Reaction of guanosine with glucose under oxidative conditions

Seidel, Wolfgang; Pischetsrieder, Monika

doi:10.1016/s0960-894x(98)00343-6

Cited by 24 publications

(18 citation statements)

References 16 publications

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“…The CMdG and CEdG adducts of deoxyguanosine are expected to be more stable. These adducts are also formed by glycation of DNA with glucose [13,20] and ascorbic acid [18]. This is not surprising, since glucose and other saccharide derivatives fragment to form glyoxal and methylglyoxal in the early stages of glycation reactions -the Namiki pathway of glycation [21].…”

Section: Glycation Of Nucleotidesmentioning

confidence: 97%

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Protecting the genome: defence against nucleotide glycation and emerging role of glyoxalase I overexpression in multidrug resistance in cancer chemotherapy

Thornalley

2003

Biochemical Society Transactions

116

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Glycation of nucleotides in DNA forms AGEs (advanced glycation end-products). Nucleotide AGEs are: the imidazopurinone derivative dG-G [3-(2'-deoxyribosyl)-6,7-dihydro-6,7-dihydroxyimidazo[2,3-b]purin-9(8)one], CMdG ( N (2)-carboxymethyldeoxyguanosine) and gdC (5-glycolyldeoxycytidine) derived from glyoxal, dG-MG [6,7-dihydro-6,7-dihydroxy-6-methylimidazo-[2,3-b]purine-9(8)one], dG-MG(2) [ N (2),7-bis-(1-hydroxy-2-oxopropyl)deoxyguanosine] and CEdG [ N (2)-(1-carboxyethyl)deoxyguanosine] derived from methylglyoxal, and dG-3DG [ N (2)-(1-oxo-2,4,5,6-tetrahydroxyhexyl)deoxyguanosine] derived from 3-deoxyglucosone and others. Glyoxal and methylglyoxal induce multi-base deletions, and base-pair substitutions - mostly occurring at G:C sites with G:C-->C:G and G:C-->T:A transversions. Suppression of nucleotide glycation by glyoxalase I and aldehyde reductases and dehydrogenases, and base excision repair, protects and recovers DNA from damaging glycation. The effects of DNA glycation may be most marked in diabetes and uraemia. Mutations arising from DNA glycation may explain the link of non-dietary carbohydrate intake to incidence of colorectal cancer. Overexpression of glyoxalase I was found in drug-resistant tumour cells and may be an example of an undesirable effect of the enzymatic protection against DNA glycation. Experimental overexpression of glyoxalase I conferred resistance to drug-induced apoptosis. Glyoxalase I-mediated drug resistance was found in human leukaemia and lung carcinoma cells. Methylglyoxal-mediated glycation of DNA may contribute to the cytotoxicity of some antitumour agents as a consequence of depletion of NAD(+) by poly(ADP-ribose) polymerase, marked increases in triosephosphate concentration and increased formation of methylglyoxal. S - p -Bromobenzylglutathione cyclopentyl diester is a cell-permeable glyoxalase I inhibitor. It countered drug resistance and was a potent antitumour agent against lung and prostate carcinoma. Glyoxalase I overexpression was also found in invasive ovarian cancer and breast cancer.

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Section: Glycation Of Nucleotidesmentioning

confidence: 97%

“…This is not surprising, since glucose and other saccharide derivatives fragment to form glyoxal and methylglyoxal in the early stages of glycation reactions -the Namiki pathway of glycation [21]. The formation of CEdG was associated with depurination of DNA [20].…”

Section: Glycation Of Nucleotidesmentioning

confidence: 99%

Protecting the genome: defence against nucleotide glycation and emerging role of glyoxalase I overexpression in multidrug resistance in cancer chemotherapy

Thornalley

2003

Biochemical Society Transactions

116

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“…Later on, it was shown that CEdG or the analogous derivatives from guanosine, guanine or 9-methylguanine -CEG, CEguanine and CEmG -were also formed from a great variety of other sugars and sugar degradation products, such as glucose, ribose, glucose-6-phosphate, dihydroxyacetone, or ascorbic acid [12,16,18,19]. In the presence of oxygen and glucose, lower concentrations of N 2 -carboxymethyl-guanosine (CMG) were additionally detectable [20,21].…”

