Trends in Pharmacology and Biochemistry. Faculdade de Ci. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. L- amino acid oxidases are enzymes found in several organisms, including venoms of snakes, where they contribute to the toxicity of ophidian envenomation. Their toxicity is primarily due to enzymatic activity, but other mechanisms have been proposed recently which require further investigation. L- amino acid oxidases exert biological and pharmacological effects, including actions on platelet aggregation and the induction of apoptosis, hemorrhage, and cytotoxicity. Amino Acids The Building Blocks for a Healthy Body and Mind. The twenty amino acids that keep you alive, healthy, and energetic. Alanine, Arginine, Asparagine. Anchovies (Engraulidae): e.g., Peruvian anchoveta (Engraulis ringens); Japanese anchovy (Engraulis japonicus). Herrings, Menhaden, Sardines and Shads (Clupeidae). These proteins present a high biotechnological potential for the development of antimicrobial, antitumor, and antiprotozoan agents. This review provides an overview of the biochemical properties and pharmacological effects of snake venom L- amino acid oxidases, their structure/activity relationship, and supposed mechanisms of action described so far. Composition of Snake Venoms. During the continuing evolution of snakes, according to Kardong . At first the discharge’s main function was to lubricate the snake’s food, but with the passage of time, some enzymes mixed with secretions allowing for the emergence of more elaborate and potentially toxic proteins, used in the immobilization of prey. A quantitative increase in the production of these secretions as well as a qualitative improvement of toxic proteins promoted a gain in absolute discretion in defense against predators . Qualitatively, snake venoms consist of a mixture of protein with or without catalytic activity such as phospholipases A2 (PLA2), proteases, hyaluronidases, L- amino acid oxidases (LAAOs), acetylcholinesterases, growth factors, protein C activators, lectins, and von Willebrand factor- binding proteins; peptides mainly comprising bradykinin potentiators and disintegrins; low molecular weight organic compounds such as carbohydrates, serotonin, histamine, citrate, and nucleosides; and inorganic ions such as calcium, cobalt, magnesium, copper, iron, and potassium, as well as enzymatic inhibitors . L- Amino Acid Oxidases. LAAOs are widely distributed in many different species including insects, fungi, bacteria, and snakes . Subsequently, Blanchard et al. Regarding snake venoms, this class of molecules was only detected in 1. Zeller and Maritiz . In 1. 97. 9, Iwanaga and Suzuki . Snake venom LAAOs (SV- LAAOs) are usually homodimeric with cofactors FAD (Flavin Adenine Dinucleotide) or FMN (Flavin Mononucleotide) covalently linked to their chemical structure. The yellow color of venoms rich in these enzymes is related to the presence of the pigment riboflavin present in the cofactors, a fact that facilitates its purification. Quantitatively, there are inter- and intraspecific variations in the content of this enzyme in the whole venom (Table 1), and therefore there is color variance between the venoms. In exceptional cases, one gland of the same individual may produce yellow venom and the other gland colorless venom as observed in Crotalus viridis helleri . LAAOs exhibit catalytic specificity for long chain hydrophobic and aromatic amino acids and are active in a wide range of p. Hs and temperatures. Their structures, molecular masses, and isoelectric points are quite varied. They are able to induce changes in platelet function, which cause local effects on plasma clotting disorders among other things. LAAOs are capable of inducing apoptosis in various cell lines and show antimicrobial and antiparasitic activity. According to Ande et al. Enzymatic Activity of L- Amino Acid Oxidases. LAAOs (EC 1. 4. 3. L- amino acids. During the reduction half- reaction, the amino acid substrate is oxidized to an imino acid, with a concomitant reduction of the FAD cofactor. The imino acid then undergoes nonenzymatic hydrolysis, yielding . Another oxidation half- reaction completes the catalytic cycle, reoxidizing FADH2 in the presence of molecular oxygen and thus generating hydrogen peroxide (Figure 1). Figure 1: Mechanism of chemical reaction catalyzed by L- amino acid oxidases (LAAOs) . Furthermore, the correlation between the production of LAAOs and their utilization in metabolic pathways involving nitrogen, as well as the production of hydrogen peroxide, opens perspectives for new applications of these enzymes as bactericidal, antiviral, and antitumor agents, making them a promising biotechnological agent. Thus various research groups have studied LAAOs isolated from different snake species . Importance of Hydrogen Peroxide. The hydrogen peroxide generated during the enzymatic reaction is a highly toxic oxygen reactive species that is capable of acting on nucleic acids, proteins, and plasma cell membranes . This reactive oxygen species, according to Ande et al. The process of necrosis could be