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

Methoxyamine     O-methylhydroxylamine

Synonyms: Methoxylamine, QMhHch@, CPD-7648, NCI-C60060, AG-L-18068, ...
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 O-methylhydroxylamine

  • Methoxyamine not only was able to increase IdUrd cytotoxicity but also increased the incorporation of IdUrd into DNA of HCT116 human colon cancer cells leading to greater radiosensitization [1].
  • Methoxylamine mutagenesis of the beta-galactosidase gene from Lactobacillus delbrückii subsp. bulgaricus was used to generate cold-sensitive variants [2].
  • A restriction fragment is inserted in each orientation into an M13 vector, single-stranded virion DNA from each recombinant phage is treated with methoxylamine, and, after reannealing of the mutagenized strands, a double-stranded restriction fragment is obtained [3].
  • By using a model oligonucleotide containing a single AP site modified with methoxyamine (MX), we show that endonuclease III and IV of E. coli are able to cleave the alkoxyamine-adducted site whereas a partially purified HeLa AP endonuclease and crude cell-free extracts from HeLa cells are inhibited by this modification [4].
  • We conclude that methoxyamine enhances manumycin-induced apoptosis in myeloid leukemia cells [5].

High impact information on O-methylhydroxylamine

  • Duplicate samples heated in the presence of methoxyamine to protect the apurinic sites from alkaline hydrolysis provided controls to assess total DNA [6].
  • Consistent with our recent publication, coadministration of IdUrd and a chemical inhibitor of BER, methoxyamine (MX), also increases the extent of MSH2 nuclear colocalization with IdUrd [7].
  • We also assessed the role of methoxyamine, a small molecule inhibitor of BER, in the response of human colon cancer cells (HCT116) to IdUrd cytotoxicity and radiosensitization [1].
  • Because methoxyamine-mediated sensitization of beta-pol wild-type and beta-pol-complemented cells to GCV did not reach the level of null cells, we suggest that both beta-pol-dependent short- and long-patch base excision repair are involved in protection of cells to GCV [8].
  • Mutagenic processing of ethylation damage in mammalian cells: the use of methoxyamine to study apurinic/apyrimidinic site-induced mutagenesis [9].

Chemical compound and disease context of O-methylhydroxylamine


Biological context of O-methylhydroxylamine


Anatomical context of O-methylhydroxylamine


Associations of O-methylhydroxylamine with other chemical compounds

  • Expression of beta-pol in the null cells restores the ability of MX to modulate sensitivity to MMS [22].
  • The relevance of these results to the molecular basis of hydroxylamine and methoxyamine mutagenesis and to the phenomenon of proton exchange in other systems is briefly discussed [23].
  • These adducts were characterized by examination of their mass spectra, by analysis of the products of their reaction with sodium cyanide, sodium borohydride, and methoxylamine and by the mass spectra derived from collision-induced dissociation in tandem mass spectrometry [24].
  • For this aim plasmid DNA was cleaved at the BamHI site, and cytosine residues of the sticky ends were modified by O-methylhydroxylamine [25].
  • The methoxyamine-treated aliquot provided gene fragments which were refractory to alkaline hydrolysis (full-length fragments), while the fragments in the untreated aliquot were cleaved at apurinic sites by hydroxide [26].

Gene context of O-methylhydroxylamine

  • The severe MMS sensitivity seen in AP endonuclease deficient strains can also be rescued by treatment of cells with the AP lyase inhibitor methoxyamine, which suggests that the product of AP lyase action on an AP site is indeed an extremely toxic lesion [27].
  • The rpsH gene, which encodes protein S8, was first inserted into an expression vector under the control of the lac promoter and subsequently mutagenized with methoxylamine or nitrous acid [28].
  • MGMT inhibitors, PARP inhibitors and methoxyamine are currently in early stages of clinical development [29].
  • We also show that 4-Amino-1,8-naphthalimide (4-AN, inhibitor of PARP) but not methoxyamine (inhibitor of base excision repair (BER)), affects IR induced G2 arrest and cell sensitivity in PARP-1+/+ cells, resulting in the phenotypes similar to those of PARP-1-/- cells [30].
  • The mechanism of interaction of methoxyamine with sheep liver serine hydroxymethyltransferase (EC (SHMT) was established by measuring changes in enzyme activity, visible absorption spectra, circular dichroism and fluorescence, and by evaluating the rate constant by stopped-flow spectrophotometry [31].

