Synonym
RA-839; RA 839; RA839;
IUPAC/Chemical Name
(3S)-1-[4-[[(2,3,5,6-Tetramethylphenyl)sulfonyl]amino]-1-naphthalenyl]-3-pyrrolidinecarboxylic acid
InChi Key
BVYWIQHJXAEJOD-IBGZPJMESA-N
InChi Code
InChI=1S/C25H28N2O4S/c1-15-13-16(2)18(4)24(17(15)3)32(30,31)26-22-9-10-23(21-8-6-5-7-20(21)22)27-12-11-19(14-27)25(28)29/h5-10,13,19,26H,11-12,14H2,1-4H3,(H,28,29)/t19-/m0/s1
SMILES Code
O=C([C@@H]1CN(C2=C3C=CC=CC3=C(NS(=O)(C4=C(C)C(C)=CC(C)=C4C)=O)C=C2)CC1)O
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
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
Biological target:
RA 839 is an Nrf2 activator; it inhibits Nrf2/Keap1 interaction (Kd = 6 μM). RA 839 suppresses LPS-induced iNOS and nitric oxide expression in macrophages and is anti-inflammatory.
In vitro activity:
RA-839 inhibits Rotavirus (RV) RNA and protein expression, viroplasm formation, yield of virion progeny and virus-induced cytopathy independent of RV strains. This study demonstrates that RA-839 is a potent antagonist of RV propagation in vitro and can be developed as anti-rotaviral therapeutics.
Reference: Antiviral Res. 2019 Jan;161:53-62. https://pubmed.ncbi.nlm.nih.gov/30465784/
In vivo activity:
RA839 prevented the induction of both inducible nitric-oxide synthase expression and nitric oxide release in response to lipopolysaccharides in macrophages. In mice, RA839 acutely induced Nrf2 target gene expression in the liver. RA839 is a selective inhibitor of the Keap1/Nrf2 interaction and a useful tool compound to study the biology of Nrf2.
Reference: J Biol Chem. 2015 Nov 20;290(47):28446-28455. https://pubmed.ncbi.nlm.nih.gov/26459563/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
45.3 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
452.57
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:
1. Patra U, Mukhopadhyay U, Sarkar R, Mukherjee A, Chawla-Sarkar M. RA-839, a selective agonist of Nrf2/ARE pathway, exerts potent anti-rotaviral efficacy in vitro. Antiviral Res. 2019 Jan;161:53-62. doi: 10.1016/j.antiviral.2018.11.009. Epub 2018 Nov 19. PMID: 30465784.
2. Winkel AF, Engel CK, Margerie D, Kannt A, Szillat H, Glombik H, Kallus C, Ruf S, Güssregen S, Riedel J, Herling AW, von Knethen A, Weigert A, Brüne B, Schmoll D. Characterization of RA839, a Noncovalent Small Molecule Binder to Keap1 and Selective Activator of Nrf2 Signaling. J Biol Chem. 2015 Nov 20;290(47):28446-28455. doi: 10.1074/jbc.M115.678136. Epub 2015 Oct 12. PMID: 26459563; PMCID: PMC4653701.
In vitro protocol:
1. Patra U, Mukhopadhyay U, Sarkar R, Mukherjee A, Chawla-Sarkar M. RA-839, a selective agonist of Nrf2/ARE pathway, exerts potent anti-rotaviral efficacy in vitro. Antiviral Res. 2019 Jan;161:53-62. doi: 10.1016/j.antiviral.2018.11.009. Epub 2018 Nov 19. PMID: 30465784.
In vivo protocol:
1. Winkel AF, Engel CK, Margerie D, Kannt A, Szillat H, Glombik H, Kallus C, Ruf S, Güssregen S, Riedel J, Herling AW, von Knethen A, Weigert A, Brüne B, Schmoll D. Characterization of RA839, a Noncovalent Small Molecule Binder to Keap1 and Selective Activator of Nrf2 Signaling. J Biol Chem. 2015 Nov 20;290(47):28446-28455. doi: 10.1074/jbc.M115.678136. Epub 2015 Oct 12. PMID: 26459563; PMCID: PMC4653701.
1: Nasiri HR, Linge S, Ullmann D. Thermodynamic profiling of inhibitors of Nrf2:Keap1 interactions. Bioorg Med Chem Lett. 2016 Jan 15;26(2):526-529. doi: 10.1016/j.bmcl.2015.11.082. Epub 2015 Nov 23. PubMed PMID: 26653613.
2: Winkel AF, Engel CK, Margerie D, Kannt A, Szillat H, Glombik H, Kallus C, Ruf S, Güssregen S, Riedel J, Herling AW, von Knethen A, Weigert A, Brüne B, Schmoll D. Characterization of RA839, a Noncovalent Small Molecule Binder to Keap1 and Selective Activator of Nrf2 Signaling. J Biol Chem. 2015 Nov 20;290(47):28446-55. doi: 10.1074/jbc.M115.678136. Epub 2015 Oct 12. PubMed PMID: 26459563; PubMed Central PMCID: PMC4653701.
3: Patra U, Mukhopadhyay U, Sarkar R, Mukherjee A, Chawla-Sarkar M. RA-839, a selective agonist of Nrf2/ARE pathway, exerts potent anti-rotaviral efficacy in vitro. Antiviral Res. 2019 Jan;161:53-62. doi: 10.1016/j.antiviral.2018.11.009. Epub 2018 Nov 19. PMID: 30465784.
