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Volumn 53, Issue 7, 2010, Pages 2843-2853

The impact of polyether chain length on the iron clearing efficiency and physiochemical properties of desferrithiocin analogues

Author keywords

[No Author keywords available]

Indexed keywords

4,5 DIHYDRO 2 [2 HYDROXY 4 (3,6 DIOXAHEPTYLOXY)PHENYL] 4 METHYL 4 THIAZOLECARBOXYLIC ACID; 4,5 DIHYDRO 2 [2 HYDROXY 4 (3,6,9 TRIOXATRIDECYLOXY)PHENYL] 4 METHYL 4 THIAZOLECARBOXYLIC ACID; 4,5 DIHYDRO 2 [2 HYDROXY 4 (3,6,9,12 TETRAOXATRIDECYLOXY)PHENYL] 4 METHYL 4 THIAZOLECARBOXYLIC ACID; DEFERITRIN; DEFERRIFERRITHIOCIN; ETHYL 4,5 DIHYDRO 2 [2 HYDROXY 4 (3,6 DIOXAHEPTYLOXY)PHENYL] 4 METHYL 4 THIAZOLECARBOXYLIC ACID; ETHYL 4,5 DIHYDRO 2 [2 HYDROXY 4 (3,6,9,12 TETRAOXATRIDECYLOXY)PHENYL] 4 METHYL 4 THIAZOLECARBOXYLIC ACID; ISOPROPYL 4,5 DIHYDRO 2 [2 HYDROXY 4 (3,6 DIOXAHEPTYLOXY)PHENYL] 4 METHYL 4 THIAZOLECARBOXYLIC ACID; UNCLASSIFIED DRUG;

EID: 77950556593     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9018146     Document Type: Article
Times cited : (9)

References (62)
  • 1
    • 0021337104 scopus 로고
    • Iron-catalyzed hydroxyl radical formation. Stringent requirement for free iron coordination site
    • Graf, E; Mahoney, J. R.; Bryant, R. G.; Eaton, J. W. Iron-Catalyzed Hydroxyl Radical Formation. Stringent Requirement for Free Iron Coordination Site J. Biol. Chem. 1984, 259, 3620 - 3624
    • (1984) J. Biol. Chem. , vol.259 , pp. 3620-3624
    • Graf, E.1    Mahoney, J.R.2    Bryant, R.G.3    Eaton, J.W.4
  • 2
    • 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
  • 4
    • 0002654177 scopus 로고    scopus 로고
    • Kinetics and mechanism of the fenton reaction: Implications for iron toxicity
    • Eds.; Saratoga: Ponte Vedra Beach, FL
    • Koppenol, W. Kinetics and Mechanism of the Fenton Reaction: Implications for Iron Toxicity. In Iron Chelators: New Development Strategies; Badman, D. G.; Bergeron, R. J.; Brittenham, G. M., Eds.; Saratoga: Ponte Vedra Beach, FL, 2000, pp 3 - 10.
