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Journal articles on the topic 'Purine synthesis'

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Published: 4 June 2021

Last updated: 25 July 2025

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1

Hasník, Zbyněk, Radek Pohl, Blanka Klepetářová, and Michal Hocek. "Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines." Collection of Czechoslovak Chemical Communications 74, no. 7-8 (2009): 1035–59. http://dx.doi.org/10.1135/cccc2009042.

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A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antivira

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2

Itakura, M., N. Maeda, and K. Yamashita. "Increased rate of purine biosynthesis in rat liver after bilateral adrenalectomy." American Journal of Physiology-Endocrinology and Metabolism 251, no. 4 (1986): E373—E378. http://dx.doi.org/10.1152/ajpendo.1986.251.4.e373.

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In bilaterally adrenalectomized rat liver the increased rate of de novo purine synthesis was shown by the increased [14C]glycine incorporation into hepatic acid-soluble purines with unchanged rapidly miscible glycine pool size and its turnover rate and by the increased rate of chasing of radiolabeled purines. At 24 h after adrenalectomy, the rate of de novo purine synthesis increased by 70%, 5-phosphoribosyl-1-pyrophosphate (PRPP) content increased by 200%, the specific activity of amidophosphoribosyltransferase (EC 2.4.2. 14; ATase) did not change, ATP and GTP showed a 33 and 24% decrease, an

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3

Allen, Shara, Julie L. Zilles, and Diana M. Downs. "Metabolic Flux in Both the Purine Mononucleotide and Histidine Biosynthetic Pathways Can Influence Synthesis of the Hydroxymethyl Pyrimidine Moiety of Thiamine in Salmonella enterica." Journal of Bacteriology 184, no. 22 (2002): 6130–37. http://dx.doi.org/10.1128/jb.184.22.6130-6137.2002.

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ABSTRACT Together, the biosyntheses of histidine, purines, and thiamine pyrophosphate (TPP) contain examples of convergent, divergent, and regulatory pathway integration. Mutations in two purine biosynthetic genes (purI and purH) affect TPP biosynthesis due to flux through the purine and histidine pathways. The molecular genetic characterization of purI mutants and their respective pseudorevertants resulted in the conclusion that <1% of the wild-type activity of the PurI enzyme was sufficient for thiamine but not for purine synthesis. The respective pseudorevertants were found to be informa

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4

Becker, Sidney, Jonas Feldmann, Stefan Wiedemann, et al. "Unified prebiotically plausible synthesis of pyrimidine and purine RNA ribonucleotides." Science 366, no. 6461 (2019): 76–82. http://dx.doi.org/10.1126/science.aax2747.

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Theories about the origin of life require chemical pathways that allow formation of life’s key building blocks under prebiotically plausible conditions. Complex molecules like RNA must have originated from small molecules whose reactivity was guided by physico-chemical processes. RNA is constructed from purine and pyrimidine nucleosides, both of which are required for accurate information transfer, and thus Darwinian evolution. Separate pathways to purines and pyrimidines have been reported, but their concurrent syntheses remain a challenge. We report the synthesis of the pyrimidine nucleoside

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5

Scott, Andrew, Weihua Zhou, Kari Wilder-Romans, et al. "DDRE-28. MECHANISTIC AND THERAPEUTIC LINKS BETWEEN PURINE BIOSYNTHESIS AND DNA DAMAGE IN GLIOBLASTOMA." Neuro-Oncology Advances 3, Supplement_1 (2021): i12. http://dx.doi.org/10.1093/noajnl/vdab024.050.

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Abstract Glioblastoma (GBM) is the most common and aggressive adult brain cancer. Radiation therapy (RT) is a critical treatment modality, and development of RT resistance is the predominant cause of recurrence and mortality in GBM patients. Using cell line models as well as patient-derived xenografts and neurospheres in orthotopic brain tumor models, we have identified increased rates and dependence upon de novo purine biosynthesis as a hallmark of GBM RT resistance. More recently, we have discovered that radiation treatment acutely stimulates flux through de novo purine synthesis in cell lin

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6

Tomlinson, Patricia Tolson, and Carol J. Lovatt. "Nucleotide Metabolism in ‘Washington’ Navel Orange Fruit: I. Pathways of Synthesis and Catabolism." Journal of the American Society for Horticultural Science 112, no. 3 (1987): 529–35. http://dx.doi.org/10.21273/jashs.112.3.529.

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Abstract The capacity of ‘Washington’ navel orange fruit [Citrus sinensis (L.) Osbeck] to synthesize and catabolize purines and pyrimidines was assessed. De novo biosynthesis of purine nucleotide was demonstrated by [14C] bicarbonate incorporation into purine nucleotides, blockage of this process by four known inhibitors, and assimilation of radiolabeled carbon from formate, both carbons of glycine, and carbon-3 of serine into the adenine ring. De novo synthesis of pyrimidines via the orotate pathway in young fruit was demonstrated by incorporation of [14C] bicarbonate and [6-14C]orotic acid i

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7

Rosiers, Christine Des, Stephan Nees, and Eckehart Gerlach. "Purine metabolism in cultured aortic and coronary endothelial cells." Biochemistry and Cell Biology 67, no. 1 (1989): 8–15. http://dx.doi.org/10.1139/o89-002.

