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Volumn 122, Issue 1, 2011, Pages 157-169

Fluorothalidomide: A characterization of maternal and developmental toxicity in rabbits and mice

Author keywords

Embryopathies; Fluorinated analog; Hydrolysis; Teratogenesis; Thalidomide

Indexed keywords

FLUOROTHALIDOMIDE; THALIDOMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79960156429     PISSN: 10966080     EISSN: 10960929     Source Type: Journal    
DOI: 10.1093/toxsci/kfr086     Document Type: Article
Times cited : (21)

References (38)
  • 2
    • 0018620980 scopus 로고
    • Chromatographic separation of racemic thalidomide and teratogenic activity of its enantiomers
    • Blaschke, G., Kraft, H. P., Fickentscher, K., and Kohler, F. (1979). Chromatographic separation of racemic thalidomide and teratogenic activity of its enantiomers. Arzneimittelforschung 29, 1640-1642.
    • (1979) Arzneimittelforschung , vol.29 , pp. 1640-1642
    • Blaschke, G.1    Kraft, H.P.2    Fickentscher, K.3    Kohler, F.4
  • 5
    • 0842327350 scopus 로고    scopus 로고
    • Effects of 3-fluorothalidomide and 3-methylthalidomide enantiomers on tumor necrosis factor production and antitumor responses to the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA)
    • Chung, F., Palmer, B. D., Muller, G. W., Man, H.W., Kestell, P., Baguley, B. C., and Ching, L. M. (2003). Effects of 3-fluorothalidomide and 3-methylthalidomide enantiomers on tumor necrosis factor production and antitumor responses to the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA). Oncol. Res. 14, 75-92.
    • (2003) Oncol. Res. , vol.14 , pp. 75-92
    • Chung, F.1    Palmer, B.D.2    Muller, G.W.3    Man, H.W.4    Kestell, P.5    Baguley, B.C.6    Ching, L.M.7
  • 6
    • 0028916174 scopus 로고
    • Stereospecific determination, chiral inversion in vitro and pharmacokinetics in humans of the enantiomers of thalidomide
    • Eriksson, T., Bjorkman, S., Roth, B., Fyge, A., and Hoglund, P. (1995). Stereospecific determination, chiral inversion in vitro and pharmacokinetics in humans of the enantiomers of thalidomide. Chirality 7, 44-52.
    • (1995) Chirality , vol.7 , pp. 44-52
    • Eriksson, T.1    Bjorkman, S.2    Roth, B.3    Fyge, A.4    Hoglund, P.5
  • 7
    • 0343627976 scopus 로고    scopus 로고
    • Intravenous formulations of the enantiomers of thalidomide: pharmacokinetic and initial pharmacodynamic characterization in man
    • Eriksson, T., Bjorkman, S., Roth, B., and Hoglund, P. (2000). Intravenous formulations of the enantiomers of thalidomide: pharmacokinetic and initial pharmacodynamic characterization in man. J. Pharm. Pharmacol. 52, 807-817.
    • (2000) J. Pharm. Pharmacol. , vol.52 , pp. 807-817
    • Eriksson, T.1    Bjorkman, S.2    Roth, B.3    Hoglund, P.4
  • 8
    • 0014116438 scopus 로고
    • The fate of [14C]thalidomide in the pregnant rabbit
    • Fabro, S., Smith, R. L., and Williams, R. T. (1967a). The fate of [14C]thalidomide in the pregnant rabbit. Biochem. J. 104, 565-569.
    • (1967) Biochem. J. , vol.104 , pp. 565-569
    • Fabro, S.1    Smith, R.L.2    Williams, R.T.3
  • 9
    • 36949061827 scopus 로고
    • Toxicity and teratogenicity of optical isomers of thalidomide
    • Fabro, S., Smith, R. L., and Williams, R. T. (1967b). Toxicity and teratogenicity of optical isomers of thalidomide. Nature 215, 296.
    • (1967) Nature , vol.215 , pp. 296
    • Fabro, S.1    Smith, R.L.2    Williams, R.T.3
  • 11
    • 0023773376 scopus 로고
    • Embryotoxic effects of thalidomide derivatives on the non-human primate Callithrix jacchus; 3,Teratogenic potency of the EM 12 enantiomers