    • (2000) Iron Chelators: New Development Strategies , pp. 3-10
    • Koppenol, W.1    Badman, D.G.2    Bergeron, R.J.3    Brittenham, G.M.4
  • 5
    • 0026683530 scopus 로고
    • Oxygen radicals in ulcerative colitis
    • Babbs, C. F. Oxygen Radicals in Ulcerative Colitis Free Radical Biol. Med. 1992, 13, 169 - 181
    • (1992) Free Radical Biol. Med. , vol.13 , pp. 169-181
    • Babbs, C.F.1
  • 6
    • 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, S. L.; d'Avignon, A.; Anderson, M. M.; Hsu, F. F.; Heinecke, J. W. 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
  • 8
    • 48749123360 scopus 로고    scopus 로고
    • Neuromelanin can protect against iron-mediated oxidative damage in system modeling iron overload of brain aging and parkinson's disease
    • Zecca, L.; Casella, L.; Albertini, A.; Bellei, C.; Zucca, F. A.; Engelen, M.; Zadlo, A.; Szewczyk, G.; Zareba, M.; Sarna, T. Neuromelanin Can Protect Against Iron-Mediated Oxidative Damage in System Modeling Iron Overload of Brain Aging and Parkinson's Disease J. Neurochem. 2008, 106, 1866 - 1875
    • (2008) J. Neurochem. , vol.106 , pp. 1866-1875
    • Zecca, L.1    Casella, L.2    Albertini, A.3    Bellei, C.4    Zucca, F.A.5    Engelen, M.6    Zadlo, A.7    Szewczyk, G.8    Zareba, M.9    Sarna, T.10
  • 9
    • 36849075284 scopus 로고    scopus 로고
    • Iron chelation beyond transfusion iron overload
    • Pietrangelo, A. Iron Chelation beyond Transfusion Iron Overload Am. J. Hematol. 2007, 82, 1142 - 1146
    • (2007) Am. J. Hematol. , vol.82 , pp. 1142-1146
    • Pietrangelo, A.1
  • 10
    • 0023623533 scopus 로고
    • Iron Overload and iron chelation therapy in thalassaemia and sickle cell haemoglobinopathies
    • Pippard, M. J. Iron Overload and Iron Chelation Therapy in Thalassaemia and Sickle Cell Haemoglobinopathies Acta. Haematol. 1987, 78, 206 - 211
    • (1987) Acta. Haematol. , vol.78 , pp. 206-211
    • Pippard, M.J.1
  • 11
    • 0035138526 scopus 로고    scopus 로고
    • Progression of iron overload in sickle cell disease
    • Olivieri, N. F. Progression of Iron Overload in Sickle Cell Disease Semin. Hematol. 2001, 38, 57 - 62
    • (2001) Semin. Hematol. , vol.38 , pp. 57-62
    • Olivieri, N.F.1
  • 12
    • 36248941352 scopus 로고    scopus 로고
    • Impact of transfusion dependency and secondary iron overload on the survival of patients with myelodysplastic syndromes
    • Malcovati, L. Impact of Transfusion Dependency and Secondary Iron Overload on the Survival of Patients with Myelodysplastic Syndromes Leukemia Res. 2007, 31, S2 - S6
    • (2007) Leukemia Res. , vol.31
    • Malcovati, L.1
  • 15
    • 0041808770 scopus 로고    scopus 로고
    • Mechanism of iron toxicity
    • Peitrangelo, A. Mechanism of Iron Toxicity Adv. Exp. Med. Biol. 2002, 509, 19 - 43
    • (2002) Adv. Exp. Med. Biol. , vol.509 , pp. 19-43
    • Peitrangelo, A.1
  • 16
    • 0346665875 scopus 로고    scopus 로고
    • Insulin sensitivity and - Cell secretion in thalassemia major with secondary haemochromatosis: Assessment by oral glucose tolerance test
    • Cario, H.; Holl, R. W.; Debatin, K. M.; Kohne, E. Insulin Sensitivity and --Cell Secretion in Thalassemia Major with Secondary Haemochromatosis: Assessment by Oral Glucose Tolerance Test Eur. J. Pediatr. 2004, 162, 139 - 146
    • (2004) Eur. J. Pediatr. , vol.162 , pp. 139-146
    • Cario, H.1    Holl, R.W.2    Debatin, K.M.3    Kohne, E.4
  • 21
    • 77950588053 scopus 로고    scopus 로고
    • Novartis Pharmaceuticals Corporation: East Hanover, NJ
    • Desferal; Novartis Pharmaceuticals Corporation: East Hanover, NJ, 2008; http://www.pharma.us.novartis.com/product/pi/pdf/desferal.pdf.