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Purine salvage pathways in cultured endothelial cells of macrovascular (pig aorta) and microvascular (guinea pig coronary system) origin were investigated by measuring the incorporation of radioactive purine bases (adenine or hypoxanthine) or nucleosides (adenosine or inosine) into purine nucleotides. These precursors were used at initial extracellular concentrations of 0.1, 5, and 500 μM. In both types of endothelial cells, purine nucleotide synthesis occurred with all four substrates. Aortic endothelial cells salvaged adenine best among purines and nucleosides when applied at 0.1 μM. At 5 an

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8

Šilhár, Peter, Radek Pohl, Ivan Votruba, and Michal Hocek. "Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides." Collection of Czechoslovak Chemical Communications 70, no. 10 (2005): 1669–95. http://dx.doi.org/10.1135/cccc20051669.

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A facile and efficient methodology of the synthesis of 6-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed based on Pd-catalyzed cross-coupling reactions of 6-halopurines or N-protected 2-amino-6-halopurines with (benzoyloxymethyl)zinc iodide followed by deprotection. Regioselective hydroxymethylations of 2,6-dihalopurines were also studied and used for the synthesis of 2-chloro-6-(hydroxymethyl)- or 2,6-bis(hydroxymethyl)purines. The 6-(hydroxymethyl)purine ribonucleoside 5f exerted high cytostatic effect and moderate inhibition of adenosine deaminase, while all the othe

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9

Vorotyntsev, S. I., A. I. Bilai, and I. M. Bilai. "Disorder of purine metabolism in the etiopathogenesis of urate nephrolithiasis." Current issues in pharmacy and medicine: science and practice 16, no. 1 (2023): 90–97. http://dx.doi.org/10.14739/2409-2932.2023.1.273835.

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Urinary stone disease (USD) is a polyetiological urological disease caused by both exogenous and endogenous factors, including hereditary ones. It is characterized by the appearance of stones in the kidneys and urinary tract, and a tendency to relapse, often with a severe course. Almost 25 % of stones consist of uric acid (UA). The leading role in the pathogenesis of urate nephrolithiasis (UN) is played by disorders of purine metabolism, which are characterized by the development of hyperuricemia (HU) and hyperuricuria. The aim of the work is to review modern literary sources on the role of pu

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10

Hocek, Michal, Hana Dvořáková, and Ivana Císařová. "Covalent Analogues of DNA Base-Pairs and Triplets V. Synthesis of Purine-Purine and Purine-Pyrimidine Conjugates Connected by Diverse Types of Acyclic Carbon Linkages." Collection of Czechoslovak Chemical Communications 67, no. 10 (2002): 1560–78. http://dx.doi.org/10.1135/cccc20021560.

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The title 1,2-bis(purin-6-yl)acetylenes, -diacetylenes, -ethylenes and -ethanes were prepared as covalent base-pair analogues starting from 6-ethynylpurines and 6-iodopurines by the Sonogashira cross-coupling or oxidative alkyne-dimerization reactions followed by hydrogenations. 6-[(1,3-Dimethyluracil-5-yl)ethynyl]purine (11) was prepared analogously and hydrogenated to the corresponding purine-pyrimidine conjugates linked via vinylene and ethylene linkers. Unlike the cytostatic bis(purin-6-yl)acetylenes and -diacetylenes, the purine-pyrimidine conjugates were inactive. Crystal structures of b

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11

Scott, Andrew J., Alexandra M. O'Brien, Weihua Zhou, et al. "Abstract 3677: DNA damage signaling activates de novo GTP synthesis to promote chemoradiation resistance in glioblastoma." Cancer Research 83, no. 7_Supplement (2023): 3677. http://dx.doi.org/10.1158/1538-7445.am2023-3677.

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Abstract Glioblastoma (GBM) is uniformly fatal due to inherent radiation (RT) and chemotherapy resistance. We have found this therapeutic resistance is mediated by alterations in tumor cellular metabolic activity. Our group and others have found that metabolites can regulate DNA repair and RT resistance in brain tumors, but little is known about how DNA damage regulates metabolic pathway activity in cancer. Here, we show that DNA damage acutely increases guanine-containing purine metabolites in multiple in vitro and intracranial GBM models. By interrogating metabolic fluxes in vitro using a va

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12

Sudhakar Rao, T., and Ganapathi R. Revankar. "Synthesis of certain alkenyl purines and purine analogs." Journal of Heterocyclic Chemistry 32, no. 3 (1995): 1043–49. http://dx.doi.org/10.1002/jhet.5570320362.

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13

Culic, Ognjen, Ulrich K. M. Decking, and Jürgen Schrader. "Metabolic adaptation of endothelial cells to substrate deprivation." American Journal of Physiology-Cell Physiology 276, no. 5 (1999): C1061—C1068. http://dx.doi.org/10.1152/ajpcell.1999.276.5.c1061.

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Endothelial cells are known to be metabolically rather robust. To study the mechanisms involved, porcine aortic endothelial cells (PAEC), cultured on microcarrier beads, were perfused with glucose (10 mM) or with substrate-free medium. Substrate-free perfusion for 2 h induced an almost complete loss of nucleoside triphosphates (31P-NMR) and decreased heat flux, a measure of total energy turnover, by >90% in parallel microcalorimetric measurements. Heat flux and nucleoside triphosphates recovered after addition of glucose. Because protein synthesis is a major energy consumer in PAEC, the rat

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14

Dewhurst, R. J., and A. J. F. Webster. "The effect of dietary sodium on the energetic efficiency of microbial yield from the rumen of sheep." Proceedings of the British Society of Animal Production (1972) 1989 (March 1989): 104. http://dx.doi.org/10.1017/s0308229600010953.

