81065-76-1 Usage
Uses
EUK-134 has been used as an antioxidant.
Biological Activity
euk 134, a synthetic superoxide dismutase (sod)/catalase mimetic, has exhibited potent antioxidant activities and inhibited the formation of β-amyloid and related amyloid fibril.
Biochem/physiol Actions
EUK-134 is a manganese-salen derivative that exhibit potent antioxidant activities. EUK-134 is a superoxide dismutase (SOD) that inhibits amyloid fibril formation, including islet amyloid polypeptide (IAPP), β-amyloid and lysozyme amyloid aggregation. It appears that EUK-134 disrupts the pre-formed amyloid fibrils. EUK-134 increases the viability of the SK-N-MC cells exposed to preformed IAPP fibrils.
in vitro
euk-134, a salen-manganese complex, showed potent catalase and cytoprotective activities and sod activity. after middle cerebral artery occlusion, euk-134 administration at 3 hr significantly reduced brain infarct size, with the highest dose apparently preventing further infarct growth[1]. administration of euk 134 (20 μm) prevented aβ-induced microglial proliferation in vitro[2]. in human neuroblastoma cell line sk-n-mc, pre-treatments with euk134 protected cells against h2o2-induced oxidative stress through inhibition of mapk pathway in a dose-dependent manner.euk134 also decreased the expression of pro-apoptotic genes p53 and bax and enhanced expression of anti-apoptotic bcl-2 gene [3]. incubation of human amylin with euk-134 significantly inhibited amyloid formation at two molar ratios of 1:1 and 5:1 (drugs to protein)[4].
in vivo
compared to the vehicle-injected rats, the euk-134-treated group at doses of 0.5 and 5.0 μmol/kg (0.25 and 2.5 mg/kg, respectively) exhibited infarct volumes that were significantly lower than those of vehicle-injected rats. at 5.0 μmol/kg, euk-134 reduced the infarct volume by 90% when compared with that of the vehicle controls [1].euk-134 protected most of the vulnerable neurons from excitotoxic cell death.euk-134 significantly reduced (p< 0.05) ka-induced neuronal damage in ca1 (22% of total neurons), an almost complete protection in ca3 (7%) and piriform cortex (14%), indicating that euk-134 prevented most but not all neuronal damage resulting from ka-induced seizure activity [5].
references
[1]. baker k, marcus c b, huffman k, et al. synthetic combined superoxide dismutase/catalase mimetics are protective as a delayed treatment in a rat stroke model: a key role for reactive oxygen species in ischemic brain injury[j]. journal of pharmacology and experimental therapeutics, 1998, 284(1): 215-221.[2]. jekabsone a, mander p k, tickler a, et al. fibrillar beta-amyloid peptide aβ 1–40 activates microglial proliferation via stimulating tnf-α release and h 2 o 2 derived from nadph oxidase: a cell culture study[j]. journal of neuroinflammation, 2006, 3(1): 1.[3]. mohammadi m, yazdanparast r. modulation of h2o2‐induced mitogen‐activated protein kinases activation and cell death in sk‐n‐mc cells by euk134, a salenderivative[j]. basic & clinical pharmacology & toxicology, 2011, 108(6): 378-384.[4]. bahramikia s, yazdanparast r. inhibition of human islet amyloid polypeptide or amylin aggregation by two manganese-salenderivatives[j]. european journal of pharmacology, 2013, 707(1): 17-25.[5]. rong y, doctrow s r, tocco g, et al. euk-134, a synthetic superoxide dismutase and catalase mimetic, prevents oxidative stress and attenuates kainate-induced neuropathology[j]. proceedings of the national academy of sciences, 1999, 96(17): 9897-9902.
Check Digit Verification of cas no
The CAS Registry Mumber 81065-76-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,0,6 and 5 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 81065-76:
(7*8)+(6*1)+(5*0)+(4*6)+(3*5)+(2*7)+(1*6)=121
121 % 10 = 1
So 81065-76-1 is a valid CAS Registry Number.
InChI:InChI=1/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;;+2/p-3/b19-11+,20-12+;;
81065-76-1Relevant academic research and scientific papers
Preparation method of guaiacol-derived diimine manganese complex
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Paragraph 0031-0033, (2021/06/06)
The invention belongs to the field of organic synthesis, fine chemicals and daily chemicals, and particularly relates to a preparation method of a guaiacol-derived diimine manganese complex. According to the method, guaiacol, formaldehyde, diamine and a manganese salt are used as raw materials, and the guaiacol-derived diimine manganese complex is synthesized in one step. Compared with a multi-step synthesis method in the prior art, the method is simple and convenient to operate, green, safe, efficient, environment-friendly and suitable for industrial production, and reagents are cheap and easy to obtain.
Bioinspired oxidation in cytochrome P450 of isomers orientin and isoorientin using Salen complexes
Chagas, Mariane B.,Pontes, Daniel O.B.,Albino, Allan V.D.,Ferreira, Emanuel J.,Alves, Jovelina S.F.,Paiva, Anallicy S.,Pontes, Daniel L.,Langansser, Silvana M.Z.,Ferreira, Leandro S.
, (2020/04/15)
Rationale: Orientin and isoorientin are C-glycosidic flavonoids, considered as markers of some plant species such as Passiflora edulis var. flavicarpa Degener, and reported in the literature to have pharmacological properties. In order to evaluate and characterize the in vitro metabolism of these flavonoids, phase I biotransformation reactions were simulated using Salen complexes. Methods: These flavonoids were oxidized separately in biomimetic reactions in different proportions, using one oxidant, m-chloroperbenzoic acid or iodosylbenzene, and one catalyst, the Jacobsen catalyst or [Mn(3-MeOSalen)Cl]. The [Mn(3-MeOSalen)Cl] catalyst was synthesized and characterized using spectrometric techniques. The oxidation potentials of the catalysts were compared. All reactions were monitored and analyzed using ultrahigh-performance liquid chromatography diode-array detection (UHPLC-DAD) and high-performance liquid chromatography/tandem mass spectrometry (HPLC/MS/MS). Results: The analysis by UHPLC-DAD and HPLC/MS/MS showed that isoorientin produces more products than orientin and that [Mn(3-MeOSalen)Cl] produces more products than the Jacobsen catalyst. In addition, [Mn(3-MeOSalen)Cl], which has a higher oxidation potential, formed products with the addition of one or two atoms of oxygen, while the Jacobsen catalyst formed compounds with only one added oxygen atom. The products with the addition of one oxygen atom were mainly epoxides, while those with two added oxygens formed an epoxide in the C-ring and incorporated the other oxygen into the glycosidic moiety. Conclusions: The formation of epoxides is common in biomimetic reactions and they may represent a safety risk in medicinal products due to their high reactivity. This study may serve as a basis for subsequent pharmacological and toxicological studies that investigate the presence of these compounds as phase I metabolites, and ensure the safe use of plant products containing orientin as a chemical marker.