Analytical, diagnostic and therapeutic context of O-methylhydroxylamine


  1. Inhibition of base excision repair potentiates iododeoxyuridine-induced cytotoxicity and radiosensitization. Taverna, P., Hwang, H.S., Schupp, J.E., Radivoyevitch, T., Session, N.N., Reddy, G., Zarling, D.A., Kinsella, T.J. Cancer Res. (2003) [Pubmed]
  2. Characterization of two cold-sensitive mutants of the beta-galactosidase from Lactobacillus delbruckii subsp. bulgaricus. Adams, R.M., Yoast, S., Mainzer, S.E., Moon, K., Palombella, A.L., Estell, D.A., Power, S.D., Schmidt, B.F. J. Biol. Chem. (1994) [Pubmed]
  3. A simple and efficient method for chemical mutagenesis of DNA. Kadonaga, J.T., Knowles, J.R. Nucleic Acids Res. (1985) [Pubmed]
  4. Processing in vitro of an abasic site reacted with methoxyamine: a new assay for the detection of abasic sites formed in vivo. Rosa, S., Fortini, P., Karran, P., Bignami, M., Dogliotti, E. Nucleic Acids Res. (1991) [Pubmed]
  5. Enhancement of manumycin A-induced apoptosis by methoxyamine in myeloid leukemia cells. She, M., Pan, I., Sun, L., Yeung, S.C. Leukemia (2005) [Pubmed]
  6. Repair of N-methylpurines in specific DNA sequences in Chinese hamster ovary cells: absence of strand specificity in the dihydrofolate reductase gene. Scicchitano, D.A., Hanawalt, P.C. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  7. Role of MutSalpha in the recognition of iododeoxyuridine in DNA. Berry, S.E., Loh, T., Yan, T., Kinsella, T.J. Cancer Res. (2003) [Pubmed]
  8. DNA polymerase beta mediates protection of mammalian cells against ganciclovir-induced cytotoxicity and DNA breakage. Tomicic, M.T., Thust, R., Sobol, R.W., Kaina, B. Cancer Res. (2001) [Pubmed]
  9. Mutagenic processing of ethylation damage in mammalian cells: the use of methoxyamine to study apurinic/apyrimidinic site-induced mutagenesis. Fortini, P., Calcagnile, A., Vrieling, H., van Zeeland, A.A., Bignami, M., Dogliotti, E. Cancer Res. (1993) [Pubmed]
  10. The mechanism of the mutagenic action of hydroxylamine XIII. Reversion of phage MS2 amber mutants in the presence of hydroxylamines. Budowsky, E.I., Klebanova, L.M., Metlitskaya, A.Z. Mutat. Res. (1978) [Pubmed]
  11. The effect of modification of cytosines in Escherichia coli 16-S rRNA on reconstitution and function of 30-S ribosomes. Wrede, A., Perzyński, S., Klita, S., Zagórska, L., Szafrański, P. Eur. J. Biochem. (1977) [Pubmed]
  12. Secondary structure of the 5' end of bacteriophage MS2 RNA Methoxyamine and kethoxal modification. Iserentant, D., Fiers, W. Eur. J. Biochem. (1979) [Pubmed]
  13. Characterization of inactivation of myxoviruses and paramyxoviruses by hydroxylamine, N-methylhydroxylamine and O-methylhydroxylamine. Newlin, G.E., Bussell, R.H. Arch. Virol. (1975) [Pubmed]
  14. Repair of abasic sites by mammalian cell extracts. Frosina, G., Fortini, P., Rossi, O., Carrozzino, F., Abbondandolo, A., Dogliotti, E. Biochem. J. (1994) [Pubmed]
  15. Methoxyamine modification of abasic sites protects CHO cells from the cytotoxic and mutagenic effects of oxygen alkylation. Fortini, P., Rosa, S., Zijno, A., Calcagnile, A., Bignami, M., Dogliotti, E. Carcinogenesis (1992) [Pubmed]
  16. Hydroxylamine mutagenesis: observation of inverted Watson-Crick base-pairing between N4-methoxycytosine and adenine with the aid of natural-abundance high-resolution 15N NMR spectroscopy. Kierdaszuk, B., Stolarski, R., Shugar, D. Eur. J. Biochem. (1983) [Pubmed]
  17. Methoxyamine potentiates iododeoxyuridine-induced radiosensitization by altering cell cycle kinetics and enhancing senescence. Yan, T., Seo, Y., Schupp, J.E., Zeng, X., Desai, A.B., Kinsella, T.J. Mol. Cancer Ther. (2006) [Pubmed]