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It has long been recognised that there is a strong positive relationship between the level of absorbed (microbial) purines and purine derivative excretion in the urine. We have used estimates based on urinary allantoin N excretion (AN) to investigate some of the factors influencing the energetic efficiency of microbial yield from the rumen (E). Figures 1 and 2 illustrate the model that has been adopted.It has been tentatively assumed that, at reasonable levels of intake, exogenous purine supply exceeds “a” moles (Figure 2) so that purine salvage is saturated (Condon & Hatfield, 1970), de n

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15

Li, Luyong, Jie Hu, Yuqing Fu, et al. "Direct Regioselective C-H Cyanation of Purines." Molecules 28, no. 3 (2023): 914. http://dx.doi.org/10.3390/molecules28030914.

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A direct regioselective C-H cyanation of purines was developed through a sequential triflic anhydride activation, nucleophilic cyanation with TMSCN, followed by a process of base-mediated elimination of triflous acid (CF3SO2H). In most cases, the direct C-H cyanation occurred on the electron-rich imidazole motif of purines, affording 8-cyanated purine derivatives in moderate to excellent yields. Various functional groups, including allyl, alkynyl, ketone, ester, nitro et al. were tolerated and acted as a C8 directing group. The electron-donating 6-diethylamino, as C2-directing group substituen

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16

Xi, Hualin, Barbara L. Schneider, and Larry Reitzer. "Purine Catabolism in Escherichia coliand Function of Xanthine Dehydrogenase in Purine Salvage." Journal of Bacteriology 182, no. 19 (2000): 5332–41. http://dx.doi.org/10.1128/jb.182.19.5332-5341.2000.

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ABSTRACT Escherichia coli is not known to utilize purines, other than adenine and adenosine, as nitrogen sources. We reinvestigated purine catabolism because a computer analysis suggested several potential ς54-dependent promoters within a 23-gene cluster whose products have homology to purine catabolic enzymes. Our results did not provide conclusive evidence that the ς54-dependent promoters are active. Nonetheless, our results suggest that some of the genes are metabolically significant. We found that even though several purines did not support growth as the sole nitrogen source, they did stim

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17

Pons, F. W., U. Neubert, and P. Müller. "Evidence for frameshift mutations in the hisH gene of Escherichia coli causing synthesis of a partially active glutamine amidotransferase." Genetics 120, no. 3 (1988): 657–65. http://dx.doi.org/10.1093/genetics/120.3.657.

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Abstract Among eight strains carrying acridine-induced mutations in hisH, five which mapped at four different sites in the promoter-distal region of the gene showed His+ phenotypes on media containing a purine. By complementation analysis, hisH enzyme was shown to be required for growth on purines. Purine-sensitive His+ revertants of strains able to grow on purines carried second-site mutations which in one case could be shown to map in hisG. Strains able to grow on purines were able to grow on 2-thiazolyl-DL-alanine, too. We conclude that frameshift mutations in the promoter-distal part of th

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18

Šilhár, Peter, Radek Pohl, Ivan Votruba, Blanka Klepetářová, and Michal Hocek. "Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 788–803. http://dx.doi.org/10.1135/cccc20060788.

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An efficient methodology of the synthesis of 6-substituted 2-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed. Regioselective Pd-catalyzed cross-coupling reactions of 6-chloro-2-iodopurines with [(benzoyloxy)methyl]zinc iodide gave 2-[(benzoyloxy)-methyl]-6-chloropurines that were converted to 2-(hydroxymethyl)adenines by reactions with ammonia and to 6-methyl- or 6-aryl-2-(hydroxymethyl)purines by cross-coupling reactions with trimethylaluminium or arylboronic acids followed by deprotection. The title 6-substituted 2-(hydroxymethyl)purine bases and nucleosides did not e

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19

Fedotov, Victor V., Evgeny N. Ulomsky, Konstantin V. Savateev, et al. "A PASE Approach to the Synthesis of Benzimidazopurines as Polycondensed Purine Derivatives." Synthesis 52, no. 23 (2020): 3622–31. http://dx.doi.org/10.1055/s-0040-1707228.

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A highly efficient PASE approach to a new class of polycyclic purine derivatives has been proposed. The strategy includes a consecutive reduction, auto-aromatization, and heterocyclization of the initial nitrobenzimidazopyrimidines obtained by a three-component condensation. It was shown that reduction of nitrobenzimidazopyrimidines by metals in acidic media was more efficient than heterogeneous hydrogenation. Novel derivatives of benz[4,5]imidazo[1,2-a]purines were obtained in good yields and the proposed structure was confirmed by X-ray crystal structure analysis. The obtained convergent b

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20

Jain, Sunny, Selina Sutchu, Patricia A. Rosa, Rebecca Byram, and Mollie W. Jewett. "Borrelia burgdorferi Harbors a Transport System Essential for Purine Salvage and Mammalian Infection." Infection and Immunity 80, no. 9 (2012): 3086–93. http://dx.doi.org/10.1128/iai.00514-12.

