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Volumn 15, Issue 7, 2003, Pages 593-599

Iron chelation promoted by desazadesferrithiocin analogs: An enantioselective barrier

Author keywords

Cebus apella; Iron clearance; Plasma concentration time curve; X ray crystallography

Indexed keywords

4' HYDROXYDESAZADESFERRITHIOCIN; CREMOPHOR; DEFEROXAMINE; DEFERRIFERRITHIOCIN; IRON; IRON CHELATING AGENT; IRON DEXTRAN; TRANSFERRIN; UNCLASSIFIED DRUG;

EID: 0041663758     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10248     Document Type: Article
Times cited : (14)

References (47)
  • 1
    • 33845559030 scopus 로고
    • Coordination chemistry and microbial iron transport
    • Raymond KN, Carrano CJ. Coordination chemistry and microbial iron transport. Acc Chem Res 1979;12:183-190.
    • (1979) Acc Chem Res , vol.12 , pp. 183-190
    • Raymond, K.N.1    Carrano, C.J.2
  • 2
    • 0000919943 scopus 로고
    • Coordination chemistry of microbial iron transport compounds. 21. Kinetics and metabolism of iron exchange in hydroxamate siderophore complexes
    • Tufano TP, Raymond KN. Coordination chemistry of microbial iron transport compounds. 21. Kinetics and metabolism of iron exchange in hydroxamate siderophore complexes. J Am Chem Soc 1981;103:6617-6624.
    • (1981) J Am Chem Soc , vol.103 , pp. 6617-6624
    • Tufano, T.P.1    Raymond, K.N.2
  • 3
    • 0001388011 scopus 로고
    • Some aspects of microbial iron metabolism
    • Neilands JB. Some aspects of microbial iron metabolism. Bacteriol Rev 1957;21:101-111.
    • (1957) Bacteriol Rev , vol.21 , pp. 101-111
    • Neilands, J.B.1
  • 4
    • 0028850367 scopus 로고
    • Siderophores: Structure and function of microbial iron transport compounds
    • Neilands JB. Siderophores: structure and function of microbial iron transport compounds. J Biol Chem 1995;270:26723-26726.
    • (1995) J Biol Chem , vol.270 , pp. 26723-26726
    • Neilands, J.B.1
  • 5
    • 0031599682 scopus 로고    scopus 로고
    • Microbial iron transport: Iron acquisition by pathogenic microorganisms
    • Byers BR, Arceneaux JE. Microbial iron transport: iron acquisition by pathogenic microorganisms. Met Ions Biol Syst 1998;35:37-66.
    • (1998) Met Ions Biol Syst , vol.35 , pp. 37-66
    • Byers, B.R.1    Arceneaux, J.E.2
  • 6
    • 0031610937 scopus 로고    scopus 로고
    • Molecular biology of iron transport in fungi
    • Leong SA, Winkelmann G. Molecular biology of iron transport in fungi. Met Ions Biol Syst 1998;35:147-186.
    • (1998) Met Ions Biol Syst , vol.35 , pp. 147-186
    • Leong, S.A.1    Winkelmann, G.2
  • 7
    • 85053654339 scopus 로고
    • Synthesis of catecholamide and hydroxamate siderophores
    • Winkelmann G, editor. Boca Raton, FL: CRC
    • Bergeron RJ, McManis JS. Synthesis of catecholamide and hydroxamate siderophores. In: Winkelmann G, editor. CRC handbook of microbial iron chelates. Boca Raton, FL: CRC; 1991. p 271-307.
    • (1991) CRC Handbook of Microbial Iron Chelates , pp. 271-307
    • Bergeron, R.J.1    McManis, J.S.2
  • 8
    • 0020419940 scopus 로고
    • Short synthesis of parabactin
    • Bergeron RJ, Kline SJ. Short synthesis of parabactin. J Am Chem Soc 1982;104:4489-4492.
    • (1982) J Am Chem Soc , vol.104 , pp. 4489-4492
    • Bergeron, R.J.1    Kline, S.J.2
  • 9
    • 0001711883 scopus 로고
    • An efficient total synthesis of agrobactin and its gallium(III) chelate
    • Bergeron RJ, McManis JS, Dionis JB, Garlich JR. An efficient total synthesis of agrobactin and its gallium(III) chelate. J Org Chem 1985;50:2780-2782.
    • (1985) J Org Chem , vol.50 , pp. 2780-2782
    • Bergeron, R.J.1    McManis, J.S.2    Dionis, J.B.3    Garlich, J.R.4
  • 10
    • 0027263215 scopus 로고
