Ebselen oxide

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

MedKoo CAT#: 525216

CAS#: 104473-83-8

Description: Ebselen oxide is a novel dose-dependent inhibitor of HDAC1, HDAC3, HDAC4, HDAC5, HDAC6, HDAC7, HDAC8, and HDAC9.


Price and Availability

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Ebselen oxide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525216
Name: Ebselen oxide
CAS#: 104473-83-8
Chemical Formula: C13H9NO2Se
Exact Mass: 290.9799
Molecular Weight: 290.18
Elemental Analysis: C, 53.81; H, 3.13; N, 4.83; O, 11.03; Se, 27.21


Synonym: Ebselen oxide

IUPAC/Chemical Name: 2-Phenyl-1,2-benzisoselenazole-1,3-dione

InChi Key: SBTLFLABILGUMK-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H9NO2Se/c15-13-11-8-4-5-9-12(11)17(16)14(13)10-6-2-1-3-7-10/h1-9H

SMILES Code: O=[Se]1N(C2=CC=CC=C2)C(C3=C1C=CC=C3)=O


Technical Data

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).

Harmonized System Code:
293490


References

¬¬¬1: Wang Y, Wallach J, Duane S, Wang Y, Wu J, Wang J, Adejare A, Ma H. Developing selective histone deacetylases (HDACs) inhibitors through ebselen and analogs. Drug Des Devel Ther. 2017 May 2;11:1369-1382. doi: 10.2147/DDDT.S124977. eCollection 2017. PubMed PMID: 28496307; PubMed Central PMCID: PMC5422321.

2: Muñoz M, López-Oliva ME, Pinilla E, Martínez MP, Sánchez A, Rodríguez C, García-Sacristán A, Hernández M, Rivera L, Prieto D. CYP epoxygenase-derived H(2)O(2) is involved in the endothelium-derived hyperpolarization (EDH) and relaxation of intrarenal arteries. Free Radic Biol Med. 2017 May;106:168-183. doi: 10.1016/j.freeradbiomed.2017.02.031. Epub 2017 Feb 14. PubMed PMID: 28212823.

3: Babiker FA, Al-Jarallah A, Joseph S. Understanding pacing postconditioning-mediated cardiac protection: a role of oxidative stress and a synergistic effect of adenosine. J Physiol Biochem. 2017 May;73(2):175-185. doi: 10.1007/s13105-016-0535-z. Epub 2016 Nov 19. PubMed PMID: 27864790.

4: Padiadpu J, Baloni P, Anand K, Munshi M, Thakur C, Mohan A, Singh A, Chandra N. Identifying and Tackling Emergent Vulnerability in Drug-Resistant Mycobacteria. ACS Infect Dis. 2016 Sep 9;2(9):592-607. Epub 2016 Aug 8. PubMed PMID: 27759382.

5: Jiang Q, Pan Y, Cheng Y, Li H, Li H. Protection of rat liver against hepatic ischemia-reperfusion injury by a novel selenocysteine-containing 7-mer peptide. Mol Med Rep. 2016 Sep;14(3):2007-15. doi: 10.3892/mmr.2016.5464. Epub 2016 Jul 1. PubMed PMID: 27431272; PubMed Central PMCID: PMC4991737.

6: Kumar S, Yan J, Poon JF, Singh VP, Lu X, Karlsson Ott M, Engman L, Kumar S. Multifunctional Antioxidants: Regenerable Radical-Trapping and Hydroperoxide-Decomposing Ebselenols. Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3729-33. doi: 10.1002/anie.201510947. Epub 2016 Feb 16. PubMed PMID: 26879742.

7: Leem YH, Oh S, Kang HJ, Kim JH, Yoon J, Chang JS. BPA-toxicity via superoxide anion overload and a deficit in β-catenin signaling in human bone mesenchymal stem cells. Environ Toxicol. 2017 Jan;32(1):344-352. doi: 10.1002/tox.22239. Epub 2016 Jan 29. PubMed PMID: 26822619; PubMed Central PMCID: PMC5217073.

8: Ozyigit F, Kucuk A, Akcer S, Tosun M, Kocak FE, Kocak C, Kocak A, Metineren H, Genc O. Different dose-dependent effects of ebselen in sciatic nerve ischemia-reperfusion injury in rats. Bosn J Basic Med Sci. 2015 Aug 26;15(4):36-43. doi: 10.17305/bjbms.2015.521. PubMed PMID: 26614850; PubMed Central PMCID: PMC4690440.

9: Mooradian AD, Onstead-Haas L, Haas MJ. Asymmetrical cross-talk between the endoplasmic reticulum stress and oxidative stress caused by dextrose. Life Sci. 2016 Jan 1;144:37-48. doi: 10.1016/j.lfs.2015.11.016. Epub 2015 Nov 19. PubMed PMID: 26603029.

