Home Methylation DNMT inhibitor Guadecitabine (SGI-110)

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Guadecitabine (SGI-110) DNMT inhibitor

Cat.No.S7013

Guadecitabine (SGI-110, S-110) is a next-generation hypomethylating agent.
Guadecitabine (SGI-110) DNMT inhibitor Chemical Structure

Chemical Structure

Molecular Weight: 579.39

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Quality Control

Batch: S701301 DMSO]100 mg/mL]false]Water]50 mg/mL]false]Ethanol]Insoluble]false Purity: 99.93%
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99.93

Solubility

In vitro
Batch:

DMSO : 100 mg/mL (172.59 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Water : 50 mg/mL

Ethanol : Insoluble

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In vivo
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Chemical Information, Storage & Stability

Molecular Weight 579.39 Formula

C18 H23 N9 O10 P . Na

 Storage (From the date of receipt)
CAS No. 929904-85-8 -- Storage of Stock Solutions

Synonyms S-110 Smiles C1C(C(OC1N2C=NC3=C2N=C(NC3=O)N)COP(=O)([O-])OC4CC(OC4CO)N5C=NC(=NC5=O)N)O.[Na+]

Mechanism of Action

Targets/IC50/Ki
DNA methyltransferase
In vitro

Guadecitabine (SGI-110) is a 5-aza-2′-deoxycytidine-containing demethylating dinucleotide that works via a mechanism similar to that of 5-aza-CdR after incorporation of its aza-moiety into DNA. However, it is well protected from deamination by cytidine deaminase. This compound (1 μM) induces a significant decrease in the level of methylation in both T24 and HCT116 cells and is able to induce robust p16 expression. It also causes depletion of extractable DNMT1 in cells at 1 μM concentration. Furthermore, it decreases the plating efficiency of T24 bladder carcinoma cells in a dose-dependent manner, with no colonies forming at 10 μM concentration, which is quite similar to 5-aza-CdR in T24 cells.

It shows immunomodulatory activity in vitro. At 1 μM, it induces/up-regulates the expression of several cancer/testis antigens (CTA) (i.e., MAGE-A1, MAGE-A2, MAGE-A3, MAGE-A4, MAGE-A10, GAGE1-2, GAGE 1-6, NY-ESO-1, and SSX 1-5) in cancer cell lines (cutaneous melanoma, mesothelioma, renal cell carcinoma, and sarcoma cells), both at mRNA and at protein levels. This compound also up-regulates the expression of HLA class I antigens and of ICAM-1, resulting in improved recognition of cancer cells by gp100-specific CTL.

In vivo

Guadecitabine (SGI-110) is as effective as 5-Aza-CdR, but is better tolerated in mice. This compound (10 mg/kg) displays potent activity on inducing p16 expression, reducing DNA methylation at the p16 promoter region, and retarding tumor growth in human xenograft. It is effective by both i.p. and s.c. deliveries.

References
  • [4] https://pubmed.ncbi.nlm.nih.gov/31060979/
  • [5] https://pubmed.ncbi.nlm.nih.gov/35843958/

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT03576963 Withdrawn
Colorectal Adenocarcinoma|CpG Island Methylator Phenotype|Metastatic Microsatellite Stable Colorectal Carcinoma|Refractory Colorectal Carcinoma|Stage IV Colorectal Cancer AJCC v8|Stage IVA Colorectal Cancer AJCC v8|Stage IVB Colorectal Cancer AJCC v8|Stage IVC Colorectal Cancer AJCC v8
University of Southern California|National Cancer Institute (NCI)|Bristol-Myers Squibb|Astex Pharmaceuticals Inc.
 January 30 2020 Phase 1|Phase 2
NCT03085849 Completed
Extensive-stage Small Cell Lung Cancer
Catherine Shu|Columbia University
 December 15 2017 Phase 1
NCT03179943 Active not recruiting
Urothelial Carcinoma
Fox Chase Cancer Center|Stand Up To Cancer|Van Andel Research Institute
 November 27 2017 Phase 2
NCT02998567 Recruiting
Castration-Resistant Prostatic Cancer|Non Small Cell Lung Cancer
Royal Marsden NHS Foundation Trust|Astex Pharmaceuticals Inc.|Merck Sharp & Dohme LLC|Institute of Cancer Research United Kingdom
 January 26 2017 Phase 1
NCT02892318 Completed
Acute Myeloid Leukemia
Hoffmann-La Roche
 October 31 2016 Phase 1

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