JQ1-Carboxylic acid
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MedKoo CAT#: 562151

CAS#: 202592-23-2 (free)

Description: JQ1-Carboxylic acid also known as JQ1 Acid, is an inhibitor of bromodomain and extra terminal domain (BET) family proteins.


Chemical Structure

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JQ1-Carboxylic acid
CAS# 202592-23-2 (free)

Theoretical Analysis

MedKoo Cat#: 562151
Name: JQ1-Carboxylic acid
CAS#: 202592-23-2 (free)
Chemical Formula: C19H17ClN4O2S
Exact Mass: 400.0761
Molecular Weight: 400.88
Elemental Analysis: C, 56.93; H, 4.27; Cl, 8.84; N, 13.98; O, 7.98; S, 8.00

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25.0mg USD 90.0 Same day
50.0mg USD 150.0 Same day
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200.0mg USD 450.0 Same day
500.0mg USD 950.0 Same day
1.0g USD 1650.0 Same day
2.0g USD 2950.0 2 Weeks
5.0g USD 6550.0 2 Weeks
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Related CAS #: 1426257-60-4 (HCl)   2069219-37-8 (TFA)   2230314-61-9 (xTFA)   202592-23-2 (free)    

Synonym: JQ1 Carboxylic Acid; JQ1-Carboxylic Acid; JQ1 Acid; JQ-1 Acid; JQ-1 Acid; 202592-23-2 (free)

IUPAC/Chemical Name: 6(S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid

InChi Key: LJOSBOOJFIRCSO-AWEZNQCLSA-N

InChi Code: InChI=1S/C19H17ClN4O2S/c1-9-10(2)27-19-16(9)17(12-4-6-13(20)7-5-12)21-14(8-15(25)26)18-23-22-11(3)24(18)19/h4-7,14H,8H2,1-3H3,(H,25,26)/t14-/m0/s1

SMILES Code: O=C(O)C[C@H]1C2=NN=C(C)N2C3=C(C(C)=C(C)S3)C(C4=CC=C(Cl)C=C4)=N1

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

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: JQ-1 carboxylic acid is a (+)-JQ1 derivative (a BET bromodomain inhibitor).
In vitro activity: In the present study, it was first noted that JQ1 can significantly affect the glycolytic metabolism of B-ALL cells by inhibiting glucose absorption and metabolic process and eventually causing the reduction of metabolic intermediates, such as lactate and ATP, which are the main materials and energy sources for cell synthesis. According to the results of RNA-seq, JQ1 suppressed the glycolytic process by inhibiting the expression of glycolysis key enzymes, including hexokinase 2, phosphofructokinase, and lactate dehydrogenase A. It was also found that the glycolysis inhibitor 2-DG blocked the cell cycle arrest of B-ALL cells induced by JQ1, suggesting JQ1 suppressed the proliferation of B-ALL by partially inhibiting glycolysis. Reference: Med Sci Monit. 2020; 26: e923411-1–e923411-10. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7165247/
In vivo activity: To further validate findings, the anti-tumor effects of JQ1 were evaluated in vivo using a xenograft mouse model transplanted with HGC27 cells subcutaneously. Twelve mice were divided into two groups: the NC group and the JQ1-treating group. After 2 weeks of JQ1 treatment, it was observed that the volumes and weights of the tumors from the JQ1-treating group were significantly decreased compared with that in the NC group (Fig. 7a, b). However, there were no obvious differences regarding body weights of the mice between the two groups (Fig. 7c). Then, total protein and mRNA were extracted from the fresh tumors. WB analysis showed that the NID1 protein expression was significantly downregulated in JQ1-treating group compared with NC group (Fig. 7d). In addition, qRT-PCR results demonstrated a significant decrease in NID1 mRNA expression after JQ1 treatment (Fig. 7e). These findings indicated that JQ1 suppressed GC tumor proliferation via inhibiting NID1 signaling in vivo. Reference: Oncogenesis. 2020 Mar; 9(3): 33. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7064486/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.92 109.56
DMSO:PBS (pH 7.2) (1:4) 0.2 0.5
DMF 20.0 49.89
Ethanol 27.55 68.72

