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MedKoo Cat#: 558418 | Name: EUK-134
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Description:

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

EUK-134 is an antioxidant compound with superoxide dismutase and catalase activity for oxidative species such as peroxynitrite, superoxide, and hydrogen peroxide.

Chemical Structure

EUK-134
EUK-134
CAS#81065-76-1

Theoretical Analysis

MedKoo Cat#: 558418

Name: EUK-134

CAS#: 81065-76-1

Chemical Formula: C18H18ClMnN2O4

Exact Mass: 416.0300

Molecular Weight: 416.74

Elemental Analysis: C, 51.88; H, 4.35; Cl, 8.51; Mn, 13.18; N, 6.72; O, 15.36

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
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Related CAS #
81065-76-1
Synonym
EUK-134; EUK-134; EUK-134;
IUPAC/Chemical Name
chloro[[2,2'-[1,2-ethanediylbis[(nitrilo-κN)methylidyne]]bis[6-methoxyphenolato-κO]]]-manganese
InChi Key
YUZJJFWCXJDFOQ-GAMUHHASSA-K
InChi Code
InChI=1S/C18H20N2O4.ClH.Mn/c1-23-15-7-3-5-13(17(15)21)11-19-9-10-20-12-14-6-4-8-16(24-2)18(14)22;;/h3-8,11-12,21-22H,9-10H2,1-2H3;1H;/q;;+3/p-3/b19-11+,20-12+;;
SMILES Code
[Cl-][Mn+3]12([N]3=CC4=CC=CC(OC)=C4[O-]2)[N](CC3)=CC5=CC=CC(OC)=C5[O-]1
Appearance
Solid powder
Purity
>97% (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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
EUK 134, a synthetic superoxide dismutase (SOD)/catalase mimetic, exhibits potent antioxidant activities, and inhibits the formation of β-amyloid and related amyloid fibril.
In vitro activity:
EUK-134 was able to significantly inhibit tunicamycin-induced increase in basal respiration (Figure 2B). Decreased spare respiratory capacity (%, also called as reserve capacity) observed after ER stress induction was significantly increased following EUK-134 treatment, even compared to the vehicle control (Figure 2E). Consistently, depressed ATP-linked OCR was observed following tunicamycin treatment, (Figure 2F), which was further enhanced by a substantial increase in leak respiration, with more than half of oxygen consumed not being used for ATP production (Figure 2G). Importantly, ER stress-induced proton leak was inhibited by EUK-134 treatment. Reference: Antioxidants (Basel). 2020 Aug; 9(8): 710. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7466046/
In vivo activity:
In the current study, EUK-134 revealed supportive effects not only on the EUK group but also in the EE group. In N2 worms, the median survival lifespans of the EE, EXER, and EUK groups were 32.5, 29.5, and 26.5 days, respectively; these lifespans are longer than that of the corresponding CON group (22.5 days). Reference: PLoS One. 2021; 16(1): e0245474. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7817057/
Solvent mg/mL mM
Solubility
DMSO 51.5 123.58
Ethanol 1.0 2.40
PBS (pH 7.2) 0.2 0.48
Water 20.0 47.99
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 416.74 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. Thoma A, Lyon M, Al-Shanti N, Nye GA, Cooper RG, Lightfoot AP. Eukarion-134 Attenuates Endoplasmic Reticulum Stress-Induced Mitochondrial Dysfunction in Human Skeletal Muscle Cells. Antioxidants (Basel). 2020 Aug 5;9(8):710. doi: 10.3390/antiox9080710. PMID: 32764412; PMCID: PMC7466046. 2. SanMartín CD, Veloso P, Adasme T, Lobos P, Bruna B, Galaz J, García A, Hartel S, Hidalgo C, Paula-Lima AC. RyR2-Mediated Ca2+ Release and Mitochondrial ROS Generation Partake in the Synaptic Dysfunction Caused by Amyloid β Peptide Oligomers. Front Mol Neurosci. 2017 Apr 25;10:115. doi: 10.3389/fnmol.2017.00115. PMID: 28487634; PMCID: PMC5403897. 3. Pham TTH, Huang WY, Chen CS, Chiu WT, Chuang HS. Effects of electrotactic exercise and antioxidant EUK-134 on oxidative stress relief in Caenorhabditis elegans. PLoS One. 2021 Jan 20;16(1):e0245474. doi: 10.1371/journal.pone.0245474. PMID: 33471830; PMCID: PMC7817057. 4. Watanabe D, Aibara C, Wada M. Treatment with EUK-134 improves sarcoplasmic reticulum Ca2+ release but not myofibrillar Ca2+ sensitivity after fatiguing contraction of rat fast-twitch muscle. Am J Physiol Regul Integr Comp Physiol. 2019 May 1;316(5):R543-R551. doi: 10.1152/ajpregu.00387.2018. Epub 2019 Feb 22. PMID: 30794441.
