SGI-1027
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MedKoo CAT#: 406558

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.


Price and Availability

Size Price Shipping out time Quantity
10mg USD 150 2 Weeks
25mg USD 250 2 Weeks
50mg USD 450 2 Weeks
100mg USD 650 2 Weeks
200mg USD 950 2 Weeks
500mg USD 1650 2 Weeks
1g USD 2850 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-06-07. Prices are subject to change without notice.

SGI-1027, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406558
Name: SGI-1027
CAS#: 1020149-73-8
Chemical Formula: C27H23N7O
Exact Mass: 461.19641
Molecular Weight: 461.52
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


Technical Data

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


Additional Information

  
 
 
 


References

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: García-Domínguez 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: García-Domínguez P, Weiss M, Lepore I, Ã