메뉴 건너뛰기




Volumn 52, Issue 5, 1997, Pages 839-845

Mitindomide is a catalytic inhibitor of DNA topoisomerase II that acts at the bisdioxopiperazine binding site

Author keywords

[No Author keywords available]

Indexed keywords

2,3 BIS(3,5 DIOXO 1 PIPERAZINYL)BUTANE; BIS(DIOXOPIPERAZINE) DERIVATIVE; ETOPOSIDE; GYRASE INHIBITOR; MITINDOMIDE; RAZOXANE; UNCLASSIFIED DRUG;

EID: 0030733491     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.52.5.839     Document Type: Article
Times cited : (52)

References (36)
  • 1
    • 1842356415 scopus 로고
    • Strategy for the discovery and development of novel anticancer agents
    • D. N. Reinhoudt, T. A. Connors, H. M. Pinedo, and L. W. van de Poll, eds.. Martinus Nijhoff, The Hague
    • Narayanan, V. L. Strategy for the discovery and development of novel anticancer agents, in Structure-Activity Relationships of Anti-Tumour Agents (D. N. Reinhoudt, T. A. Connors, H. M. Pinedo, and L. W. van de Poll, eds.). Martinus Nijhoff, The Hague, 5-22 (1983).
    • (1983) Structure-Activity Relationships of Anti-Tumour Agents , pp. 5-22
    • Narayanan, V.L.1
  • 2
    • 85036676602 scopus 로고    scopus 로고
    • Chevron Research, assignee. Use of a tricyclodecene-3,4,7,8-tetracarboxylic acid diimide as an anti-murine tumor agent. U.S. Patent 4,877,806 (1989)
    • Neighbors, R. P., and J. R. Riden, inventors. Chevron Research, assignee. Use of a tricyclodecene-3,4,7,8-tetracarboxylic acid diimide as an anti-murine tumor agent. U.S. Patent 4,877,806 (1989).
    • Neighbors, R.P.1    Riden, J.R.2
  • 4
    • 1842348500 scopus 로고
    • Cross-linking of DNA by diimide antitumor agents and the relationship to cytotoxicity in A204 rhabdomyosarcoma cells
    • Moore, D. J., G. Powis, D. C. Melder, H. M. Deutsch, and L. H. Zalkow. Cross-linking of DNA by diimide antitumor agents and the relationship to cytotoxicity in A204 rhabdomyosarcoma cells. J. Cell. Pharmacol. 1:103-108 (1990).
    • (1990) J. Cell. Pharmacol. , vol.1 , pp. 103-108
    • Moore, D.J.1    Powis, G.2    Melder, D.C.3    Deutsch, H.M.4    Zalkow, L.H.5
  • 5
    • 0022646959 scopus 로고
    • 2,5]dec-9-ene-3,4,7,8-tetracarboxylic acid diimide: Formulation and stability studies
    • 2,5]dec-9-ene-3,4,7,8-tetracarboxylic acid diimide: formulation and stability studies. J. Pharm. Sci. 75:301-303 (1986).
    • (1986) J. Pharm. Sci. , vol.75 , pp. 301-303
    • Vishnuvajjala, B.R.1    Cradock, J.C.2
  • 8
    • 85036675755 scopus 로고    scopus 로고
    • United States of America, assignee. Substituted N-methyl derivatives of mitindomide. U.S. Patent 4,803,202 (1984)
    • Haugwitz, R. D., V. Narayanan, L. H. Zalkow, H. M. Deutch, and L. Gelbaum, inventors. United States of America, assignee. Substituted N-methyl derivatives of mitindomide. U.S. Patent 4,803,202 (1984).
    • Haugwitz, R.D.1    Narayanan, V.2    Zalkow, L.H.3    Deutch, H.M.4    Gelbaum, L.5
  • 9
    • 85036683240 scopus 로고    scopus 로고
    • Formaldehyde derivatives of mitindomide. United States of America, assignee. U.S. Patent 4,670,461 (1987)
    • Haugwitz, R. D., V. L. Narayanan, L. H. Zalkow, and H. M. Deutsch. Formaldehyde derivatives of mitindomide. United States of America, assignee. U.S. Patent 4,670,461 (1987).
    • Haugwitz, R.D.1    Narayanan, V.L.2    Zalkow, L.H.3    Deutsch, H.M.4
  • 10
    • 0023628873 scopus 로고
    • Stability indicating assay for fetindomide (NSC 373965), a potential prodrug of mitindomide (NSC 284356), employing high-performance liquid chromatography
