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Peroxidation
Lipid peroxidation is the chain of reactions of oxidative degradation of lipids. It is the process in which free radicals "steal" electrons from the lipids in cell membranes, resulting in cell damage. This process proceeds by a free radical chain reaction mechanism. It most often affects polyunsaturated fatty acids, because they contain multiple double bonds in between which lie methylene bridges (-CH2-) that possess especially reactive hydrogen atoms. As with any radical reaction, the reaction consists of three major steps: initiation, propagation, and termination. The chemical products of this oxidation are known as lipid peroxides or lipid oxidation products (LOPs). Initiation Initiation is the step in which a fatty acid radical is produced. The most notable initiators in living cells are reactive oxygen species (ROS), such as OH· and HOO·, which combines with a hydrogen atom to make water and a fatty acid radical. Propagation The fatty acid radical is not a very ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isotope Effect On Lipid Peroxidation
Kinetic isotope effect, Isotope effect is observed when molecules containing heavier isotopes of the same atoms (for example, deuterium instead of hydrogen) are engaged in a chemical reaction at a slower rate. Reinforced lipids, Deuterium-reinforced lipids can be used for the protection of Cell (biology), living cells by slowing the chain reaction of lipid peroxidation. The lipid bilayer of the Cell (biology), cell and organelle membranes contain polyunsaturated fatty acids (PUFA) are key components of cell and organelle membranes. Any process that either increases oxidation of PUFAs or hinders their ability to be replaced can lead to serious disease. Correspondingly, drugs that stop the chain reaction of lipid peroxidation have preventive and therapeutic potential. Mechanism of isotope effect in general The mass of the atoms forming a chemical bond affects the bond’s strength. When two different isotopes of the same element exist, the heavier ones form stronger bonds. Stronger ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Di-deuterated Linoleic Acid Ethyl Ester
Di-deuterated ethyl linoleate (also known as RT001, di-deuterated linoleic acid ethyl ester, 11,11-''d2''-ethyl linoleate, or ethyl 11,11-''d2''-linoleate) is an experimental, orally-bioavailable synthetic deuterated polyunsaturated fatty acid (PUFA), a part of reinforced lipids. It is an isotopologue of linoleic acid, an essential omega-6 PUFA. The deuterated compound, while identical to natural linoleic acid except for the presence of deuterium, is resistant to lipid peroxidation which makes studies of its cell-protective properties worthwhile. Mechanism of action Di-deuterated linoleic acid is recognized by cells as identical to the natural linoleic acid. But when taken up, it is converted into 13,13-''d2''-arachidonic acid, a heavy isotope version of arachidonic acid, that gets incorporated into lipid membranes. The deuterated compound resists the non-enzymatic lipid peroxidation (LPO) through isotope effect — a non-antioxidant based mechanism that protects mitochond ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Malondialdehyde
Malondialdehyde (MDA) is the organic compound with the nominal formula CH2(CHO)2. A colorless liquid, malondialdehyde is a highly reactive compound that occurs as the enol. It occurs naturally and is a marker for oxidative stress. Structure and synthesis Malondialdehyde mainly exists as the enol:V. Nair, C. L. O'Neil, P. G. Wang "Malondialdehyde", ''Encyclopedia of Reagents for Organic Synthesis'', 2008, John Wiley & Sons, New York. Article Online Posting Date: March 14, 2008 :CH2(CHO)2 → HOC(H)=CH-CHO In organic solvents, the ''cis''-isomer is favored, whereas in water the ''trans''-isomer predominates. The equilibrium is rapid and is inconsequential for many purposes. In the laboratory it can be generated in situ by hydrolysis of its acetal 1,1,3,3-tetramethoxypropane, which is commercially available and shelf-stable, unlike malondialdehyde. Malondialdehyde is easily deprotonated to give the sodium salt of the enolate (m.p. 245 °C). Biosynthesis and reactivity ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
4-hydroxynonenal
4-Hydroxynonenal, or 4-hydroxy-2-nonenal or 4-HNE or HNE, (), is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion. Early identification and characterization of 4-hydroxynonenal was reported by Esterbauer, et al., who also obtained the same compound synthetically. The topic has since been often reviewed. Synthesis 4-Hydroxynonenal is generated in the oxidation of lipids containing polyunsaturated omega-6 acyl groups, such as arachidonic or linoleic groups, and of the corresponding fatty acids viz., the hydroperoxy p ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Radical (chemistry)
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes. A notable example of a radical is the hydroxyl radical (HO·), a molecule that has one unpaired electron on the oxygen atom. Two other examples are triplet oxygen and triplet carbene (꞉) which have two unpaired electrons. Radicals may be generated in a number of ways, but typical methods involve redox reactions. Ionizing radiation, heat, electrical discharges, and electrolysis are known to produce radicals. Radicals are intermediates in many chemical reactions, more so than is apparent from the balanced equations. Radicals are important in combustion, atmospheric chemistry, polymerization, plasma chemistry, biochemistry, and many other chemical processes. A majority ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Deuterated Drug