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ABSTRACTBorrelia burgdorferiis the tick-borne bacterium that causes the multistage inflammatory disease Lyme disease.B. burgdorferihas a reduced genome and lacks the enzymes required forde novosynthesis of purines for synthesis of RNA and DNA. Therefore, this obligate pathogen is dependent upon the tick vector and mammalian host environments for salvage of purine bases for nucleic acid biosynthesis. This pathway is vital forB. burgdorferisurvival throughout its infectious cycle, as key enzymes in the purine salvage pathway are essential for the ability of the spirochete to infect mice and crit

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21

Enos-Berlage, Jodi L., and Diana M. Downs. "Biosynthesis of the Pyrimidine Moiety of Thiamine Independent of the PurF Enzyme (Phosphoribosylpyrophosphate Amidotransferase) in Salmonella typhimurium: Incorporation of Stable Isotope-Labeled Glycine and Formate." Journal of Bacteriology 181, no. 3 (1999): 841–48. http://dx.doi.org/10.1128/jb.181.3.841-848.1999.

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ABSTRACT Genetic analyses have suggested that the pyrimidine moiety of thiamine can be synthesized independently of the first enzyme of de novo purine synthesis, phosphoribosylpyrophosphate amidotransferase (PurF), in Salmonella typhimurium. To obtain biochemical evidence for and to further define this proposed synthesis, stable isotope labeling experiments were performed with two compounds, [2-13C]glycine and [13C]formate. These compounds are normally incorporated into thiamine pyrophosphate (TPP) via steps in the purine pathway subsequent to PurF. Gas chromatography-mass spectrometry analyse

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22

Hristov, A. N., T. A. McAllister, D. R. Ouellet, and G. A. Broderick. "Comparison of purines and nitrogen-15 as microbial flow markers in beef heifers fed barley- or corn-based diets." Canadian Journal of Animal Science 85, no. 2 (2005): 211–22. http://dx.doi.org/10.4141/a04-054.

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The objective of this study was to estimate the contribution of microbial purine bases to duodenal purines and to purine derivatives [allantoin and uric acid (PD)] excreted in the urine. Additionally, microbial protein (MCP) flow estimated using duodenal flow of purine bases was compared to estimates using 15N as a microbial marker. Four beef heifers were fed two diets, barley silage/barley grain/soybean meal (diet B) or corn silage/corn grain/corn gluten meal (diet C), in a cross-over design study. (15NH4)2SO4 was infused in the rumen for 8 d to label ruminal microorganisms and their purine b

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23

Boss, G. R. "Purine deoxynucleosides and adenosine dialdehyde decrease 5-amino-4-imidazolecarboxamide (Z-base)-dependent purine nucleotide synthesis in cultured T and B lymphoblasts." Biochemical Journal 242, no. 2 (1987): 425–31. http://dx.doi.org/10.1042/bj2420425.

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Deoxyadenosine (dAdo) and deoxyguanosine (dGuo) decrease methionine synthesis from homocysteine in cultured lymphoblasts; because of the possible trapping of 5-methyltetrahydrofolate this could lead to decreased purine nucleotide synthesis. Since purine deoxynucleosides could also inhibit purine synthesis de novo at an early step not involving folate metabolism, we measured in azaserine-treated cells 5-amino-4-imidazolecarboxamide (Z-base)-dependent purine nucleotide synthesis using [14C]formate. In the T lymphoblasts, Z-base-dependent purine nucleotide synthesis was decreased 26% by 0.3 micro

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24

Itakura, M., N. Maeda, M. Tsuchiya, and K. Yamashita. "Glucagon infusion increases rate of purine synthesis de novo in rat liver." American Journal of Physiology-Endocrinology and Metabolism 253, no. 6 (1987): E684—E690. http://dx.doi.org/10.1152/ajpendo.1987.253.6.e684.

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Based on the parallel increases of glucagon, the second peak of hepatic cAMP, and the rate of purine synthesis de novo in the prereplicative period in regenerating rat liver after a 70% hepatectomy, it was hypothesized that glucagon is responsible for the increased rate of purine synthesis de novo. To test this hypothesis, the effect of glucagon or dibutyryl cAMP infusion on the rate of purine synthesis de novo in rat liver was studied. Glucagon infusion but not insulin or glucose infusion increased the rate of purine synthesis de novo, which was assayed by [14C]glycine or [14C]formate incorpo

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25

Xu, Zhongnan, Yuqing Wang, Yucheng Zheng, Zhixing Huang, Lutz Ackermann, and Zhixiong Ruan. "Manganese- and rhenium-catalyzed C–H enaminylation: expedient access to novel indole–purine hybrids with anti-tumor bioactivities." Organic Chemistry Frontiers 7, no. 22 (2020): 3709–14. http://dx.doi.org/10.1039/d0qo01120g.

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The C–H enaminylation of novel 6-(1H-indol-1-yl)-purines with ketenimines was accomplished by means of aqueous manganese and rhenium catalysis, which sets the stage for the facile synthesis of indole–purine hybrids with anti-tumor bioactivities.

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26

Glockzin, Kayla, Thomas D. Meek, and Ardala Katzfuss. "Characterization of adenine phosphoribosyltransferase (APRT) activity in Trypanosoma brucei brucei: Only one of the two isoforms is kinetically active." PLOS Neglected Tropical Diseases 16, no. 2 (2022): e0009926. http://dx.doi.org/10.1371/journal.pntd.0009926.

