C-DIM8 | DIM-C-pPhOH | CAS#151358-47-3 | Nur77 Antagonist

MedKoo Cat#: 407870 | Name: C-DIM8

Description:

WARNING: This product is for research use only, not for human or veterinary use.

DIM-C-pPhOH is a Nur77 Antagonist. DIM-C-pPhOH inhibits lung cancer cell and tumor growth in a metastasis model.

Chemical Structure

C-DIM8

CAS#151358-47-3

Theoretical Analysis

MedKoo Cat#: 407870

Name: C-DIM8

CAS#: 151358-47-3

Chemical Formula: C23H18N2O

Exact Mass: 338.1419

Molecular Weight: 338.41

Elemental Analysis: C, 81.63; H, 5.36; N, 8.28; O, 4.73

Price and Availability

Size	Price	Availability
100mg	USD 550.00	2 Weeks
200mg	USD 950.00	2 Weeks
500mg	USD 1,850.00	2 Weeks
1g	USD 2,850.00	2 Weeks
2g	USD 5,150.00	2 Weeks

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Synonym

DIM-C-pPhOH; C-DIM8; C-DIM 8; C-DIM-8; CDIM 8

IUPAC/Chemical Name

1,1-Bis(3'-indolyl)-1-(p-hydroxyphenyl)methane

InChi Key

QCPDFNWJBQMXLI-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H18N2O/c26-16-11-9-15(10-12-16)23(19-13-24-21-7-3-1-5-17(19)21)20-14-25-22-8-4-2-6-18(20)22/h1-14,23-26H

SMILES Code

OC1=CC=C(C(C2=CNC3=C2C=CC=C3)C4=CNC5=C4C=CC=C5)C=C1

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

More Info

Nuclear receptor 4A1(NR4A1) (testicular receptor 3 (TR3), nuclear hormone receptor (Nur)77) is a member of the nuclear receptor superfamily of transcription factors and is highly expressed in multiple tumor types. RNA interference studies indicate that NR4A1 exhibits growth-promoting, angiogenic and prosurvival activity in most cancers.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

DIM-C-pPhOH is a nuclear receptor 4A1 (NR4A1) antagonist.

In vitro activity:

Treatment of MDA-MB-231 cells with 5 ng/ml TGF-β significantly induced cell migration (Fig. 5A) as previously described, and knockdown of NR4A1 or treatment with DIM-C-pPhOH or DIM-C-pPhCO2Me blocked TGF-β-induced migration and significantly decreased overall migration, similar to that observed after knockdown of NR4A1 or treatment with the NR4A1 antagonists alone (Fig. 4A to C). Reference: Mol Cell Biol. 2016 Apr 15;36(9):1383-94. https://pubmed.ncbi.nlm.nih.gov/26929200/

In vivo activity:

Since inhibition of TR3 by RNA interference or DIM-C-pPhOH induces apoptosis and inhibits growth of pancreatic cancer cells, this study investigated the anticancer activity of DIM-C-pPhOH in a murine orthotopic model for pancreatic cancer using L3.6pL cells. The results in Figures 7A demonstrate that DIM-C-pPhOH significantly inhibited tumor volumes and weights compared to the corn oil control tumors. Reference: Cancer Res. 2010 Sep 1;70(17):6824-36. https://pubmed.ncbi.nlm.nih.gov/20660371/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	44.32
	DMF:PBS (pH 7.2) (1:6)	0.1	0.41
	DMSO	59.2	174.97
	Ethanol	37.3	110.16