Preparing Stock Solutions

The following data is based on the product molecular weight 400.88 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: 1. Zhang MY, Liu SL, Huang WL, Tang DB, Zheng WW, Zhou N, Zhou H, Abudureheman T, Tang ZH, Zhou BS, Duan CW. Bromodomains and Extra-Terminal (BET) Inhibitor JQ1 Suppresses Proliferation of Acute Lymphocytic Leukemia by Inhibiting c-Myc-Mediated Glycolysis. Med Sci Monit. 2020 Apr 8;26:e923411. doi: 10.12659/MSM.923411. PMID: 32266878; PMCID: PMC7165247. 2. Qian Z, Shuying W, Ranran D. Inhibitory effects of JQ1 on listeria monocytogenes-induced acute liver injury by blocking BRD4/RIPK1 axis. Biomed Pharmacother. 2020 May;125:109818. doi: 10.1016/j.biopha.2020.109818. Epub 2020 Feb 25. PMID: 32106368. 3. Li F, MacKenzie KR, Jain P, Santini C, Young DW, Matzuk MM. Metabolism of JQ1, an inhibitor of bromodomain and extra terminal bromodomain proteins, in human and mouse liver microsomes†. Biol Reprod. 2020 Aug 4;103(2):427-436. doi: 10.1093/biolre/ioaa043. PMID: 32285106; PMCID: PMC7401416. 4. Zhou S, Zhang S, Wang L, Huang S, Yuan Y, Yang J, Wang H, Li X, Wang P, Zhou L, Yang J, Xu Y, Gao H, Zhang Y, Lv Y, Zou X. BET protein inhibitor JQ1 downregulates chromatin accessibility and suppresses metastasis of gastric cancer via inactivating RUNX2/NID1 signaling. Oncogenesis. 2020 Mar 10;9(3):33. doi: 10.1038/s41389-020-0218-z. PMID: 32157097; PMCID: PMC7064486.
In vitro protocol: 1. Zhang MY, Liu SL, Huang WL, Tang DB, Zheng WW, Zhou N, Zhou H, Abudureheman T, Tang ZH, Zhou BS, Duan CW. Bromodomains and Extra-Terminal (BET) Inhibitor JQ1 Suppresses Proliferation of Acute Lymphocytic Leukemia by Inhibiting c-Myc-Mediated Glycolysis. Med Sci Monit. 2020 Apr 8;26:e923411. doi: 10.12659/MSM.923411. PMID: 32266878; PMCID: PMC7165247. 2. Qian Z, Shuying W, Ranran D. Inhibitory effects of JQ1 on listeria monocytogenes-induced acute liver injury by blocking BRD4/RIPK1 axis. Biomed Pharmacother. 2020 May;125:109818. doi: 10.1016/j.biopha.2020.109818. Epub 2020 Feb 25. PMID: 32106368.
In vivo protocol: 1. Li F, MacKenzie KR, Jain P, Santini C, Young DW, Matzuk MM. Metabolism of JQ1, an inhibitor of bromodomain and extra terminal bromodomain proteins, in human and mouse liver microsomes†. Biol Reprod. 2020 Aug 4;103(2):427-436. doi: 10.1093/biolre/ioaa043. PMID: 32285106; PMCID: PMC7401416. 2. Zhou S, Zhang S, Wang L, Huang S, Yuan Y, Yang J, Wang H, Li X, Wang P, Zhou L, Yang J, Xu Y, Gao H, Zhang Y, Lv Y, Zou X. BET protein inhibitor JQ1 downregulates chromatin accessibility and suppresses metastasis of gastric cancer via inactivating RUNX2/NID1 signaling. Oncogenesis. 2020 Mar 10;9(3):33. doi: 10.1038/s41389-020-0218-z. PMID: 32157097; PMCID: PMC7064486.

