Guadecitabine

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

MedKoo CAT#: 205629

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.


Price and Availability

Size
Price

1g
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Size
Price

2g
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Size
Price

5g
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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 sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205629
Name: Guadecitabine
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


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


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


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.