The tandem of free radicals and methylglyoxal

Kalapos, Miklös Péter

doi:10.1016/j.cbi.2007.11.009

Cited by 222 publications

(171 citation statements)

References 133 publications

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“…We have previously reported a remarkable stereoselective reaction of methylglyoxal (MG, pyruvaldehyde) with α-aminoazaheterocycles, as 2-aminopyridine, the nucleic base adenine and adenine nucleosides, leading in high yield to cyclic adducts in water under mild conditions at 50 to 70° C (Figure 8) [26][27]. On another hand, the reactions of MG with the guanidinine function of arginine residues in proteins are considered to be involved in diabete complications because of the MG production by degradation of glucose in vivo [28][29][30]. The formations of fluorescent 3-hydroxypyrimidine biomarkers called Argpyrimidines and of MG adducts from arginine residues have been independently demonstrated in vivo and/or in vitro from the corresponding amino acid derivatives ( Figure 9) but were not related [31][32][33].…”

Section: Prebiotic Synthesis Of Pyridoxal (Vitamin B6) and Related Comentioning

confidence: 99%

Key steps from the “RNA World” to the “DNA World”

Renard

Maurin

Chambert

et al. 2014

BIO Web of Conferences

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Abstract. In the « RNA World » hypothesis of the origin of life, RNAs are assumed to be the central macromolecules able to self-replicate, conserve information and catalyze the reactions necessary for a primitive metabolism and many enzymatic cofactors may be regarded as molecular fossils of the "RNA World". In the key steps involved in the transition from the RNA World to the DNA World, two main steps can be distinguished: (i) the synthesis of 2'-deoxyribonucleotides from ribonucleotides catalyzed nowadays by the enzyme ribonucleotide reductase and (ii) the synthesis of thymine, a base specific for DNA, from uracil which is a base specific for RNA, catalyzed today by the enzyme thymidylate synthase. In regard to the chemistry of sulfur used by both enzymes for achieving their respective catalysis, we were interested in the search for simple sulfur reactions able to catalyze such transformations and report here on first results in an approach from thionucleosides to the catalysis involved in the conversion of uracil to thymine. In the RNA World, the recruitment of cofactors was crucial to expand the catalytic repertoire of RNA and we also describe interesting preliminary results obtained in the prebiotic synthesis of pyridoxal (vitamin B6) that is the precursor of the key coenzyme pyridoxal phosphate (PLP) able to catalyze nowadays seven different enzymatic reactions.

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Section: Prebiotic Synthesis Of Pyridoxal (Vitamin B6) and Related Comentioning

confidence: 99%

Key steps from the “RNA World” to the “DNA World”

Renard

Maurin

Chambert

et al. 2014

BIO Web of Conferences

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“…Oxidation of some amino acids can also lead to MGO formation under physiological conditions. For example, threonine and glycine can be converted to aminoacetone and succinylacetone, MGO precursors (Kalapos, 2008a). It should be noted that MGO can be formed from dihydroxyacetone phosphate in the reaction catalysed by bacterial MGO synthase, however, it is unknown whether this enzyme and this kind of MGO generation also exist in animals (Kalapos, 2008b).…”

Section: Enzymatic Reactionsmentioning

confidence: 99%

“…The concentration of fructosamine in blood plasma of healthy individuals has been found about 140 µM (Kato et al, 1989). Physiological steady-state concentrations of MGO ranged from 120 to 650 nM (Kalapos, 2008a;Talukdar et al, 2009). Since there are no standard methods to evaluate the steady-state levels of RCS, different techniques applying in various laboratories yield different results.…”

Section: Steady-state Concentration Of Carbonyl Compounds In Vivo Andmentioning

confidence: 99%

“…Low molecular mass reactive carbonyls (e.g. MGO) were found to decrease the level of reduced gluthatione (GSH) in different cells in vivo (Kalapos, 2008a). The situation seems to be more dramatic if one would take into account that GSH is a cofactor for certain antioxidant and antiglycated enzymes, thus an effective cellular protector against both oxidative and carbonyl stresses.…”

Section: Wwwintechopencommentioning

confidence: 99%

“…It is well known that single stranded nucleic acids are particularly susceptible to modification by RS. The mutagenicity of such RCS as MGO and involvement of ROS in this effect is known for a long time (Kalapos, 2008a). Reactive carbonyl and oxygen species induce mutations frequently detected in oncogenes or tumor suppressor genes from human tumors, and correlate to alterations in cell cycle control and gene expression.…”

Section: Cytotoxic Genotoxic and Mutagenic Effectsmentioning

confidence: 99%

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Oxidative stress is among the major causes of toxicity due to interaction of reactive oxygen species (ROS) with cellular macromolecules and structures and interference with signal transduction pathways. ROS originate from exogenous and endogenous sources; among the former are UV and ionizing radiation and xenobiotics, the latter are represented by a number of metabolic reactions. The mitochondrial respiratory chain, specially from Complexes I and III, is considered the main origin of ROS particularly under conditions of high membrane potential, but several other sources may be important for ROS generation, such as mitochondrial p66 Shc , monoamine oxidase, α‐ketoglutarate dehydrogenase and extramitochondrial xanthine oxidase, cytochrome P450, nitric oxide synthase, peroxisomal enzymes, plasma membrane NADPH oxidases, and lipoxygenase, with the participation of redox‐active metal ions. ROS are able to oxidatively modify lipids, proteins, carbohydrates and nucleic acids and to activate/inactivate signalling pathways by oxidative modification of redox‐active factors. Cells are endowed with several defence mechanisms, including repair or removal of damaged molecules, and antioxidant systems, either enzymatic or nonenzymatic. Oxidative stress is at the basis of ageing and many pathological disorders, such as ischaemic diseases, neurodegenerative diseases, diabetes and cancer, although the underlying mechanisms are not always completely understood.

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The tandem of free radicals and methylglyoxal

Cited by 222 publications

References 133 publications

Key steps from the “RNA World” to the “DNA World”

Key steps from the “RNA World” to the “DNA World”

Interplay Between Oxidative and Carbonyl Stresses: Molecular Mechanisms, Biological Effects and Therapeutic Strategies of Protection

Reactive Oxygen Species in the Induction of Toxicity

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