RA190 HCl
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Hodoodo CAT#: H533301

CAS#: 1617495-03-0 (HCl)

Description: RA190 is a potent Rpn13 inhibitor and ADRM1 inhibitor, suppressing intrahepatic cholangiocarcinoma by inducing NF-kappaB-mediated cell apoptosis.

Chemical Structure

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RA190 HCl
CAS# 1617495-03-0 (HCl)
Instruction

Theoretical Analysis

Hodoodo Cat#: H533301
Name: RA190 HCl
CAS#: 1617495-03-0 (HCl)
Chemical Formula: C28H23Cl5N2O2
Exact Mass: 594.02
Molecular Weight: 596.750
Elemental Analysis: C, 56.36; H, 3.89; Cl, 29.70; N, 4.69; O, 5.36

Price and Availability

Size Price Availability Quantity
50mg USD 550 2 Weeks
100mg USD 1050 2 Weeks
200mg USD 1850 2 Weeks
500mg USD 3650 2 Weeks
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Related CAS #: 1617572-02-7 (free base)   1617495-03-0 (HCl)    

Synonym: RA190; RA-190; RA 190; RA190 HCl; RA190 hydrochloride

IUPAC/Chemical Name: 1-(L-Phenylalanyl)-3,5-bis((E)-3,4-dichlorobenzylidene)piperidin-4-one hydrochloride

InChi Key: UMWXLEVUBFNYIK-VXWDMQPRSA-N

InChi Code: InChI=1S/C28H22Cl4N2O2.ClH/c29-22-8-6-18(12-24(22)31)10-20-15-34(28(36)26(33)14-17-4-2-1-3-5-17)16-21(27(20)35)11-19-7-9-23(30)25(32)13-19;/h1-13,26H,14-16,33H2;1H/b20-10+,21-11+;/t26-;/m0./s1

SMILES Code: O=C1/C(CN(C([C@H](CC2=CC=CC=C2)N)=O)C/C1=C\C3=CC=C(Cl)C(Cl)=C3)=C/C4=CC=C(Cl)C(Cl)=C4.[H]Cl

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: To be determined

Shelf Life: >3 years if stored properly

Drug Formulation: To be determined

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:

Preparing Stock Solutions

The following data is based on the product molecular weight 596.75 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.

Recalculate based on batch purity %
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:

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1: Du T, Song Y, Ray A, Chauhan D, Anderson KC. Proteomic analysis identifies mechanism(s) of overcoming bortezomib resistance via targeting ubiquitin receptor Rpn13. Leukemia. 2020 May 18. doi: 10.1038/s41375-020-0865-2. Epub ahead of print. PMID: 32424294.


2: Soong RS, Anchoori RK, Roden RBS, Cho RL, Chen YC, Tseng SC, Huang YL, Liao PC, Shyu YC. Bis-benzylidine Piperidone RA190 treatment of hepatocellular carcinoma via binding RPN13 and inhibiting NF-κB signaling. BMC Cancer. 2020 May 6;20(1):386. doi: 10.1186/s12885-020-06896-0. PMID: 32375699; PMCID: PMC7201939.


3: Sherman DJ, Li J. Proteasome Inhibitors: Harnessing Proteostasis to Combat Disease. Molecules. 2020 Feb 5;25(3):671. doi: 10.3390/molecules25030671. PMID: 32033280; PMCID: PMC7037493.


4: Anchoori RK, Tan M, Tseng SH, Peng S, Soong RS, Algethami A, Foran P, Das S, Wang C, Wang TL, Liang H, Hung CF, Roden RBS. Structure-function analyses of candidate small molecule RPN13 inhibitors with antitumor properties. PLoS One. 2020 Jan 15;15(1):e0227727. doi: 10.1371/journal.pone.0227727. PMID: 31940398; PMCID: PMC6961910.


5: Ray A, Song Y, Chauhan D, Anderson KC. Blockade of ubiquitin receptor Rpn13 in plasmacytoid dendritic cells triggers anti-myeloma immunity. Blood Cancer J. 2019 Aug 12;9(8):64. doi: 10.1038/s41408-019-0224-6. PMID: 31406111; PMCID: PMC6690908.


6: Song Y, Park PMC, Wu L, Ray A, Picaud S, Li D, Wimalasena VK, Du T, Filippakopoulos P, Anderson KC, Qi J, Chauhan D. Development and preclinical validation of a novel covalent ubiquitin receptor Rpn13 degrader in multiple myeloma. Leukemia. 2019 Nov;33(11):2685-2694. doi: 10.1038/s41375-019-0467-z. Epub 2019 Apr 8. PMID: 30962579; PMCID: PMC6783320.