    • (2008) Desferal
  • 23
    • 0030058376 scopus 로고    scopus 로고
    • Long-term therapy with deferiprone
    • Olivieri, N. F. Long-Term Therapy with Deferiprone Acta Haematol. 1996, 95, 37 - 48
    • (1996) Acta Haematol. , vol.95 , pp. 37-48
    • Olivieri, N.F.1
  • 25
    • 0035336822 scopus 로고    scopus 로고
    • The controversial role of deferiprone in the treatment of thalassemia
    • Richardson, D. R. The Controversial Role of Deferiprone in the Treatment of Thalassemia J. Lab. Clin. Med. 2001, 137, 324 - 329
    • (2001) J. Lab. Clin. Med. , vol.137 , pp. 324-329
    • Richardson, D.R.1
  • 27
    • 0037906104 scopus 로고    scopus 로고
    • Safety, tolerability, and pharmacokinetics of ICL670, a new orally active iron-chelating agent in patients with transfusion-dependent iron overload due to - Thalassemia
    • Galanello, R.; Piga, A.; Alberti, D.; Rouan, M.-C.; Bigler, H.; Séchaud, R. Safety, Tolerability, and Pharmacokinetics of ICL670, a New Orally Active Iron-Chelating Agent in Patients with Transfusion-Dependent Iron Overload Due to -Thalassemia J. Clin. Pharmacol. 2003, 43, 565 - 572
    • (2003) J. Clin. Pharmacol. , vol.43 , pp. 565-572
    • Galanello, R.1    Piga, A.2    Alberti, D.3    Rouan, M.-C.4    Bigler, H.5    Séchaud, R.6
  • 28
    • 14544276809 scopus 로고    scopus 로고
    • Iron-chelating therapy with the new oral agent ICL670 (exjade)
    • Cappellini, M. D. Iron-Chelating Therapy with the New Oral Agent ICL670 (Exjade) Best Pract. Res. Clin. Haematol. 2005, 18, 289 - 298
    • (2005) Best Pract. Res. Clin. Haematol. , vol.18 , pp. 289-298
    • Cappellini, M.D.1
  • 29
    • 67651231740 scopus 로고    scopus 로고
    • Novartis Pharmaceuticals Corporation: East Hanover, NJ, December
    • Exjade Prescribing Information; Novartis Pharmaceuticals Corporation: East Hanover, NJ, December, 2007; http://www.pharma.us.novartis.com/product/pi/ pdf/exjade.pdf.
    • (2007) Exjade Prescribing Information
  • 31
    • 0024521376 scopus 로고
    • Desferrioxamine-induced iron excretion in humans
    • Pippard, M. J. 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
  • 32
    • 0034783438 scopus 로고    scopus 로고
    • Chelation therapy in - Thalassemia: An optimistic update
    • Giardina, P. J.; Grady, R. W. Chelation Therapy in --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
  • 33
    • 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
  • 34
    • 33646441572 scopus 로고    scopus 로고
    • (S)-4,5-dihydro-2-(2-hydroxy-4-hydroxyphenyl)-4-methyl-4- thiazolecarboxylic acid Polyethers: A solution to nephrotoxicity
    • Bergeron, R. J.; Wiegand, J.; McManis, J. S.; Vinson, J. R. T.; Yao, H.; Bharti, N.; Rocca, J. R. (S)-4,5-Dihydro-2-(2-hydroxy-4-hydroxyphenyl)-4-methyl- 4-thiazolecarboxylic Acid Polyethers: A Solution to Nephrotoxicity J. Med. Chem. 2006, 49, 2772 - 2783
    • (2006) J. Med. Chem. , vol.49 , pp. 2772-2783
    • Bergeron, R.J.1    Wiegand, J.2    McManis, J.S.3    Vinson, J.R.T.4    Yao, H.5    Bharti, N.6    Rocca, J.R.7
  • 35
    • 0025552882 scopus 로고
    • Pyridoxal isonicotinoyl hydrazone. effective iron chelation after oral administration
