≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Guadecitabine sodium (SGI-110 sodium) is a second-generation DNA methyltransferases ( DNMT ) inhibitor for research of acute myeloid leukemia (AML) and myelodysplastic syndromes (MDS)
In Vitro
After HCT116 colorectal carcinoma cells are treated for 6 days, a dose-dependent increase in p16expression is observed with Guadecitabine sodium (SGI-110 sodium). In addition, T24 and HCT116 cells treated with Guadecitabine sodium or 5-aza-CdR for 3 days show a dose-dependent increase in the level of p16 protein, showing the competence of Guadecitabine sodium to inhibit DNA methylation and induce p16 at both mRNA and protein levels as well as 5-aza-CdR. Thus, Guadecitabine sodium is able to inhibit DNA methylation at 5′-region and induce the expression of the p16 gene in T24 and HCT116 cells at concentrations comparable to 5-aza-CdR, and the induction of p16 expression by both agents correlates with the demethylation at the 5′-end region of the gene in both cell lines. Guadecitabine sodium is slightly less toxic than 5-aza-CdR at the doses tested up to 1 μM concentration but displaying similar toxicity at 10 μM concentration. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Guadecitabine sodium (SGI-110 sodium) at 10mg/kg is an effective dose at reducing DNA methylation and retarding tumor growth, and caused roughly the same level of toxicity as 5-Aza-CdR. Guadecitabine sodium is effective in vivo at reactivating the expression of the p16 gene, which is heavily methylated in the parent EJ6 cells. Guadecitabine sodium is effective in reducing the level of DNA methylation in vivo at the p16 promoter region. Guadecitabine sodium is better tolerated than 5-Aza-CdR in vivo , suggesting that it can be an attractive alternative for potential clinical use. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Animal administration
Mouse: Athymic nu/nu mice are inoculated subcutaneously in the right hind flank with 10 7 EJ6 bladder cancer cells. After tumors reach 0.5 cm in diameter, animals are stratified into three groups with eight animals per group to begin treatments. Doses and dosing schedules are designed so that each group received molar equivalents of either S-110 or 5-Aza-CdR. The agents are administered SQ once weekly at a dose of 12.2 mg/kg for S-110 and 5.0 mg/kg for 5-Aza-CdR for three weeks. The study includes an appropriate PBS control group. Tumor sizes by caliper and body weight measurements are taken twice weekly to monitor tumor growth inhibition and tolerability . aladdin has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:DNMT1
| Canonical Smiles | C1C(C(OC1N2C=NC3=C2N=C(NC3=O)N)COP(=O)([O-])OC4CC(OC4CO)N5C=NC(=NC5=O)N)O.[Na+] |
|---|---|
| IUPAC Name | sodium;[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3S,5R)-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] phosphate |
| InChIKey | XLHBNJPXFOZFNJ-BYKQGDNKSA-M |
| INCHI | 1S/C18H24N9O10P.Na/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);/q;+1/p-1/t7-,8-,9+,10+,11+,12+;/m0./s1 |
| Isomeric SMILES | C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(NC3=O)N)COP(=O)([O-])O[C@H]4C[C@@H](O[C@@H]4CO)N5C=NC(=NC5=O)N)O.[Na+] |
| Molecular Weight | 579.39 |
| Reaxy-Rn | 15477452 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=15477452&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Nucleosides, nucleotides, and analogues |
| Class | Purine nucleotides |
| Subclass | Purine deoxyribonucleotides |
| Intermediate Tree Nodes | Purine deoxyribonucleoside monophosphates |
| Direct Parent | Purine 2'-deoxyribonucleoside monophosphates |
| Alternative Parents | 6-oxopurines Hypoxanthines Triazinones Pyrimidones Aminopyrimidines and derivatives Aminotriazines Dialkyl phosphates 1,3,5-triazines N-substituted imidazoles Vinylogous amides Oxolanes Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Organic sodium salts Organic zwitterions Primary alcohols Primary amines |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Purine 2'-deoxyribonucleoside monophosphate - 6-oxopurine - Hypoxanthine - Imidazopyrimidine - Purine - Aminopyrimidine - Amino-1,3,5-triazine - Aminotriazine - Pyrimidone - Triazinone - Dialkyl phosphate - N-substituted imidazole - Organic phosphoric acid derivative - Phosphoric acid ester - 1,3,5-triazine - Pyrimidine - Triazine - Alkyl phosphate - Vinylogous amide - Azole - Heteroaromatic compound - Imidazole - Oxolane - Secondary alcohol - Organic alkali metal salt - Organoheterocyclic compound - Azacycle - Oxacycle - Organic oxide - Organonitrogen compound - Alcohol - Organic nitrogen compound - Organooxygen compound - Amine - Primary alcohol - Primary amine - Hydrocarbon derivative - Organic sodium salt - Organic oxygen compound - Organic zwitterion - Organic salt - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. |
| External Descriptors | Not available |
| Solubility | H2O : 50 mg/mL (86.30 mM; Need ultrasonic and warming) DMSO : 50 mg/mL (86.30 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 579.400 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 8 |
| Exact Mass | 579.12 Da |
| Monoisotopic Mass | 579.12 Da |
| Topological Polar Surface Area | 274.000 Ų |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Complexity | 1110.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 2 |