Section: Dna Glycation: From Browning To Structuresmentioning

confidence: 99%

“…Since quenching in the ion source by co-eluting matrix components is often observed, Glucose Guanosine 2-(␤-d-Glucopyranosylamino)-guanosine [13] Only at elevated temperatures Glucose Guanosine N 2 -(1-Carboxymethyl)-guanosine (CMG) [20] In the presence of oxygen; also from glyoxal at elevated temperatures Glucose 2 -Deoxyguanosine 2-(␤-d-Glucopyranosylamino)-guanine [13] Only at elevated temperatures Glucose 2 -Deoxyguanosine N 2 -(1-Carboxy-3,4,5-trihydroxypentyl)-2 -deoxyguanosine (CTPdG A,B ) [14] In the presence of propylamine…”

Section: Lc-ms Analysis Of Dna-adductsmentioning

confidence: 99%

Analysis of DNA-bound advanced glycation end-products by LC and mass spectrometry

Bidmon¹,

Frischmann²,

Pischetsrieder³

2007

Journal of Chromatography B

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“…The reaction products, which have been isolated so far, are almost exclusively adducts of 29-desoxyguanosine, which are alkylated at the exocyclic amino group, such as the two diastereomers of N 2 -carboxyethyl-29-deoxyguanosine (CEdG A,B , Scheme 1) or N 2 -carboxymethyl-29-deoxyguanosine [11,14]. There is strong evidence that DNA-AGEs cause loss of the genomic integrity and are therefore potentially genotoxic: consequences of DNA glycation are, for example, depurination [15], singlestrand breaks, and an increase in mutation frequencies [16].…”

Section: Introductionmentioning

confidence: 99%

Detection of DNA‐bound advanced glycation end‐products by immunoaffinity chromatography coupled to HPLC‐diode array detection

Schneider

Georgescu²,

Bidmon

et al. 2006

Molecular Nutrition Food Res

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Sugars and sugar degradation products are formed during food processing, but also endogenously in vivo. In vitro, nucleosides and DNA react readily with these carbonyl compounds during the formation of the two diastereomers of N(2)-carboxyethyl-2'-deoxyguanosine (CEdG(A,B)), leading to a loss of DNA integrity. Only little is known about DNA glycation in vivo and about the influence of nutrition on CEdG formation. In this study, we developed a sensitive method to analyze DNA glycation by HPLC. For this purpose, immunoaffinity chromatography (IAC) using a polyclonal antibody against N(2)-carboxyethylguanine (CEguanine) was coupled to HPLC-DAD. In some samples, peak identity was confirmed by LC-MS/MS. The recovery of CEguanine from the IAC columns was 52.5% +/- 3.6 (n = 4). Thus, it was possible for the first time to detect CEdG(A,B), N(2)-carboxyethylguanosine (CEG(A,B)), and CEguanine in 11 human urine samples. However, due to imprecision of IAC, valid quantification of the adducts could not be achieved. Furthermore, CEdG was also detected in the DNA of cultured human smooth muscle cells (SMCs) and bovine aorta endothelium cells (BAECs). In BAECs, CEdG(A,B) were found by HPLC-DAD and LC-MS/MS after immunoaffinity purification, whereas in SMCs DNA-advanced glycation end-products were only detected with the more sensitive LC-MS/MS method.

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Reaction of guanosine with glucose under oxidative conditions

Cited by 24 publications

References 16 publications

Protecting the genome: defence against nucleotide glycation and emerging role of glyoxalase I overexpression in multidrug resistance in cancer chemotherapy

Protecting the genome: defence against nucleotide glycation and emerging role of glyoxalase I overexpression in multidrug resistance in cancer chemotherapy

Analysis of DNA-bound advanced glycation end-products by LC and mass spectrometry

Detection of DNA‐bound advanced glycation end‐products by immunoaffinity chromatography coupled to HPLC‐diode array detection

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