    • Synthesis of the thiazoline-based siderophore (S)-desferrithiocin
    • Mulqueen GC, Pattenden G, Whiting DA. Synthesis of the thiazoline-based siderophore (S)-desferrithiocin. Tetrahedron 1993;49:5359-5364.
    • (1993) Tetrahedron , vol.49 , pp. 5359-5364
    • Mulqueen, G.C.1    Pattenden, G.2    Whiting, D.A.3
  • 12
    • 0042370320 scopus 로고    scopus 로고
    • A search for clinically effective iron chelators
    • Badman DG, Bergeron RJ, Brittenham GM, editors. Ponte Vedra Beach, FL: Saratoga
    • Bergeron RJ, McManis JS, Wiegand J, Weimar WR. A search for clinically effective iron chelators. In: Badman DG, Bergeron RJ, Brittenham GM, editors. Iron chelators: new development strategies. Ponte Vedra Beach, FL: Saratoga; 2000. p 253-292.
    • (2000) Iron Chelators: New Development Strategies , pp. 253-292
    • Bergeron, R.J.1    McManis, J.S.2    Wiegand, J.3    Weimar, W.R.4
  • 13
    • 0025288378 scopus 로고
    • Coordination chemistry of microbial iron transport. 42. Structural and spectroscopic characterization of diastereomeric Cr(III) and Co(III) complexes of desferriferrithiocin
    • Hahn FE, McMurry TJ, Hugi A, Raymond KN. Coordination chemistry of microbial iron transport. 42. Structural and spectroscopic characterization of diastereomeric Cr(III) and Co(III) complexes of desferriferrithiocin. J Am Chem Soc 1990;112:1854-1860.
    • (1990) J Am Chem Soc , vol.112 , pp. 1854-1860
    • Hahn, F.E.1    McMurry, T.J.2    Hugi, A.3    Raymond, K.N.4
  • 14
    • 0025088608 scopus 로고
    • Metal complex formation of a new siderophore desferiithiocin and of three related ligands
    • Anderegg G, Räber M. Metal complex formation of a new siderophore desferiithiocin and of three related ligands. J Chem Soc Chem Commun 1990:1194-1196.
    • (1990) J Chem Soc Chem Commun , pp. 1194-1196
    • Anderegg, G.1    Räber, M.2
  • 15
    • 0021997134 scopus 로고
    • Mechanism and stereospecificity of the parabactin-mediated iron-transport system in Paracoccus denitrificans
    • Bergeron RJ, Dionis JB, Elliott GT, Kline SJ. Mechanism and stereospecificity of the parabactin-mediated iron-transport system in Paracoccus denitrificans. J Biol Chem 1985;260:7936-7944.
    • (1985) J Biol Chem , vol.260 , pp. 7936-7944
    • Bergeron, R.J.1    Dionis, J.B.2    Elliott, G.T.3    Kline, S.J.4
  • 17
    • 0031963449 scopus 로고    scopus 로고
    • Function and regulation of transferrin and ferritin
    • Ponka P, Beaumont C, Richardson DR. Function and regulation of transferrin and ferritin. Semin Hematol 1998;35:35-54.
    • (1998) Semin Hematol , vol.35 , pp. 35-54
    • Ponka, P.1    Beaumont, C.2    Richardson, D.R.3
  • 18
    • 0012341790 scopus 로고    scopus 로고
    • Ferritin mineralization: Ferroxidation and beyond
    • Theil EC, Huynh BH. Ferritin mineralization: ferroxidation and beyond. J Inorg Biochem 1997;67:30.
    • (1997) J Inorg Biochem , vol.67 , pp. 30
    • Theil, E.C.1    Huynh, B.H.2
  • 19
    • 0001250740 scopus 로고
    • Physiology and pathophysiology of iron metabolism: Implications for iron chelation therapy in iron overload
    • Bergeron RJ, Brittenham GM, editors. Boca Raton, FL: CRC
    • Ponka P. Physiology and pathophysiology of iron metabolism: implications for iron chelation therapy in iron overload. In: Bergeron RJ, Brittenham GM, editors. The development of iron chelators for clinical use. Boca Raton, FL: CRC; 1994. p 1-29.
    • (1994) The Development of Iron Chelators for Clinical Use , pp. 1-29
    • Ponka, P.1
  • 20
    • 0026683530 scopus 로고
    • Oxygen radicals in ulcerative colitis
    • Babbs CF. Oxygen radicals in ulcerative colitis. Free Radic Biol Med 1992;13:169-181.
    • (1992) Free Radic Biol Med , vol.13 , pp. 169-181
    • Babbs, C.F.1
  • 21
