Guadecitabine

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H205629

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.

Chemical Structure

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Guadecitabine
CAS# 929901-49-5
Instruction

Theoretical Analysis

Hodoodo Cat#: H205629
Name: Guadecitabine
CAS#: 929901-49-5
Chemical Formula: C18H24N9O10P
Exact Mass: 557.14
Molecular Weight: 557.411
Elemental Analysis: C, 38.79; H, 4.34; N, 22.62; O, 28.70; P, 5.56

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 929904-85-8 (Na); 929901-49-5  

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

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 DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

More Info: Related CAS# 929901-49-5 (Guadecitabine) 929904-85-8 (Guadecitabine sodium)    

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 557.41 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.