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

MedKoo CAT#: 406634

CAS#: 550-24-3

Description: Embelin is the only known non-peptide small-molecule X-linked inhibitor of the apoptosis protein (XIAP) - an anti-apoptotic protein considered a promising cancer therapeutic target. Embelin acts as an NF-κB blocker and potential suppressor of tumorigenesis. It also exhibits potent cytotoxic, antioxidant and cancer chemopreventive effects. Given the potential uses of embelin, it is recommended that further investigations take place to properly explore its pharmacological and clinical effects.


Chemical Structure

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Embelin
CAS# 550-24-3

Theoretical Analysis

MedKoo Cat#: 406634
Name: Embelin
CAS#: 550-24-3
Chemical Formula: C17H26O4
Exact Mass: 294.18311
Molecular Weight: 294.39
Elemental Analysis: C, 69.36; H, 8.90; O, 21.74

Price and Availability

Size Price Availability Quantity
10.0mg USD 235.0 2 Weeks
25.0mg USD 375.0 2 Weeks
50.0mg USD 600.0 2 Weeks
100.0mg USD 850.0 2 Weeks
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Synonym: NSC91874; NSC91874; NSC 91874; Embelin; Emberine; Embelic acid.

IUPAC/Chemical Name: 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione

InChi Key: IRSFLDGTOHBADP-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3

SMILES Code: O=C1C(O)=C(CCCCCCCCCCC)C(C(O)=C1)=O

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 to 10 mM in ethanol with gentle warming and to 100 mM in DMSO, not soluble 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

Product Data:

Biological target: Embelin (Embelic acid), a potent, nonpeptidic XIAP inhibitor (IC50=4.1 μM), inhibits cell growth, induces apoptosis, and activates caspase-9 in prostate cancer cells with high levels of XIAP.
In vitro activity: This study used an MTT assay to examine the cytotoxic impact of embelin within 0 to 100 μM concentration range for 24 and 48 h on three breast cancer cell lines MDA-MB-231, MCF-7, and MDA-MB-453. The results of treatment for 24 and 48 h showed that three breast cancer cell lines exhibited dose-dependent cytotoxicity in 0 to 50 μM treatment of embelin. Reference: Sci Rep. 2021; 11: 14720. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8289868/
In vivo activity: Embelin (EMB) treatment increased the seizure threshold to hind limb extension (HLE) in the ICES test and decreased the seizure scores in the kindling experiment. Significantly low levels of IL-1β, IL-1Ra, IL-6, and TNF-α were observed in the hippocampus of PTZ + EMB (10 and 20 mg/kg)-treated mouse groups compared with PTZ+ vehicle-treated group. Reference: Epilepsy Behav. 2021 Mar;116:107788. https://pubmed.ncbi.nlm.nih.gov/33581600/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 35.36 120.11
DMF 5.0 16.98
DMF:PBS (pH 7.2) (1:1) 0.5 1.7
Ethanol 7.47 25.37

Preparing Stock Solutions

The following data is based on the product molecular weight 294.39 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. Liang YH, Wu JM, Teng JW, Hung E, Wang HS. Embelin downregulated cFLIP in breast cancer cell lines facilitate anti-tumor effect of IL-1β-stimulated human umbilical cord mesenchymal stem cells. Sci Rep. 2021 Jul 19;11(1):14720. doi: 10.1038/s41598-021-94006-w. PMID: 34282169; PMCID: PMC8289868. 2. Reis-Silva CSM, Branco PC, Lima K, Silva FL, Moreno PRH, Guallar V, Costa-Lotufo LV, Machado-Neto JA. Embelin potentiates venetoclax-induced apoptosis in acute myeloid leukemia cells. Toxicol In Vitro. 2021 Jul 1;76:105207. doi: 10.1016/j.tiv.2021.105207. Epub ahead of print. PMID: 34216723. 3. Hoda U, Jain S, Samim M, Jain GK, Agarwal NB. Embelin ameliorates cognitive dysfunction and progression of kindling in pentylenetetrazol-induced kindling in mice by attenuating brain inflammation. Epilepsy Behav. 2021 Mar;116:107788. doi: 10.1016/j.yebeh.2021.107788. Epub 2021 Feb 10. PMID: 33581600. 4. Nakajima K, Ino Y, Yamazaki-Itoh R, Naito C, Shimasaki M, Takahashi M, Esaki M, Nara S, Kishi Y, Shimada K, Hiraoka N. IAP inhibitor, Embelin increases VCAM-1 levels on the endothelium, producing lymphocytic infiltration and antitumor immunity. Oncoimmunology. 2020 Oct 27;9(1):1838812. doi: 10.1080/2162402X.2020.1838812. PMID: 33178497; PMCID: PMC7595596.
In vitro protocol: 1. Liang YH, Wu JM, Teng JW, Hung E, Wang HS. Embelin downregulated cFLIP in breast cancer cell lines facilitate anti-tumor effect of IL-1β-stimulated human umbilical cord mesenchymal stem cells. Sci Rep. 2021 Jul 19;11(1):14720. doi: 10.1038/s41598-021-94006-w. PMID: 34282169; PMCID: PMC8289868. 2. Reis-Silva CSM, Branco PC, Lima K, Silva FL, Moreno PRH, Guallar V, Costa-Lotufo LV, Machado-Neto JA. Embelin potentiates venetoclax-induced apoptosis in acute myeloid leukemia cells. Toxicol In Vitro. 2021 Jul 1;76:105207. doi: 10.1016/j.tiv.2021.105207. Epub ahead of print. PMID: 34216723.
In vivo protocol: 1. Hoda U, Jain S, Samim M, Jain GK, Agarwal NB. Embelin ameliorates cognitive dysfunction and progression of kindling in pentylenetetrazol-induced kindling in mice by attenuating brain inflammation. Epilepsy Behav. 2021 Mar;116:107788. doi: 10.1016/j.yebeh.2021.107788. Epub 2021 Feb 10. PMID: 33581600. 2. Nakajima K, Ino Y, Yamazaki-Itoh R, Naito C, Shimasaki M, Takahashi M, Esaki M, Nara S, Kishi Y, Shimada K, Hiraoka N. IAP inhibitor, Embelin increases VCAM-1 levels on the endothelium, producing lymphocytic infiltration and antitumor immunity. Oncoimmunology. 2020 Oct 27;9(1):1838812. doi: 10.1080/2162402X.2020.1838812. PMID: 33178497; PMCID: PMC7595596.