    • Umprayn, K., V. J. Stella, and C. M. Riley. Stability indicating assay for fetindomide (NSC 373965), a potential prodrug of mitindomide (NSC 284356), employing high-performance liquid chromatography. J. Pharm. Biomed. Anal. 5:675-685 (1987).
    • (1987) J. Pharm. Biomed. Anal. , vol.5 , pp. 675-685
    • Umprayn, K.1    Stella, V.J.2    Riley, C.M.3
  • 11
    • 0026425654 scopus 로고
    • Inhibition of intracellular topoisomerase II by antitumor bis(2,6-dioxopiperazine) derivatives: Mode of cell growth inhibition distinct from that of cleavable complex-forming type inhibitors
    • Ishida, R., T. Miki, T. Narita, R. Yui, M. Sato, K. R. Utsumi, K. Tanabe, and T. Andoh. Inhibition of intracellular topoisomerase II by antitumor bis(2,6-dioxopiperazine) derivatives: mode of cell growth inhibition distinct from that of cleavable complex-forming type inhibitors. Cancer Res. 51:4909-4916 (1991).
    • (1991) Cancer Res. , vol.51 , pp. 4909-4916
    • Ishida, R.1    Miki, T.2    Narita, T.3    Yui, R.4    Sato, M.5    Utsumi, K.R.6    Tanabe, K.7    Andoh, T.8
  • 12
    • 0028810791 scopus 로고
    • A QSAR study comparing the cytotoxicity and DNA topoisomerase II inhibitory effects of bisdioxopiperazine analogs of ICRF-187 (dexrazoxane)
    • Hasinoff, B. B., T. I. Kuschak, J. C. Yalowich, and A. M. Creighton. A QSAR study comparing the cytotoxicity and DNA topoisomerase II inhibitory effects of bisdioxopiperazine analogs of ICRF-187 (dexrazoxane). Biochem. Pharmacol. 50:953-958 (1995).
    • (1995) Biochem. Pharmacol. , vol.50 , pp. 953-958
    • Hasinoff, B.B.1    Kuschak, T.I.2    Yalowich, J.C.3    Creighton, A.M.4
  • 13
    • 0014691658 scopus 로고
    • Antitumour activity in a series of bisdiketopiperazines
    • Creighton, A. M., K. Hellmann, and S. Whitecross. Antitumour activity in a series of bisdiketopiperazines. Nature (Lond.) 22:384-385 (1969).
    • (1969) Nature (Lond.) , vol.22 , pp. 384-385
    • Creighton, A.M.1    Hellmann, K.2    Whitecross, S.3
  • 15
    • 0027740137 scopus 로고
    • The one-ring open hydrolysis product intermediates of the cardioprotective agent ICRF-187 (dexrazoxane) displace iron from iron-anthracycline complexes
    • Buss, J. L., and B. B. Hasinoff. The one-ring open hydrolysis product intermediates of the cardioprotective agent ICRF-187 (dexrazoxane) displace iron from iron-anthracycline complexes. Agents Actions 40:86-95 (1993).
    • (1993) Agents Actions , vol.40 , pp. 86-95
    • Buss, J.L.1    Hasinoff, B.B.2
  • 16
    • 0027381810 scopus 로고
    • When good enzymes go bad: Conversion of topoisomerase II to a cellular toxin by antineoplastic drugs
    • Corbett, A. H., and N. Osheroff. When good enzymes go bad: conversion of topoisomerase II to a cellular toxin by antineoplastic drugs. Chem. Res. Toxicol. 6:585-597 (1993).
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 585-597
    • Corbett, A.H.1    Osheroff, N.2
  • 20
    • 0025988304 scopus 로고
    • Antagonistic effect of aclarubicin on daunorubicin-induced cytotoxicity in human small cell lung cancer cells: Relationship to DNA integrity and topoisomerase II
    • Jensen, P. B., P. S. Jensen, E. J. F. Demant, E. Friche, B. S. Sorensen, M. Sehested, K. Wassermann, L. Vindelov, O. Westergaard, and H. H. Hansen. Antagonistic effect of aclarubicin on daunorubicin-induced cytotoxicity in human small cell lung cancer cells: relationship to DNA integrity and topoisomerase II. Cancer Res. 51:5093-5099 (1991).
    • (1991) Cancer Res. , vol.51 , pp. 5093-5099
    • Jensen, P.B.1    Jensen, P.S.2    Demant, E.J.F.3    Friche, E.4    Sorensen, B.S.5    Sehested, M.6    Wassermann, K.7    Vindelov, L.8    Westergaard, O.9    Hansen, H.H.10
