Amidox

• CAT Number: I021992
• CAS Number: 95933-72-5
• Molecular Formula: C7H8N2O3
• Molecular Weight: 168.152
• Purity: 98%
• Synonyms: Amidox; VF 236
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Benzenecarboximidamide, N,3,4-trihydroxy-
• InChI: InChI=1S/C7H8N2O3/c8-7(9-12)4-1-2-5(10)6(11)3-4/h1-3,10-12H,(H2,8,9)
• InChIKey: JOAASNKBYBFGDN-UHFFFAOYSA-N
• SMILES: N=C(C1=CC=C(O)C(O)=C1)NO

Amidox(CAT: I021992) assumes a significant role as a ribonucleotide reductase inhibitor. This compound’s activity centers around the inhibition of ribonucleotide reductase, an essential enzyme responsible for catalyzing the conversion of ribonucleotides to deoxyribonucleotides, a critical step in DNA synthesis. By targeting ribonucleotide reductase, Amidox interferes with DNA replication and cell division, making it a potential candidate for anti-proliferative and cytotoxic therapies.

Reference

1: Fritzer-Szekeres M, Novotny L, Vachalkova A, Findenig G, Elford HL, Szekeres T. Iron binding capacity of didox (3,4-dihydroxybenzohydroxamic acid) and amidox (3,4-dihydroxybenzamidoxime) new inhibitors of the enzyme ribonucleotide reductase. Life Sci. 1997;61(22):2231-7. PubMed PMID: 9393942.
2: Fritzer-Szekeres M, Novotny L, Vachalkova A, Göbl R, Elford HL, Szekeres T. Iron binding capacity of didox (3,4 dihydroxybenzohydroxamic acid) and amidox (3,4 dihydroxybenzamidoxime) two inhibitors of the enzyme ribonucleotide reductase. Adv Exp Med Biol. 1998;431:599-604. PubMed PMID: 9598136.
3: Bauer W, Horvath Z, Höchtl T, Saiko P, Karl D, Fritzer-Szekeres M, Szekeres T. Amidox, an inhibitor of ribonucleotide reductase, potentiates the action of Ara-C in HL-60 human promyelocytic leukemia cells. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1541-4. PubMed PMID: 15571294.
4: Tryka AF. ICRF 187 and polyhydroxyphenyl derivatives fail to protect against bleomycin induced lung injury. Toxicology. 1989 Dec 1;59(2):127-38. PubMed PMID: 2479996.
5: Höchtl T, Horvath Z, Bauer W, Karl D, Saiko P, Elford HL, Fritzer-Szekeres M, Szekeres T. Biochemical modulation of Ara-C effects by amidox, an inhibitor of ribonucleotide reductase in HL-60 promyelocytic human leukemia cells. Life Sci. 2004 Jan 16;74(9):1071-80. PubMed PMID: 14687648.
6: Tabélé C, Cohen A, Curti C, Bouhlel A, Hutter S, Remusat V, Primas N, Terme T, Azas N, Vanelle P. New series of monoamidoxime derivatives displaying versatile antiparasitic activity. Eur J Med Chem. 2014 Nov 24;87:440-53. doi: 10.1016/j.ejmech.2014.07.113. Epub 2014 Sep 30. PubMed PMID: 25282267.
7: Grusch M, Fritzer-Szekeres M, Fuhrmann G, Rosenberger G, Luxbacher C, Elford HL, Smid K, Peters GJ, Szekeres T, Krupitza G. Activation of caspases and induction of apoptosis by novel ribonucleotide reductase inhibitors amidox and didox. Exp Hematol. 2001 May;29(5):623-32. PubMed PMID: 11376876.
8: Salamon A, Vielnascher E, Hagenauer B, Szekeres T, Szekeres-Fritzer M, Thalhammer T, Jäger W. Metabolism of the new ribonucleotide reductase inhibitor amidox in the isolated perfused rat liver. Anticancer Res. 2000 Sep- Oct;20(5B):3521-6. PubMed PMID: 11131656.
9: Vielnascher E, Romanová D, Novotný L, Szekeres T, Elfort HL, Thalhammer T, Jäger W. Simultaneous determination of the new anticancer agent amidox and its metabolites in rat bile and plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1997 Aug 29;696(2):267-74. PubMed PMID: 9323547.
10: Plitzko B, Ott G, Reichmann D, Henderson CJ, Wolf CR, Mendel R, Bittner F, Clement B, Havemeyer A. The involvement of mitochondrial amidoxime reducing components 1 and 2 and mitochondrial cytochrome b5 in N-reductive metabolism in human cells. J Biol Chem. 2013 Jul 12;288(28):20228-37. doi: 10.1074/jbc.M113.474916. Epub 2013 May 23. PubMed PMID: 23703616; PubMed Central PMCID: PMC3711290.
11: Miadoková E, Macáková K, Podstavková S, Vlcek D. Genotoxic properties of the newly synthesized antineoplastic agents amidox, didox and trimidox. Pharmazie. 1997 Jul;52(7):540-4. PubMed PMID: 9266591.
12: El-Shishtawy RM, El-Zawahry MM, Abdelghaffar F, Ahmed NS. Nucleophilic addition of reactive dyes on amidoximated acrylic fabrics. ScientificWorldJournal. 2014;2014:305930. doi: 10.1155/2014/305930. Epub 2014 Aug 28. PubMed PMID: 25258720; PubMed Central PMCID: PMC4166449.
13: Myette MS, Elford HL, Chitambar CR. Interaction of gallium nitrate with other inhibitors of ribonucleotide reductase: effects on the proliferation of human leukemic cells. Cancer Lett. 1998 Jul 17;129(2):199-204. PubMed PMID: 9719462.
14: Tihan T, Elford HL, Cory JG. Studies on the mechanisms of inhibition of L1210 cell growth by 3,4-dihydroxybenzohydroxamic acid and 3,4-dihydroxybenzamidoxime. Adv Enzyme Regul. 1991;31:71-83. PubMed PMID: 1877400.
15: Romanova D, Vachalkova A, Szekeres T, Elford HL, Novotny L. The new inhibitors of ribonucleotide reductase–comparison of some physico-chemical properties. J Pharm Biomed Anal. 1997 Apr;15(7):951-6. PubMed PMID: 9160261.
16: Rauko P, Romanova D, Miadokova E, Macakova K, Novotny L, Elford HL, Szekeres T. DNA-protective activity of new ribonucleotide reductase inhibitors. Anticancer Res. 1997 Sep-Oct;17(5A):3437-40. PubMed PMID: 9413183.
17: Oresmaa L, Aulaskari P, Vainiotalo P. Electrospray ionization mass spectrometric studies of some imidazole amidoximes and nitrolic acids and their esters. Rapid Commun Mass Spectrom. 2006;20(7):1071-6. PubMed PMID: 16498595.