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 338.41 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. Hedrick E, Lee SO, Doddapaneni R, Singh M, Safe S. NR4A1 Antagonists Inhibit β1-Integrin-Dependent Breast Cancer Cell Migration. Mol Cell Biol. 2016 Apr 15;36(9):1383-94. doi: 10.1128/MCB.00912-15. Erratum in: Mol Cell Biol. 2017 Aug 28;37(18): PMID: 26929200; PMCID: PMC4836213. 2. Hedrick E, Lee SO, Kim G, Abdelrahim M, Jin UH, Safe S, Abudayyeh A. Nuclear Receptor 4A1 (NR4A1) as a Drug Target for Renal Cell Adenocarcinoma. PLoS One. 2015 Jun 2;10(6):e0128308. doi: 10.1371/journal.pone.0128308. PMID: 26035713; PMCID: PMC4452731. 3. Lee SO, Abdelrahim M, Yoon K, Chintharlapalli S, Papineni S, Kim K, Wang H, Safe S. Inactivation of the orphan nuclear receptor TR3/Nur77 inhibits pancreatic cancer cell and tumor growth. Cancer Res. 2010 Sep 1;70(17):6824-36. doi: 10.1158/0008-5472.CAN-10-1992. Epub 2010 Jul 21. PMID: 20660371; PMCID: PMC2988472. 4. Luo Q, Tang Y, Jiang Z, Bao H, Fu Q, Zhang H. hUCMSCs reduce theca interstitial cells apoptosis and restore ovarian function in premature ovarian insufficiency rats through regulating NR4A1-mediated mitochondrial mechanisms. Reprod Biol Endocrinol. 2022 Aug 19;20(1):125. doi: 10.1186/s12958-022-00992-5. PMID: 35986315; PMCID: PMC9389823.

In vitro protocol:

In vivo protocol:

1. Lee SO, Abdelrahim M, Yoon K, Chintharlapalli S, Papineni S, Kim K, Wang H, Safe S. Inactivation of the orphan nuclear receptor TR3/Nur77 inhibits pancreatic cancer cell and tumor growth. Cancer Res. 2010 Sep 1;70(17):6824-36. doi: 10.1158/0008-5472.CAN-10-1992. Epub 2010 Jul 21. PMID: 20660371; PMCID: PMC2988472. 2. Luo Q, Tang Y, Jiang Z, Bao H, Fu Q, Zhang H. hUCMSCs reduce theca interstitial cells apoptosis and restore ovarian function in premature ovarian insufficiency rats through regulating NR4A1-mediated mitochondrial mechanisms. Reprod Biol Endocrinol. 2022 Aug 19;20(1):125. doi: 10.1186/s12958-022-00992-5. PMID: 35986315; PMCID: PMC9389823.