  • 21
    • 0030739460 scopus 로고    scopus 로고
    • Characterization of a Chinese hamster ovary cell line with acquired resistance to the bisdioxopiperazine dexrazoxane (ICRF-187) catalytic inhibitor of topoisomerase II
    • Hasinoff, B. B., T. I. Kuschak, A. M. Creighton, C. L. Fattman, W. P. Allan, P. Thampatty, and J. C. Yalowich. Characterization of a Chinese hamster ovary cell line with acquired resistance to the bisdioxopiperazine dexrazoxane (ICRF-187) catalytic inhibitor of topoisomerase II. Biochem. Pharmacol. 53:1843-1853 (1997).
    • (1997) Biochem. Pharmacol. , vol.53 , pp. 1843-1853
    • Hasinoff, B.B.1    Kuschak, T.I.2    Creighton, A.M.3    Fattman, C.L.4    Allan, W.P.5    Thampatty, P.6    Yalowich, J.C.7
  • 22
    • 0027214092 scopus 로고
    • Antagonistic effect of the cardioprotector (+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane (ICRF-187) on DNA breaks and cytotoxicity induced by the topoisomerase II directed drugs daunorubicin and etoposide (VP-16)
    • Sehested, M., P. B. Jensen, B. S. Sorensen, B. Holm, E. Friche, and E. J. F. Demant. Antagonistic effect of the cardioprotector (+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane (ICRF-187) on DNA breaks and cytotoxicity induced by the topoisomerase II directed drugs daunorubicin and etoposide (VP-16). Biochem. Pharmacol. 46:389-393 (1993).
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 389-393
    • Sehested, M.1    Jensen, P.B.2    Sorensen, B.S.3    Holm, B.4    Friche, E.5    Demant, E.J.F.6
  • 23
    • 0029982836 scopus 로고    scopus 로고
    • Collateral sensitivity to the bisdioxopiperazine dexrazoxane (ICRF-187) in etoposide (VP-16) resistant human leukemia K562 cells
    • Fattman, C., W. P. Allan, B. B. Hasinoff, and J. C. Yalowich. Collateral sensitivity to the bisdioxopiperazine dexrazoxane (ICRF-187) in etoposide (VP-16) resistant human leukemia K562 cells. Biochem. Pharmacol. 52: 635-642 (1996).
    • (1996) Biochem. Pharmacol. , vol.52 , pp. 635-642
    • Fattman, C.1    Allan, W.P.2    Hasinoff, B.B.3    Yalowich, J.C.4
  • 24
    • 0029796045 scopus 로고    scopus 로고
    • The effect of dexrazoxane (ICRF-187) on doxorubicin and daunorubicin-mediated growth inhibition of Chinese hamster ovary (CHO) cells
    • Hasinoff, B. B., J. C. Yalowich, Y. Ling, and J. L. Buss. The effect of dexrazoxane (ICRF-187) on doxorubicin and daunorubicin-mediated growth inhibition of Chinese hamster ovary (CHO) cells. Anticancer Drugs 7:558-567 (1996).
    • (1996) Anticancer Drugs , vol.7 , pp. 558-567
    • Hasinoff, B.B.1    Yalowich, J.C.2    Ling, Y.3    Buss, J.L.4
  • 26
    • 1842284357 scopus 로고
    • A comparative study of the properties of the tumour-inhibitory photosynthetic benzene-maleimide adduct (NSC 284, 356 and ICRF 159)
    • Creighton, A. M., J. Long, and S. J. Kenwrick. A comparative study of the properties of the tumour-inhibitory photosynthetic benzene-maleimide adduct (NSC 284, 356 and ICRF 159). Imperial Cancer Res. Fund Sci. Report-1983. 143-144 (1984).
    • (1984) Imperial Cancer Res. Fund Sci. Report-1983 , pp. 143-144
    • Creighton, A.M.1    Long, J.2    Kenwrick, S.J.3
  • 27
    • 0022524870 scopus 로고
    • A quantitative decatenation assay for type II topoisomerases
    • Sahai, B. M., and J. G. Kaplan. A quantitative decatenation assay for type II topoisomerases. Anal. Biochem. 156:364-379 (1986).
    • (1986) Anal. Biochem. , vol.156 , pp. 364-379
    • Sahai, B.M.1    Kaplan, J.G.2
  • 28
