4-oxo-2-Nonenal
(Synonyms: 4-ONE) 目录号 : GC42464A lipid peroxidation product
Cas No.:103560-62-9
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
4-hydroxy Nonenal is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid and linoleic acid. [1] [2] It exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity and has been widely used as a marker of lipid peroxidation.[1][2][3] 4-oxo-2-Nonenal is a more recently identified product of lipid peroxidation.[4][5][6] It actively modifies histidine and lysine residues on proteins and causes protein cross-linking. [7][8] 4-oxo-2-Nonenal also modifies 2’-deoxyguanosine, further implicating lipid peroxidation in mutagenesis and carcinogenesis.[4]
Reference:
[1]. Pryor, W.A., and Porter, N.A. Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids. Free Radical Biology & Medicine 8, 541-543 (1990).
[2]. Esterbauer, H., Schaur, R.J., and Zoliner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydes. Free Radical Biology & Medicine 11, 81-128 (1991).
[3]. Sodum, R.S., and Chung, F.L. 1,N2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Research 48, 320-323 (1988).
[4]. Rindgen, D., Nakajima, M., Wehrli, S., et al. Covalent modifications to 2'-deoxyguanosine by 4-oxo-nonenal, a novel product of lipid peroxidation. Chemical Research in Toxicology 12, 1195-1204 (1999).
[5]. Lee, S.H., and Blair, I.A. Characterization of 4-oxo-2-nonenal as a novel product of lipid peroxidation. Chemical Research in Toxicology 13, 698-702 (2000).
[6]. Spiteller, P., Kern, W., Reiner, J., et al. Aldehydic lipid peroxidation products derived from linoleic acid. Biochimica et Biophysica Acta 1531, 188-208 (2001).
[7]. Liu, Z., Minkler, P.E., and Sayre, L.M. Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenal. Chemical Research in Toxicology 16, 901-911 (2003).
[8]. Zhang, W.H., Liu, J., Xu, G., et al. Model studies on protein side chain modification by 4-oxo-2-nonenal. Chemical Research in Toxicology 16, 512-523 (2003).
| Cas No. | 103560-62-9 | SDF | |
| 别名 | 4-ONE | ||
| 化学名 | 4-oxo-2E-nonenal | ||
| Canonical SMILES | CCCCCC(=O)/C=C\C=O | ||
| 分子式 | C9H14O2 | 分子量 | 154.2 |
| 溶解度 | DMF: 50 mg/ml,DMSO: 50 mg/ml,Ethanol: 50 mg/ml,PBS (pH 7.2): 0.5 mg/ml | 储存条件 | Store at -80°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 6.4851 mL | 32.4254 mL | 64.8508 mL |
| 5 mM | 1.297 mL | 6.4851 mL | 12.9702 mL |
| 10 mM | 0.6485 mL | 3.2425 mL | 6.4851 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Scavenging 4-oxo-2-Nonenal
Chem Res Toxicol 2015 Oct 19;28(10):1888-90.PMID:26355561DOI:10.1021/acs.chemrestox.5b00301.
4-oxo-2-Nonenal (ONE), a product of cellular lipid oxidation, reacts nonspecifically with the lysine residues of proteins and is generated in increased amounts during degenerative diseases and cancer. We show that pyridoxamine, salicylamine, and related 2-aminomethylphenols react with ONE, to form pyrrolo[2,1-b][1,3]oxazines with the participation of both the amino and the phenolic groups. 2-Aminomethylphenols react with ONE as well as with the Michael adducts of ONE much more rapidly than lysine, suggesting their use for therapeutically scavenging ONE.
4-oxo-2-Nonenal (4-ONE)-Induced Degradation of Bovine Skeletal Muscle Proteins
J Agric Food Chem 2022 Oct 5;70(39):12641-12650.PMID:36129340DOI:10.1021/acs.jafc.2c05550.
Lipids are an important component of meat, as they provide desirable sensory characteristics and nutritional benefits. However, lipids are susceptible to degradation through oxidation and produce toxic oxidative byproducts. 4-oxo-2-Nonenal (4-ONE) is an oxidative byproduct that is highly reactive and cytotoxic. In this study, we investigated the influence of 4-ONE-induced protein degradation on fresh and gastric digested bovine skeletal muscle proteins. The results indicated that 4-ONE naturally forms in fresh muscle proteins. We report here for the first time that 4-ONE causes severe degradation of bovine skeletal muscle proteins. An SDS-PAGE gel analysis showed evidence that the skeletal muscle proteins attenuated over the incubation time, as the density of the protein bands faded significantly after 120 h. Additionally, protein and band density analyses showed a significant decrease in protein abundance and band densities throughout the incubation time. This study revealed that the lipid oxidation byproduct, 4-oxo-2-Nonenal (4-ONE) is responsible for causing skeletal muscle protein degradation. Future studies should assess the bioprotective role of antioxidants and other food ingredients for their potential to prevent the formation and/or detoxification of 4-ONE in meat.
Effects of 4-oxo-2-Nonenal on biochemical properties of bovine heart mitochondria
Food Sci Nutr 2022 Mar 9;10(6):1830-1840.PMID:35702292DOI:10.1002/fsn3.2799.