    • 0027991050 scopus 로고
    • Free radicals and antioxidants: A personal view
    • Halliwell B. Free radicals and antioxidants: a personal view. Nutr Rev 1994;52:253-265.
    • (1994) Nutr Rev , vol.52 , pp. 253-265
    • Halliwell, B.1
  • 22
    • 0032570808 scopus 로고    scopus 로고
    • Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to oxidize α-amino acids to a family of reactive aldehydes. Mechanistic studies identifying labile intermediates along the reaction pathway
    • Hazen SL, d'Avignon A, Anderson MM, Hsu FF, Heinecke JW. Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to oxidize α-amino acids to a family of reactive aldehydes. Mechanistic studies identifying labile intermediates along the reaction pathway. J Biol Chem 1998;273:4997-5005.
    • (1998) J Biol Chem , vol.273 , pp. 4997-5005
    • Hazen, S.L.1    D'Avignon, A.2    Anderson, M.M.3    Hsu, F.F.4    Heinecke, J.W.5
  • 23
    • 0001854599 scopus 로고
    • Iron, oxidative damage, and chelating agents
    • Bergeron RJ, Brittenham GM, editors. Boca Raton, FL: CRC
    • Halliwell B. Iron, oxidative damage, and chelating agents. In: Bergeron RJ, Brittenham GM, editors. The development of iron chelators for clinical use. Boca Raton, FL: CRC; 1994. p 33-56.
    • (1994) The Development of Iron Chelators for Clinical Use , pp. 33-56
    • Halliwell, B.1
  • 24
    • 0031001278 scopus 로고    scopus 로고
    • Iron-chelating therapy and the treatment of thalassemia
    • Olivieri NF, Brittenham GM. 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
  • 25
    • 0034783438 scopus 로고    scopus 로고
    • Chelation therapy in β-thalassemia: An optimistic update
    • Giardina PJ, Grady RW. Chelation therapy in β-thalassemia: an optimistic update. Semin Hematol 2001;38:360-366.
    • (2001) Semin Hematol , vol.38 , pp. 360-366
    • Giardina, P.J.1    Grady, R.W.2
  • 26
    • 0022637547 scopus 로고
    • Iron chelation using subcutaneous infusions of diethylene triamine penta-acetic acid (DTPA)
    • Pippard MJ, Jackson MJ, Hoffman K, Petrou M, Modell CB. Iron chelation using subcutaneous infusions of diethylene triamine penta-acetic acid (DTPA). Scand J Haematol 1986;36:466-472.
    • (1986) Scand J Haematol , vol.36 , pp. 466-472
    • Pippard, M.J.1    Jackson, M.J.2    Hoffman, K.3    Petrou, M.4    Modell, C.B.5
  • 27
    • 0024521376 scopus 로고
    • Desferrioxamine-induced iron excretion in humans
    • Pippard MJ. Desferrioxamine-induced iron excretion in humans. Bailliere's Clin Haematol 1989;2:323-343.
    • (1989) Bailliere's Clin Haematol , vol.2 , pp. 323-343
    • Pippard, M.J.1
  • 28
    • 0033168448 scopus 로고    scopus 로고
    • Effects of C-4 stereochemistry and C-4′ hydroxylation on the iron clearing efficiency and toxicity of desferrithiocin analogues
    • Bergeron RJ, Wiegand J, McManis JS, McCosar BH, Weimar WR, Brittenham GM, Smith RE. Effects of C-4 stereochemistry and C-4′ hydroxylation on the iron clearing efficiency and toxicity of desferrithiocin analogues. J Med Chem 1999;42:2432-2440.
    • (1999) J Med Chem , vol.42 , pp. 2432-2440
    • Bergeron, R.J.1    Wiegand, J.2    McManis, J.S.3    McCosar, B.H.4    Weimar, W.R.5    Brittenham, G.M.6    Smith, R.E.7
  • 30
  • 32
    • 0026520355 scopus 로고
    • A comparison of the iron-clearing properties of 1,2-dimethyl-3-hydroxypyrid-4-one, 1,2-diethyl-3-hydroxypyrid-4-one, and deferoxamine
    • Bergeron RJ, Streiff RR, Wiegand J, Luchetta G, Creary EA, Peter HH. A comparison of the iron-clearing properties of 1,2-dimethyl-3-hydroxypyrid-4-one, 1,2-diethyl-3-hydroxypyrid-4-one, and deferoxamine. Blood 1992;79:1882-1890.
    • (1992) Blood , vol.79 , pp. 1882-1890
    • Bergeron, R.J.1    Streiff, R.R.2    Wiegand, J.3    Luchetta, G.4    Creary, E.A.5    Peter, H.H.6