A deuterated drug is a small molecule medicinal product in which one or more of the hydrogen atoms contained in the drug molecule have been replaced by its heavier stable isotope deuterium. Because of the kinetic isotope effect, deuterium-containing drugs may have significantly lower rates of metabolism, and hence a longer half-life. Mode of action Hydrogen is a chemical element with an atomic number of 1. It has just one proton and one electron. Deuterium is the heavier naturally occurring, non-radioactive, stable isotope of hydrogen. Deuterium was discovered by Harold Urey in 1931, for which he received the Nobel Prize in 1934. The deuterium isotope effect has become an important tool in the elucidation the mechanism of chemical reactions. Deuterium contains one proton, one electron, and a neutron, effectively doubling the mass of the deuterium isotope without changing its properties significantly. However, the C–D bond is a bit shorter, and it has reduced electronic polarizabi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Reactive Oxygen Species
In chemistry, reactive oxygen species (ROS) are highly reactive chemicals formed from diatomic oxygen (). Examples of ROS include peroxides, superoxide, hydroxyl radical, singlet oxygen, and alpha-oxygen. The reduction of molecular oxygen () produces superoxide (), which is the precursor to most other reactive oxygen species: :O2 + e^- -> \ ^\bullet O2- Dismutation of superoxide produces hydrogen peroxide (): :2 H+ + \ ^\bullet O2^- + \ ^\bullet O2^- -> H2O2 + O2 Hydrogen peroxide in turn may be partially reduced, thus forming hydroxide ions and hydroxyl radicals (), or fully reduced to water: :H2O2 + e^- -> HO^- + \ ^\bullet OH :2 H+ + 2 e- + H2O2 -> 2 H2O In a biological context, ROS are byproducts of the normal metabolism of oxygen. ROS have roles in cell signaling and homeostasis. ROS are intrinsic to cellular functioning, and are present at low and stationary levels in normal cells. In plants, ROS are involved in metabolic processes related to photoprotection and toleran ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mutagenic
In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in animals, such mutagens can therefore be carcinogens, although not all necessarily are. All mutagens have characteristic mutational signatures with some chemicals becoming mutagenic through cellular processes. The process of DNA becoming modified is called mutagenesis. Not all mutations are caused by mutagens: so-called "spontaneous mutations" occur due to spontaneous hydrolysis, errors in DNA replication, repair and recombination. Discovery The first mutagens to be identified were carcinogens, substances that were shown to be linked to cancer. Tumors were described more than 2,000 years before the discovery of chromosomes and DNA; in 500 B.C., the Greek physician Hippocrates named tumors resembling a crab ''karkinos'' (from which the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroperoxyl
The hydroperoxyl radical, also known as the hydrogen superoxide, is the protonated form of superoxide with the chemical formula HO2. This species plays an important role in the atmosphere and as a reactive oxygen species in cell biology. Structure and reactions The molecule has a bent structure. The superoxide anion, , and the hydroperoxyl radical exist in equilibrium in aqueous solution: : + H2O HO2 + OH− The p''K''a of HO2 is 4.88. Therefore, about 0.3% of any superoxide present in the cytosol of a typical cell is in the protonated form. It oxidizes nitric oxide to nitrogen dioxide: :NO + HO2 → NO2 + HO Reactive oxygen species in biology Together with its conjugate base superoxide, hydroperoxyl is an important reactive oxygen species. Unlike , which has reducing properties, HO2 can act as an oxidant in a number of biologically important reactions, such as the abstraction of hydrogen atoms from tocopherol and polyunstaturated fatty acids in the lipid bilaye ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroxyl Radical
The hydroxyl radical is the diatomic molecule . The hydroxyl radical is very stable as a dilute gas, but it decays very rapidly in the condensed phase. It is pervasive in some situations. Most notably the hydroxyl radicals are produced from the decomposition of hydroperoxides (ROOH) or, in atmospheric chemistry, by the reaction of excited atomic oxygen with water. It is also important in the field of radiation chemistry, since it leads to the formation of hydrogen peroxide and oxygen, which can enhance corrosion and SCC in coolant systems subjected to radioactive environments. In organic synthesis, hydroxyl radicals are most commonly generated by photolysis of 1-hydroxy-2(1''H'')-pyridinethione. Notation The unpaired electron of the hydroxyl radical is officially represented by a middle dot, •, beside the O. Biology Hydroxyl radicals can occasionally be produced as a byproduct of immune action. Macrophages and microglia most frequently generate this compound when expos ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polyunsaturated Fatty Acid
Polyunsaturated fatty acids (PUFAs) are fatty acids that contain more than one double bond in their backbone. This class includes many important compounds, such as essential fatty acids and those that give drying oils their characteristic property. Polyunsaturated fatty acids can be classified in various groups by their chemical structure: * methylene-interrupted polyenes * conjugated fatty acids * other PUFAs Based on the length of their carbon backbone, they are sometimes classified in two groups: * short chain polyunsaturated fatty acids (SC-PUFA), with 18 carbon atoms * long-chain polyunsaturated fatty acids (LC-PUFA) with 20 or more carbon atoms Dietary sources Types Methylene-interrupted polyenes These fatty acids have 2 or more ''Cis-trans isomerism, cis'' double bonds that are separated from each other by a single methylene bridge (--). This form is also sometimes called a ''divinylmethane pattern''. The essential fatty acids are all omega-3 and -6 methylene-i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lipid Peroxidation Pathway
Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology. Lipids may be broadly defined as hydrophobic or amphiphilic small molecules; the amphiphilic nature of some lipids allows them to form structures such as vesicles, multilamellar/ unilamellar liposomes, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": ketoacyl and isoprene groups. Using this approach, lipids may be divided into eight categories: fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, saccharolipids, and polyketides (derived from con ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