    • 0028325365 scopus 로고
    • Altered stability of etoposide-induced topoisomerase II-DNA complexes in resistant human leukemia K562 cells
    • Ritke, M. K., D. Roberts, W. P. Allan, J. Raymond, V. V. Bergoltz, and J. C. Yalowich. Altered stability of etoposide-induced topoisomerase II-DNA complexes in resistant human leukemia K562 cells. Br. J. Cancer 69:687-697 (1994).
    • (1994) Br. J. Cancer , vol.69 , pp. 687-697
    • Ritke, M.K.1    Roberts, D.2    Allan, W.P.3    Raymond, J.4    Bergoltz, V.V.5    Yalowich, J.C.6
  • 30
    • 0027209306 scopus 로고
    • Topoisomerase II inhibition prevents anaphase chromatid segregation in mammalian cells independently of the generation of DNA strand breaks
    • Clarke, D. J., R. T. Johnson, and C. S. Downes. Topoisomerase II inhibition prevents anaphase chromatid segregation in mammalian cells independently of the generation of DNA strand breaks. J. Cell Sci. 105:563-569 (1993).
    • (1993) J. Cell Sci. , vol.105 , pp. 563-569
    • Clarke, D.J.1    Johnson, R.T.2    Downes, C.S.3
  • 31
    • 0019942448 scopus 로고
    • Stereochemistry of the antitumor agent 4,4′-(1,2-propanediyl)bis(4-piperazine-2,6-dione): Crystal and molecular structures of the racemate (ICRF-159) and a soluble enantiomer (ICRF-187)
    • Hempel, A., N. Camerman, and A. Camerman. Stereochemistry of the antitumor agent 4,4′-(1,2-propanediyl)bis(4-piperazine-2,6-dione): crystal and molecular structures of the racemate (ICRF-159) and a soluble enantiomer (ICRF-187). J. Am. Chem. Soc. 105:3453-3456 (1982).
    • (1982) J. Am. Chem. Soc. , vol.105 , pp. 3453-3456
    • Hempel, A.1    Camerman, N.2    Camerman, A.3
  • 33
    • 0141654021 scopus 로고
    • Antineoplastic agents. 90. The structure of the benzene-maleimide photosynthetic product (mitindomide)
    • Pettit, G. R., K. D. Paull, C. L. Herald, D. L. Herald, and J. R. Riden. Antineoplastic agents. 90. The structure of the benzene-maleimide photosynthetic product (mitindomide). Can. J. Chem. 61:2291-2294 (1983).
    • (1983) Can. J. Chem. , vol.61 , pp. 2291-2294
    • Pettit, G.R.1    Paull, K.D.2    Herald, C.L.3    Herald, D.L.4    Riden, J.R.5
  • 34
    • 0020459342 scopus 로고
    • Isolation and characterization of a subline of CHO cells with induced resistance to ICRF 159
    • Kenwrick, S. J., and A. M. Creighton. Isolation and characterization of a subline of CHO cells with induced resistance to ICRF 159. Br. J. Cancer 46:504-505 (1982).
    • (1982) Br. J. Cancer , vol.46 , pp. 504-505
    • Kenwrick, S.J.1    Creighton, A.M.2
  • 35
    • 0028345406 scopus 로고
    • Antitumor bisdioxopiperazines inhibit yeast DNA topoisomerase II by trapping the enzyme in the form of a closed protein clamp
    • Roca, J., R. Ishida, J. M. Berger, T. Andoh, and J. C. Wang. Antitumor bisdioxopiperazines inhibit yeast DNA topoisomerase II by trapping the enzyme in the form of a closed protein clamp. Proc. Natl. Acad. Sci. USA 91:1781-1785 (1994).
    • (1994) Proc. Natl. Acad. Sci. USA , vol.91 , pp. 1781-1785
    • Roca, J.1    Ishida, R.2    Berger, J.M.3    Andoh, T.4    Wang, J.C.5
  • 36
    • 0026448670 scopus 로고
    • The capture of a DNA double helix by an ATP-dependent protein clamp: A key step in DNA transport by type II DNA topoisomerases
    • Roca, J., and J. C. Wang. The capture of a DNA double helix by an ATP-dependent protein clamp: a key step in DNA transport by type II DNA topoisomerases. Cell 71:833-840 (1992).
    • (1992) Cell , vol.71 , pp. 833-840
    • Roca, J.1    Wang, J.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.