10: Sharma A, Yuen D, Huet O, Pickering R, Stefanovic N, Bernatchez P, de Haan JB. Lack of glutathione peroxidase-1 facilitates a pro-inflammatory and activated vascular endothelium. Vascul Pharmacol. 2016 Apr;79:32-42. doi: 10.1016/j.vph.2015.11.001. Epub 2015 Nov 11. PubMed PMID: 26569096.

11: Maleki J, Nourbakhsh M, Shabani M, Korani M, Nourazarian SM, Ostadali Dahaghi MR, Moghadasi MH. 17β-Estradiol Stimulates Generation of Reactive Species Oxygen and Nitric Oxide in Ovarian Adenocarcinoma Cells (OVCAR 3). Iran J Cancer Prev. 2015 May;8(3):e2332. doi: 10.17795/ijcp2332. Epub 2015 May 22. PubMed PMID: 26413252; PubMed Central PMCID: PMC4581366.

12: Ruiz-Ramírez A, Barrios-Maya MA, López-Acosta O, Molina-Ortiz D, El-Hafidi M. Cytochrome c release from rat liver mitochondria is compromised by increased saturated cardiolipin species induced by sucrose feeding. Am J Physiol Endocrinol Metab. 2015 Nov 1;309(9):E777-86. doi: 10.1152/ajpendo.00617.2014. Epub 2015 Sep 8. PubMed PMID: 26353385.

13: Mordente A, Silvestrini A, Martorana GE, Tavian D, Meucci E. Inhibition of Anthracycline Alcohol Metabolite Formation in Human Heart Cytosol: A Potential Role for Several Promising Drugs. Drug Metab Dispos. 2015 Nov;43(11):1691-701. doi: 10.1124/dmd.115.065110. Epub 2015 Aug 11. PubMed PMID: 26265744.

14: Młochowski J, Wójtowicz-Młochowska H. Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents. Molecules. 2015 Jun 3;20(6):10205-43. doi: 10.3390/molecules200610205. Review. PubMed PMID: 26046320.

15: Tovmasyan A, Maia CG, Weitner T, Carballal S, Sampaio RS, Lieb D, Ghazaryan R, Ivanovic-Burmazovic I, Ferrer-Sueta G, Radi R, Reboucas JS, Spasojevic I, Benov L, Batinic-Haberle I. A comprehensive evaluation of catalase-like activity of different classes of redox-active therapeutics. Free Radic Biol Med. 2015 Sep;86:308-21. doi: 10.1016/j.freeradbiomed.2015.05.018. Epub 2015 May 28. PubMed PMID: 26026699; PubMed Central PMCID: PMC4554972.

16: Di Marco E, Jha JC, Sharma A, Wilkinson-Berka JL, Jandeleit-Dahm KA, de Haan JB. Are reactive oxygen species still the basis for diabetic complications? Clin Sci (Lond). 2015 Jul;129(2):199-216. doi: 10.1042/CS20150093. Review. PubMed PMID: 25927680.

17: Tan SM, Deliyanti D, Figgett WA, Talia DM, de Haan JB, Wilkinson-Berka JL. Ebselen by modulating oxidative stress improves hypoxia-induced macroglial Müller cell and vascular injury in the retina. Exp Eye Res. 2015 Jul;136:1-8. doi: 10.1016/j.exer.2015.04.015. Epub 2015 Apr 24. PubMed PMID: 25912997.

18: Bartolini D, Piroddi M, Tidei C, Giovagnoli S, Pietrella D, Manevich Y, Tew KD, Giustarini D, Rossi R, Townsend DM, Santi C, Galli F. Reaction kinetics and targeting to cellular glutathione S-transferase of the glutathione peroxidase mimetic PhSeZnCl and its D,L-polylactide microparticle formulation. Free Radic Biol Med. 2015 Jan;78:56-65. doi: 10.1016/j.freeradbiomed.2014.10.008. Epub 2014 Oct 18. PubMed PMID: 25452145; PubMed Central PMCID: PMC4451065.

19: Rifaioglu MM, Motor S, Davarci I, Tuzcu K, Sefil F, Davarci M, Nacar A. Protective effect of ebselen on experimental testicular torsion and detorsion injury. Andrologia. 2014 Dec;46(10):1134-40. doi: 10.1111/and.12204. Epub 2013 Dec 8. PubMed PMID: 25388506.

20: Li CF, Fang FM, Lan J, Wang JW, Kung HJ, Chen LT, Chen TJ, Li SH, Wang YH, Tai HC, Yu SC, Huang HY. AMACR amplification in myxofibrosarcomas: a mechanism of overexpression that promotes cell proliferation with therapeutic relevance. Clin Cancer Res. 2014 Dec 1;20(23):6141-52. doi: 10.1158/1078-0432.CCR-14-1182. Epub 2014 Nov 10. PubMed PMID: 25384383.