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1: Zhou XL, Huang L, Cao J. Embelin Reduces Systemic Inflammation and Ameliorates Organ Injuries in Septic Rats Through Downregulating STAT3 and NF-κB Pathways. Inflammation. 2015 Feb 15. [Epub ahead of print] PubMed PMID: 25682469.

2: Narayanaswamy R, Shymatak M, Chatterjee S, Wai LK, Arumugam G. Inhibition of Angiogenesis and Nitric Oxide Synthase (NOS), by Embelin & Vilangin Using in vitro, in vivo & in Silico Studies. Adv Pharm Bull. 2014 Dec;4(Suppl 2):543-8. doi: 10.5681/apb.2014.080. Epub 2014 Dec 31. PubMed PMID: 25671187; PubMed Central PMCID: PMC4312403.

3: Joy B, Kumar SN, Radhika AR, Abraham A. Embelin (2,5-Dihydroxy-3-undecyl-p-benzoquinone) for photodynamic therapy: study of their cytotoxicity in cancer cells. Appl Biochem Biotechnol. 2015 Jan;175(2):1069-79. doi: 10.1007/s12010-014-1266-7. Epub 2014 Oct 31. PubMed PMID: 25359675.

4: Yang T, Lan J, Huang Q, Chen X, Sun X, Liu X, Yang P, Jin T, Wang S, Mou X. Embelin sensitizes acute myeloid leukemia cells to TRAIL through XIAP inhibition and NF-κB inactivation. Cell Biochem Biophys. 2015 Jan;71(1):291-7. doi: 10.1007/s12013-014-0197-9. PubMed PMID: 25358405.

5: Dhanjal JK, Nigam N, Sharma S, Chaudhary A, Kaul SC, Grover A, Wadhwa R. Embelin inhibits TNF-α converting enzyme and cancer cell metastasis: molecular dynamics and experimental evidence. BMC Cancer. 2014 Oct 22;14:775. doi: 10.1186/1471-2407-14-775. PubMed PMID: 25336399; PubMed Central PMCID: PMC4210574.

6: Hu R, Yang Y, Liu Z, Jiang H, Zhu K, Li J, Xu W. The XIAP inhibitor Embelin enhances TRAIL-induced apoptosis in human leukemia cells by DR4 and DR5 upregulation. Tumour Biol. 2015 Feb;36(2):769-77. doi: 10.1007/s13277-014-2702-6. Epub 2014 Oct 8. PubMed PMID: 25293521.

7: Singh B, Guru SK, Sharma R, Bharate SS, Khan IA, Bhushan S, Bharate SB, Vishwakarma RA. Synthesis and anti-proliferative activities of new derivatives of embelin. Bioorg Med Chem Lett. 2014 Oct 15;24(20):4865-70. doi: 10.1016/j.bmcl.2014.08.052. Epub 2014 Sep 1. PubMed PMID: 25240254.

8: Joy B, Nishanth Kumar S, Soumya MS, Radhika AR, Vibin M, Abraham A. Embelin (2,5-dihydroxy-3-undecyl-p-benzoquinone): a bioactive molecule isolated from Embelia ribes as an effective photodynamic therapeutic candidate against tumor in vivo. Phytomedicine. 2014 Sep 25;21(11):1292-7. doi: 10.1016/j.phymed.2014.07.001. Epub 2014 Jul 30. PubMed PMID: 25172792.

9: Poojari RJ. Embelin, a small molecule quinone with a co-clinical power for castrate-resistant prostate cancer. Front Pharmacol. 2014 Aug 8;5:184. doi: 10.3389/fphar.2014.00184. eCollection 2014. PubMed PMID: 25152733; PubMed Central PMCID: PMC4126039.

10: Peng M, Huang B, Zhang Q, Fu S, Wang D, Cheng X, Wu X, Xue Z, Zhang L, Zhang D, Da Y, Dai Y, Yang Q, Yao Z, Qiao L, Zhang R. Embelin inhibits pancreatic cancer progression by directly inducing cancer cell apoptosis and indirectly restricting IL-6 associated inflammatory and immune suppressive cells. Cancer Lett. 2014 Nov 28;354(2):407-16. doi: 10.1016/j.canlet.2014.08.011. Epub 2014 Aug 13. PubMed PMID: 25128650.

Embelin

10.0mg / USD 235.0


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