MedKoo product information:

  Methoxyamine

Description og Methoxyamine: Methoxyamine is an orally bioavailable small molecule inhibitor with potential adjuvant activity. Methoxyamine covalently binds to apurinic/apyrimidinic (AP) DNA damage sites and inhibits base excision repair (BER), which may result in an increase in DNA strand breaks and apoptosis. This agent may potentiate the anti-tumor activity of alkylating agents. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Current developer:    TRACON Pharmaceuticals

1: She MR, Guo KY, Niu XQ, Lu XX. [Effects of manumycin combined with methoxyamine on apoptosis in myeloid leukemia U937 cells]. Ai Zheng. 2008 Aug;27(8):835-9. Chinese. PubMed PMID: 18710617.

2: Yan L, Bulgar A, Miao Y, Mahajan V, Donze JR, Gerson SL, Liu L. Combined treatment with temozolomide and methoxyamine: blocking apurininc/pyrimidinic site repair coupled with targeting topoisomerase IIalpha. Clin Cancer Res. 2007 Mar 1;13(5):1532-9. PubMed PMID: 17332299.

3: Yan T, Seo Y, Schupp JE, Zeng X, Desai AB, Kinsella TJ. Methoxyamine potentiates iododeoxyuridine-induced radiosensitization by altering cell cycle kinetics and enhancing senescence. Mol Cancer Ther. 2006 Apr;5(4):893-902. PubMed PMID: 16648559.

4: Liao YC, Yang S, Syu MJ, Xu Y. Development and validation of an HPLC-UV method for the analysis of methoxyamine using 4-(diethylamino)benzaldehyde as a derivatizing agent. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):724-9. PubMed PMID: 15951147.

5: She M, Pan I, Sun L, Yeung SC. Enhancement of manumycin A-induced apoptosis by methoxyamine in myeloid leukemia cells. Leukemia. 2005 Apr;19(4):595-602. PubMed PMID: 15744347.

6: Liu L, Gerson SL. Therapeutic impact of methoxyamine: blocking repair of abasic sites in the base excision repair pathway. Curr Opin Investig Drugs. 2004 Jun;5(6):623-7. Review. PubMed PMID: 15242251.

7: Yang S, Liu L, Gerson SL, Xu Y. Measurement of anti-cancer agent methoxyamine in plasma by tandem mass spectrometry with on-line sample extraction. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Oct 5;795(2):295-307. PubMed PMID: 14522034.

8: Wang E, Struble E, Liu P, Cheung AP. A new sensitive HPLC assay for methoxyamine and its analogs. J Pharm Biomed Anal. 2002 Oct 15;30(3):415-27. PubMed PMID: 12367666.

9: Taverna P, Liu L, Hwang HS, Hanson AJ, Kinsella TJ, Gerson SL. Methoxyamine potentiates DNA single strand breaks and double strand breaks induced by temozolomide in colon cancer cells. Mutat Res. 2001 May 10;485(4):269-81. PubMed PMID: 11585361.

10: Gdaniec Z, Ban B, Sowers LC, Fazakerley GV. Methoxyamine-induced mutagenesis of nucleic acids. A proton NMR study of oligonucleotides containing N4-methoxycytosine paired with adenine or guanine. Eur J Biochem. 1996 Dec 1;242(2):271-9. PubMed PMID: 8973643.

11: Gdaniec Z, Sowers LC, Fazakerley GV. Methoxyamine attack on cytosine produces ambivalent base pairing properties of the modified base. Acta Biochim Pol. 1996;43(1):95-105. PubMed PMID: 8790715.

12: Dietzen DJ, Koenig J, Turk J. Facilitation of thin-layer chromatographic identification of opiates by derivatization with acetic anhydride or methoxyamine. J Anal Toxicol. 1995 Sep;19(5):299-303. PubMed PMID: 7500616.

13: Nedderman AN, Stone MJ, Williams DH, Lin PK, Brown DM. Molecular basis for methoxyamine-initiated mutagenesis: 1H nuclear magnetic resonance studies of oligonucleotide duplexes containing base-modified cytosine residues. J Mol Biol. 1993 Apr 5;230(3):1068-76. PubMed PMID: 8478918.

14: Fortini P, Calcagnile A, Vrieling H, van Zeeland AA, Bignami M, Dogliotti E. Mutagenic processing of ethylation damage in mammalian cells: the use of methoxyamine to study apurinic/apyrimidinic site-induced mutagenesis. Cancer Res. 1993 Mar 1;53(5):1149-55. PubMed PMID: 8439960.

15: Fortini P, Rosa S, Zijno A, Calcagnile A, Bignami M, Dogliotti E. Methoxyamine modification of abasic sites protects CHO cells from the cytotoxic and mutagenic effects of oxygen alkylation. Carcinogenesis. 1992 Jan;13(1):87-93. PubMed PMID: 1370769.

16: Stone MJ, Nedderman AN, Williams DH, Lin PK, Brown DM. Molecular basis for methoxyamine initiated mutagenesis. 1H nuclear magnetic resonance studies of base-modified oligodeoxynucleotides. J Mol Biol. 1991 Dec 5;222(3):711-23. PubMed PMID: 1660932.

17: Rosa S, Fortini P, Karran P, Bignami M, Dogliotti E. Processing in vitro of an abasic site reacted with methoxyamine: a new assay for the detection of abasic sites formed in vivo. Nucleic Acids Res. 1991 Oct 25;19(20):5569-74. PubMed PMID: 1719478; PubMed Central PMCID: PMC328958.

18: Acharya JK, Prakash V, Rao AG, Savithri HS, Rao NA. Interactions of methoxyamine with pyridoxal-5'-phosphate-Schiff's base at the active site of sheep liver serine hydroxymethyltransferase. Indian J Biochem Biophys. 1991 Oct-Dec;28(5-6):381-8. PubMed PMID: 1812071.

