The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Azomycin     2-nitro-1H-imidazole

Synonyms: Amicin, nitroimidazole, PubChem7616, Azomycin [MI], SureCN10049, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Amicin


High impact information on Amicin

  • Infections with the sexually transmitted protozoan Trichomonas vaginalis are usually treated with metronidazole, a 5-nitroimidazole drug derived from the antibiotic azomycin [6].
  • Preclinical evaluation of the fluorinated 2-nitroimidazole N-(2-hydroxy-3,3,3-trifluoropropyl)-2-(2-nitro-1-imidazolyl) acetamide (SR-4554) as a probe for the measurement of tumor hypoxia [7].
  • We have shown that VEGF expression is predominantly localized in interior spheroid cells that are sufficiently hypoxic to bioreductively activate the 2-nitroimidazole and produce immunologically detectable adducts of the EF5 compound [8].
  • The bisnitroimidazole N-[2-(2-methyl-5-nitroimidazolyl)ethyl]-4-(2-nitroimidazolyl)butanamide (NNB, NSC 639862), in which a 2-nitroimidazole and 5-nitroimidazole moiety are joined via a carboxamide linker, is highly selective for hypoxic AA8 Chinese hamster cells (200-fold by 8 h) relative to mononitroimidazoles (5-25-fold) [9].
  • The effect of elevated temperature (44 degrees) on the intracellular uptake of the 2-nitroimidazole hypoxic cell radiosensitizer, misonidazole (MIS), and analogues more hydrophilic than MIS was studied in Chinese hamster ovary cells [10].

Chemical compound and disease context of Amicin


Biological context of Amicin


Anatomical context of Amicin


Associations of Amicin with other chemical compounds


Gene context of Amicin

  • The amplification of P450 reductase activity within cells was always much larger than the resultant increase in 2-nitroimidazole binding rate, suggesting an enzyme kinetic process less than first order and possibly of 1/2-order [31].
  • The largest tumor/blood (T/B) and tumor/muscle (T/M) ratios were observed for compounds of the azomycin nucleoside class in EMT-6 tumor-bearing scid mice [18].
  • RESULTS: A 1,000-fold overexpression of DT-diaphorase resulted in a small but significant increase in 2-nitroimidazole binding rate [31].
  • An 80-fold overexpression of cytochrome P450 reductase resulted in a 5-7-fold increase in the binding rate of 2-nitroimidazole [31].
  • At a concentration of 0.5 mM, NLP-1 is 8 times more toxic to hypoxic than aerobic cells at 37 degrees C. This concentration is 40 times less than the concentration of misonidazole, a non-intercalating 2-nitroimidazole, required for the same degree of hypoxic cell toxicity [32].