  • 33
    • 0014249766 scopus 로고
    • The metabolism of iron-dextran given as a total-dose infusion to iron deficient Jamaican subjects
    • Wood JK, Milner PF, Pathak UN. The metabolism of iron-dextran given as a total-dose infusion to iron deficient Jamaican subjects. Br J Haematol 1968;14:119-129.
    • (1968) Br J Haematol , vol.14 , pp. 119-129
    • Wood, J.K.1    Milner, P.F.2    Pathak, U.N.3
  • 35
    • 0032519770 scopus 로고    scopus 로고
    • HBED: A potential alternative to deferoxamine for iron-chelating therapy
    • Bergeron RJ, Wiegand J, Brittenham GM. HBED: A potential alternative to deferoxamine for iron-chelating therapy. Blood 1998;91:1446-1452.
    • (1998) Blood , vol.91 , pp. 1446-1452
    • Bergeron, R.J.1    Wiegand, J.2    Brittenham, G.M.3
  • 37
    • 0032908391 scopus 로고    scopus 로고
    • HBED: The continuing development of a potential alternative to deferoxamine for iron-chelating therapy
    • Bergeron RJ, Wiegand J, Brittenham GM. HBED: The continuing development of a potential alternative to deferoxamine for iron-chelating therapy. Blood 1999;93:370-375.
    • (1999) Blood , vol.93 , pp. 370-375
    • Bergeron, R.J.1    Wiegand, J.2    Brittenham, G.M.3
  • 38
    • 0031822561 scopus 로고    scopus 로고
    • The origin of the differences in (R)- and (S)-desmethyldesferrithiocin: Iron-clearing properties
    • Bergeron RJ, Wiegand J, Ratliff-Thompson K, Weimar WR. The origin of the differences in (R)- and (S)-desmethyldesferrithiocin: Iron-clearing properties. Ann NY Acad Sci 1998;850:202-216.
    • (1998) Ann NY Acad Sci , vol.850 , pp. 202-216
    • Bergeron, R.J.1    Wiegand, J.2    Ratliff-Thompson, K.3    Weimar, W.R.4
  • 39
    • 0032751521 scopus 로고    scopus 로고
    • Pharmacokinetics of orally administered desferrithiocin analogs in Cebus apella primates
    • Bergeron RJ, Weimar WR, Wiegand J. Pharmacokinetics of orally administered desferrithiocin analogs in Cebus apella primates. Drug Metab Dispos 1999;27:1496-1498.
    • (1999) Drug Metab Dispos , vol.27 , pp. 1496-1498
    • Bergeron, R.J.1    Weimar, W.R.2    Wiegand, J.3
  • 43
    • 0042115456 scopus 로고
    • Study on the structure and properties of 4-(2-pyridylazo)resorcinol (PAR) and its derivatives
    • Zhao F, Liang Y, Zhang Y, Tong S. Study on the structure and properties of 4-(2-pyridylazo)resorcinol (PAR) and its derivatives. Chin Chem Lett 1992;3:107-108.
    • (1992) Chin Chem Lett , vol.3 , pp. 107-108
    • Zhao, F.1    Liang, Y.2    Zhang, Y.3    Tong, S.4
  • 44
    • 0012363412 scopus 로고
    • Resonance raman spectra of tautomeric forms of 1-(2-pyridylazo)-2-naphthol and 4-(2-pyridylazo)resorcinol
    • Drozdzewski PM. Resonance raman spectra of tautomeric forms of 1-(2-pyridylazo)-2-naphthol and 4-(2-pyridylazo)resorcinol. Spectrochim Acta A: Mol Biomol Spectrosc 1985;41A:1035-1039.
    • (1985) Spectrochim Acta A: Mol Biomol Spectrosc , vol.41 A , pp. 1035-1039
    • Drozdzewski, P.M.1
  • 45
    • 0019801634 scopus 로고
    • Synthesis of iron chelators. Enterobactin, enantioenterobactin, and a chiral analogue
    • Rastetter WH, Erickson TJ, Venuti MC. Synthesis of iron chelators. Enterobactin, enantioenterobactin, and a chiral analogue. J Org Chem 1981;46:3579-3590.
    • (1981) J Org Chem , vol.46 , pp. 3579-3590
    • Rastetter, W.H.1    Erickson, T.J.2    Venuti, M.C.3
  • 47
    • 0022586690 scopus 로고
    • Iron: A controlling nutrient in proliferative processes
    • Bergeron RJ. Iron: a controlling nutrient in proliferative processes. Trends Biochem Sci 1986;11:133-136.
    • (1986) Trends Biochem Sci , vol.11 , pp. 133-136
    • Bergeron, R.J.1


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