Embelin | CAS#550-24-3 | XIAP inhibitor

MedKoo Cat#: 406634 | Name: Embelin

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Description:

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

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

Embelin

CAS#550-24-3

Theoretical Analysis

MedKoo Cat#: 406634

Name: Embelin

CAS#: 550-24-3

Chemical Formula: C17H26O4

Exact Mass: 294.1831

Molecular Weight: 294.39

Elemental Analysis: C, 69.36; H, 8.90; O, 21.74

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Related CAS #

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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

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Product Data

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	35.4	120.11
	DMF	5.0	16.98
	DMF:PBS (pH 7.2) (1:1)	0.5	1.70
	Ethanol	7.5	25.37

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 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.

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:

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.

1: Danquah M. Embelin and Its Derivatives: Design, Synthesis, and Potential Delivery Systems for Cancer Therapy. Pharmaceuticals (Basel). 2022 Sep 9;15(9):1131. doi: 10.3390/ph15091131. PMID: 36145352; PMCID: PMC9505931. 2: Lu H, Wang J, Wang Y, Qiao L, Zhou Y. Embelin and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;928:397-418. doi: 10.1007/978-3-319-41334-1_16. PMID: 27671825. 3: Basha NJ, Basavarajaiah SM, Baskaran S, Kumar P. A comprehensive insight on the biological potential of embelin and its derivatives. Nat Prod Res. 2022 Jun;36(12):3054-3068. doi: 10.1080/14786419.2021.1955361. Epub 2021 Jul 26. PMID: 34304655. 4: Devi Daimary U, Girisa S, Parama D, Verma E, Kumar A, Kunnumakkara AB. Embelin: A novel XIAP inhibitor for the prevention and treatment of chronic diseases. J Biochem Mol Toxicol. 2022 Feb;36(2):e22950. doi: 10.1002/jbt.22950. Epub 2021 Nov 29. PMID: 34842329. 5: Sheng Z, Ge S, Gao M, Jian R, Chen X, Xu X, Li D, Zhang K, Chen WH. Synthesis and Biological Activity of Embelin and its Derivatives: An Overview. Mini Rev Med Chem. 2020;20(5):396-407. doi: 10.2174/1389557519666191015202723. PMID: 31644404. 6: Poojari R. Embelin - a drug of antiquity: shifting the paradigm towards modern medicine. Expert Opin Investig Drugs. 2014 Mar;23(3):427-44. doi: 10.1517/13543784.2014.867016. Epub 2014 Jan 8. PMID: 24397264. 7: Prabhu KS, Achkar IW, Kuttikrishnan S, Akhtar S, Khan AQ, Siveen KS, Uddin S. Embelin: a benzoquinone possesses therapeutic potential for the treatment of human cancer. Future Med Chem. 2018 Apr 1;10(8):961-976. doi: 10.4155/fmc-2017-0198. Epub 2018 Apr 5. PMID: 29620447. 8: Ko JH, Lee SG, Yang WM, Um JY, Sethi G, Mishra S, Shanmugam MK, Ahn KS. The Application of Embelin for Cancer Prevention and Therapy. Molecules. 2018 Mar 9;23(3):621. doi: 10.3390/molecules23030621. PMID: 29522451; PMCID: PMC6017120. 9: Zappavigna S, Cossu AM, Grimaldi A, Bocchetti M, Ferraro GA, Nicoletti GF, Filosa R, Caraglia M. Anti-Inflammatory Drugs as Anticancer Agents. Int J Mol Sci. 2020 Apr 9;21(7):2605. doi: 10.3390/ijms21072605. PMID: 32283655; PMCID: PMC7177823. 10: Shuveksh PS, Ahmed K, Padhye S, Schobert R, Biersack B. Chemical and Biological Aspects of the Natural 1,4-Benzoquinone Embelin and its (semi-)Synthetic Derivatives. Curr Med Chem. 2017;24(18):1998-2009. doi: 10.2174/0929867324666170116125731. PMID: 28093981. 11: Azman S, Sekar M, Wahidin S, Gan SH, Vaijanathappa J, Bonam SR, Alvala M, Lum PT, Thakur V, Beladiya JV, Mehta AA. Embelin Alleviates Severe Airway Inflammation in OVA-LPS-Induced Rat Model of Allergic Asthma. J Asthma Allergy. 2021 Dec 15;14:1511-1525. doi: 10.2147/JAA.S298613. PMID: 34938083; PMCID: PMC8685448. 12: Kundap UP, Bhuvanendran S, Kumari Y, Othman I, Shaikh MF. Plant Derived Phytocompound, Embelin in CNS Disorders: A Systematic Review. Front Pharmacol. 2017 Feb 27;8:76. doi: 10.3389/fphar.2017.00076. PMID: 28289385; PMCID: PMC5326771. 13: 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 Oct;76:105207. doi: 10.1016/j.tiv.2021.105207. Epub 2021 Jul 1. PMID: 34216723. 14: Durg S, Veerapur VP, Neelima S, Dhadde SB. Antidiabetic activity of Embelia ribes, embelin and its derivatives: A systematic review and meta-analysis. Biomed Pharmacother. 2017 Feb;86:195-204. doi: 10.1016/j.biopha.2016.12.001. Epub 2016 Dec 13. PMID: 27984799. 15: Bhuvanendran S, Paudel YN, Kumari Y, Othman I, Shaikh MF. Embelin prevents amyloid-beta accumulation via modulation of SOD1 in a Streptozotocin-induced AD- like condition: An evidence from in vitro investigation. Curr Res Neurobiol. 2022 Feb 22;3:100032. doi: 10.1016/j.crneur.2022.100032. PMID: 36518345; PMCID: PMC9743048. 16: Bai X, Wang J, Ding S, Yang S, Pei B, Yao M, Zhu X, Jiang M, Zhang M, Mu W, Guo S. Embelin protects against apoptosis and inflammation by regulating PI3K/Akt signaling in IL-1β-stimulated human nucleus pulposus cells. Tissue Cell. 2023 Jun;82:102089. doi: 10.1016/j.tice.2023.102089. Epub 2023 Apr 11. PMID: 37075678. 17: Ramachandra VH, Sivanesan S, Koppal A, Anandakumar S, Howell MD, Sukumar E, Vijayaraghavan R. Embelin and levodopa combination therapy for improved Parkinson's disease treatment. Transl Neurosci. 2022 Jun 29;13(1):145-162. doi: 10.1515/tnsci-2022-0224. PMID: 35855085; PMCID: PMC9245559. 18: Yao W, Wang T, Huang L, Bao Z, Wen S, Huang F. Embelin alleviates weaned piglets intestinal inflammation and barrier dysfunction via PCAF/NF-κB signaling pathway in intestinal epithelial cells. J Anim Sci Biotechnol. 2022 Dec 14;13(1):139. doi: 10.1186/s40104-022-00787-z. PMID: 36514139; PMCID: PMC9749222. 19: Wang H, Zhang H, Wang Y, Yang L, Wang D. Embelin can protect mice from thioacetamide-induced acute liver injury. Biomed Pharmacother. 2019 Oct;118:109360. doi: 10.1016/j.biopha.2019.109360. Epub 2019 Aug 21. PMID: 31545222. 20: Ning NZ, Liu X, Chen F, Zhou P, Hu L, Huang J, Li Z, Huang J, Li T, Wang H. Embelin Restores Carbapenem Efficacy against NDM-1-Positive Pathogens. Front Microbiol. 2018 Jan 25;9:71. doi: 10.3389/fmicb.2018.00071. PMID: 29422890; PMCID: PMC5789148.