19: Liuzzi M, Talpaert-Borlé M. Characterization of damage in gamma-irradiated and OsO4-treated DNA using methoxyamine. Int J Radiat Biol. 1988 Nov;54(5):709-22. PubMed PMID: 2902166.

20: Liuzzi M, Weinfeld M, Paterson MC. Selective inhibition by methoxyamine of the apurinic/apyrimidinic endonuclease activity associated with pyrimidine dimer-DNA glycosylases from Micrococcus luteus and bacteriophage T4. Biochemistry. 1987 Jun 16;26(12):3315-21. PubMed PMID: 2443160.

21: Liuzzi M, Talpaert-Borlé M. A new approach to the study of the base-excision repair pathway using methoxyamine. J Biol Chem. 1985 May 10;260(9):5252-8. PubMed PMID: 2580833.

22: Stolarski R, Kierdaszuk B, Hagberg CE, Shugar D. Hydroxylamine and methoxyamine mutagenesis: displacement of the tautomeric equilibrium of the promutagen N6-methoxyadenosine by complementary base pairing. Biochemistry. 1984 Jun 19;23(13):2906-13. PubMed PMID: 6466624.

23: Kierdaszuk B, Stolarski R, Shugar D. Hydroxylamine and methoxyamine mutagenesis: tautomeric equilibrium of the promutagenic, N6-methoxyadenosine in solvents of different polarities. Acta Biochim Pol. 1984;31(1):49-64. PubMed PMID: 6720194.

24: Talpaert-Borlé M, Liuzzi M. Reaction of apurinic/apyrimidinic sites with [14C]methoxyamine. A method for the quantitative assay of AP sites in DNA. Biochim Biophys Acta. 1983 Sep 9;740(4):410-6. PubMed PMID: 6349690.

25: Castello D, Sacchetti L, Brero P, Poncini L. [Results of a clinical trial of the use of a methoxyamine (cefuroxime) in respiratory tract infections in children]. Minerva Pediatr. 1981 Sep 15;33(17):881-6. Italian. PubMed PMID: 7031458.

26: Iserentant D, Fiers W. Secondary structure of the 5' end of bacteriophage MS2 RNA Methoxyamine and kethoxal modification. Eur J Biochem. 1979 Dec 17;102(2):595-604. PubMed PMID: 118878.

27: Iserentant D, Fiers W. Proceedings: Chemical modification of some hairpin loops of the MS2 genome with the methoxyamine reagent. Arch Int Physiol Biochim. 1976 Feb;84(1):165-6. PubMed PMID: 60941.

28: Filipowicz W, Wodnar-Filipowicz A, Szafrański P. Activity of methoxyamine-modified f2 RNA in initiation and elongation steps of protein synthesis. Acta Biochim Pol. 1976;23(2-3):243-59. PubMed PMID: 788415.

29: Wodnar-Filipowicz A, Filipowicz W, Szafrański P. Preparation and characteristics of the structure of methoxyamine-modified f2 RNA. Acta Biochim Pol. 1975;22(1):11-24. PubMed PMID: 236625.

30: Piper PW, Clark BF. The selective reaction of methoxyamine with cytidine residues in mammalian initiator transfer ribonucleic acid. Nucleic Acids Res. 1974 Jan;1(1):45-51. PubMed PMID: 10793658; PubMed Central PMCID: PMC343322.

31: Putrament A, Baranowska H, Pachecka J. Mutagenic action of hydroxylamine and methoxyamine on yeast. II. Methoxyamine. Mol Gen Genet. 1973 Mar 27;122(1):73-80. PubMed PMID: 4573264.

32: Putrament A, Baranowska H. Mutagenic action of hydroxylamine and methoxyamine on yeast. I. Hydroxylamine. Mol Gen Genet. 1973 Mar 27;122(1):61-72. PubMed PMID: 4573263.

33: Filipowicz W, Wodnar A, Zagórska L, Szafrański P. f2 RNA structure and peptide chain initiation: fMet-tRNA binding directed by methoxyamine-modified unfolded or native-like f2 RNAs. Biochem Biophys Res Commun. 1972 Dec 4;49(5):1272-9. PubMed PMID: 4566675.

34: Steinschneider A, Leshem B. Nearest-neighbour effects: reactivity towards methoxyamine of cytidine, cytidine monophosphates and cytidine dinucleoside monophosphates. J Mol Biol. 1972 Jun 20;67(2):333-7. PubMed PMID: 5040375.

35: Filipowicz W, Wodnar A, Szafrański P. Reaction of methoxyamine with phage f2 RNA and activity of modified messenger. FEBS Lett. 1972 Jun 15;23(2):249-53. PubMed PMID: 4564151.

36: Fraenkel-Conrat H, Singer B. The chemical basis for the mutagenicity of hydroxylamine and methoxyamine. Biochim Biophys Acta. 1972 Mar 24;262(3):264-8. PubMed PMID: 4338936.

37: Cashmore AR, Brown DM, Smith JD. Selective reaction of methoxyamine with cytosine bases in tyrosine transfer ribonucleic acid. J Mol Biol. 1971 Jul 28;59(2):359-73. PubMed PMID: 4935788.

38: Cashmore AR. Aminoacylation of methoxyamine modified tyrosine transfer RNA. FEBS Lett. 1970 Dec 28;12(2):90-95. PubMed PMID: 11945549.

39: Small GD, Gordon MP. Reaction of hydroxylamine and methoxyamine with the ultraviolet-induced hydrate of cytidine. J Mol Biol. 1968 Jul 14;34(2):281-91. PubMed PMID: 5760460.