Synonym
RA-9; RA 9; RA9; Proteasome-IN-3
IUPAC/Chemical Name
N2-[[(3E,5E)-3,5-bis[(3,4-dichlorophenyl)methylene]-4-oxo-1-piperidinyl]carbonyl]-L-arginyl-L-lysine
InChi Key
BNQKHLJMLJIRBI-PMWHKEQESA-N
InChi Code
InChI=1S/C32H37Cl4N7O5/c33-22-8-6-18(14-24(22)35)12-20-16-43(17-21(28(20)44)13-19-7-9-23(34)25(36)15-19)32(48)42-26(5-3-11-40-31(38)39)29(45)41-27(30(46)47)4-1-2-10-37/h6-9,12-15,26-27H,1-5,10-11,16-17,37H2,(H,41,45)(H,42,48)(H,46,47)(H4,38,39,40)/b20-12+,21-13+/t26-,27-/m0/s1
SMILES Code
NCCCC[C@@H](C(O)=O)NC([C@H](CCCNC(N)=N)NC(N1C/C(C(/C(C1)=C/C2=CC=C(Cl)C(Cl)=C2)=O)=C\C3=CC=C(Cl)C(Cl)=C3)=O)=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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
741.49
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 |
1: De Winter LM, Hansen WL, van Steenbergen HW, Geusens P, Lenaerts J, Somers K, Stinissen P, van der Helm-van Mil AH, Somers V. Autoantibodies to two novel peptides in seronegative and early rheumatoid arthritis. Rheumatology (Oxford). 2016 Aug;55(8):1431-6. doi: 10.1093/rheumatology/kew198. Epub 2016 Apr 19. PubMed PMID: 27094600.
2: Vogel RI, Coughlin K, Scotti A, Iizuka Y, Anchoori R, Roden RB, Marastoni M, Bazzaro M. Simultaneous inhibition of deubiquitinating enzymes (DUBs) and autophagy synergistically kills breast cancer cells. Oncotarget. 2015 Feb 28;6(6):4159-70. PubMed PMID: 25784654; PubMed Central PMCID: PMC4414179.
3: Coughlin K, Anchoori R, Iizuka Y, Meints J, MacNeill L, Vogel RI, Orlowski RZ, Lee MK, Roden RB, Bazzaro M. Small-molecule RA-9 inhibits proteasome-associated DUBs and ovarian cancer in vitro and in vivo via exacerbating unfolded protein responses. Clin Cancer Res. 2014 Jun 15;20(12):3174-86. doi: 10.1158/1078-0432.CCR-13-2658. Epub 2014 Apr 11. PubMed PMID: 24727327; PubMed Central PMCID: PMC4269153.
4: Issaenko OA, Amerik AY. Chalcone-based small-molecule inhibitors attenuate malignant phenotype via targeting deubiquitinating enzymes. Cell Cycle. 2012 May 1;11(9):1804-17. doi: 10.4161/cc.20174. Epub 2012 May 1. Erratum in: Cell Cycle. 2012 Sep 15;11(18):3518. PubMed PMID: 22510564; PubMed Central PMCID: PMC3372381.
5: van der Poel EP, Stevens RJ, Lohse D. Connecting flow structures and heat flux in turbulent Rayleigh-Bénard convection. Phys Rev E Stat Nonlin Soft Matter Phys. 2011 Oct;84(4 Pt 2):045303. Epub 2011 Oct 19. PubMed PMID: 22181218.
6: Zhu GY, Li YW, Hau DK, Jiang ZH, Yu ZL, Fong WF. Acylated protopanaxadiol-type ginsenosides from the root of Panax ginseng. Chem Biodivers. 2011 Oct;8(10):1853-63. doi: 10.1002/cbdv.201000196. PubMed PMID: 22006713.