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PubMed1998

UV light-induced cross-linking of nucleosides, nucleotides and a dinucleotide to the carboxy-terminal heptad repeat peptide of RNA polymerase II as studied by mass spectrometry.

We report here the results of a study to assess the usefulness of mass spectrometry as a method for rapidly locating cross-linking sites in peptides modified by UV irradiation in the presence of nucleic acid components. For this study, we selected two nucleosides (thymidine and 5-bromo-2'-deoxyuridine), two nucleotides (thymidine-5'-monophosphate and 5-bromo-2'-deoxyuridine-5'-monophosphate) and a dinucleotide (thymidylyl-[3'-->5']-2'-deoxyadenosine). The peptide picked was SPSYSPT (L-seryl-L-prolyl-L-seryl-L-tyrosyl-L-seryl-L-prolyl-L-threonine), the heptad repeat unit found in the largest subunit of the RNA polymerase II multiprotein complex. Modified peptides were isolated by reversed-phase HPLC. Molecular mass measurements confirmed that covalent adducts had been formed. High-energy tandem collision-induced dissociation mass spectrometry pinpointed the location of cross-linking in each modified peptide as being at the tyrosine residue. These results indicate that mass spectrometry is a potentially applicable technique for location of cross-linking sites in peptides, modified by attachment of nucleosides, nucleotides and dinucleotides. Such modified peptides would be among the products expected after application of standard proteolytic and nucleolytic digestion protocols to digestion of cross-linked DNA-protein complexes.

Amino Acid Sequence↗
PubMed1983

Current high performance liquid chromatographic methodology in analysis of nucleotides, nucleosides, and their bases. II.

This review of HPLC technology is presented in two parts, the first of which appeared in Volume 1, Number 5 of this journal. Part I presented an introduction to chromatography, sample preparation, and basic information on chromatographic theory and terminology, modes, and instrumentation. Also covered in Part I was a discussion of stationary and mobile phase parameters which can be varied to optimize separations. Part II of the review which follows covers peak identification, quantification, and selected applications of HPLC for metabolic profiling, for assays of adenosine and cyclic nucleotides in studies of disease processes and for enzyme assays. The paper concludes with a short discussion of future trends for HPLC in biomedical research and clinical chemistry.

Adenosine Deaminase↗
PubMed1983

Current high-performance liquid chromatographic methodology in analysis of nucleotides, nucleosides, and their bases. I.

This review of HPLC technology is presented in two parts. An introduction to chromatography, sample preparation, and basic information on chromatographic theory and terminology, modes, and instrumentation is presented here. A discussion of stationary and mobile phase parameters which can be varied to optimize separations is also presented here. The second part of the review, which will appear in the next issue, will cover peak identification, quantification, and selected applications. The applications include short discussions of applications of HPLC for metabolic profiling, for assays of adenosine and cyclic nucleotides in studies of disease processes, and for enzyme assays. The paper concludes with a short discussion of future trends for HPLC in biomedical research and clinical chemistry.

Chromatography, High Pressure Liquid↗
PubMed1981

Effect of renal failure on erythrocyte purine nucleotide, nucleoside and base concentrations and some related enzyme activities.

1. We have studied purine metabolism in renal failure using high-pressure liquid chromatography to determine metabolite concentrations in erythrocytes and plasma, and microradiochemical assays of enzyme activity in erythrocytes. 2. The mean activities of some of the enzymes involved in purine metabolism were raised in renal failure. Significant elevations of adenylate kinase (EC 2.7.4.3), purine nucleoside phosphorylase (EC 2.4.2.1), hypoxanthine phosphoribosyltransferase (EC 2.4.2.8) and adenosine deaminase (EC 3.5.4.4) but not of adenine phosphoribosyltransferase (EC 2.4.2.7) and ribosephosphate pyrophosphokinase (phosphoribosylpyrophosphate synthetase; EC 2.7.6.1) activities were demonstrated. However, there was an overlap between results from patients with renal failure and normal (control) subjects. Erythrocyte phosphoribosylpyrophosphate levels were also unchanged. 3. Erythrocyte nucleotide concentrations especially those of inosine were raised in renal failure. 4. The plasma inosine was reduced in renal failure. 5. The significance of these changes is discussed.