In vitro protocol:
1. Thoma A, Lyon M, Al-Shanti N, Nye GA, Cooper RG, Lightfoot AP. Eukarion-134 Attenuates Endoplasmic Reticulum Stress-Induced Mitochondrial Dysfunction in Human Skeletal Muscle Cells. Antioxidants (Basel). 2020 Aug 5;9(8):710. doi: 10.3390/antiox9080710. PMID: 32764412; PMCID: PMC7466046. 2. SanMartín CD, Veloso P, Adasme T, Lobos P, Bruna B, Galaz J, García A, Hartel S, Hidalgo C, Paula-Lima AC. RyR2-Mediated Ca2+ Release and Mitochondrial ROS Generation Partake in the Synaptic Dysfunction Caused by Amyloid β Peptide Oligomers. Front Mol Neurosci. 2017 Apr 25;10:115. doi: 10.3389/fnmol.2017.00115. PMID: 28487634; PMCID: PMC5403897.
In vivo protocol:
1. Pham TTH, Huang WY, Chen CS, Chiu WT, Chuang HS. Effects of electrotactic exercise and antioxidant EUK-134 on oxidative stress relief in Caenorhabditis elegans. PLoS One. 2021 Jan 20;16(1):e0245474. doi: 10.1371/journal.pone.0245474. PMID: 33471830; PMCID: PMC7817057. 2. Watanabe D, Aibara C, Wada M. Treatment with EUK-134 improves sarcoplasmic reticulum Ca2+ release but not myofibrillar Ca2+ sensitivity after fatiguing contraction of rat fast-twitch muscle. Am J Physiol Regul Integr Comp Physiol. 2019 May 1;316(5):R543-R551. doi: 10.1152/ajpregu.00387.2018. Epub 2019 Feb 22. PMID: 30794441.
1: Magder S, Parthenis DG, Ghouleh IA. Preservation of renal blood flow by the antioxidant EUK-134 in LPS-treated pigs. Int J Mol Sci. 2015 Mar 25;16(4):6801-17. doi: 10.3390/ijms16046801. PubMed PMID: 25815596; PubMed Central PMCID: PMC4424988. 2: Kumar A, Shukla S, Chauhan AK, Singh D, Pandey HP, Singh C. The manganese-salen compound EUK-134 and N-acetyl cysteine rescue from zinc- and paraquat-induced toxicity in rat polymorphonuclear leukocytes. Chem Biol Interact. 2015 Apr 25;231:18-26. doi: 10.1016/j.cbi.2015.02.012. Epub 2015 Feb 24. PubMed PMID: 25724285. 3: Lawler JM, Kunst M, Hord JM, Lee Y, Joshi K, Botchlett RE, Ramirez A, Martinez DA. EUK-134 ameliorates nNOSμ translocation and skeletal muscle fiber atrophy during short-term mechanical unloading. Am J Physiol Regul Integr Comp Physiol. 2014 Apr 1;306(7):R470-82. doi: 10.1152/ajpregu.00371.2013. Epub 2014 Jan 29. PubMed PMID: 24477538; PubMed Central PMCID: PMC3962621. 4: Purushothaman S, Nair RR. Mitoprotective antioxidant EUK-134 stimulates fatty acid oxidation and prevents hypertrophy in H9C2 cells. Mol Cell Biochem. 2016 Sep;420(1-2):185-94. doi: 10.1007/s11010-016-2788-9. Epub 2016 Aug 11. PubMed PMID: 27514538. 5: Howard MD, Greineder CF, Hood ED, Muzykantov VR. Endothelial targeting of liposomes encapsulating SOD/catalase mimetic EUK-134 alleviates acute pulmonary inflammation. J Control Release. 2014 Mar 10;177:34-41. doi: 10.1016/j.jconrel.2013.12.035. Epub 2014 Jan 9. PubMed PMID: 24412573; PubMed Central PMCID: PMC4593476. 6: Ni X, Yang ZJ, Carter EL, Martin LJ, Koehler RC. Striatal neuroprotection from neonatal hypoxia-ischemia in piglets by antioxidant treatment with EUK-134 or edaravone. Dev Neurosci. 2011;33(3-4):299-311. doi: 10.1159/000327243. Epub 2011 Jun 24. PubMed PMID: 21701140; PubMed Central PMCID: PMC3225250. 7: Chen SY, Dehart DB, Sulik KK. Protection from ethanol-induced limb malformations by the superoxide dismutase/catalase mimetic, EUK-134. FASEB J. 2004 Aug;18(11):1234-6. Epub 2004 Jun 18. PubMed PMID: 15208273. 8: Samai M, Sharpe MA, Gard PR, Chatterjee PK. Comparison of the effects of the superoxide dismutase mimetics EUK-134 and tempol on paraquat-induced nephrotoxicity. Free Radic Biol Med. 2007 Aug 15;43(4):528-34. Epub 2007 May 16. PubMed PMID: 17640563. 