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4: Nilsson LM, Green LC, Muralidharan SV, Demir D, Welin M, Bhadury J, Logan DT, Walse B, Nilsson JA. Cancer Differentiating Agent Hexamethylene Bisacetamide Inhibits BET Bromodomain Proteins. Cancer Res. 2016 Apr 15;76(8):2376-83. doi: 10.1158/0008-5472.CAN-15-2721. Epub 2016 Mar 3. PubMed PMID: 26941288.

5: Shahbazi J, Liu PY, Atmadibrata B, Bradner JE, Marshall GM, Lock RB, Liu T. The Bromodomain Inhibitor JQ1 and the Histone Deacetylase Inhibitor Panobinostat Synergistically Reduce N-Myc Expression and Induce Anticancer Effects. Clin Cancer Res. 2016 May 15;22(10):2534-44. doi: 10.1158/1078-0432.CCR-15-1666. Epub 2016 Jan 5. PubMed PMID: 26733615.

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7: Borbely G, Haldosen LA, Dahlman-Wright K, Zhao C. Induction of USP17 by combining BET and HDAC inhibitors in breast cancer cells. Oncotarget. 2015 Oct 20;6(32):33623-35. doi: 10.18632/oncotarget.5601. PubMed PMID: 26378038; PubMed Central PMCID: PMC4741790.

8: Gopalakrishnan R, Matta H, Tolani B, Triche T Jr, Chaudhary PM. Immunomodulatory drugs target IKZF1-IRF4-MYC axis in primary effusion lymphoma in a cereblon-dependent manner and display synergistic cytotoxicity with BRD4 inhibitors. Oncogene. 2016 Apr 7;35(14):1797-810. doi: 10.1038/onc.2015.245. Epub 2015 Jun 29. PubMed PMID: 26119939; PubMed Central PMCID: PMC4486341.

9: Lu J, Qian Y, Altieri M, Dong H, Wang J, Raina K, Hines J, Winkler JD, Crew AP, Coleman K, Crews CM. Hijacking the E3 Ubiquitin Ligase Cereblon to Efficiently Target BRD4. Chem Biol. 2015 Jun 18;22(6):755-63. doi: 10.1016/j.chembiol.2015.05.009. Epub 2015 Jun 4. PubMed PMID: 26051217; PubMed Central PMCID: PMC4475452.

10: Phthalimide-Conjugated Ligands Promote Selective Protein Destabilization. Cancer Discov. 2015 Jul;5(7):691. doi: 10.1158/2159-8290.CD-RW2015-104. Epub 2015 Jun 4. PubMed PMID: 26045013.

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13: Fiskus W, Sharma S, Qi J, Valenta JA, Schaub LJ, Shah B, Peth K, Portier BP, Rodriguez M, Devaraj SG, Zhan M, Sheng J, Iyer SP, Bradner JE, Bhalla KN. Highly active combination of BRD4 antagonist and histone deacetylase inhibitor against human acute myelogenous leukemia cells. Mol Cancer Ther. 2014 May;13(5):1142-54. doi: 10.1158/1535-7163.MCT-13-0770. Epub 2014 Jan 16. PubMed PMID: 24435446.

14: Bartholomeeusen K, Xiang Y, Fujinaga K, Peterlin BM. Bromodomain and extra-terminal (BET) bromodomain inhibition activate transcription via transient release of positive transcription elongation factor b (P-TEFb) from 7SK small nuclear ribonucleoprotein. J Biol Chem. 2012 Oct 19;287(43):36609-16. doi: 10.1074/jbc.M112.410746. Epub 2012 Sep 5. Erratum in: J Biol Chem. 2013 Apr 26;288(17):12214. PubMed PMID: 22952229; PubMed Central PMCID: PMC3476326.

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