Analytical, diagnostic and therapeutic context of Amicin


  1. The farnesyltransferase inhibitor L744,832 reduces hypoxia in tumors expressing activated H-ras. Cohen-Jonathan, E., Evans, S.M., Koch, C.J., Muschel, R.J., McKenna, W.G., Wu, J., Bernhard, E.J. Cancer Res. (2001) [Pubmed]
  2. Differences in the toxicity and metabolism of the 2-nitroimidazole misonidazole (Ro-07-0582) in HeLa and Chinese hamster ovary cells. Taylor, Y.C., Rauth, A.M. Cancer Res. (1978) [Pubmed]
  3. Stimulation by localized tumor hyperthermia of reductive bioactivation of 2-nitroimidazole benznidazole in mice. Walton, M.I., Bleehen, N.M., Workman, P. Cancer Res. (1989) [Pubmed]
  4. Addition of 2-nitroimidazole radiosensitizers to cis-diamminedichloroplatinum(II) with radiation and with or without hyperthermia in the murine FSaIIC fibrosarcoma. Herman, T.S., Teicher, B.A., Holden, S.A., Pfeffer, M.R., Jones, S.M. Cancer Res. (1990) [Pubmed]
  5. BRU59-21, a second-generation 99mTc-labeled 2-nitroimidazole for imaging hypoxia in tumors. Melo, T., Duncan, J., Ballinger, J.R., Rauth, A.M. J. Nucl. Med. (2000) [Pubmed]
  6. Treatment of infections caused by metronidazole-resistant Trichomonas vaginalis. Cudmore, S.L., Delgaty, K.L., Hayward-McClelland, S.F., Petrin, D.P., Garber, G.E. Clin. Microbiol. Rev. (2004) [Pubmed]
  7. Preclinical evaluation of the fluorinated 2-nitroimidazole N-(2-hydroxy-3,3,3-trifluoropropyl)-2-(2-nitro-1-imidazolyl) acetamide (SR-4554) as a probe for the measurement of tumor hypoxia. Aboagye, E.O., Maxwell, R.J., Kelson, A.B., Tracy, M., Lewis, A.D., Graham, M.A., Horsman, M.R., Griffiths, J.R., Workman, P. Cancer Res. (1997) [Pubmed]
  8. Mapping of the vascular endothelial growth factor-producing hypoxic cells in multicellular tumor spheroids using a hypoxia-specific marker. Waleh, N.S., Brody, M.D., Knapp, M.A., Mendonca, H.L., Lord, E.M., Koch, C.J., Laderoute, K.R., Sutherland, R.M. Cancer Res. (1995) [Pubmed]
  9. N-[2-(2-methyl-5-nitroimidazolyl)ethyl]-4-(2-nitroimidazolyl)butanamide (NSC 639862), a bisnitroimidazole with enhanced selectivity as a bioreductive drug. Moselen, J.W., Hay, M.P., Denny, W.A., Wilson, W.R. Cancer Res. (1995) [Pubmed]
  10. Influence of heat on the intracellular uptake and radiosensitization of 2-nitroimidazole hypoxic cell sensitizers in vitro. Brown, D.M., Cohen, M.S., Sagerman, R.H., Gonzalez-Mendez, R., Hahn, G.M., Brown, J.M. Cancer Res. (1983) [Pubmed]
  11. Chronic enteral ethanol treatment causes hypoxia in rat liver tissue in vivo. Arteel, G.E., Iimuro, Y., Yin, M., Raleigh, J.A., Thurman, R.G. Hepatology (1997) [Pubmed]
  12. The synthesis and radiolabeling of 2-nitroimidazole derivatives of cyclam and their preclinical evaluation as positive markers of tumor hypoxia. Engelhardt, E.L., Schneider, R.F., Seeholzer, S.H., Stobbe, C.C., Chapman, J.D. J. Nucl. Med. (2002) [Pubmed]
  13. In vitro and in vivo evaluation of a technetium-99m-labeled 2-nitroimidazole (BMS181321) as a marker of tumor hypoxia. Ballinger, J.R., Kee, J.W., Rauth, A.M. J. Nucl. Med. (1996) [Pubmed]
  14. Reperfusion injury in livers due to gentle in situ organ manipulation during harvest involves hypoxia and free radicals. Schemmer, P., Connor, H.D., Arteel, G.E., Raleigh, J.A., Bunzendahl, H., Mason, R.P., Thurman, R.G. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  15. Detection by PCR of the nim genes encoding 5-nitroimidazole resistance in Bacteroides spp. Trinh, S., Reysset, G. J. Clin. Microbiol. (1996) [Pubmed]
  16. Fluorescent markers for hypoxic cells: a study of nitroaromatic compounds, with fluorescent heterocyclic side chains, that undergo bioreductive binding. Hodgkiss, R.J., Jones, G.W., Long, A., Middleton, R.W., Parrick, J., Stratford, M.R., Wardman, P., Wilson, G.D. J. Med. Chem. (1991) [Pubmed]
  17. Fluorinated 2-nitroimidazole derivative hypoxic cell radiosensitizers: radiosensitizing activities and pharmacokinetics. Sasai, K., Iwai, H., Yoshizawa, T., Nishimoto, S., Shibamoto, Y., Oya, N., Shibata, T., Abe, M. Int. J. Radiat. Oncol. Biol. Phys. (1994) [Pubmed]
  18. Preclinical assessment of hypoxic marker specificity and sensitivity. Iyer, R.V., Engelhardt, E.L., Stobbe, C.C., Schneider, R.F., Chapman, J.D. Int. J. Radiat. Oncol. Biol. Phys. (1998) [Pubmed]
