Aminooxyacetic acid

Source: Wikipedia, the free encyclopedia.
Aminooxyacetic acid
Names
Preferred IUPAC name
(Aminooxy)acetic acid
Other names
Carboxymethoxylamine
Hydroxylamineacetic acid
U-7524
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
DrugBank
IUPHAR/BPS
MeSH Aminooxyacetic+Acid
UNII
  • InChI=1S/C2H5NO3/c3-6-1-2(4)5/h1,3H2,(H,4,5) checkY
    Key: NQRKYASMKDDGHT-UHFFFAOYSA-N checkY
  • InChI=1/C2H5NO3/c3-6-1-2(4)5/h1,3H2,(H,4,5)
    Key: NQRKYASMKDDGHT-UHFFFAOYAB
  • O=C(O)CON
  • NOCC(O)=O
Properties
C2H5NO3
Molar mass 91.066
Density 1.375 g/cm3
Melting point 138 °C (280 °F; 411 K)
Boiling point 326.7 °C (620.1 °F; 599.8 K)
Hazards
Flash point 151 °C (304 °F; 424 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N (what is checkY☒N ?)

Aminooxyacetic acid, often abbreviated AOA or AOAA, is a compound that inhibits

gamma-aminobutyric acid (GABA) being broken down.[1] Subsequently, the level of GABA is increased in tissues. At concentrations high enough to fully inhibit 4-aminobutyrate aminotransferase activity, aminooxyacetic acid is indicated as a useful tool to study regional GABA turnover in rats.[2]

Aminooxyacetic acid is a general inhibitor of pyridoxal phosphate (PLP)-dependent enzymes (this includes GABA-T).[3] It functions as an inhibitor by attacking the Schiff base linkage between PLP and the enzyme, forming oxime type complexes.[3]

Aminooxyacetic acid inhibits

drowsiness, ataxia, seizures, and psychosis when the dosage was increased beyond 2 mg per kilogram per day.[6] Also, the inhibition of aspartate aminotransferase by aminooxyacetic acid has clinical implications for the treatment of breast cancer, since a decrease in glycolysis disrupts breast adenocarcinoma cells more than normal cells.[7]

Moreover, selective inhibition of aspartate aminotransferase with aminooxyacetic acid ameliorated experimental

autoimmune encephalomyelitis in a therapeutic mouse model by reprograming the differentiation of pro-inflammatory T helper 17 cells, that boost the immune system, towards induced anti-inflammatory regulatory T cells.[8]

Aminooxyacetic acid has been studied as a treatment for

disequilibrium.[11] Thus, the investigators of the study concluded that the incidence of the side effects makes aminooxyacetic acid unsuitable to treat tinnitus.[11]

Aminooxyacetic acid also has anticonvulsant properties.[12] At high dosages, it can act as a convulsant agent in mice and rats.[13]

Aminooxyacetic acid can also inhibit

1-aminocyclopropane-1-carboxylate synthase preventing ethylene synthesis, which can increase the vase life of cut flowers.[14]

History

Aminooxyacetic acid was first described by Werner in 1893, and was prepared by the hydrolysis of ethylbenzhydroximinoacetic acid.[15][16][17][18] In 1936, Anchel and Shoenheimer used aminooxyacetic acid to isolate ketones from natural sources.[17] Also in 1936, Kitagawa and Takani described the preparation of aminooxyacetic acid by the condensation of benzhydroxamic acid and ethyl bromoacetate, followed by hydrolysis by hydrochloric acid.[19]

References

  1. PMID 13782815
    .
  2. S2CID 39248295
    .
  3. ^
    PMID 8458
    .
  4. ^
    PMID 3620514
    .
  5. S2CID 27982816
    .
  6. ^
    S2CID 10190223
    .
  7. PMID 18922152
    .
  8. PMID 28783731
    .
  9. PMID 2415097
    .
  10. PMID 3734755
    .
  11. ^
    S2CID 7789128
    .
  12. PMID 13883717
    .
  13. S2CID 45193391
    .
  14. doi:10.1016/0304-4238(81)90038-8
    .
  15. doi:10.1002/cber.18930260274
    .
  16. doi:10.1002/cber.189402703141
    .
  17. ^
    doi:10.1016/S0021-9258(18)74826-6
    . Retrieved 2011-05-20.
  18. doi:10.1021/ja01301a058
    .
  19. doi:10.1093/oxfordjournals.jbchem.a125537
    .
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