An inhibitor of adenylosuccinate synthase
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L-Alanosine

Item No. 19545

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(hydroxynitrosoamino)-L-alanine
CAS Number
5854-93-3
Synonyms
  • NSC 153353
  • NSC 529469
  • SDX-102
Molecular Formula
C3H7N3O4
Formula Weight
149.1
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
100 mM HCl: 1 mg/ml100 mM NaOH: 1 mg/mlWater: 1 mg/ml
λmax
250 nm
SMILES
ON(N=O)C[C@H](N)C(O)=O
InChi Code
InChI=1S/C3H7N3O4/c4-2(3(7)8)1-6(10)5-9/h2,10H,1,4H2,(H,7,8)/t2-/m0/s1
InChi Key
MLFKVJCWGUZWNV-REOHCLBHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $42

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    5 mg

    $200

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    10 mg

    $377

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    25 mg

    $836

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    Cayman Chemical
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    Product Description

    L-Alanosine is an antibiotic derived from bacterium S. alanosinicus with antineoplastic activity in cells deficient in methylthioadenosine phosphorylase (MTAP) (mean IC50 = 4.8 μM and 10 μM in T-ALL and CAK-1 cells, respectively).1,2 L-Alanosine inhibits adenylosuccinate synthetase to disrupt de novo purine biosynthesis, inhibiting cellular metabolism in MTAP-deficient tumor cells.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Batova, A., Diccianni, M.B., Omura-Minamisawa, M., et al. Use of alanosine as a methylthioadenosine phosphorylase-selective therapy for T-cell acute lymphoblastic leukemia in vitro. Cancer Res. 59(7), 1492-1497 (1999).

    2. Karikari, C.A., Mullendore, M., Esheleman, J.R., et al. Homozygous deletions of methylthioadenosine phosphorylase in human biliary tract cancers. Mol. Cancer Ther. 4(12), 1860-1866 (2005).

    3. Gale, G.R., Ostrander, W.E., and Atkins, L.M. Effects of alanosine on purine and pyrimidine synthesis. Biochem. Pharmacol. 19(9), 1823-1832 (1968).

    4. Li, C.-F., Fang, F.-M., Kung, H.-J., et al. Downregulated MTAP expression in myxofibrosarcoma: A characterization of inactivating mechanisms, tumor suppressive function, and therapeutic relevance. Oncotarget 5(22), 11428-11441 (2014).

    5. Kindler, H.L., Burris, H.A., III, Sandler, A.B., et al. A phase II multicenter study of L-alanosine, a potent inhibitor of adenine biosynthesis, in patients with MTAP-deficient cancer. Invest New Drugs 27(1), 75-81 (2009).