WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H406558
CAS#: 1020149-73-8
Description: SGI-1027 is a potent DNMT inhibitor, which reactivates tumor suppressor genes by blocking DNA methyltransferase 1 activity and inducing its degradation. Treatment of different cancer cell lines with SGI-1027 resulted in selective degradation of DNMT1 with minimal or no effects on DNMT3A and DNMT3B. At a concentration of 2.5 to 5 micromol/L (similar to that of decitabine), complete degradation of DNMT1 protein was achieved within 24 h without significantly affecting its mRNA level. SGI-1027 may have the potential for use in epigenetic cancer therapy.
Hodoodo Cat#: H406558
Name: SGI-1027
CAS#: 1020149-73-8
Chemical Formula: C27H23N7O
Exact Mass: 461.20
Molecular Weight: 461.520
Elemental Analysis: C, 70.27; H, 5.02; N, 21.24; O, 3.47
Synonym: SGI1027; SGI 1027; SGI1027.
IUPAC/Chemical Name: N-(4-((2-amino-6-methylpyrimidin-4-yl)amino)phenyl)-4-(quinolin-4-ylamino)benzamide
InChi Key: QSYLKMKIVWJAAK-UHFFFAOYSA-N
InChi Code: InChI=1S/C27H23N7O/c1-17-16-25(34-27(28)30-17)32-20-10-12-21(13-11-20)33-26(35)18-6-8-19(9-7-18)31-24-14-15-29-23-5-3-2-4-22(23)24/h2-16H,1H3,(H,29,31)(H,33,35)(H3,28,30,32,34)
SMILES Code: O=C(NC1=CC=C(NC2=NC(N)=NC(C)=C2)C=C1)C3=CC=C(NC4=CC=NC5=CC=CC=C45)C=C3
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: >2 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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 20.0 | 43.30 |
The following data is based on the product molecular weight 461.52 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Ronen M, Avrahami D, Gerber D. A sensitive microfluidic platform for a high throughput DNA methylation assay. Lab Chip. 2014 Jul 7;14(13):2354-62. doi: 10.1039/c4lc00150h. Epub 2014 May 19. PubMed PMID: 24841578.
2: Rilova E, Erdmann A, Gros C, Masson V, Aussagues Y, Poughon-Cassabois V, Rajavelu A, Jeltsch A, Menon Y, Novosad N, Gregoire JM, Vispé S, Schambel P, Ausseil F, Sautel F, Arimondo PB, Cantagrel F. Design, synthesis and biological evaluation of 4-amino-N- (4-aminophenyl)benzamide analogues of quinoline-based SGI-1027 as inhibitors of DNA methylation. ChemMedChem. 2014 Mar;9(3):590-601. doi: 10.1002/cmdc.201300420. PubMed PMID: 24678024.
3: Fagan RL, Cryderman DE, Kopelovich L, Wallrath LL, Brenner C. Laccaic acid A is a direct, DNA-competitive inhibitor of DNA methyltransferase 1. J Biol Chem. 2013 Aug 16;288(33):23858-67. doi: 10.1074/jbc.M113.480517. Epub 2013 Jul 9. PubMed PMID: 23839987; PubMed Central PMCID: PMC3745332.
4: Gamage SA, Brooke DG, Redkar S, Datta J, Jacob ST, Denny WA. Structure-activity relationships for 4-anilinoquinoline derivatives as inhibitors of the DNA methyltransferase enzyme DNMT1. Bioorg Med Chem. 2013 Jun 1;21(11):3147-53. doi: 10.1016/j.bmc.2013.03.033. Epub 2013 Apr 6. PubMed PMID: 23639684.
5: Yoo J, Choi S, Medina-Franco JL. Molecular modeling studies of the novel inhibitors of DNA methyltransferases SGI-1027 and CBC12: implications for the mechanism of inhibition of DNMTs. PLoS One. 2013 Apr 25;8(4):e62152. doi: 10.1371/journal.pone.0062152. Print 2013. PubMed PMID: 23637988; PubMed Central PMCID: PMC3636198.
6: GarcÃa-DomÃnguez P, Dell'aversana C, Alvarez R, Altucci L, de Lera AR. Synthetic approaches to DNMT inhibitor SGI-1027 and effects on the U937 leukemia cell line. Bioorg Med Chem Lett. 2013 Mar 15;23(6):1631-5. doi: 10.1016/j.bmcl.2013.01.085. Epub 2013 Jan 30. PubMed PMID: 23402879.
7: GarcÃa-DomÃnguez P, Weiss M, Lepore I, Ã