7: Anchoori RK, Jiang R, Peng S, Soong RS, Algethami A, Rudek MA, Anders N, Hung CF, Chen X, Lu X, Kayode O, Dyba M, Walters KJ, Roden RBS. Covalent Rpn13-Binding Inhibitors for the Treatment of Ovarian Cancer. Version 2. ACS Omega. 2018 Sep 30;3(9):11917-11929. doi: 10.1021/acsomega.8b01479. Epub 2018 Sep 27. PMID: 30288466; PMCID: PMC6166221.


8: Yu GY, Wang X, Zheng SS, Gao XM, Jia QA, Zhu WW, Lu L, Jia HL, Chen JH, Dong QZ, Lu M, Qin LX. RA190, a Proteasome Subunit ADRM1 Inhibitor, Suppresses Intrahepatic Cholangiocarcinoma by Inducing NF-KB-Mediated Cell Apoptosis. Cell Physiol Biochem. 2018;47(3):1152-1166. doi: 10.1159/000490210. Epub 2018 Jun 15. PMID: 29913454.


9: Jiang RT, Yemelyanova A, Xing D, Anchoori RK, Hamazaki J, Murata S, Seidman JD, Wang TL, Roden RBS. Early and consistent overexpression of ADRM1 in ovarian high-grade serous carcinoma. J Ovarian Res. 2017 Aug 7;10(1):53. doi: 10.1186/s13048-017-0347-y. PMID: 28784174; PMCID: PMC5547474.


10: Lu X, Nowicka U, Sridharan V, Liu F, Randles L, Hymel D, Dyba M, Tarasov SG, Tarasova NI, Zhao XZ, Hamazaki J, Murata S, Burke TR Jr, Walters KJ. Structure of the Rpn13-Rpn2 complex provides insights for Rpn13 and Uch37 as anticancer targets. Nat Commun. 2017 Jun 9;8:15540. doi: 10.1038/ncomms15540. PMID: 28598414; PMCID: PMC5494190.


11: Soong RS, Anchoori RK, Yang B, Yang A, Tseng SH, He L, Tsai YC, Roden RB, Hung CF. RPN13/ADRM1 inhibitor reverses immunosuppression by myeloid-derived suppressor cells. Oncotarget. 2016 Oct 18;7(42):68489-68502. doi: 10.18632/oncotarget.12095. PMID: 27655678; PMCID: PMC5340091.


12: Song Y, Ray A, Li S, Das DS, Tai YT, Carrasco RD, Chauhan D, Anderson KC. Targeting proteasome ubiquitin receptor Rpn13 in multiple myeloma. Leukemia. 2016 Sep;30(9):1877-86. doi: 10.1038/leu.2016.97. Epub 2016 Apr 27. PMID: 27118409; PMCID: PMC5749253.


13: Randles L, Anchoori RK, Roden RB, Walters KJ. The Proteasome Ubiquitin Receptor hRpn13 and Its Interacting Deubiquitinating Enzyme Uch37 Are Required for Proper Cell Cycle Progression. J Biol Chem. 2016 Apr 15;291(16):8773-83. doi: 10.1074/jbc.M115.694588. Epub 2016 Feb 23. PMID: 26907685; PMCID: PMC4861445.


14: Fejzo MS, Anderson L, Chen HW, Anghel A, Zhuo J, Anchoori R, Roden R, Slamon DJ. ADRM1-amplified metastasis gene in gastric cancer. Genes Chromosomes Cancer. 2015 Aug;54(8):506-515. doi: 10.1002/gcc.22262. Epub 2015 Jun 6. PMID: 26052681.


15: Trader DJ, Simanski S, Kodadek T. A reversible and highly selective inhibitor of the proteasomal ubiquitin receptor rpn13 is toxic to multiple myeloma cells. J Am Chem Soc. 2015 May 20;137(19):6312-9. doi: 10.1021/jacs.5b02069. Epub 2015 May 8. PMID: 25914958; PMCID: PMC4455945.


16: Anchoori RK, Karanam B, Peng S, Wang JW, Jiang R, Tanno T, Orlowski RZ, Matsui W, Zhao M, Rudek MA, Hung CF, Chen X, Walters KJ, Roden RB. A bis- benzylidine piperidone targeting proteasome ubiquitin receptor RPN13/ADRM1 as a therapy for cancer. Cancer Cell. 2013 Dec 9;24(6):791-805. doi: 10.1016/j.ccr.2013.11.001. PMID: 24332045; PMCID: PMC3881268.