1: Hedrick E, Lee SO, Safe S. The nuclear orphan receptor NR4A1 regulates β1-integrin expression in pancreatic and colon cancer cells and can be targeted by NR4A1 antagonists. Mol Carcinog. 2017 Sep;56(9):2066-2075. doi: 10.1002/mc.22662. Epub 2017 May 9. PubMed PMID: 28418095; PubMed Central PMCID: PMC5546981. 2: Jiang Y, Zeng Y, Huang X, Qin Y, Luo W, Xiang S, Sooranna SR, Pinhu L. Nur77 attenuates endothelin-1 expression via downregulation of NF-κB and p38 MAPK in A549 cells and in an ARDS rat model. Am J Physiol Lung Cell Mol Physiol. 2016 Dec 1;311(6):L1023-L1035. doi: 10.1152/ajplung.00043.2016. Epub 2016 Oct 7. PubMed PMID: 27765761; PubMed Central PMCID: PMC5206403. 3: Lacey A, Hedrick E, Li X, Patel K, Doddapaneni R, Singh M, Safe S. Nuclear receptor 4A1 (NR4A1) as a drug target for treating rhabdomyosarcoma (RMS). Oncotarget. 2016 May 24;7(21):31257-69. doi: 10.18632/oncotarget.9112. PubMed PMID: 27144436; PubMed Central PMCID: PMC5058754. 4: Hedrick E, Lee SO, Doddapaneni R, Singh M, Safe S. NR4A1 Antagonists Inhibit β1-Integrin-Dependent Breast Cancer Cell Migration. Mol Cell Biol. 2016 Apr 15;36(9):1383-94. doi: 10.1128/MCB.00912-15. Print 2016 May. Erratum in: Mol Cell Biol. 2017 Aug 28;37(18):. PubMed PMID: 26929200; PubMed Central PMCID: PMC4836213. 5: Hedrick E, Lee SO, Doddapaneni R, Singh M, Safe S. Nuclear receptor 4A1 as a drug target for breast cancer chemotherapy. Endocr Relat Cancer. 2015 Oct;22(5):831-40. doi: 10.1530/ERC-15-0063. Epub 2015 Jul 30. PubMed PMID: 26229035. 6: Hedrick E, Lee SO, Kim G, Abdelrahim M, Jin UH, Safe S, Abudayyeh A. Nuclear Receptor 4A1 (NR4A1) as a Drug Target for Renal Cell Adenocarcinoma. PLoS One. 2015 Jun 2;10(6):e0128308. doi: 10.1371/journal.pone.0128308. eCollection 2015. PubMed PMID: 26035713; PubMed Central PMCID: PMC4452731. 7: De Miranda BR, Popichak KA, Hammond SL, Miller JA, Safe S, Tjalkens RB. Novel para-phenyl substituted diindolylmethanes protect against MPTP neurotoxicity and suppress glial activation in a mouse model of Parkinson's disease. Toxicol Sci. 2015 Feb;143(2):360-73. doi: 10.1093/toxsci/kfu236. Epub 2014 Nov 17. PubMed PMID: 25406165; PubMed Central PMCID: PMC4306720. 8: Lee SO, Li X, Hedrick E, Jin UH, Tjalkens RB, Backos DS, Li L, Zhang Y, Wu Q, Safe S. Diindolylmethane analogs bind NR4A1 and are NR4A1 antagonists in colon cancer cells. Mol Endocrinol. 2014 Oct;28(10):1729-39. doi: 10.1210/me.2014-1102. Epub 2014 Aug 6. PubMed PMID: 25099012; PubMed Central PMCID: PMC4179635. 9: Lee SO, Jin UH, Kang JH, Kim SB, Guthrie AS, Sreevalsan S, Lee JS, Safe S. The orphan nuclear receptor NR4A1 (Nur77) regulates oxidative and endoplasmic reticulum stress in pancreatic cancer cells. Mol Cancer Res. 2014 Apr;12(4):527-538. doi: 10.1158/1541-7786.MCR-13-0567. Epub 2014 Feb 10. PubMed PMID: 24515801; PubMed Central PMCID: PMC4407472. 10: Andey T, Patel A, Jackson T, Safe S, Singh M. 1,1-Bis (3'-indolyl)-1-(p-substitutedphenyl)methane compounds inhibit lung cancer cell and tumor growth in a metastasis model. Eur J Pharm Sci. 2013 Oct 9;50(2):227-41. doi: 10.1016/j.ejps.2013.07.007. Epub 2013 Jul 23. PubMed PMID: 23892137; PubMed Central PMCID: PMC3838903. 11: Lee SO, Andey T, Jin UH, Kim K, Singh M, Safe S. The nuclear receptor TR3 regulates mTORC1 signaling in lung cancer cells expressing wild-type p53. Oncogene. 2012 Jul 5;31(27):3265-76. doi: 10.1038/onc.2011.504. Epub 2011 Nov 14. Erratum in: Oncogene. 2012 Jul 5;31(27):3310. Sachdeva, M [corrected to Singh, M]. PubMed PMID: 22081070; PubMed Central PMCID: PMC3299891. 12: Lee SO, Li X, Khan S, Safe S. Targeting NR4A1 (TR3) in cancer cells and tumors. Expert Opin Ther Targets. 2011 Feb;15(2):195-206. doi: 10.1517/14728222.2011.547481. Epub 2011 Jan 5. Review. PubMed PMID: 21204731; PubMed Central PMCID: PMC4407471. 13: Lee SO, Abdelrahim M, Yoon K, Chintharlapalli S, Papineni S, Kim K, Wang H, Safe S. Inactivation of the orphan nuclear receptor TR3/Nur77 inhibits pancreatic cancer cell and tumor growth. Cancer Res. 2010 Sep 1;70(17):6824-36. doi: 10.1158/0008-5472.CAN-10-1992. Epub 2010 Jul 21. PubMed PMID: 20660371; PubMed Central PMCID: PMC2988472.