(+)-JQ1
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MedKoo CAT#: 406669

CAS#: 1268524-70-4

Description: (+)-JQ1 is a BET potent BET bromodomain Inhibitor. Bromodomain and extra terminal domain (BET) proteins are important epigenetic regulators facilitating the transcription of genes in chromatin areas linked to acetylated histones. JQ1 has antiproliferative activity against many cancers, mainly through inhibition of c-MYC and upregulation of p21. JQ1 suppresses tumor growth through downregulating LDHA in ovarian cancer. JQ1 suppresses growth of pancreatic ductal adenocarcinoma in patient-derived xenograft models. JQ1 disrupts human dendritic cell maturation by inhibiting STAT5.


Chemical Structure

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(+)-JQ1
CAS# 1268524-70-4

Theoretical Analysis

MedKoo Cat#: 406669
Name: (+)-JQ1
CAS#: 1268524-70-4
Chemical Formula: C23H25ClN4O2S
Exact Mass: 456.13867
Molecular Weight: 456.99
Elemental Analysis: C, 60.45; H, 5.51; Cl, 7.76; N, 12.26; O, 7.00; S, 7.02

Price and Availability

Size Price Availability Quantity
50.0mg USD 110.0 Same day
100.0mg USD 190.0 Same day
200.0mg USD 340.0 Same day
500.0mg USD 760.0 Same day
1.0g USD 1350.0 Same day
2.0g USD 2430.0 2 Weeks
5.0g USD 4950.0 2 Weeks
10.0g USD 6450.0 2 Weeks
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Synonym: (+)-JQ1; (+)-JQ-1; (+)-JQ 1; Bromodomain Inhibitor

IUPAC/Chemical Name: tert-butyl (S)-2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

InChi Key: DNVXATUJJDPFDM-KRWDZBQOSA-N

InChi Code: InChI=1S/C23H25ClN4O2S/c1-12-13(2)31-22-19(12)20(15-7-9-16(24)10-8-15)25-17(11-18(29)30-23(4,5)6)21-27-26-14(3)28(21)22/h7-10,17H,11H2,1-6H3/t17-/m0/s1

SMILES Code: O=C(OC(C)(C)C)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, 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

Biological target: (+)-JQ-1 (JQ1) is a reversible BET bromodomain inhibitor, with IC50s of 77 and 33 nM for the first and second bromodomain (BRD4(1/2)).
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. JQ1 not only affected glycolysis, but also altered the mitochondrial oxidative phosphorylation metabolism of B-ALL cells, but the mechanism is unclear. As a BRD4-specific inhibitor, JQ1 can mediate the proliferation and apoptosis of a variety of tumor cells by c-Myc. In this study, the level of c-Myc decreased in B-ALL cells after JQ1 treatment. Because c-Myc plays an important part in cell metabolism, it was hypothesized that glycolysis repression mediated by JQ1 is due to the reduction of the c-Myc level. Then, this study carried out a rescue experiment by overexpressing c-Myc, and observed that the effect of JQ1 decreased, accompanied by the relief of cell cycle arrest and glycolysis, suggesting that the inhibited glycolysis and cell cycle arrest of JQ1 was mediated by c-Myc. 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 47.93 104.87
DMF 16.0 35.01
DMF:PBS (pH 7.2) (1:9) 0.1 0.22
Ethanol 50.23 109.91

Preparing Stock Solutions

The following data is based on the product molecular weight 456.99 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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1: Garcia PL, Miller AL, Kreitzburg KM, Council LN, Gamblin TL, Christein JD, Heslin MJ, Arnoletti JP, Richardson JH, Chen D, Hanna CA, Cramer SL, Yang ES, Qi J, Bradner JE, Yoon KJ. The BET bromodomain inhibitor JQ1 suppresses growth of pancreatic ductal adenocarcinoma in patient-derived xenograft models. Oncogene. 2015 May 11. doi: 10.1038/onc.2015.126. [Epub ahead of print] PubMed PMID: 25961927.

2: Wang Y, Ma LM, Wang XZ, Wang T. [Mechanism of Notch1 Pathway in SUP-B15 Cell Apoptosis Induced by JQ1]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2015 Apr;23(2):364-8. doi: 10.7534/j.issn.1009-2137.2015.02.013. Chinese. PubMed PMID: 25948186.

3: Fowler T, Ghatak P, Price DH, Conaway R, Conaway J, Chiang CM, Bradner JE, Shilatifard A, Roy AL. Correction: Regulation of MYC Expression and Differential JQ1 Sensitivity in Cancer Cells. PLoS One. 2015 Apr 22;10(4):e0126328. doi: 10.1371/journal.pone.0126328. eCollection 2015. PubMed PMID: 25902070; PubMed Central PMCID: PMC4406619.

4: Jung KH, Das A, Chai JC, Kim SH, Morya N, Park KS, Lee YS, Chai YG. RNA sequencing reveals distinct mechanisms underlying BET inhibitor JQ1-mediated modulation of the LPS-induced activation of BV-2 microglial cells. J Neuroinflammation. 2015 Feb 24;12(1):36. doi: 10.1186/s12974-015-0260-5. PubMed PMID: 25890327; PubMed Central PMCID: PMC4359438.

5: Kumar K, Raza SS, Knab LM, Chow CR, Kwok B, Bentrem DJ, Popovic R, Ebine K, Licht JD, Munshi HG. GLI2-dependent c-MYC upregulation mediates resistance of pancreatic cancer cells to the BET bromodomain inhibitor JQ1. Sci Rep. 2015 Mar 25;5:9489. doi: 10.1038/srep09489. PubMed PMID: 25807524.

6: Qiu H, Jackson AL, Kilgore JE, Zhong Y, Chan LL, Gehrig PA, Zhou C, Bae-Jump VL. JQ1 suppresses tumor growth through downregulating LDHA in ovarian cancer. Oncotarget. 2015 Mar 30;6(9):6915-30. PubMed PMID: 25762632.

7: Toniolo PA, Liu S, Yeh JE, Moraes-Vieira PM, Walker SR, Vafaizadeh V, Barbuto JA, Frank DA. Inhibiting STAT5 by the BET bromodomain inhibitor JQ1 disrupts human dendritic cell maturation. J Immunol. 2015 Apr 1;194(7):3180-90. doi: 10.4049/jimmunol.1401635. Epub 2015 Feb 27. PubMed PMID: 25725100; PubMed Central PMCID: PMC4369449.

8: Ghurye RR, Stewart HJ, Chevassut TJ. Bromodomain inhibition by JQ1 suppresses lipopolysaccharide-stimulated interleukin-6 secretion in multiple myeloma cells. Cytokine. 2015 Feb;71(2):415-7. doi: 10.1016/j.cyto.2014.11.013. Epub 2014 Dec 4. PubMed PMID: 25482841.

9: Horne GA, Stewart HJ, Dickson J, Knapp S, Ramsahoye B, Chevassut T. Nanog requires BRD4 to maintain murine embryonic stem cell pluripotency and is suppressed by bromodomain inhibitor JQ1 together with Lefty1. Stem Cells Dev. 2015 Apr 1;24(7):879-91. doi: 10.1089/scd.2014.0302. Epub 2014 Dec 17. PubMed PMID: 25393219; PubMed Central PMCID: PMC4367495.

10: Hogg SJ, Johnstone RW, Shortt J. Letter to the Editor, "BET inhibitor JQ1 blocks inflammation and bone destruction". J Dent Res. 2015 Jan;94(1):229. doi: 10.1177/0022034514557673. Epub 2014 Nov 11. PubMed PMID: 25389001.

(+)-JQ1

50.0mg / USD 110.0


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