    • Heger, W., Klug, S., Schmahl, H. J., Nau, H., Merker, H. J., and Neubert, D. (1988). Embryotoxic effects of thalidomide derivatives on the non-human primate Callithrix jacchus; 3. Teratogenic potency of the EM 12 enantiomers. Arch. Toxicol. 62, 205-208.
    • (1988) Arch. Toxicol. , vol.62 , pp. 205-208
    • Heger, W.1    Klug, S.2    Schmahl, H.J.3    Nau, H.4    Merker, H.J.5    Neubert, D.6
  • 12
    • 2542509655 scopus 로고    scopus 로고
    • A double-blind study of the sedative effects of the thalidomide enantiomers in humans
    • Hoglund, P., Eriksson, T., and Bjorkman, S. (1998). A double-blind study of the sedative effects of the thalidomide enantiomers in humans. J. Pharmacokinet. Biopharm. 26, 363-383.
    • (1998) J. Pharmacokinet. Biopharm. , vol.26 , pp. 363-383
    • Hoglund, P.1    Eriksson, T.2    Bjorkman, S.3
  • 13
    • 79960175072 scopus 로고    scopus 로고
    • Embryopathic effects of thalidomide and its hydrolysis products in rabbit embryo culture: evidence for a prostaglandin H synthase (PHS)-dependent, reactive oxygen species (ROS)-mediated mechanism
    • Accessed April 18, 2011. doi:10.1096/fj.10-178814 fj.10-178814
    • Lee, C. J. J., Goncxalves, L. L., and Wells, P. G. (2011a). Embryopathic effects of thalidomide and its hydrolysis products in rabbit embryo culture: evidence for a prostaglandin H synthase (PHS)-dependent, reactive oxygen species (ROS)-mediated mechanism. FASEB J. Accessed April 18, 2011. doi:10.1096/fj.10-178814 fj.10-178814.
    • (2011) FASEB J
    • Lee, C.J.J.1    Goncxalves, L.L.2    Wells, P.G.3
  • 14
    • 79960187844 scopus 로고    scopus 로고
    • Resistance of CD-1 and ogg1 DNA repair-deficient mice to thalidomide and hydrolysis product embryopathies in culture
    • Accessed April 19, 2011. doi:10.1093/toxsci/KFR084
    • Lee, C. J. J., Goncxalves, L. L., and Wells, P. G. (2011b). Resistance of CD-1 and ogg1 DNA repair-deficient mice to thalidomide and hydrolysis product embryopathies in culture. Toxicol. Sci Accessed April 19, 2011. doi:10.1093/toxsci/KFR084.
    • (2011) Toxicol. Sci
    • Lee, C.J.J.1    Goncxalves, L.L.2    Wells, P.G.3
  • 15
    • 0023789803 scopus 로고
    • A short history of thalidomide embryopathy
    • Lenz, W. (1988). A short history of thalidomide embryopathy. Teratology 38, 203-215.
    • (1988) Teratology , vol.38 , pp. 203-215
    • Lenz, W.1
  • 18
    • 0023832112 scopus 로고
    • Embryotoxic effects of thalidomide-derivatives in the non-human primate Callithrix jacchus. I. Effects of 3-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-dioxopiperidine (EM12) on skeletal development
    • Merker, H. J., Heger, W., Sames, K., Sturje, H., and Neubert, D. (1988). Embryotoxic effects of thalidomide-derivatives in the non-human primate Callithrix jacchus. I. Effects of 3-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-dioxopiperidine (EM12) on skeletal development. Arch. Toxicol. 61, 165-179.
    • (1988) Arch. Toxicol. , vol.61 , pp. 165-179
    • Merker, H.J.1    Heger, W.2    Sames, K.3    Sturje, H.4    Neubert, D.5
  • 19
    • 0030590082 scopus 로고    scopus 로고
    • Cell-type/inducer-specific bidirectional regulation by thalidomide and phenylphthalimides of tumor necrosis factor-alpha production and its enantio-dependence
    • Miyachi, H., Azuma, A., Hioki, E., Iwasaki, S., Kobayashi, Y., and Hashimoto, Y. (1996). Cell-type/inducer-specific bidirectional regulation by thalidomide and phenylphthalimides of tumor necrosis factor-alpha production and its enantio-dependence. Biochem. Biophsy. Res. Commun. 224, 426-430.
    • (1996) Biochem. Biophsy. Res. Commun. , vol.224 , pp. 426-430
    • Miyachi, H.1    Azuma, A.2    Hioki, E.3    Iwasaki, S.4    Kobayashi, Y.5    Hashimoto, Y.6
  • 20
    • 0031873804 scopus 로고    scopus 로고