    • Brittenham, G. M. Pyridoxal Isonicotinoyl Hydrazone. Effective Iron Chelation after Oral Administration Ann. N. Y. Acad. Sci. 1990, 612, 315 - 326
    • (1990) Ann. N. Y. Acad. Sci. , vol.612 , pp. 315-326
    • Brittenham, G.M.1
  • 36
    • 84985071864 scopus 로고
    • Metabolites of microorganisms. Part 193. Ferrithiocin
    • Naegeli, H.-U.; Zohner, H. Metabolites of Microorganisms. Part 193. Ferrithiocin Helv. Chim. Acta 1980, 63, 1400 - 1406
    • (1980) Helv. Chim. Acta , vol.63 , pp. 1400-1406
    • Naegeli, H.-U.1    Zohner, H.2
  • 37
    • 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, F. E.; McMurry, T. J.; Hugi, A.; Raymond, K. N. 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
  • 38
    • 0025088608 scopus 로고
    • Metal complex formation of a new siderophore desferrithiocin and of three related ligands
    • Anderegg, G.; Rober, M. Metal Complex Formation of a New Siderophore Desferrithiocin 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    Rober, M.2
  • 41
    • 0027401142 scopus 로고
    • A comparative study of the iron-clearing properties of desferrithiocin analogues with desferrioxamine b in a cebus monkey model
    • Bergeron, R. J.; Streiff, R. R.; Creary, E. A.; Daniels, R. D., Jr.; King, W.; Luchetta, G.; Wiegand, J.; Moerker, T.; Peter, H. H. A Comparative Study of the Iron-Clearing Properties of Desferrithiocin Analogues with Desferrioxamine B in a Cebus Monkey Model Blood 1993, 81, 2166 - 2173
    • (1993) Blood , vol.81 , pp. 2166-2173
    • Bergeron, R.J.1    Streiff, R.R.2    Creary, E.A.3    Daniels Jr., R.D.4    King, W.5    Luchetta, G.6    Wiegand, J.7    Moerker, T.8    Peter, H.H.9
  • 42
    • 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, R. J.; Wiegand, J.; McManis, J. S.; McCosar, B. H.; Weimar, W. R.; Brittenham, G. M.; Smith, R. E. 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
  • 45
    • 33845351575 scopus 로고    scopus 로고
    • The design, synthesis, and evaluation of organ-specific iron chelators
    • Bergeron, R. J.; Wiegand, J.; McManis, J. S.; Bharti, N. The Design, Synthesis, and Evaluation of Organ-Specific Iron Chelators J. Med. Chem. 2006, 49, 7032 - 7043
    • (2006) J. Med. Chem. , vol.49 , pp. 7032-7043
    • Bergeron, R.J.1    Wiegand, J.2    McManis, J.S.3    Bharti, N.4
  • 46
    • 34447523769 scopus 로고    scopus 로고
    • Impact of the 3,6,9-trioxadecyloxy group on desazadesferrithiocin analogue iron clearance and organ distribution
    • Bergeron, R. J.; Wiegand, J.; Bharti, N.; Singh, S.; Rocca, J. R. Impact of the 3,6,9-Trioxadecyloxy Group on Desazadesferrithiocin Analogue Iron Clearance and Organ Distribution J. Med. Chem. 2007, 50, 3302 - 3313
    • (2007) J. Med. Chem. , vol.50 , pp. 3302-3313
    • Bergeron, R.J.1    Wiegand, J.2    Bharti, N.3    Singh, S.4    Rocca, J.R.5
  • 47
    • 46849115983 scopus 로고    scopus 로고
    • Design, synthesis, and testing of non-nephrotoxic desazadesferrithiocin polyether analogues
    • Bergeron, R. J.; Wiegand, J.; McManis, J. S.; Bharti, N.; Singh, S. Design, Synthesis, and Testing of Non-Nephrotoxic Desazadesferrithiocin Polyether Analogues J. Med. Chem. 2008, 51, 3913 - 3923
