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Chemical Compound Review

Nitrosourea     nitrosourea

Synonyms: N-Nitrosourea, Urea, nitroso-, AG-D-61014, AC1Q5JJR, CTK0H5660, ...
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Disease relevance of nitrosourea


Psychiatry related information on nitrosourea


High impact information on nitrosourea


Chemical compound and disease context of nitrosourea


Biological context of nitrosourea

  • The objective of this study was to determine if HeLa cells irreversibly arrested in G2 phase of the cell cycle by a brief exposure to a nitrosourea compound were deficient in certain proteins when compared with G2-synchronized cells [16].
  • These studies show that nitrosourea resistance in myeloid leukemic cells can be abrogated by inactivation of the DNA repair protein O6-alkylguanine-DNA alkyltransferase [17].
  • These data suggest that the lethal damage of nitrosourea alkylation in human bone marrow is principally expressed in transcriptionally active regions of chromatin [18].
  • Long-term protection of hematopoiesis against the cytotoxic effects of multiple doses of nitrosourea by retrovirus-mediated expression of human O6-alkylguanine-DNA-alkyltransferase [19].
  • In contrast, resting lymphocytes do not rapidly synthesize new alkyltransferase molecules after nitrosourea exposure and appear susceptible to DNA damage caused by persistent O6-alkylguanine adducts [20].

Anatomical context of nitrosourea


Associations of nitrosourea with other chemical compounds


Gene context of nitrosourea

  • Transient induction of the MRP/GS-X pump and gamma-glutamylcysteine synthetase by 1-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3- nitrosourea in human glioma cells [30].
  • Msh2 deficiency reduced the apoptotic response to each agent, but only led to increased crypt survival after NMNU treatment [31].
  • These findings highlight the importance of MGMT methylation as a specific predictive factor for responsiveness to nitrosourea chemotherapy [32].
  • These results indicate that the MDR1-MGMT bicistronic retrovirus vectors would be useful to protect normal hematopoietic cells from nitrosourea-induced mutagenesis, and drug-selectable bicistronic constructs would have great advantage over non-selectable vectors [33].
  • With the exception of the monofunctional nitrosourea, streptozotocin, both recA and uvrA gene products contribute to the repair of DNA damage caused by the alkylating agents tested [34].