Adolescent↗
PubMed1982

Interconversion and uptake of nucleotides, nucleosides, and purine bases by the marine bacterium MB22.

Whole cells and isolated membranes of the marine bacterium MB22 converted nucleotides present in the external medium rapidly into nucleosides and then into bases. Nucleosides and purine bases formed were taken up by distinct transport systems. We found a high-affinity common transport system for adenine, guanine, and hypoxanthine, with a Km of 40 nM. This system was inhibited noncompetitively by purine nucleosides. In addition, two transport systems for nucleosides were present: one for guanosine with a Km of 0.8 microM and another one for inosine and adenosine with a Km of 1.4 microM. The nucleoside transport systems exhibited both mixed and noncompetitive inhibition by different nucleosides other than those translocated; purine and pyrimidine bases had no effect. The transport of nucleosides and purine bases was inhibited by dinitrophenol or azide, thus suggesting that transport is energy dependent. Inside the cell all of the substrates were converted mainly into guanosine, xanthine, and uric acid, but also anabolic products, such as nucleotides and nucleic acids, could be found.

Adenine↗
PubMed1997

Effects of OG-VI, a nucleoside-nucleotide mixture, on ischemic myocardial metabolism in dogs.

BACKGROUND: OG-VI is a solution composed of 30 mmol/l inosine, 30 mmol/l sodium 5'-guanylate, 30 mmol/l cytidine, 22.5 mmol/l uridine, and 7.5 mmol/l thymidine, which is known to improve myocardial stunning. OBJECTIVE: To study the effect of OG-VI on myocardial energy and carbohydrate metabolism during ischemia. METHODS: Ischemia was induced in pentobarbital-anesthetized open-chested dogs for 3 min by left anterior descending coronary artery ligation. Saline, 1.2 mmol/kg per min OG-VI, or 12 mmol/kg per min OG-VI was infused at 0.1 ml/kg per min, starting 30 min before the onset of ischemia. The myocardium was extracted 3 min after the onset of ischemia, and used to determine the tissue levels of energy and carbohydrate metabolites. RESULTS: Ischemia decreased the levels of ATP and fructose 1,6 diphosphate significantly, and increased those of AMP, glucose 6 phosphate, fructose 6 phosphate and lactate. OG-VI infusion preserved the adenine nucleotide levels significantly in 3 min ischemic hearts, and attenuated the ischemia-induced alteration of carbohydrate metabolism. CONCLUSION: OG-VI may improve the myocardial metabolic derangement induced by ischemia.

Animals↗
PubMed2006

Palladium-catalyzed direct N-arylation of nucleosides, nucleotides, and oligonucleotides for efficient preparation of dG-N2 adducts with carcinogenic amino-/nitroarenes.

A method for direct palladium-catalyzed N-arylation reaction of nucleobases was developed for the convenient synthesis of DNA adducts with carcinogenic compounds. Using xantphos as the phosphine ligand and tetraethylammonium fluoride as the base in DMSO, several o-iodonitroarenes could be efficiently coupled with 2'-deoxyguanosine, 2'-deoxyadenosine, and 2'-deoxycytidine. The presence of a 3'-phosphate group in the deoxyribose moiety was found to be compatible with this N-arylation reaction; further, oligonucleotides could serve as substrates. The facile nitroreduction of the coupling compounds (12) yielded 2'-deoxyguanosin-N2-ylarylamine adducts, which are known to be biologically important. Compound 12 was easily converted to phosphoramidite derivatives, allowing the preparation of site-specific modified oligonucleotides with arylamine after the nitroreduction.

Carcinogens↗
PubMed1976

Isocratic separation of some purine nucleotide, nucleoside, and base metabolites from biological extracts by high-performance liquid chromatography.

Separation of ATP, ADP, AMP, adenine, adenosine, cAMP, ITP, IDP, IMP, hypoxanthine, inosine, cIMP, the guanine series, NAD, NADPH, xanthine, 3-methylxanthine, theobromine, theophylline, and caffeine was accomplished using high-performance liquid chromatography with a microparticulate reversed-phase column. Under isocratic conditions all compounds could be eluted with reasonable resolution and retention time. Quantitation by peak height for several of the compounds was used to the 10-ng level.

Adenine Nucleotides↗