Types of Free Radicals
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1 Terminology Lipid Oxidation and Lipid peroxidation Free Radicals and Reactive oxygen species Fatty acyl group and methylene group Hydroperoxides and lipid peroxides Peroxyl radicals and alkoxyl radicals Oxidation and reduction Homolytic and heterolytic fission Fenton Reaction Haber-Weiss reaction (Metal-catalyzed Fenton reaction) Ferryl and perferryl Heme and non-heme iron Ischemic conditions
2 Types of Free Radicals Reactive Oxygen Species Peroxyl, alkoxyl rdaicals, and Lipid (alkyl) radicals Thiyl radicals Nitric oxide radical Carbon-centered radicals
3 Reactive Oxygen Species Ground-state oxygen ( 3 O 2 ) Superoxide anion (O 2- ) Singlet oxygen ( 1 O 2 ) Ozone (O 3 ) Hydrogen peroxide (H 2 O 2 ) Hydroperoxyl radical (HO2.) Hydroxyl radical (OH )
4 Free Radical Half-Life at 37ºC Radical Symbol Half-Life Time Hydroxyl.OH one nanosecond Singlet Oxygen 1 O 2 one microsecond Superoxide.O 2 one microsecond Alkoxyl.OL one microsecond Peroxyl LOO. ten milliseconds Nitric Oxide NO. few seconds
5 Orbitals Electrons has some of the properties of a particle, and some of the properties of a wave motion As a result, the position of an electron at a given time cannot be precisely located, but only the region of space where it is most likely to be. These regions are referred to as orbitals
6 Sketches of the electron density for the first three shells
7 Orbitals available in the principal electron shells Principal Sublevels in number of number of number of electrons quantum main energy electrons orbitals (n 2 ) electrons per main energy per sublevel number level (n sublevel) level (2n 2 ) 1 s s p s p d s p 3 6 d 5 10 f 7 14
8 Quantum numbers Four quantum numbers: 1. Principal quantum number (n): Indicates the main energy levels occupied by the electron Values of n are positive integers: n=1 is closest to the nucleus, and lowest in energy The number of orbitals possible per energy level is equal to n 2 2. Angular momentum quantum number Governs the shape of the orbitals number of orbital shapes = n: shapes are designated s,p,d,f 3. Spin quantum number Indicates the fundamental spin state of an electron in an orbital Two possible values for spin: +½ or -1/2 A single orbital can contain only 2 electrons, which have opposite spin
9 Electron configuration Aufbau Principle: An electron occupies the lowest energy orbital that can receive it. Hund s rule: If orbitals of equal energy are available (e.g., 2p orbitals in the L-shell), each is filled with one electron before any receives two. Also, all electrons in singly occupied orbitals must have the same spin. Pauli s exclusion principle: an atomic orbital cannot contain more than two electrons. The order of electron filling 1s 2s 2p 3s 3p 4s 3d 4p 5s 4d 5p 6s 4f 5d 6p 7s 5f
10 Electron Configuration of Atoms
11 Electron States of ROS
12 Transition metal Some of the d-block elements with their inner shell of electrons is not complete (the electrons in the fourth shell are filled, but all the d-orbitals of the third sell are not yet full)
13 Bond Energy and Lipid Oxidation Bond Strength (kcal/mol) H-O-H, 119; RO-H, ; ROO-H, ~90; Ar-H, 112; ArO-H, 85; NH 2 -H, 107, RS-H, ~90; ArS-H, ~84 Bond energies in kcal/mol of C-H bonds in polyunsaturated fatty acids H H H H H H H C C C C=C C C= C C C H H H H H H H H H H
14 Unsaturated fatty acids Oleic acid: CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 COOH Alpha-linolenic acid: CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH Linoleic acid: CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH Arachidonic acid CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 3 COOH Eicosapentaenoic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH (CH 2 ) 5 COOH Docosahexaenoic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH =CH(CH 2 ) 3 COOH
15 Enzymatic peroxidation Cyclooxygenase and lipoxygenase catalyze the reactions between oxygen and polyunsaturated fatty acids The main function of enzymes are generating superoxide, which serves as a reducing agent for ferric iron complexes in microsomes Enzymic lipid peroxidation in skeletal muscle microsomes is dependent on NADH or NADPH and requires ADP and Fe(II) or Fe(III) for maximum rate. Iron(II) and its complexes stimulate membrane peroxidation more than does iron(iii)
16 Photo-oxidation A quicker reaction than autoxidation Singlet oxygen is involved In the presence of sensitizers: chlorophyll, porphyrins, myoglobin, riboflavin, bilirubin, erythrosine, rose bengal, methylene blue... Inhibited by carotenoids: through an interference with the formation of singlet oxygen from the oxygen molecule Tocopherols inhibit photo oxidation by quenching the previously formed singlet oxygen
17 Homolytic and heterolytic fission Homolytic fission: A:B -----> A. + B. H 2 O -----> HO. + H. Heterolytic fission: A:B -----> A:- + B + H 2 O -----> HO - + H +
18 Function of Iron Fenton Reaction Fe 2+ -dependent decomposition of H 2 O 2 (Fenton reaction) Fe 2+ + H 2 O > Fe 3+ +.OH + OH - Fe 2+ + H 2 O > ferryl? -----> Fe 3+ +.OH + OH - Sources of iron for the Fenton reaction in vivo: released iron from injured tissues by cell damages through toxin and other mechanisms
19 Haber-Weiss Reaction Fe 3+ + O > Fe 2+ + O 2 Fe 2+ + H 2 O > Fe 3+ +.OH + OH - Net O 2- + H 2 O > O 2 +.OH + OH - (metal-catalyzed Haber-Weiss reaction or superoxidedriven Fention reaction)
20 MECHANISMS OF FATTY ACID OXIDATION
21 Process of Lipid Oxidation - Autoxidation Initiation RH + (reactive oxygen species) OH -->R + H 2 O Propagation R + O > ROO ROO + RH > R + ROOH ROOH > RO + HO - Termination R + R > RR R + ROO > ROOR ROO + ROO > ROOR + O 2
22 Initiation The attack of a ROS able to abstract a hydrogen atom from a methylene group (- CH 2 -). Generates easily free radicals from polyunsaturated fatty acids..oh is the most efficient ROS to do that attack Energy requirement for radical production by rupture of a CH bond is about 80 kcal
23 Initiation - continued The presence of a double bond in the fatty acid weakens the C-H bonds on the carbon atom adjacent to the double bond and so makes H-removal easier Metal activation, enzyme catalysis or photooxidation: Less energy is required Inhibited by tocopherols, mannitol and formate
24 Degree of unsaturation in Fatty Acids
25 1. Diene Conjugation Propagation
26 2. Oxygen uptake Propagation - Continued
27 Propagation - Continued 3. Autoxidation ROOH + Fe 2+ -complex --- Fe 3+ -complex --- RO. + OH - ROOH + Fe 3+ -complex --- ROO. + H + + Fe 2+ -complex
28 Termination Formation of hydroperoxides: ften achieved by reaction of a peroxyl radical with a-tocopherol: chain breaking Radical-Radical reactions R + R > RR R + ROO > ROOR ROO + ROO > ROOR + O 2
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