M.1    Hartman, A.2    Di Luzio, N.R.3


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