    • Tumor necrosis factor-alpha production enhancing activity of substituted 3'-methylthalidomide: influence of substituents at the phthaloyl moiety on the activity and stereoselectivity
    • Miyachi, H., Kioso, Y., Shirai, R., Niwayama, S., Liu, J. O., and Hashimoto, Y. (1998). Tumor necrosis factor-alpha production enhancing activity of substituted 3'-methylthalidomide: influence of substituents at the phthaloyl moiety on the activity and stereoselectivity. Chem. Pharm. Bull. 46, 1165-1168.
    • (1998) Chem. Pharm. Bull. , vol.46 , pp. 1165-1168
    • Miyachi, H.1    Kioso, Y.2    Shirai, R.3    Niwayama, S.4    Liu, J.O.5    Hashimoto, Y.6
  • 22
    • 0028302647 scopus 로고
    • (S)-form of alphamethyl-N(alpha)-phthalimidoglutarimide, but not its (R)-form, enhanced phorbol ester-induced tumor necrosis factor-alpha production in human leukemia cell HL-60: implication of optical resolution of thalidomide effects
    • Nishimura, K., Hashimoto, Y., and Iwasaki, S. (1994). (S)-form of alphamethyl-N(alpha)-phthalimidoglutarimide, but not its (R)-form, enhanced phorbol ester-induced tumor necrosis factor-alpha production in human leukemia cell HL-60: implication of optical resolution of thalidomide effects. Chem. Pharm. Bull. 42, 1157-1159.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 1157-1159
    • Nishimura, K.1    Hashimoto, Y.2    Iwasaki, S.3
  • 23
    • 0032080615 scopus 로고    scopus 로고
    • Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-alpha production is associated with a change of mechanism of action
    • Niwayama, S., Loh, C., Turk, B. E., Liu, J. O., Miyachi, H., and Hashimoto, Y. (1998). Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-alpha production is associated with a change of mechanism of action. Bioorg. Med. Chem. Lett. 8, 1071-1076.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1071-1076
    • Niwayama, S.1    Loh, C.2    Turk, B.E.3    Liu, J.O.4    Miyachi, H.5    Hashimoto, Y.6
  • 25
    • 0032920883 scopus 로고    scopus 로고
    • Free radical-mediated oxidative DNA damage in the mechanism of thalidomide teratogenicity
    • Parman, T., Wiley, M. J., and Wells, P. G. (1999). Free radical-mediated oxidative DNA damage in the mechanism of thalidomide teratogenicity. Nat. Med. 5, 582-585.
    • (2001) Nat. Med , vol.5 , pp. 582-585
    • Parman, T.1    Wiley, M.J.2    Wells, P.G.3
  • 26
    • 0032989357 scopus 로고    scopus 로고
    • Development of a morphologicallybased scoring system for postimplantation New Zealand White rabbit embryos
    • Pitt, J. A., and Carney, E. W. (1999a). Development of a morphologicallybased scoring system for postimplantation New Zealand White rabbit embryos. Teratology 59, 88-101.
    • (1999) Teratology , vol.59 , pp. 88-101
    • Pitt, J.A.1    Carney, E.W.2
  • 27
    • 0033060375 scopus 로고    scopus 로고
    • Evaluation of various toxicants in rabbit whole embryo culture using a new morphologically-based evaluation system
    • Pitt, J. A., and Carney, E. W. (1999b). Evaluation of various toxicants in rabbit whole embryo culture using a new morphologically-based evaluation system. Teratology 59, 102-109.
    • (1999) Teratology , vol.59 , pp. 102-109
    • Pitt, J.A.1    Carney, E.W.2
  • 29
    • 0014267139 scopus 로고
    • A comparison of the teratogenic activity of thalidomide in rabbits and rats
    • Schumacher, H., Blake, D. A., Gurian, J. M., and Gillette, J. R. (1968). A comparison of the teratogenic activity of thalidomide in rabbits and rats. J. Pharmacol. Exp. Ther. 160, 189-200.
    • (1968) J. Pharmacol. Exp. Ther. , vol.160 , pp. 189-200
    • Schumacher, H.1    Blake, D.A.2    Gurian, J.M.3    Gillette, J.R.4
  • 30
    • 67649297606 scopus 로고    scopus 로고