  19. A novel amine-dioxime chelator for technetium-99m: synthesis and evaluation of 2-nitroimidazole-containing analogues as markers for hypoxic cells. Su, Z.F., Ballinger, J.R., Rauth, A.M., Abrams, D.N., Billinghurst, M.W. Bioconjug. Chem. (2000) [Pubmed]
  20. The pharmacokinetics, bioavailability and biodistribution in mice of a rationally designed 2-nitroimidazole hypoxia probe SR-4554. Aboagye, E.O., Lewis, A.D., Graham, M.A., Tracy, M., Kelson, A.B., Ryan, K.J., Workman, P. Anticancer Drug Des. (1996) [Pubmed]
  21. Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170. Kaneta, T., Takai, Y., Kagaya, Y., Yamane, Y., Wada, H., Yuki, M., Iwata, R., Tsujitani, M., Takahashi, S., Yamada, S. J. Nucl. Med. (2002) [Pubmed]
  22. Characterization of the tuberculous granuloma in murine and human lungs: cellular composition and relative tissue oxygen tension. Tsai, M.C., Chakravarty, S., Zhu, G., Xu, J., Tanaka, K., Koch, C., Tufariello, J., Flynn, J., Chan, J. Cell. Microbiol. (2006) [Pubmed]
  23. The novel fluorinated 2-nitroimidazole hypoxia probe SR-4554: reductive metabolism and semiquantitative localisation in human ovarian cancer multicellular spheroids as measured by electron energy loss spectroscopic analysis. Aboagye, E.O., Lewis, A.D., Johnson, A., Workman, P., Tracy, M., Huxham, I.M. Br. J. Cancer (1995) [Pubmed]
  24. A novel hypoxia-dependent 2-nitroimidazole KIN-841 inhibits tumour-specific angiogenesis by blocking production of angiogenic factors. Shimamura, M., Nagasawa, H., Ashino, H., Yamamoto, Y., Hazato, T., Uto, Y., Hori, H., Inayama, S. Br. J. Cancer (2003) [Pubmed]
  25. Tacrolimus (FK506) Limits Accumulation of Granulocytes and Platelets and Protects against Brain Damage after Transient Focal Cerebral Ischemia in Rat. Noto, T., Furuichi, Y., Ishiye, M., Matsuoka, N., Aramori, I., Mutoh, S., Yanagihara, T. Biol. Pharm. Bull. (2007) [Pubmed]
  26. Initial results of a phase I trial of continuous infusion SR 2508 (etanidazole): a radiation therapy oncology group study. Coleman, C.N., Noll, L., Howes, A.E., Harris, J.R., Zakar, J., Kramer, R.A. Int. J. Radiat. Oncol. Biol. Phys. (1989) [Pubmed]
  27. Evidence that hypoxia markers detect oxygen gradients in liver: pimonidazole and retrograde perfusion of rat liver. Arteel, G.E., Thurman, R.G., Yates, J.M., Raleigh, J.A. Br. J. Cancer (1995) [Pubmed]
  28. RSU 1069, a 2-nitroimidazole containing an alkylating group: high efficiency as a radio- and chemosensitizer in vitro and in vivo. Adams, G.E., Ahmed, I., Sheldon, P.W., Stratford, I.J. Int. J. Radiat. Oncol. Biol. Phys. (1984) [Pubmed]
  29. Heat-stimulated nitroreductive bioactivation of the 2-nitroimidazole benznidazole in vitro. Walton, M.I., Bleehen, N.M., Workman, P. Biochem. Pharmacol. (1987) [Pubmed]
  30. Studies on the toxicity of RSU-1069. Whitmore, G.F., Gulyas, S. Int. J. Radiat. Oncol. Biol. Phys. (1986) [Pubmed]
  31. The role of specific reductases in the intracellular activation and binding of 2-nitroimidazoles. Joseph, P., Jaiswal, A.K., Stobbe, C.C., Chapman, J.D. Int. J. Radiat. Oncol. Biol. Phys. (1994) [Pubmed]
  32. NLP-1: a DNA intercalating hypoxic cell radiosensitizer and cytotoxin. Panicucci, R., Heal, R., Laderoute, K., Cowan, D., McClelland, R.A., Rauth, A.M. Int. J. Radiat. Oncol. Biol. Phys. (1989) [Pubmed]
  33. Measurement of PDT-induced hypoxia in Dunning prostate tumors by iodine-123-iodoazomycin arabinoside. Moore, R.B., Chapman, J.D., Mercer, J.R., Mannan, R.H., Wiebe, L.I., McEwan, A.J., McPhee, M.S. J. Nucl. Med. (1993) [Pubmed]
  34. Oncogenic transforming potential of etanidazole. Hall, E.J., Hei, T.K. Int. J. Radiat. Oncol. Biol. Phys. (1992) [Pubmed]
  35. Development of an ELISA for the detection of 2-nitroimidazole hypoxia markers bound to tumor tissue. Raleigh, J.A., Zeman, E.M., Rathman, M., LaDine, J.K., Cline, J.M., Thrall, D.E. Int. J. Radiat. Oncol. Biol. Phys. (1992) [Pubmed]
  36. Immunohistochemical detection of a hypoxia marker in spontaneous canine tumours. Cline, J.M., Thrall, D.E., Page, R.L., Franko, A.J., Raleigh, J.A. Br. J. Cancer (1990) [Pubmed]
  37. Correlations between in vivo tumor weight, oxygen pressure, 31P NMR spectroscopy, hypoxic microenvironment marking by beta-D-iodinated azomycin galactopyranoside (beta-D-IAZGP), and radiation sensitivity. Saitoh, J., Sakurai, H., Suzuki, Y., Muramatsu, H., Ishikawa, H., Kitamoto, Y., Akimoto, T., Hasegawa, M., Mitsuhashi, N., Nakano, T. Int. J. Radiat. Oncol. Biol. Phys. (2002) [Pubmed]
WikiGenes - Universities