  18. DNA excision repair profiles of normal and leukemic human lymphocytes: functional analysis at the single-cell level. Buschfort, C., Muller, M.R., Seeber, S., Rajewsky, M.F., Thomale, J. Cancer Res. (1997) [Pubmed]
  19. Microsomal metabolism of the 5-lipoxygenase inhibitor L-739,010: evidence for furan bioactivation. Zhang, K.E., Naue, J.A., Arison, B., Vyas, K.P. Chem. Res. Toxicol. (1996) [Pubmed]
  20. Recognition of initiation codons in modified f2 RNA by Escherichia coli ribosomes. Szkopińska, A., Zagórski, W., Zagórska, L., Szafrański, P. Eur. J. Biochem. (1975) [Pubmed]
  21. Modulation of base excision repair alters cellular sensitivity to UVA1 but not to UVB1. Kim, K.J., Chakrabarty, I., Li, G.Z., Grösch, S., Kaina, B., Rünger, T.M. Photochem. Photobiol. (2002) [Pubmed]
  22. Protection against methylation-induced cytotoxicity by DNA polymerase beta-dependent long patch base excision repair. Horton, J.K., Prasad, R., Hou, E., Wilson, S.H. J. Biol. Chem. (2000) [Pubmed]
  23. Mechanism of hydroxylamine mutagenesis: tautomeric shifts and proton exchange between the promutagen N6-methoxyadenosine and cytidine. Stolarski, R., Kierdaszuk, B., Hagberg, C.E., Shugar, D. Biochemistry (1987) [Pubmed]
  24. Characterization of the lysyl adducts formed from prostaglandin H2 via the levuglandin pathway. Boutaud, O., Brame, C.J., Salomon, R.G., Roberts, L.J., Oates, J.A. Biochemistry (1999) [Pubmed]
  25. Cluster of point mutations predetermined by a quasipalindromic nucleotide sequence in plasmid pBR322 DNA. Salganik, R.I., Dianov, G.L., Medvedev, O.A. FEBS Lett. (1990) [Pubmed]
  26. Two expressed human genes sustain slightly more DNA damage after alkylating agent treatment than an inactive gene. Bartlett, J.D., Scicchitano, D.A., Robison, S.H. Mutat. Res. (1991) [Pubmed]
  27. Involvement of two endonuclease III homologs in the base excision repair pathway for the processing of DNA alkylation damage in Saccharomyces cerevisiae. Hanna, M., Chow, B.L., Morey, N.J., Jinks-Robertson, S., Doetsch, P.W., Xiao, W. DNA Repair (Amst.) (2004) [Pubmed]
  28. Mutagenesis of ribosomal protein S8 from Escherichia coli: defects in regulation of the spc operon. Wower, I., Kowaleski, M.P., Sears, L.E., Zimmermann, R.A. J. Bacteriol. (1992) [Pubmed]
  29. The emerging role of DNA repair proteins as predictive, prognostic and therapeutic targets in cancer. Madhusudan, S., Middleton, M.R. Cancer Treat. Rev. (2005) [Pubmed]
  30. A stronger DNA damage-induced G2 checkpoint due to over-activated CHK1 in the absence of PARP-1. Lu, H.R., Wang, X., Wang, Y. Cell Cycle (2006) [Pubmed]
  31. Interactions of methoxyamine with pyridoxal-5'-phosphate-Schiff's base at the active site of sheep liver serine hydroxymethyltransferase. Acharya, J.K., Prakash, V., Rao, A.G., Savithri, H.S., Rao, N.A. Indian J. Biochem. Biophys. (1991) [Pubmed]
  32. Trace determination of hydroxyl radical in biological systems. Li, B., Gutierrez, P.L., Blough, N.V. Anal. Chem. (1997) [Pubmed]
  33. Base-pairing properties of N4-methoxydeoxycytidine 5'-triphosphate during DNA synthesis on natural templates, catalyzed by DNA polymerase I of Escherichia coli. Reeves, S.T., Beattie, K.L. Biochemistry (1985) [Pubmed]
  34. Epinephrine, norepinephrine, and dopamine during a 4-day head-down bed rest. Pequignot, J.M., Guell, A., Gauquelin, G., Jarsaillon, E., Annat, G., Bes, A., Peyrin, L., Gharib, C. J. Appl. Physiol. (1985) [Pubmed]
  35. The biosynthesis of 1a, 1b-dihomo-PGF2 and 1a,1b-dihomo-PGF2 alpha from 7, 10, 13, 16-docosatetraenoic acid by an acetone-pentane powder of sheep vesicular gland microsomes. Tobias, L.D., Vane, F.M., Paulsrud, J.R. Prostaglandins (1975) [Pubmed]
WikiGenes - Universities