WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205629
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.
MedKoo Cat#: 205629
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
Guadecitabine (SGI-110) is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to firstname.lastname@example.org to inquire quote.
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
InChi Key: GUWXKKAWLCENJA-ZNSALQAWSA-N
InChi Code: InChI=1S/C18H24N9O10P/c19-16-22-6-27(18(31)25-16)12-2-8(9(3-28)35-12)37-38(32,33)34-4-10-7(29)1-11(36-10)26-5-21-13-14(26)23-17(20)24-15(13)30/h5-12,28-29H,1-4H2,(H,32,33)(H2,19,25,31)(H3,20,23,24,30)/t7-,8+,9-,10+,11-,12-/m1/s1
SMILES Code: O=P(OC[C@@H]1O[C@@H](N2C=NC3=C2N=C(N)NC3=O)C[C@H]1O)(O[C@@H]4[C@@H](CO)O[C@@H](N5C(N=C(N)N=C5)=O)C4)O
The following data is based on the product molecular weight 557.41122 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: 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.
929904-85-8 (Guadecitabine sodium)