Anti-crosslinking properties of carnosine: Significance of histidine

Hobart, Laura J.; Seibel, Ines; Yeargans, George S; Seidler, Norbert W.

doi:10.1016/j.lfs.2004.05.002

Cited by 130 publications

(100 citation statements)

References 34 publications

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“…Synthesized endogenously by carnosine-anserine synthetase in many eukaryotes, it is found in long-lived mammalian tissues (such as neurons and muscle tissue) at concentrations up to 20 mM (37,41). It has been shown that protein cross-links induced in vitro by methyglyoxal are eliminated in the presence of carnosine (24). Carnosine may react directly with MG and sequester it; its amino group and imidazole ring may bind to reactive dicarbonyl groups (3,7,24), although the structure of MG-carnosine adducts has yet to be determined (37).…”

Section: Discussionmentioning

confidence: 99%

“…Although its mechanism of action has not been fully determined, there is evidence that both the free amino group derived from the ␤-alanine and the imidazole ring of histidine compete with amino groups of proteins in the presence of reactive dicarbonyl compounds (7,24). In this study we designed assays to determine the effect of carnosine (and other compounds) on survival of cultures of E. coli under a variety of experimental conditions.…”

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confidence: 99%

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Antiglycation Effects of Carnosine and Other Compounds on the Long-Term Survival of Escherichia coli

Pepper

Farrell

Nord

et al. 2010

Appl Environ Microbiol

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Glycation, or nonenzymatic glycosylation, is a chemical reaction between reactive carbonyl-containing compounds and biomolecules containing free amino groups. Carbonyl-containing compounds include reducing sugars such as glucose or fructose, carbohydrate-derived compounds such as methylglyoxal and glyoxal, and nonsugars such as polyunsaturated fatty acids. The latter group includes molecules such as proteins, DNA, and amino lipids. Glycation-induced damage to these biomolecules has been shown to be a contributing factor in human disorders such as Alzheimer's disease, atherosclerosis, and cataracts and in diabetic complications. Glycation also affects Escherichia coli under standard laboratory conditions, leading to a decline in bacterial population density and long-term survival. Here we have shown that as E. coli aged in batch culture, the amount of carboxymethyl lysine, an advanced glycation end product, accumulated over time and that this accumulation was affected by the addition of glucose to the culture medium. The addition of excess glucose or methylglyoxal to the culture medium resulted in a dose-dependent loss of cell viability. We have also demonstrated that glyoxylase enzyme GloA plays a role in cell survival during glycation stress. In addition, we have provided evidence that carnosine, folic acid, and aminoguanidine inhibit glycation in prokaryotes. These agents may also prove to be beneficial to eukaryotes since the chemical processes of glycation are similar in these two domains of life.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Antiglycation Effects of Carnosine and Other Compounds on the Long-Term Survival of Escherichia coli

Pepper

Farrell

Nord

et al. 2010

Appl Environ Microbiol

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“…[25] These properties are, in fact, also a reflection of its antioxidant properties. There is also evidence that carnosine acts as quenchers of reactive and cytotoxic carbonyl species through its ability to form adducts with them.…”

Section: Discussionmentioning

confidence: 99%

Lithium ascorbate as a protector of human blood biomolecules under ethanol impact

Plotnikov¹,

Prokopieva²,

Yarygina³

et al. 2017

Natl J Physiol Pharm Pharmacol

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Background: Alcoholism is an acute social problem worldwide for negative impact on health. This problem is closely associated with social stress and drinking traditions. Previously, it was established exhaustion of blood antioxidant in alcoholism patients. It requires development and investigation of substances with protective properties under ethanol impact, on both cells and biomolecules. Aims and Objectives: Lithium salts are widely used in medicine as mood stabilizers for mental pathologies, including alcoholism. In this work, we investigate lithium ascorbate for the protection of human blood plasma lipids and proteins under ethanol impact. Materials and Methods: Well-known antioxidants -carnosine and ascorbic acid -were used as reference drugs. Heparinized venous blood was used as an experimental substrate. The ethanol and tested substances in the form of water (physiological)solutions were added to blood in vitro. Protection effects were measured and estimated as concentrations of carbonyls proteins and products of lipid peroxidation in blood plasma. Results: It was shown similar protective action of lithium ascorbate and carnosine on human plasma biomolecules against damaging action of ethanol. No protective effect revealed for ascorbic acid. Conclusion: Lithium ascorbate and carnosine were proved to possess the protection effects for blood lipids and proteins under ethanol impact. Normothymic and bloodprotective properties are desirable for psychotropic drugs, and thus, lithium salts could be considered as prospective agents in the treatment of addictions and other pathologies associated with oxidative stress.

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“…Carnosine-like compounds can prevent AGE-induced crosslinking (21). Recently, Seidler et al (22) suggested that histidine is the representative structure for an anti-crosslinking agent. And they proposed that imidazolium group of histidine may stabilize adducts formed at the primary amino group because methylation at N-1 position of imidazole abolished anti-crosslinking activity of histidine.…”

Section: Discussionmentioning

confidence: 99%

Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine

Dai¹,

Nemet²,

Shen³

et al. 2007

Archives of Biochemistry and Biophysics

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We isolated a novel acid-labile yellow chromophore from the incubation of lysine, histidine and Dthreose and identified its chemical structure by one and two-dimensional 1 H and DEPT NMR spectroscopy combined with LC-tandem mass spectrometry. This new cross-link exhibits a UV absorbance maximum at 305 nm and a molecular mass of 451 Da. The proposed structure is 2-amino-5-(3-((4-(2-amino-2-carboxyethyl)-1H-imidazol-1-yl)methyl)-4-(1,2-dihydroxyethyl)-2-formyl-1H-pyrrol-1-yl)pentatonic acid, a cross-link between lysine and histidine with addition of two threose molecules. It was in part deduced and confirmed through synthesis of the analogous compound from n-butylamine, imidazole and D-threose. We assigned the compound the trivial name histidino-threosidine. Systemic incubation revealed that histidino-threosidine can be formed in low amounts from fructose, glyceraldehyde, methylglyoxal, glycolaldehyde, ascorbic acid, and dehydroascorbic acid, but at a much higher yield with degradation products of ascorbic acid, i.e. threose, erythrose, and erythrulose. Bovine lens protein incubated with 10 and 50 mM threose for two weeks yielded 560 and 2840 pmol/mg histidino-threosidine. Histidino-threosidine is to our knowledge the first Maillard reaction product known to involve histidine in a crosslink.

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Anti-crosslinking properties of carnosine: Significance of histidine

Cited by 130 publications

References 34 publications

Antiglycation Effects of Carnosine and Other Compounds on the Long-Term Survival of Escherichia coli

Antiglycation Effects of Carnosine and Other Compounds on the Long-Term Survival of Escherichia coli

Lithium ascorbate as a protector of human blood biomolecules under ethanol impact

Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine

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