WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200130
Description: Alanosine, also known as L-alanosine, is an amino acid analogue and antibiotic derived from the bacterium Streptomyces alanosinicus with antimetabolite and potential antineoplastic activities. L-alanosine inhibits adenylosuccinate synthetase, which converts inosine monophospate (IMP) into adenylosuccinate, an intermediate in purine metabolism. L-alanosine-induced disruption of de novo purine biosynthesis is potentiated by methylthioadenosine phosphorylase (MTAP) deficiency. The clinical use of this agent may be limited by its toxicity profile. MTAP is a key enzyme in the adenine and methionine salvage pathways.
MedKoo Cat#: 200130
Chemical Formula: C3H7N3O4
Exact Mass: 149.04366
Molecular Weight: 149.11
Elemental Analysis: C, 24.17; H, 4.73; N, 28.18; O, 42.92
Synonym: SDX102; SDX-102; SDX 102; alanosine; L-alanosine.
IUPAC/Chemical Name: (S)-2-amino-3-(hydroxy(nitroso)amino)propanoic acid
InChi Key: MLFKVJCWGUZWNV-REOHCLBHSA-N
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
SMILES Code: O=C(O)[C@@H](N)CN(O)N=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in water
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in water
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 149.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Kindler HL, Burris HA 3rd, Sandler AB, Oliff IA. A phase II multicenter study of L-alanosine, a potent inhibitor of adenine biosynthesis, in patients with MTAP-deficient cancer. Invest New Drugs. 2009 Feb;27(1):75-81. doi: 10.1007/s10637-008-9160-1. Epub 2008 Jul 11. PubMed PMID: 18618081.
2: Li XM, Kanekal S, CrÃ©pin D, Guettier C, CarriÃ¨re J, Elliott G, LÃ©vi F. Circadian pharmacology of L-alanosine (SDX-102) in mice. Mol Cancer Ther. 2006 Feb;5(2):337-46. PubMed PMID: 16505107.
3: Huang J, Lipscomb WN. T-state active site of aspartate transcarbamylase: crystal structure of the carbamyl phosphate and L-alanosine ligated enzyme. Biochemistry. 2006 Jan 17;45(2):346-52. PubMed PMID: 16401065.
4: Batova A, Cottam H, Yu J, Diccianni MB, Carrera CJ, Yu AL. EFA (9-beta-D-erythrofuranosyladenine) is an effective salvage agent for methylthioadenosine phosphorylase-selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine. Blood. 2006 Feb 1;107(3):898-903. Epub 2005 Oct 18. PubMed PMID: 16234352; PubMed Central PMCID: PMC1895892.
5: Li W, Su D, Mizobuchi H, Martin DS, Gu B, Gorlick R, Cole P, Bertino JR. Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells. Oncol Res. 2004;14(7-8):373-9. PubMed PMID: 15301428.
6: Gantverg A, Elliott G, Pineault J, Demers R. Determination of derivatized l-alanosine in plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Apr 25;803(2):311-5. PubMed PMID: 15063341.
7: Efferth T, Gebhart E, Ross DD, Sauerbrey A. Identification of gene expression profiles predicting tumor cell response to L-alanosine. Biochem Pharmacol. 2003 Aug 15;66(4):613-21. PubMed PMID: 12906926.
8: Yu J. Alanosine (UCSD). Curr Opin Investig Drugs. 2001 Nov;2(11):1623-30. Review. PubMed PMID: 11763167.
9: Batova A, Diccianni MB, Omura-Minamisawa M, Yu J, Carrera CJ, Bridgeman LJ, Kung FH, Pullen J, Amylon MD, Yu AL. Use of alanosine as a methylthioadenosine phosphorylase-selective therapy for T-cell acute lymphoblastic leukemia in vitro. Cancer Res. 1999 Apr 1;59(7):1492-7. PubMed PMID: 10197619.
10: Guicherit OM, Cooper BF, Rudolph FB, Kellems RE. Amplification of an adenylosuccinate synthetase gene in alanosine-resistant murine T-lymphoma cells. Molecular cloning of a cDNA encoding the "non-muscle" isozyme. J Biol Chem. 1994 Feb 11;269(6):4488-96. PubMed PMID: 8308018.