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Human African Trypanosomiasis (HAT), also known as sleeping sickness, is a Neglected Tropical Disease endemic to 36 African countries, with approximately 70 million people currently at risk for infection. Current therapeutics are suboptimal due to toxicity, adverse side effects, and emerging resistance. Thus, both effective and affordable treatments are urgently needed. The causative agent of HAT is the protozoan Trypanosoma brucei ssp. Annotation of its genome confirms previous observations that T. brucei is a purine auxotroph. Incapable of de novo purine synthesis, these protozoan parasites

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27

Carreira, Ana R. F., Telma Veloso, Nicolas Schaeffer, et al. "Synthesis of Purine-Based Ionic Liquids and Their Applications." Molecules 26, no. 22 (2021): 6958. http://dx.doi.org/10.3390/molecules26226958.

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Bio-based ionic liquids (ILs) are being increasingly sought after, as they are more sustainable and eco-friendly. Purines are the most widely distributed, naturally occurring N-heterocycles, but their low water-solubility limits their application. In this work, four purines (theobromine, theophylline, xanthine, and uric acid) were combined with the cation tetrabutylammonium to synthesize bio-based ILs. The physico–chemical properties of the purine-based ILs were characterized, including their melting and decomposition temperatures and water-solubility. The ecotoxicity against the microalgae Ra

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Hřebabecký, Hubert, Milena Masojídková, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 871–88. http://dx.doi.org/10.1135/cccc20060871.

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(1R*,2R*,3R*,4R*,5R*,6S*)-3-Amino-5-(benzyloxy)-6-(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (18) was prepared in seven easy steps from benzyl (1R*,2S*,3S*,4S*)-3-(benzyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate (10). Reaction of amine18with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded 1-[(1R*,2R*,3R*,4R*,5S*,6R*)-6-(benzyloxy)-3-hydroxy-5- (hydroxymethyl)bicyclo[2.2.1]heptan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (21) and after deprotection by transfer hydrogenation, free thymine analogue22. The thymine derivative21was converted to 2,3'-anhydronucleoside26. Treatment of the benzyl d

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29

Archambault, Anne-Sophie, Lauar de Brito Monteiro, Lucas Starchuck, et al. "Purine catabolism regulates the production of IL-1beta in macrophages." Journal of Immunology 212, no. 1_Supplement (2024): 0286_4533. http://dx.doi.org/10.4049/jimmunol.212.supp.0286.4533.

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Abstract Activation of pro-inflammatory (M1-like) macrophages leads to the production of pro-inflammatory cytokines, such as IL-1b, TNFa and IL-6. Those cytokines are important in the control of infections, but overproduction can lead to chronic inflammation. M1-like macrophages undergo metabolic remodeling, including the upregulation of purine metabolism. Using inhibitors of purine breakdown or purine synthesis, we aimed to identify the role of purine metabolism in M1-like macrophage function. Blocking purine synthesis or purine breakdown did not affect the frequency of CD80+CD86+iNOS+macroph

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Hung, Man-Hsin, Ching Wen Chang, Kathy Cheng Wang, et al. "Abstract 3683: Activation of purine anabolism creates a therapeutic vulnerability in hepatocellular carcinoma via m6A-mediated epitranscriptomic regulation." Cancer Research 83, no. 7_Supplement (2023): 3683. http://dx.doi.org/10.1158/1538-7445.am2023-3683.

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Abstract Introduction Purines are building blocks for genomics and the abundance of purine nucleotides is controlled by purine synthesis and purine degradation. Imbalance of purine nucleotide pool in tumors has been shown, but how synthesis and degradation of purine integrates in tumors has not been well characterized. Hepatocellular carcinoma (HCC) is the most common liver cancer with a high mortality rate and limited treatments. Aberrant purine metabolism was observed in HCC, but the functional status of global purine metabolism in HCC and how that drive HCC fitness and therapeutic response

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31

Zhou, Weihua, Yangyang Yao, Andrew Scott, et al. "DDRE-24. TARGETING PURINE METABOLISM TO OVERCOME GLIOBLASTOMA THERAPY RESISTANCE." Neuro-Oncology Advances 3, Supplement_1 (2021): i11. http://dx.doi.org/10.1093/noajnl/vdab024.046.

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Abstract Intratumoral genomic heterogeneity in glioblastoma (GBM) is a barrier to overcoming radiation (RT) resistance. To discover genotype-independent mediators of RT resistance, we correlated RT resistance with the concentration of approximately 700 metabolites across 23 GBM cell lines. Purine metabolites, especially those containing the base guanine, were most correlated with RT resistance. Similarly, increased abundance of tumor purines was associated with decreased survival in GBM patients treated with RT. This relationship is causal. Purine supplementation protected RT-sensitive GBMs fr

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32

Šála, Michal, Hubert Hřebabecký, Martin Dračínský, et al. "Synthesis of novel racemic carbocyclic nucleosides derived from 5,6-disubstituted norbornene." Collection of Czechoslovak Chemical Communications 75, no. 1 (2009): 1–20. http://dx.doi.org/10.1135/cccc2009116.

