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MedKoo product information:

 

Alanosine

  

Description of L-alanosine: 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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

 

Current developer:    Gilead (Originator)

 

MedKoo Code#:  200130

Name:  Alanosine

CAS#:  16931-22-9

  

Synonym:   alanosine; L-alanosine sodium;   Code name: SDX-102. 

  

IUPAC/Chemical name: 

(S)-2-amino-3-(hydroxy(nitroso)amino)propanoic acid

 

Chemical structure Theoretical analysis

 

 

 

Chemical Formula: C3H7N3O4

Exact Mass: 149.04366

Molecular Weight: 149.10

Elemental Analysis: C, 24.17; H, 4.73; N, 28.18; O, 42.92

 

  

Availability and price:

 

Alanosine is available through custom synthesis.

  

To inquire quotation and lead time or to ask questions, please send email to sales@medkoo.com to describe your needs. A representative will respond your email shortly. We offer big discount for orders of bulk quantities.

 

Quality control data:

Product will be shipped with supporting analytical data.

 

 

Information about this agent

  

References

 1: Efferth T. Personalized Cancer Medicine: From Molecular Diagnostics to Targeted Therapy with Natural Products. Planta Med. 2010 May 19. [Epub ahead of print] PubMed PMID: 20486071.

2: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Sep;31(7):463-93. PubMed PMID: 19907722.

3: 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. Epub 2008 Jul 11. PubMed PMID: 18618081.

4: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Dec;29(10):697-735. PubMed PMID: 18200333.

5: Bonomo J, Lynch MD, Warnecke T, Price JV, Gill RT. Genome-scale analysis of anti-metabolite directed strain engineering. Metab Eng. 2008 Mar;10(2):109-20. Epub 2007 Nov 5. PubMed PMID: 18093856.

6: Bilodeau-Goeseels S, Sasseville M, Guillemette C, Richard FJ. Effects of adenosine monophosphate-activated kinase activators on bovine oocyte nuclear maturation in vitro. Mol Reprod Dev. 2007 Aug;74(8):1021-34. PubMed PMID: 17290417.

7: Marcé S, Balagué O, Colomo L, Martinez A, Höller S, Villamor N, Bosch F, Ott G, Rosenwald A, Leoni L, Esteller M, Fraga MF, Montserrat E, Colomer D, Campo E. Lack of methylthioadenosine phosphorylase expression in mantle cell lymphoma is associated with shorter survival: implications for a potential targeted therapy. Clin Cancer Res. 2006 Jun 15;12(12):3754-61. PubMed PMID: 16778103.

8: Li XM, Kanekal S, Crépin D, Guettier C, Carrière J, Elliott G, Lévi F. Circadian pharmacology of L-alanosine (SDX-102) in mice. Mol Cancer Ther. 2006 Feb;5(2):337-46. PubMed PMID: 16505107.

9: 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.

10: Karikari CA, Mullendore M, Eshleman JR, Argani P, Leoni LM, Chattopadhyay S, Hidalgo M, Maitra A. Homozygous deletions of methylthioadenosine phosphorylase in human biliary tract cancers. Mol Cancer Ther. 2005 Dec;4(12):1860-6. PubMed PMID: 16373701.

11: 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.

12: Powell EL, Leoni LM, Canto MI, Forastiere AA, Iocobuzio-Donahue CA, Wang JS, Maitra A, Montgomery E. Concordant loss of MTAP and p16/CDKN2A expression in gastroesophageal carcinogenesis: evidence of homozygous deletion in esophageal noninvasive precursor lesions and therapeutic implications. Am J Surg Pathol. 2005 Nov;29(11):1497-504. PubMed PMID: 16224217.

13: Huang Y, Dai Z, Barbacioru C, Sadée W. Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance. Cancer Res. 2005 Aug 15;65(16):7446-54. PubMed PMID: 16103098.

14: Capella G, Caldas C. MTAP homozygous deletion: an Achilles heel of human cancers ready for clinical use? Cancer Biol Ther. 2005 Mar;4(3):347. Epub 2005 Mar 9. PubMed PMID: 15876862.

15: 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.

16: 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.

17: 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.

18: Illei PB, Rusch VW, Zakowski MF, Ladanyi M. Homozygous deletion of CDKN2A and codeletion of the methylthioadenosine phosphorylase gene in the majority of pleural mesotheliomas. Clin Cancer Res. 2003 Jun;9(6):2108-13. PubMed PMID: 12796375.

19: Harasawa H, Yamada Y, Kudoh M, Sugahara K, Soda H, Hirakata Y, Sasaki H, Ikeda S, Matsuo T, Tomonaga M, Nobori T, Kamihira S. Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL). Leukemia. 2002 Sep;16(9):1799-807. PubMed PMID: 12200696.

 

 

 

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