Analytical, diagnostic and therapeutic context of nitrosourea


  1. Delayed pulmonary fibrosis after nitrosourea therapy. Limper, A.H., McDonald, J.A. N. Engl. J. Med. (1990) [Pubmed]
  2. Renal-failure anemia and nitrosourea therapy. Baker, J.J., Lokey, J.L., Price, N.A., Winokur, S.H., Chang, M. N. Engl. J. Med. (1979) [Pubmed]
  3. Leukemia and preleukemia after adjuvant treatment of gastrointestinal cancer with semustine (methyl-CCNU). Boice, J.D., Greene, M.H., Killen, J.Y., Ellenberg, S.S., Keehn, R.J., McFadden, E., Chen, T.T., Fraumeni, J.F. N. Engl. J. Med. (1983) [Pubmed]
  4. The prevention of thymic lymphomas in transgenic mice by human O6-alkylguanine-DNA alkyltransferase. Dumenco, L.L., Allay, E., Norton, K., Gerson, S.L. Science (1993) [Pubmed]
  5. Serologic analysis of nitrosourea-induced rat gliomas. Pfreundschuh, M., Cravioto, H., Hochwald, G., Ransohoff, J. J. Natl. Cancer Inst. (1982) [Pubmed]
  6. Dementia following treatment of brain tumors with radiotherapy administered alone or in combination with nitrosourea-based chemotherapy: a clinical and pathological study. Vigliani, M.C., Duyckaerts, C., Hauw, J.J., Poisson, M., Magdelenat, H., Delattre, J.Y. J. Neurooncol. (1999) [Pubmed]
  7. Glutathione, cell proliferation, and 1,3-bis-(2-chloroethyl)-1-nitrosourea in K562 leukemia. Frischer, H., Kennedy, E.J., Chigurupati, R., Sivarajan, M. J. Clin. Invest. (1993) [Pubmed]
  8. Enhancement of nitrosourea activity in medulloblastoma and glioblastoma multiforme. Friedman, H.S., Dolan, M.E., Moschel, R.C., Pegg, A.E., Felker, G.M., Rich, J., Bigner, D.D., Schold, S.C. J. Natl. Cancer Inst. (1992) [Pubmed]
  9. Interim report of phase II study of new nitrosourea S 10036 in disseminated malignant melanoma. Khayat, D., Bizzari, J.P., Frenay, M., Naman, H., Weil, M., Goupil, A., Namer, M., Rouesse, J., Banzet, P., Jacquillat, C. J. Natl. Cancer Inst. (1988) [Pubmed]
  10. Significance of DNA cross-links on 1-(4-amino-2-methylpyrimidin-5-yl)methyl-3-(2-chloroethyl)-3- nitrosourea (ACNU)-induced cytotoxicity against ACNU-sensitive and -resistant lines of 9L rat glioma cells. Kokunai, T., Tamaki, N., Matsumoto, S. J. Natl. Cancer Inst. (1987) [Pubmed]
  11. Treatment of aggressive multiple myeloma by high-dose chemotherapy and total body irradiation followed by blood stem cells autologous graft. Fermand, J.P., Levy, Y., Gerota, J., Benbunan, M., Cosset, J.M., Castaigne, S., Seligmann, M., Brouet, J.C. Blood (1989) [Pubmed]
  12. Phase II trial of carmustine plus O(6)-benzylguanine for patients with nitrosourea-resistant recurrent or progressive malignant glioma. Quinn, J.A., Pluda, J., Dolan, M.E., Delaney, S., Kaplan, R., Rich, J.N., Friedman, A.H., Reardon, D.A., Sampson, J.H., Colvin, O.M., Haglund, M.M., Pegg, A.E., Moschel, R.C., McLendon, R.E., Provenzale, J.M., Gururangan, S., Tourt-Uhlig, S., Herndon, J.E., Bigner, D.D., Friedman, H.S. J. Clin. Oncol. (2002) [Pubmed]
  13. Sensitization of nitrosourea-resistant Mer+ human tumor cells to N-(2-chloroethyl)-N'-cyclohexyl-N-nitrosourea by mild (41 degrees C) hyperthermia. Mulcahy, R.T., Gipp, J.J., Tanner, M.A. Cancer Res. (1988) [Pubmed]
  14. Protein metabolism in the small intestine during cancer cachexia and chemotherapy in mice. Samuels, S.E., Knowles, A.L., Tilignac, T., Debiton, E., Madelmont, J.C., Attaix, D. Cancer Res. (2000) [Pubmed]
  15. Chlorozotocin, 2-(3-(2-chloroethyl)-3-nitrosoureido)-D-glucopyranose, an antitumor agent with modified bone marrow toxicity. Anderson, T., McMenamin, M.G., Schein, P.S. Cancer Res. (1975) [Pubmed]
  16. G2 phase-specific proteins of HeLa cells. Al-Bader, A.A., Orengo, A., Rao, P.N. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  17. Modulation of nitrosourea resistance in myeloid leukemias. Gerson, S.L., Trey, J.E. Blood (1988) [Pubmed]
  18. Cellular and molecular mechanisms of the bone marrow sparing effects of the glucose chloroethylnitrosourea chlorozotocin. Byrne, P., Tew, K., Jemionek, J., MacVittie, T., Erickson, L., Schein, P. Blood (1984) [Pubmed]
  19. Long-term protection of hematopoiesis against the cytotoxic effects of multiple doses of nitrosourea by retrovirus-mediated expression of human O6-alkylguanine-DNA-alkyltransferase. Jelínek, J., Fairbairn, L.J., Dexter, T.M., Rafferty, J.A., Stocking, C., Ostertag, W., Margison, G.P. Blood (1996) [Pubmed]
  20. Regeneration of O6-alkylguanine-DNA alkyltransferase in human lymphocytes after nitrosourea exposure. Gerson, S.L. Cancer Res. (1988) [Pubmed]
