L-Alanosine

L-Alanosine (NSC-153353), an antibiotic from Streptomyces alanosinicus, has antineoplastic activity. L-Alanosine (NSC-153353) inhibits adenylosuccinate synthetase, which converts inosine monophospate (IMP) into adenylosuccinate. L-Alanosine is the inhibitor for methylthioadenosine phosphorylase (MTAP) [1][2][3].

Product Specifications

CAS Number

[5854-93-3]

Product Name Alternative

NSC-153353; SDX-102

UNSPSC

12352211

Hazard Statement

H302

Target

Antibiotic; DNA/RNA Synthesis

Type

Reference compound

Related Pathways

Anti-infection; Cell Cycle/DNA Damage

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/l-alanosine.html

Purity

99.85

Solubility

H2O : 15 mg/mL (ultrasonic; adjust pH to 8 with NaOH) |H2O : 50 mg/mL (ultrasonic)

Smiles

N[C@@H](CN(O)N=O)C(O)=O

Molecular Formula

C3H7N3O4

Molecular Weight

149.11

Precautions

H302

References & Citations

[1]Efferth T, et al. Identification of gene expression profiles predicting tumor cell response to L-alanosine. Biochem Pharmacol. 2003 Aug 15;66 (4) :613-21.|[2]Chitnis MP, et al. Antitumor effect of L-alanosine (NSC 153553) on sensitive and resistant sublines of murine leukemias. Tumori. 1984 Aug 31;70 (4) :317-20.|[3]Tyagi AK, et al. Identification of the antimetabolite of L-alanosine, L-alanosyl-5-amino-4-imidazolecarboxylic acid ribonucleotide, in tumors and assessment of its inhibition of adenylosuccinate synthetase. Cancer Res. 1980 Dec;40 (12) :4390-7.|[4]Singh SX, et al., Purine Synthesis Inhibitor L-Alanosine Impairs Mitochondrial Function and Stemness of Brain Tumor Initiating Cells. Biomedicines. 2022 Mar 23;10 (4) :751.