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Novel class of the carbocyclic nucleosides based on bicyclo[2.2.1]heptene/heptane was prepared by two approaches. Thymine analogues were synthesized starting from methyl (1R*,4S*)-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate1by Michael addition of the thymine salt to the double bond as the key step. The yield and ratio of the isomers of this reaction depended on the used base (DBU, K2CO3). Purine nucleoside analogues were synthesized by the linear synthesis, the purine nucleobase was build-up on the amino group. The amino groups (exo/endoconfiguration) were introduced to the scaffold by the Cur

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Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 5,5- and 6,6-Bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol." Collection of Czechoslovak Chemical Communications 70, no. 4 (2005): 519–38. http://dx.doi.org/10.1135/cccc20050519.

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(1R*,2R*,3R*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (13) was prepared from (bicyclo[2.2.1]hept-5-ene-2,2-diyl)dimethyl dibenzoate (7) viacis-diol8, cyclic sulfate10, and azide12. (1R*,2R*,3S*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]-heptan-2-ol (18) and (1R*,2S*,3S*,4S*)-3-amino-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (19) were obtained by addition of chromyl azide to double bond of7, chromatographic separation, debenzoylation and hydrogenation of resulting azides14and16. The amines13,18, and19were used to build (1R*,2R*,3R*,4S*)- (21a), (1R*,2R*,3S*,4S*)

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De Vitto, Humberto, Danushka B. Arachchige, Brian C. Richardson, and Jarrod B. French. "The Intersection of Purine and Mitochondrial Metabolism in Cancer." Cells 10, no. 10 (2021): 2603. http://dx.doi.org/10.3390/cells10102603.

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Nucleotides are essential to cell growth and survival, providing cells with building blocks for DNA and RNA, energy carriers, and cofactors. Mitochondria have a critical role in the production of intracellular ATP and participate in the generation of intermediates necessary for biosynthesis of macromolecules such as purines and pyrimidines. In this review, we highlight the role of purine and mitochondrial metabolism in cancer and how their intersection influences cancer progression, especially in ovarian cancer. Additionally, we address the importance of metabolic rewiring in cancer and how th

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Saathoff, Miranda, Jack Shireman, Eunus Ali, Cheol Park, Issam Ben-Sahra, and Atique Ahmed. "DRES-09. REGULATORY EFFECTS OF THE CILIARY GTPASE ARL13B ON PURINE METABOLISM IN GBM." Neuro-Oncology 21, Supplement_6 (2019): vi73. http://dx.doi.org/10.1093/neuonc/noz175.297.

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Abstract Glioblastoma (GBM) is the most common form of adult primary brain cancer. Despite an aggressive treatment regimen – surgical resection, irradiation, and temozolomide (TMZ) chemotherapy – patients’ prognosis is still grim. TMZ acts by methylating purines, specifically at the O6 and N7 positions of guanine, to induce cytotoxic DNA double-strand breaks. We thus wanted to explore how purine metabolism may contribute to TMZ-resistance. In mammalian cells, purine nucleotides can be recycled by the salvage pathway or generated via de novo synthesis. The salvage pathway is energetically inexp

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RAO, T. S., and G. R. REVANKAR. "ChemInform Abstract: Synthesis of Certain Alkenyl Purines and Purine Analogues." ChemInform 26, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199547188.

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Sousa, L. B., M. L. A. Pereira, H. G. O. Silva, et al. "Creatinine and purine derivatives excretion and microbial synthesis in lambs fed rain tree pod meal." Arquivo Brasileiro de Medicina Veterinária e Zootecnia 74, no. 1 (2022): 160–68. http://dx.doi.org/10.1590/1678-4162-12376.

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ABSTRACT Evaluated the levels of rain tree (Samanea saman) pod meal (RTPM) (0, 10, 15, 20 and 25%) replacing maize in the dry matter of the diet on intake of DM, CP and ME, creatinine and total purine derivatives excretion in urine and microbial protein synthesis in lambs. Twenty-five uncastrated Bergamasca lambs were used, with an initial body weight of 24±5kg and an average age of 120 days. The experimental design was completely randomized, with five treatments and five replications. The trial lasted 84 days and the 24h and spot urine collections were performed in the last day of the experim

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Umemura, Yoshie, Andrew J. Scott, Wajd Al-Holou, et al. "Abstract 1093: Measuring and inhibiting purine metabolism in patients with glioblastoma." Cancer Research 83, no. 7_Supplement (2023): 1093. http://dx.doi.org/10.1158/1538-7445.am2023-1093.

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Abstract Introduction: We have previously found that purine metabolism is an important metabolic mediator of treatment resistance in glioblastoma (GBM). Mycophenolate mofetil (MMF), an inhibitor of purine synthesis, synergizes with radiation and temozolomide in mouse models of GBM. No measurements of purine synthesis have been performed in human cancer patients, nor has the purine inhibitor MMF been used clinically for patients with GBM. Methods: We infused clinical-grade 13C6 glucose into patients undergoing craniotomy for presumed GBM and used mass spectrometry to measure carbon incorporatio

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Ma, Qian, Qiuhua Yang, Jiean Xu, et al. "ATIC-Associated De Novo Purine Synthesis Is Critically Involved in Proliferative Arterial Disease." Circulation 146, no. 19 (2022): 1444–60. http://dx.doi.org/10.1161/circulationaha.121.058901.

