Guadecitabine
CAS#: 929901-49-5
Description: Guadecitabine, aslo known as SGI-110, is a dinucleotide antimetabolite of a decitabine linked via phosphodiester bond to a guanosine, with potential antineoplastic activity. Following metabolic activation by phosphorylation and incorporation into DNA, SGI-110 inhibits DNA methyltransferase, thereby causing genome-wide and non-specific hypomethylation and inducing cell cycle arrest at S-phase. This agent is resistant to cytidine deaminase, hence may result in gradual release of decitabine both extra- and intracellularly, leading to more prolonged exposures to decitabine.
Synonym: SGI110; SGI-110; SGI 110; S110; Guadecitabine
IUPAC/Chemical Name: (2R,3S,5R)-5-(4-amino-2-oxo-1,3,5-triazin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl (((2S,3R,5R)-5-(2-amino-6-oxo-1H-purin-9(6H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl) hydrogen phosphate
PRICE AND AVAILABILITY
THEORETICAL ANALYSIS
Name: Guadecitabine (SGI-110)
CAS#: 929901-49-5
Chemical Formula: C18H24N9O10P
Exact Mass: 557.13837
Molecular Weight: 557.41122
Elemental Analysis: C, 38.79; H, 4.34; N, 22.62; O, 28.70; P, 5.56
TECHNICAL DATA
ADDITIONAL INFORMATION
Related CAS#
929901-49-5 (Guadecitabine)
929904-85-8 (Guadecitabine sodium)
REFERENCES
1: Lavelle D, Saunthararajah Y, Vaitkus K, Singh M, Banzon V, Phiasivongsva P, Redkar S, Kanekal S, Bearss D, Shi C, Inloes R, DeSimone J. S110, a novel decitabine dinucleotide, increases fetal hemoglobin levels in baboons (P. anubis). J Transl Med. 2010 Oct 8;8:92. PubMed PMID: 20932295; PubMed Central PMCID: PMC2958909.
2: Chuang JC, Warner SL, Vollmer D, Vankayalapati H, Redkar S, Bearss DJ, Qiu X, Yoo CB, Jones PA. S110, a 5-Aza-2′-deoxycytidine-containing dinucleotide, is an effective DNA methylation inhibitor in vivo and can reduce tumor growth. Mol Cancer Ther. 2010 May;9(5):1443-50. Epub 2010 May 4. PubMed PMID: 20442312; PubMed Central PMCID: PMC2868087.
3: Yoo CB, Jeong S, Egger G, Liang G, Phiasivongsa P, Tang C, Redkar S, Jones PA. Delivery of 5-aza-2′-deoxycytidine to cells using oligodeoxynucleotides. Cancer Res. 2007 Jul 1;67(13):6400-8. PubMed PMID: 17616700.
4: Taylor JS, Garrett DS, Cohrs MP. Solution-state structure of the Dewar pyrimidinone photoproduct of thymidylyl-(3′—-5′)-thymidine. Biochemistry. 1988 Sep 20;27(19):7206-15. PubMed PMID: 3207670.