  21. Long-term studies on carcinogenicity and promoting effect of phenylbutazone in DONRYU rats. Meakawa, A., Onodera, H., Tanigawa, H., Furuta, K., Kanno, J., Matsuoka, C., Ogiu, T., Hayashi, Y. J. Natl. Cancer Inst. (1987) [Pubmed]
  22. 5-Fluorouracil, 1,3-bis(2-chloroethyl)-1-nitrosourea, and 1-(2-chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea: effect on the human granulopoietic system. Lohrmann, H.P., Lepp, K.A., Schreml, W. J. Natl. Cancer Inst. (1982) [Pubmed]
  23. The expression of sarcomeric muscle-specific contractile protein genes in BC3H1 cells: BC3H1 cells resemble skeletal myoblasts that are defective for commitment to terminal differentiation. Taubman, M.B., Smith, C.W., Izumo, S., Grant, J.W., Endo, T., Andreadis, A., Nadal-Ginard, B. J. Cell Biol. (1989) [Pubmed]
  24. DNA damage induced by a new 2-chloroethyl nitrosourea on malignant melanoma cells. Godeneche, D., Rapp, M., Thierry, A., Laval, F., Madelmont, J.C., Chollet, P., Veyre, A. Cancer Res. (1990) [Pubmed]
  25. Selective activation of human heat shock gene transcription by nitrosourea antitumor drugs mediated by isocyanate-induced damage and activation of heat shock transcription factor. Kroes, R.A., Abravaya, K., Seidenfeld, J., Morimoto, R.I. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  26. O6-benzylguanine potentiates the antitumor effect of locally delivered carmustine against an intracranial rat glioma. Rhines, L.D., Sampath, P., Dolan, M.E., Tyler, B.M., Brem, H., Weingart, J. Cancer Res. (2000) [Pubmed]
  27. Modulation of human lymphocyte O6-alkylguanine-DNA alkyltransferase by streptozotocin in vivo. Gerson, S.L. Cancer Res. (1989) [Pubmed]
  28. Chemotherapy inhibits skeletal muscle ubiquitin-proteasome-dependent proteolysis. Tilignac, T., Temparis, S., Combaret, L., Taillandier, D., Pouch, M.N., Cervek, M., Cardenas, D.M., Le Bricon, T., Debiton, E., Samuels, S.E., Madelmont, J.C., Attaix, D. Cancer Res. (2002) [Pubmed]
  29. Antitumor activity and bone marrow toxicity of aminoglucose mustard anticancer agents in mice. Cantrell, J.E., Green, D., Schein, P.S. Cancer Res. (1986) [Pubmed]
  30. Transient induction of the MRP/GS-X pump and gamma-glutamylcysteine synthetase by 1-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3- nitrosourea in human glioma cells. Gomi, A., Shinoda, S., Masuzawa, T., Ishikawa, T., Kuo, M.T. Cancer Res. (1997) [Pubmed]
  31. The ability to engage enterocyte apoptosis does not predict long-term crypt survival in p53 and Msh2 deficient mice. Sansom, O.J., Clarke, A.R. Oncogene (2002) [Pubmed]
  32. O6-methylguanine-DNA methyltransferase methylation and TP53 mutation in malignant astrocytomas and their relationships with clinical course. Watanabe, T., Katayama, Y., Komine, C., Yoshino, A., Ogino, A., Ohta, T., Fukushima, T. Int. J. Cancer (2005) [Pubmed]
  33. Efficient protection of cells from the genotoxicity of nitrosoureas by the retrovirus-mediated transfer of human O6-methylguanine-DNA methyltransferase using bicistronic vectors with human multidrug resistance gene 1. Suzuki, M., Sugimoto, Y., Tsuruo, T. Mutat. Res. (1998) [Pubmed]
  34. Mutagenesis and repair of DNA damage caused by nitrogen mustard, N,N'-bis(2-chloroethyl)-N-nitrosourea (BCNU), streptozotocin, and mitomycin C in E. coli. Fram, R.J., Sullivan, J., Marinus, M.G. Mutat. Res. (1986) [Pubmed]
  35. Procarbazine and high-dose tamoxifen as a second-line regimen in recurrent high-grade gliomas: a phase II study. Brandes, A.A., Ermani, M., Turazzi, S., Scelzi, E., Berti, F., Amistà, P., Rotilio, A., Licata, C., Fiorentino, M.V. J. Clin. Oncol. (1999) [Pubmed]
  36. Differential sensitivity of human and mouse alkyltransferase to O6-benzylguanine using a transgenic model. Liu, L., Lee, K., Wasan, E., Gerson, S.L. Cancer Res. (1996) [Pubmed]
  37. 2-Chloroethyl (methylsulfonyl)methanesulfonate (NSC-338947), a more selective DNA alkylating agent than the chloroethylnitrosoureas. Gibson, N.W., Hartley, J.A., Strong, J.M., Kohn, K.W. Cancer Res. (1986) [Pubmed]
  38. Salvage chemotherapy with paclitaxel for recurrent oligodendrogliomas. Chamberlain, M.C., Kormanik, P.A. J. Clin. Oncol. (1997) [Pubmed]
  39. Immunity to transplantable nitrosourea-induced neurogenic tumors. III. Systemic adoptive transfer of immunity. Shibuya, N., Hochgeschwender, U., Kida, Y., Hochwald, G.M., Thorbecke, G.J., Cravioto, H. J. Neuropathol. Exp. Neurol. (1984) [Pubmed]
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