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Chemical Compound Review:

CHEMBL281021 O-(3-aminopropyl)hydroxylamine

Synonyms: AG-H-99840, CHEBI:136103, CTK3I7322, DNC013220, AKOS006348478, ...

Hyvönen, T. et al., Hyvönen, T. et al., Keinänen, T.A. et al., Milovica, V. et al., Hyvönen, T. et al., et al.

Milovica, Turchanowa, Khomutov, Khomutov, Caspary, Stein,

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Disease relevance of AIDS-087115

The effects of 1-aminooxy-3-aminopropane and S-(5'-deoxy-5'-adenosyl)methylthioethylhydroxylamine on ornithine decarboxylase and S-adenosyl-L-methionine decarboxylase from Escherichia coli [1].
We evaluated highly specific and reportedly non-toxic hydroxylamine-containing inhibitors of ODC (1-aminooxy-3-aminopropane, APA) and SAMDC (S-(5'-deoxy-5'-adenosyl)-methylthioethyl-hydroxylamine, AMA) in human colon cancer cells (Caco-2 and HT-29) in culture [2].

High impact information on AIDS-087115

The effects on cultured baby hamster kidney cells of 1-aminooxy-3-aminopropane, a potent new inhibitor of mammalian ornithine and S-adenosylmethionine decarboxylases and of spermidine synthase, were studied [3].
The potential of 1-aminooxy-3-aminopropane as a tool for studies on fungal polyamine metabolism and for the control of plant diseases of fungal origin is discussed [4].
Pharmacological properties of the ornithine decarboxylase inhibitor 3-aminooxy-1-propanamine and several structural analogues [5].
The method was used to measure the stability of aminooxy analogues of putrescine (1-aminooxy-3-aminopropane) and spermidine [N-(2-aminooxyethyl)-1,4-diaminobutane and 1-aminooxy-3-N-(3-aminopropyl)aminopropane] in cell culture media and the uptake into cultured baby hamster kidney (BHK21/C13) cells [6].
1- or 3-methylated derivatives and oximes of 1-aminooxy-3-aminopropane (APA) with pyridoxal (PL) and pyridoxal 5'-phosphate (PLP) were synthesized to examine whether the stability of the parent APA molecule could be increased without loss of its inhibitory capacity towards ornithine decarboxylase [7].

Biological context of AIDS-087115

Regulation of S-adenosyl-L-methionine decarboxylase by 1-aminooxy-3-aminopropane: enzyme kinetics and effects on the enzyme activity in cultured cells [8].

Anatomical context of AIDS-087115

In cell-free systems, however, 1-aminooxy-3-aminopropane is likely to find use in unraveling the reaction mechanism of S-adenosylmethionine decarboxylase [8].

Gene context of AIDS-087115

So, 1-aminooxy-3-aminopropane is a very weak inhibitor of S-adenosylmethionine decarboxylase and the cellular effects can be correlated primarily with its inhibitory effects on ornithine decarboxylase and spermidine synthase [8].

References

The effects of 1-aminooxy-3-aminopropane and S-(5'-deoxy-5'-adenosyl)methylthioethylhydroxylamine on ornithine decarboxylase and S-adenosyl-L-methionine decarboxylase from Escherichia coli. Paulin, L. FEBS Lett. (1986) [Pubmed]
Hydroxylamine-containing inhibitors of polyamine biosynthesis and impairment of colon cancer cell growth. Milovica, V., Turchanowa, L., Khomutov, A.R., Khomutov, R.M., Caspary, W.F., Stein, J. Biochem. Pharmacol. (2001) [Pubmed]
1-Aminooxy-3-aminopropane reversibly prevents the proliferation of cultured baby hamster kidney cells by interfering with polyamine synthesis. Hyvönen, T., Alakuijala, L., Andersson, L., Khomutov, A.R., Khomutov, R.M., Eloranta, T.O. J. Biol. Chem. (1988) [Pubmed]
The putrescine analogue 1-aminooxy-3-aminopropane perturbs polyamine metabolism in the phytopathogenic fungus Sclerotinia sclerotiorum. Gárriz, A., Dalmasso, M.C., Pieckenstain, F.L., Ruiz, O.A. Arch. Microbiol. (2003) [Pubmed]
Pharmacological properties of the ornithine decarboxylase inhibitor 3-aminooxy-1-propanamine and several structural analogues. Mett, H., Stanek, J., Lopez-Ballester, J.A., Jänne, J., Alhonen, L., Sinervirta, R., Frei, J., Regenass, U. Cancer Chemother. Pharmacol. (1993) [Pubmed]
Monitoring of the uptake and metabolism of aminooxy analogues of polyamines in cultured cells by high-performance liquid chromatography. Hyvönen, T., Keinänen, T.A., Khomutov, A.R., Khomutov, R.M., Eloranta, T.O. J. Chromatogr. (1992) [Pubmed]
Derivatives of 1-aminooxy-3-aminopropane as polyamine antimetabolites: stability and effects on BHK21/C13 cells. Keinänen, T.A., Hyvönen, T., Pankaskie, M.C., Vepsäläinen, J.J., Eloranta, T.O. J. Biochem. (1994) [Pubmed]
Regulation of S-adenosyl-L-methionine decarboxylase by 1-aminooxy-3-aminopropane: enzyme kinetics and effects on the enzyme activity in cultured cells. Hyvönen, T., Eloranta, T.O. J. Biochem. (1990) [Pubmed]

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