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Background: Proliferation of vascular smooth muscle cells (VSMCs) is a hallmark of arterial diseases, especially in arterial restenosis after angioplasty or stent placement. VSMCs reprogram their metabolism to meet the increased requirements of lipids, proteins, and nucleotides for their proliferation. De novo purine synthesis is one of critical pathways for nucleotide synthesis. However, its role in proliferation of VSMCs in these arterial diseases has not been defined. Methods: De novo purine synthesis in proliferative VSMCs was evaluated by liquid chromatography-tandem mass spectrometry. Th

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Derzelle, Sylviane, Alexander Bolotin, Michel-Yves Mistou, and Françoise Rul. "Proteome Analysis of Streptococcus thermophilus Grown in Milk Reveals Pyruvate Formate-Lyase as the Major Upregulated Protein." Applied and Environmental Microbiology 71, no. 12 (2005): 8597–605. http://dx.doi.org/10.1128/aem.71.12.8597-8605.2005.

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ABSTRACT We investigated the adaptation to milk of Streptococcus thermophilus LMG18311 using a proteomic approach. Two-dimensional electrophoresis of cytosolic proteins were performed after growth in M17 medium or in milk. A major modification of the proteome concerned proteins involved in the supply of amino acids, like the peptidase PepX, and several enzymes involved in amino acid biosynthesis. In parallel, we observed the upregulation of the synthesis of seven enzymes directly involved in the synthesis of purines, as well as formyl-tetrahydrofolate (THF) synthetase and serine hydroxy-methyl

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Zilles, Julie L., T. Joseph Kappock, JoAnne Stubbe, and Diana M. Downs. "Altered Pathway Routing in a Class ofSalmonella enterica Serovar Typhimurium Mutants Defective in Aminoimidazole Ribonucleotide Synthetase." Journal of Bacteriology 183, no. 7 (2001): 2234–40. http://dx.doi.org/10.1128/jb.183.7.2234-2240.2001.

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ABSTRACT In Salmonella enterica serovar Typhimurium, purine nucleotides and thiamine are synthesized by a branched pathway. The last known common intermediate, aminoimidazole ribonucleotide (AIR), is formed from formylglycinamidine ribonucleotide (FGAM) and ATP by AIR synthetase, encoded by the purI gene in S. enterica. Reduced flux through the first five steps of de novo purine synthesis results in a requirement for purines but not necessarily thiamine. To examine the relationship between the purine and thiamine biosynthetic pathways, purI mutants were made (J. L. Zilles and D. M. Downs, Gene

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Kapadiya, Khushal, Kishor Kavadia, Jyoti Gohel, and Ranjan Khunt. "Regioselective synthesis of triazolo[3,4-e]purine derivatives and their anti-cancer activity against NCI-60 cell-lines." Folia Medica 63, no. 2 (2021): 213–20. http://dx.doi.org/10.3897/folmed.63.e52891.

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Introduction: Due to the vast medicinal importance of purine nucleoside, a hybrid molecule of triazole with purine ring might&nbsp;explode a lead molecule in the pharma sector and based on the last decade&rsquo;s studies suggested that the nitrogen-rich molecules possess a wide range of medicinal importance. Aim: Due to the vast application of purine nucleoside itself in the field of cancer research, we synthesized triazolo[3,4-e]purines and screened them for their anti-cancer study against NCI-60 cell lines by the protocol used by NIH. Materials and methods: The targeted molecules, 4-

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Šála, Michal, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "Synthesis of Novel Racemic Conformationally Locked Carbocyclic Nucleosides Derived from 7-Substituted Bicyclo[2.2.1]hept-5-ene-2,2-dimethanols." Collection of Czechoslovak Chemical Communications 71, no. 5 (2006): 635–49. http://dx.doi.org/10.1135/cccc20060635.

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(1R*,4R*,7S*)-7-Aminobicyclo[2.2.1]hept-5-ene-2,2-dimethanol (15) was prepared in four easy steps from bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (10). Reaction of amine 15 with ethyl N-((E)-3-ethoxymethacryloyl)carbamate afforded thymine derivatives 17a. The amine 15 was used to construct 6-chloro-9H-purine derivative 19a, 2-amino-6-chloro-9H-purine derivative 22a. Ammonolysis of 19a led to the adenine derivative 20a. Treatment of 22a with trifluoroacetic acid afforded guanine nucleoside 23a. (1R*,4R*,7S*)-7-[6-(Cyclopropylamino)-9H-purin-9-yl]bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (21a) and (1

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Rouchal, Michal, Jana Rudolfová, Vladimír Kryštof, Veronika Vojáčková, Richard Čmelík та Robert Vícha. "Adamantane-Substituted Purines and Their β-Cyclodextrin Complexes: Synthesis and Biological Activity". International Journal of Molecular Sciences 22, № 23 (2021): 12675. http://dx.doi.org/10.3390/ijms222312675.

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Cyclin-dependent kinases (CDKs) play an important role in the cell-division cycle. Synthetic inhibitors of CDKs are based on 2,6,9-trisubstituted purines and are developed as potential anticancer drugs; however, they have low solubility in water. In this study, we proved that the pharmaco-chemical properties of purine-based inhibitors can be improved by appropriate substitution with the adamantane moiety. We prepared ten new purine derivatives with adamantane skeletons that were linked at position 6 using phenylene spacers of variable geometry and polarity. We demonstrated that the adamantane

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Jiménez, Alberto, María A. Santos, Markus Pompejus, and José L. Revuelta. "Metabolic Engineering of the Purine Pathway for Riboflavin Production in Ashbya gossypii." Applied and Environmental Microbiology 71, no. 10 (2005): 5743–51. http://dx.doi.org/10.1128/aem.71.10.5743-5751.2005.