The effects of lipid peroxidation products 4-Hydroxy-2-nonenal (4-HNE) and 4-oxo-2-Nonenal (4-ONE) were evaluated using bovine heart mitochondria. Oxygen consumption rate (OCR), ultrastructure, antioxidant activity, and membrane permeability were examined to compare their effects on isolated mitochondria from beef cardiac muscle. For the mitochondrial morphology, the final concentration of mitochondria and 4-ONE or 4-HNE in the reaction tube were 10 mg/ml and 1 mM, respectively. For the OCR experiment, mitochondria (2.5 mg/ml) were incubated with 0.20 mM ONE or in a Clark electrode chamber at 25°C. Mitochondrial membrane permeability was determined by incubating 0.5 mg/ml of mitochondrial protein with either 0.05 mM ONE or HNE or ethanol control at pH 5.6 and 7.4 at 25°C. Transmission electron microscopy (TEM) revealed that the size of 4-ONE treated mitochondria at pH 7.4 increased (p < .05), as did permeability (p < .05), unlike ethanol controls. However, mitochondria incubated with 4-ONE at pH 5.6 showed a decrease in volume (p < .05). Incubating mitochondria with 4-ONE at pH 5.6 and pH increased oxygen consumption rate 7.4 caused less oxygen consumption than either 4-HNE treatment or ethanol control. The hydrogen peroxide assay (H2O2), ferric reducing antioxidant properties (FRAP), and 2,2'-azinobis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS.+) assays revealed that 4-ONE is a more potent inhibitor of the endogenous antioxidant system of mitochondria than 4-HNE (p < .05).
Characterization of 4-oxo-2-Nonenal as a novel product of lipid peroxidation
Chem Res Toxicol 2000 Aug;13(8):698-702.PMID:10956056DOI:10.1021/tx000101a.
Fe(II)-mediated decomposition of 13-[S-(Z,E)]-9, 11-hydroperoxyoctadecadienoic (hydroperoxylinoleic) acid resulted in the formation of three alpha,beta-unsaturated aldehydes. At low Fe(II) concentrations or at early time points after the addition of Fe(II), two major products were observed. The least polar product had chromatographic properties that were identical with those of 4-oxo-2-Nonenal. Conversion of this product to its bis-oxime derivative with hydroxylamine hydrochloride resulted in two syn- and two anti-oxime isomers that had chromatographic and mass spectral properties identical with the properties of products derived from an authentic standard of 4-oxo-2-Nonenal. This confirmed for the first time that 4-oxo-2-Nonenal is a major product of the Fe(II)-mediated breakdown of lipid hydroperoxides. The more polar product had chromatographic properties that were similar to those of 4-hydroperoxy-2-nonenal. LC/MS analysis of its syn- and anti-oxime isomers confirmed this structural assignment. Thus, 4-hydroperoxy-2-nonenal is a previously unrecognized major product of lipid hydroperoxide decomposition. At high Fe(II) concentrations and at longer incubation times, a third more polar product was observed with chromatographic properties that were identical to those of 4-hydroxy-2-nonenal. The syn- and anti-oxime isomers had chromatographic and mass spectral properties identical with the properties of products derived from an authentic standard of 4-hydroxy-2-nonenal. It appears that 4-hydroperoxy-2-nonenal is formed initially and that it is then converted to 4-hydroxy-2-nonenal in the presence of high Fe(II) concentrations or by extended incubations in the presence of low Fe(II) concentrations. It is conceivable that some of the 4-hydroperoxy-2-nonenal is also converted to 4-oxo-2-Nonenal. However, we cannot rule out the possibility that it is also formed by a concerted mechanism from a rearrangement product of 13-[S-(Z,E)]-9, 11-hydroperoxyoctadecadienoic acid.
Low molar excess of 4-oxo-2-Nonenal and 4-hydroxy-2-nonenal promote oligomerization of alpha-synuclein through different pathways
Free Radic Biol Med 2017 Sep;110:421-431.PMID:28690195DOI:10.1016/j.freeradbiomed.2017.07.004.
Aggregated alpha-synuclein is the main component of Lewy bodies, intraneuronal inclusions found in brains with Parkinson's disease and dementia with Lewy bodies. A body of evidence implicates oxidative stress in the pathogenesis of these diseases. For example, a large excess (30:1, aldehyde:protein) of the lipid peroxidation end products 4-oxo-2-Nonenal (ONE) or 4-hydroxy-2-nonenal (HNE) can induce alpha-synuclein oligomer formation. The objective of the study was to investigate the effect of these reactive aldehydes on alpha-synuclein at a lower molar excess (3:1) at both physiological (7.4) and acidic (5.4) pH. As observed by size-exclusion chromatography, ONE rapidly induced the formation of alpha-synuclein oligomers at both pH values, but the effect was less pronounced under the acidic condition. In contrast, only a small proportion of alpha-synuclein oligomers were formed with low excess HNE-treatment at physiological pH and no oligomers at all under the acidic condition. With prolonged incubation times (up to 96h), more alpha-synuclein was oligomerized at physiological pH for both ONE and HNE. As determined by Western blot, ONE-oligomers were more SDS-stable and to a higher-degree cross-linked as compared to the HNE-induced oligomers. However, as shown by their greater sensitivity to proteinase K treatment, ONE-oligomers, exhibited a less compact structure than HNE-oligomers. As indicated by mass spectrometry, ONE modified most Lys residues, whereas HNE primarily modified the His50 residue and fewer Lys residues, albeit to a higher degree than ONE. Taken together, our data show that the aldehydes ONE and HNE can modify alpha-synuclein and induce oligomerization, even at low molar excess, but to a higher degree at physiological pH and seemingly through different pathways.