A glutamine antagonist with anti-tumorigenic activity
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Acivicin

Item No. 14003

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
αS-amino-3-chloro-4,5S-dihydro-5-isoxazoleacetic acid
CAS Number
42228-92-2
Synonyms
  • Antibiotic AT-125
  • NSC 163501
  • U 42126
Molecular Formula
C5H7ClN2O3
Formula Weight
178.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 1.4 mg/ml
λmax
219 nm
SMILES
ClC1=NO[C@@]([C@H](N)C(O)=O)([H])C1
InChi Code
InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1
InChi Key
QAWIHIJWNYOLBE-OKKQSCSOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $55

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    10 mg

    $304

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    Cayman Chemical
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    Product Description

    Acivicin is a glutamine analog that irreversibly inhibits glutamine-dependent amidotransferases involved in nucleotide and amino acid biosynthesis (Kis = 10 and 560 μM for anthranilate synthase and glutamate synthase, respectively).1,2 It also reversibly inhibits γ-glutamyl transpeptidase.3,4 Acividin has been used to elucidate aspects of glutathione metabolism and has known anti-tumorigenic activity.2,5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tso, J.Y., Bower, S.G., and Zalkin, H. Mechanism of inactivation of glutamine amidotransferases by the antitumor drug L-(αS, 5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125). The Journal of Biological Chemisty 255(14), 6734-6738 (1980).

    2. Lyons, S.D., Sant, M.E., and Christopherson, R.I. Cytotoxic mechanisms of glutamine antagonists in mouse L1210 leukemia. The Journal of Biological Chemisty 265(19), 11377-11381 (1990).

    3. Stole, E., Smith, T.K., Manning, J.M., et al. Interaction of γ-glutamyl transpeptidase with acivicin. The Journal of Biological Chemisty 269(34), 21435-21439 (1994).

    4. Smith, T.K., Ikeda, Y., Fujii, J., et al. Different sites of acivicin binding and inactivation of γ-glutamyl transpeptidases. Proc. Natl. Acad. Sci. USA 92(6), 2360-2364 (1995).

    5. Griffith, O.W., and Meister, A. Excretion of cysteine and γ-glutamylcysteine moieties in human and experimental animal γ-glutamyl transpeptidase deficiency. Proc. Natl. Acad. Sci. USA 77(6), 3384-3387 (1980).

    6. Meck, R.A., Clubb, K.J., Allen, L.M., et al. Inhibition of cell cycle progression of human pancreatic carcinoma cells in vitro by L-(αS,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid, acivicin (NSC 163501). Cancer Res. 41(11 Pt 1), 4547-4553 (1981).

    7. Willoughby, L.F., Schlosser, T., Manning, S.A., et al. An in vivo large-scale chemical screening platform using Drosophila for anti-cancer drug discovery. Dis. Model. Mech. 6(2), 521-529 (2012).