    • (2008) J. Med. Chem. , vol.51 , pp. 3913-3923
    • Bergeron, R.J.1    Wiegand, J.2    McManis, J.S.3    Bharti, N.4    Singh, S.5
  • 49
    • 9244264422 scopus 로고    scopus 로고
    • Carboplatin-containing porphyrin-platinum complexes as cytotoxic and phototoxic antitumor agents
    • Brunner, H; Gruber, N. Carboplatin-Containing Porphyrin-Platinum Complexes as Cytotoxic and Phototoxic Antitumor Agents Inorg. Chim. Acta 2004, 357, 4423 - 4451
    • (2004) Inorg. Chim. Acta , vol.357 , pp. 4423-4451
    • Brunner, H.1    Gruber, N.2
  • 51
    • 0041663758 scopus 로고    scopus 로고
    • Iron chelation promoted by desazadesferrithiocin analogues: An enantioselective barrier
    • Bergeron, R. J.; Wiegand, J.; Weimar, W. R.; McManis, J. S.; Smith, R. E.; Abboud, K. A. Iron Chelation Promoted by Desazadesferrithiocin Analogues: An Enantioselective Barrier Chirality 2003, 15, 593 - 599
    • (2003) Chirality , vol.15 , pp. 593-599
    • Bergeron, R.J.1    Wiegand, J.2    Weimar, W.R.3    McManis, J.S.4    Smith, R.E.5    Abboud, K.A.6
  • 53
    • 0017094116 scopus 로고
    • The effect of chelating agents on iron mobilization in chang cell cultures
    • White, G. P.; Jacobs, A.; Grady, R. W.; Cerami, A. The Effect of Chelating Agents on Iron Mobilization in Chang Cell Cultures Blood 1976, 48, 923 - 929
    • (1976) Blood , vol.48 , pp. 923-929
    • White, G.P.1    Jacobs, A.2    Grady, R.W.3    Cerami, A.4
  • 54
    • 0017135357 scopus 로고
    • The effect of chelating agents on cellular iron metabolism
    • White, G. P.; Bailey-Wood, R.; Jacobs, A. The Effect of Chelating Agents on Cellular Iron Metabolism Clin. Sci. Mol. Med. 1976, 50, 145 - 52
    • (1976) Clin. Sci. Mol. Med. , vol.50 , pp. 145-52
    • White, G.P.1    Bailey-Wood, R.2    Jacobs, A.3
  • 57
    • 77950570196 scopus 로고    scopus 로고
    • SHELXTL6; Bruker-AXS: Madison, WI.
    • SHELXTL6; Bruker-AXS: Madison, WI, 2000.
    • (2000)
  • 58
    • 0031822561 scopus 로고    scopus 로고
    • The origin of the differences in (r)- and (s)-desmethyldesferrithiocin: iron-clearing properties
    • Bergeron, R. J.; Wiegand, J.; Ratliff-Thompson, K.; Weimar, W. R. The Origin of the Differences in (R)- and (S)-Desmethyldesferrithiocin: Iron-Clearing Properties Ann. N. Y. Acad. Sci. 1998, 850, 202 - 216
    • (1998) Ann. N. Y. Acad. Sci. , vol.850 , pp. 202-216
    • Bergeron, R.J.1    Wiegand, J.2    Ratliff-Thompson, K.3    Weimar, W.R.4
  • 59
    • 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, R. J.; Streiff, R. R.; Wiegand, J.; Luchetta, G.; Creary, E. A.; Peter, H. H. 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
  • 60
    • 0014249766 scopus 로고
    • The metabolism of iron-dextran given as a total-dose infusion to iron deficient jamaican subjects
    • Wood, J. K.; Milner, P. F.; Pathak, U. N. 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
  • 61
    • 0032519770 scopus 로고    scopus 로고
    • HBED: A potential alternative to deferoxamine for iron-chelating therapy
    • Bergeron, R. J.; Wiegand, J.; Brittenham, G. M. 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


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