    • Chiral toxicology: it's the same thing... only different
    • Smith, S. W. (2009). Chiral toxicology: it's the same thing... only different. Toxicol. Sci. 110, 4-30.
    • (2009) Toxicol. Sci. , vol.110 , pp. 4-30
    • Smith, S.W.1
  • 31
    • 0003163821 scopus 로고
    • Thalidomide and congenital abnormalities
    • Somers, G. F. (1962). Thalidomide and congenital abnormalities. Lancet 279, 912-913.
    • (1962) Lancet , vol.279 , pp. 912-913
    • Somers, G.F.1
  • 32
    • 0001093384 scopus 로고    scopus 로고
    • (R)- and (S)-3-fluorothalidomides: isosteric analogues of thalidomide
    • Takeuchi, Y., Tomoki, S., Kenichi, K., Suzuki, E., and Shibata, N. (1999). (R)- and (S)-3-fluorothalidomides: isosteric analogues of thalidomide. Org. Lett. 1, 1571-1573.
    • (1999) Org. Lett. , vol.1 , pp. 1571-1573
    • Takeuchi, Y.1    Tomoki, S.2    Kenichi, K.3    Suzuki, E.4    Shibata, N.5
  • 33
    • 0037263658 scopus 로고    scopus 로고
    • Chiral inversion of the second generation IMiD CC-4047 (ACTIMID) in human plasma and phosphate-buffered saline
    • Teo, S. K., Chen, Y.,Muller, G. W., Chen, R. S., Thomas, S. D., Stirling, D. I., and Chandula, R. S. (2003). Chiral inversion of the second generation IMiD CC-4047 (ACTIMID) in human plasma and phosphate-buffered saline. Chirality 15, 348-351.
    • (2003) Chirality , vol.15 , pp. 348-351
    • Teo, S.K.1    Chen, Y.2    Muller, G.W.3    Chen, R.S.4    Thomas, S.D.5    Stirling, D.I.6    Chandula, R.S.7
  • 34
    • 66649093493 scopus 로고    scopus 로고
    • Thalidomide induces limb defects by preventing angiogenic outgrowth during early limb formation
    • Therapontos, C., Erskine, L., Gardner, E. R., Figg, W. D., and Vargesson, N. (2009). Thalidomide induces limb defects by preventing angiogenic outgrowth during early limb formation. Proc. Natl. Acad. Sci. U.S.A. 106, 8573-8578.
    • (2009) Proc. Natl. Acad. Sci. U.S.A. , vol.106 , pp. 8573-8578
    • Therapontos, C.1    Erskine, L.2    Gardner, E.R.3    Figg, W.D.4    Vargesson, N.5
  • 35
    • 0030971749 scopus 로고    scopus 로고
    • A review of the contribution of whole embryo culture to the determination of hazard and risk in teratogenicity testing
    • Webster, S. W., Brown-Woodman, P. C. D., and Ritchie, H. E. (1997). A review of the contribution of whole embryo culture to the determination of hazard and risk in teratogenicity testing. Int. J. Dev. Biol. 41, 329-335.
    • (1997) Int. J. Dev. Biol. , vol.41 , pp. 329-335
    • Webster, S.W.1    Brown-Woodman, P.C.D.2    Ritchie, H.E.3
  • 36
    • 0014278061 scopus 로고
    • Thalidomide. A study of biochemical teratology
    • Williams, R. T. (1968). Thalidomide. A study of biochemical teratology. Arch. Environ. Health 16, 493-502.
    • (1968) Arch. Environ. Health , vol.16 , pp. 493-502
    • Williams, R.T.1
  • 37
    • 0036447393 scopus 로고    scopus 로고
    • Evidence for Ras-dependent signal transduction in phenytoin teratogenicity
    • Winn, L. M., and Wells, P. G. (2002). Evidence for Ras-dependent signal transduction in phenytoin teratogenicity. Toxicol. Appl. Pharm. 184, 144-152.
    • (2002) Toxicol. Appl. Pharm. , vol.184 , pp. 144-152
    • Winn, L.M.1    Wells, P.G.2
  • 38
    • 0029990823 scopus 로고    scopus 로고
    • Enantioselective inhibition of TNF-alpha release by thalidomide and thalidomide-analogues
    • Wnendt, S., Finkam, M., Winter, W., Ossig, J., Raabe, G., and Zwingenberger, K. (1996). Enantioselective inhibition of TNF-alpha release by thalidomide and thalidomide-analogues. Chirality 8, 390-396.
    • (1996) Chirality , vol.8 , pp. 390-396
    • Wnendt, S.1    Finkam, M.2    Winter, W.3    Ossig, J.4    Raabe, G.5    Zwingenberger, K.6


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