9: Bianca Rd, Wayman NS, McDonald MC, Pinto A, Shape MA, Chatterjee PK, Thiemermann C. Superoxide dismutase mimetic with catalase activity, EUK-134, attenuates the multiple organ injury and dysfunction caused by endotoxin in the rat. Med Sci Monit. 2002 Jan;8(1):BR1-7. PubMed PMID: 11796957. 10: Decraene D, Smaers K, Gan D, Mammone T, Matsui M, Maes D, Declercq L, Garmyn M. A synthetic superoxide dismutase/catalase mimetic (EUK-134) inhibits membrane-damage-induced activation of mitogen-activated protein kinase pathways and reduces p53 accumulation in ultraviolet B-exposed primary human keratinocytes. J Invest Dermatol. 2004 Feb;122(2):484-91. PubMed PMID: 15009734. 11: Shah MH, Liu GS, Thompson EW, Dusting GJ, Peshavariya HM. Differential effects of superoxide dismutase and superoxide dismutase/catalase mimetics on human breast cancer cells. Breast Cancer Res Treat. 2015 Apr;150(3):523-34. doi: 10.1007/s10549-015-3329-z. Epub 2015 Mar 21. PubMed PMID: 25794772. 12: Chatterjee PK, Patel NS, Kvale EO, Brown PA, Stewart KN, Mota-Filipe H, Sharpe MA, Di Paola R, Cuzzocrea S, Thiemermann C. EUK-134 reduces renal dysfunction and injury caused by oxidative and nitrosative stress of the kidney. Am J Nephrol. 2004 Mar-Apr;24(2):165-77. Epub 2004 Jan 29. PubMed PMID: 14752229. 13: Rezazadeh A, Yazdanparast R, Molaei M. Amelioration of diet-induced nonalcoholic steatohepatitis in rats by Mn-salen complexes via reduction of oxidative stress. J Biomed Sci. 2012 Feb 29;19:26. doi: 10.1186/1423-0127-19-26. PubMed PMID: 22375551; PubMed Central PMCID: PMC3311616. 14: Wu L, Shan Y, Liu D. Stability, disposition, and penetration of catalytic antioxidants Mn-porphyrin and Mn-salen and of methylprednisolone in spinal cord injury. Cent Nerv Syst Agents Med Chem. 2012 Jun;12(2):122-30. PubMed PMID: 22640221; PubMed Central PMCID: PMC4288768. 15: Chen Z, Wen L, Martin M, Hsu CY, Fang L, Lin FM, Lin TY, Geary MJ, Geary GG, Zhao Y, Johnson DA, Chen JW, Lin SJ, Chien S, Huang HD, Miller YI, Huang PH, Shyy JY. Oxidative stress activates endothelial innate immunity via sterol regulatory element binding protein 2 (SREBP2) transactivation of microRNA-92a. Circulation. 2015 Mar 3;131(9):805-14. doi: 10.1161/CIRCULATIONAHA.114.013675. Epub 2014 Dec 30. PubMed PMID: 25550450; PubMed Central PMCID: PMC4351177. 16: Himori K, Abe M, Tatebayashi D, Lee J, Westerblad H, Lanner JT, Yamada T. Superoxide dismutase/catalase mimetic EUK-134 prevents diaphragm muscle weakness in monocrotalin-induced pulmonary hypertension. PLoS One. 2017 Feb 2;12(2):e0169146. doi: 10.1371/journal.pone.0169146. eCollection 2017. PubMed PMID: 28152009; PubMed Central PMCID: PMC5289453. 17: Ni X, Yang ZJ, Wang B, Carter EL, Larson AC, Martin LJ, Koehler RC. Early antioxidant treatment and delayed hypothermia after hypoxia-ischemia have no additive neuroprotection in newborn pigs. Anesth Analg. 2012 Sep;115(3):627-37. doi: 10.1213/ANE.0b013e31825d3600. Epub 2012 Jun 28. PubMed PMID: 22745113; PubMed Central PMCID: PMC3425722. 18: Bahramikia S, Yazdanparast R. Inhibition of human islet amyloid polypeptide or amylin aggregation by two manganese-salen derivatives. Eur J Pharmacol. 2013 May 5;707(1-3):17-25. doi: 10.1016/j.ejphar.2013.03.017. Epub 2013 Mar 23. PubMed PMID: 23528352. 19: Shopova VL, Dancheva VY, Salovsky PT, Stoyanova AM. Protective effects of a superoxide dismutase/catalase mimetic compound against paraquat pneumotoxicity in rat lung. Respirology. 2009 May;14(4):504-10. doi: 10.1111/j.1440-1843.2009.01531.x. PubMed PMID: 19645869. 20: Wedgwood S, Black SM. Induction of apoptosis in fetal pulmonary arterial smooth muscle cells by a combined superoxide dismutase/catalase mimetic. Am J Physiol Lung Cell Mol Physiol. 2003 Aug;285(2):L305-12. Epub 2003 Mar 28. PubMed PMID: 12665466.