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ABSTRACT Purine nucleotides are essential precursors for living organisms because they are involved in many important processes, such as nucleic acid synthesis, energy supply, and the biosynthesis of several amino acids and vitamins such as riboflavin. GTP is the immediate precursor for riboflavin biosynthesis, and its formation through the purine pathway is subject to several regulatory mechanisms in different steps. Extracellular purines repress the transcription of most genes required for de novo ATP and GTP synthesis. Additionally, three enzymes of the pathway, phosphoribosyl pyrophosphate

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Cicero, Arrigo F. G., Federica Fogacci, Valentina Di Micoli, Cristina Angeloni, Marina Giovannini, and Claudio Borghi. "Purine Metabolism Dysfunctions: Experimental Methods of Detection and Diagnostic Potential." International Journal of Molecular Sciences 24, no. 8 (2023): 7027. http://dx.doi.org/10.3390/ijms24087027.

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Purines, such as adenine and guanine, perform several important functions in the cell. They are found in nucleic acids; are structural components of some coenzymes, including NADH and coenzyme A; and have a crucial role in the modulation of energy metabolism and signal transduction. Moreover, purines have been shown to play an important role in the physiology of platelets, muscles, and neurotransmission. All cells require a balanced number of purines for growth, proliferation, and survival. Under physiological conditions, enzymes involved in purines metabolism maintain a balanced ratio between

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Bertrand, Jeanluc, Hana Dostálová, Vladimír Kryštof, et al. "Design, Synthesis, In Silico Studies and Inhibitory Activity towards Bcr-Abl, BTK and FLT3-ITD of New 2,6,9-Trisubstituted Purine Derivatives as Potential Agents for the Treatment of Leukaemia." Pharmaceutics 14, no. 6 (2022): 1294. http://dx.doi.org/10.3390/pharmaceutics14061294.

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We report 31 new compounds designed, synthesized and evaluated on Bcr-Abl, BTK and FLT3-ITD as part of our program to develop 2,6,9-trisubstituted purine derivatives as inhibitors of oncogenic kinases. The design was inspired by the chemical structures of well-known kinase inhibitors and our previously developed purine derivatives. The synthesis of these purines was simple and used a microwave reactor for the final step. Kinase assays showed three inhibitors with high selectivity for each protein that were identified: 4f (IC50 = 70 nM for Bcr-Abl), 5j (IC50 = 0.41 μM for BTK) and 5b (IC50 = 0.

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Kiehl, R., and G. Ionescu. "A defective purine nucleotide synthesis pathway in psoriatic patients." Acta Dermato-Venereologica 72, no. 4 (1992): 253–55. http://dx.doi.org/10.2340/0001555572253255.

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Purine nucleotide concentrations in skin- and blood-cells of psoriatic patients are abnormal: The increase in the steady state level of cGMP and the decrease in the cAMP concentrations are associated with an enhanced rate of cellular proliferation. Concomitantly we found in the present study decreased ADP and ATP concentrations in blood cells (p less than 0.0001). The change in nucleotide concentrations suggests a defective purine nucleotide synthesis pathway. Stimulation of the Krebs cycle with fumaric acid raises ATP (p less than 0.0001) and most probably cAMP levels and at the same time slo

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ZINN, R. A., and F. N. OWENS. "A RAPID PROCEDURE FOR PURINE MEASUREMENT AND ITS USE FOR ESTIMATING NET RUMINAL PROTEIN SYNTHESIS." Canadian Journal of Animal Science 66, no. 1 (1986): 157–66. http://dx.doi.org/10.4141/cjas86-017.

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A rapid method for separation and quantitation of purines was applied to ruminal and intestinal digesta for estimating net microbial protein synthesis in the rumen. The procedure combines standard literature methods for hydrolysis of nucleotides by perchloric acid followed by precipitation of free purines with silver nitrate to separate the purines from interfering compounds. Acid resolubilized purines were quantitated spectrophotometrically at 260 nm. Microbial protein was estimated by the ratio of purines to N of isolated bacteria. The procedure is rapid, simple, precise and not costly. Duod

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Onidani, Kaoru, Nami Miura, Yuki Sugiura, et al. "Possible Therapeutic Strategy Involving the Purine Synthesis Pathway Regulated by ITK in Tongue Squamous Cell Carcinoma." Cancers 13, no. 13 (2021): 3333. http://dx.doi.org/10.3390/cancers13133333.

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The epidermal growth factor receptor is the only available tyrosine kinase molecular target for treating oral cancer. To improve the prognosis of tongue squamous cell carcinoma (TSCC) patients, a novel molecular target for tyrosine kinases is thus needed. We examined the expression of interleukin-2–inducible T-cell kinase (ITK) using immunohistochemistry, and the biological function of ITK was investigated using biochemical, phosphoproteomic, and metabolomic analyses. We found that ITK is overexpressed in TSCC patients with poor outcomes. The proliferation of oral cancer cell lines expressing

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