related to the direct action of hydrogen peroxide on the plasma cell membrane, since within the mechanism of apoptosis the development of morphological, biochemical, and molecular changes leads to cell death. The most common morphological changes were chromatin condensation, reduction and disintegration of nucleolus volume, and others. It also seems to be involved in the cytotoxic mechanisms of the enzyme which may ultimately represent another defense mechanism of the organism in response to the environment. Enzymatic Kinetics of L- Amino Acid Oxidases. Kinetic studies suggest that LAAOs present preferential catalytic specificity for hydrophobic and aromatic L- amino acids (Table 1), whereas their affinity for polar and basic amino acids is low . Positively charged amino acids such as L- lysine and L- arginine present unfavorable electrostatic interactions with the catalytic site of the enzyme . The kinetic parameters and Kcat shown in Table 2 are very useful for the study and comparison of different enzymes in relation to their substrate. Each enzyme presents optimal and Kcat values that reflect the cellular environment, substrate concentration, and chemical characteristics of the reaction catalyzed. The maximum velocity () reached in each enzymatic reaction is associated with the concentration of the substrate present in the medium and with and is also specific for each substrate . Effect of p. H on the Enzymatic Kinetics of L- Amino Acid Oxidases. The oxidation of L- amino acids by LAAOs happens in a wide range of p. Hs. This maximal specific activity of each LAAO is related to the optimum p. H for each type of amino acid acting as the substrate . Other amino acids such as L- isoleucine, L- tryptophan, and L- lysine showed optimum p. Hs of 7. 5, 8. 0 and 9. LAAOs also catalyze specific oxidoreduction reactions within a broad range of medium p. Hs . The different profiles of specificity in terms of substrate and p. H are related to the acid- base behavior of the enzyme in response to the amino acid. At a certain p. H, both the enzyme and the substrate are in ionic equilibrium, permitting a better fit of the substrate in the active site of the enzyme and consequent maximum oxidation. Snake venom LAAOs can suffer two types of reversible inactivation. One factor inducing inactivation is a change in p. H to values close to neutral, resulting in a spontaneous structural change of the enzyme to its inactive configuration. If the p. H is lowered, the active conformation of the enzyme is restored. The steady state is reached at a p. H ranging from 5. H levels . This type of inactivation can be prevented by the addition of monovalent anions, substrates, and substrate analogs and is characterized by high activation energy. Effect of Metal Ions and Enzymatic Inhibitors on the Enzymatic Kinetics of L- Amino Acid Oxidases. Mackessy . The activity of these enzymes, including that of the LAAOs, was inhibited in the presence of EDTA, N- ethylmaleimide, and 1,1. PMSF and glutathione. In the presence of enzymatic inhibitors, as mentioned above, LAAO cofactors NAD or FAD are reduced, causing inactivation of the enzyme . The LAAO of Crotalus adamanteus requires Mg. Other ions such as manganese and calcium do not affect the activity of these enzymes. The inhibitory action of these ions might be related to their ability to reversibly bind to thiol groups of cysteines present in the active site of the enzyme, reducing its activity . Effect of Temperature on the Enzymatic Activity of L- Amino Acid Oxidases. The specific activity of some LAAOs depends on the experimental temperature. These enzymes remain active for a variable period of time at a broad range of temperatures (0. Exposure to temperatures higher than 5. Temperatures lower than 2. Moreover, LAAOs are also progressively inactivated when submitted to freezing or lyophilization . These types of inactivation by freezing, and also by alterations in p. H as cited above, induce substantial conformational changes that can be demonstrated by circular dichroism . These changes involve alterations in the binding of the enzyme to substrates and lack of binding to arachidonic acid (competitive inhibitor), as well as alterations in the affinity of the flavin coenzyme for electrons. Reversible inactivation by freezing involves specific regions of the catalytic site of the enzyme, affecting the redox properties of the cofactor- substrate complex . Purification of L- Amino Acid Oxidases. The first reports of isolation of LAAOs date back to the 1. Singer and Kearney . Later Wellner and Meister . A large number of these proteins have been isolated using basically the same chromatographic strategy, that is, fractionation of the venom by size exclusion chromatography, followed by hydrophobic interaction chromatography of the fractions of interest. This step can be repeated and, finally, the highly purified protein is applied to reverse- phase HPLC. However, each research group has adapted the steps of isolation to its specific protein and laboratory conditions.
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