Relevant bibliographies by topics / '-deoxy purine nucleosides

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Academic literature on the topic ''-deoxy purine nucleosides'

Author: Grafiati
Published: 4 June 2021
Last updated: 6 February 2022

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Journal articles on the topic "'-deoxy purine nucleosides"

1

Ren, Hang, Haoyun An, Paul J. Hatala, William C. Stevens, Jingchao Tao, and Baicheng He. "Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides." Beilstein Journal of Organic Chemistry 11 (December 9, 2015): 2509–20. http://dx.doi.org/10.3762/bjoc.11.272.

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A unified synthetic strategy accessing novel 3'-fluorinated purine nucleoside derivatives and their biological evaluation were achieved. Novel 3’-fluorinated analogues were constructed from a common 3’-deoxy-3’-fluororibofuranose intermediate. Employing Suzuki and Stille cross-coupling reactions, fifteen 3’-fluororibose purine nucleosides 1–15 and eight 3’-fluororibose 2-chloro/2-aminopurine nucleosides 16–23 with various substituents at position 6 of the purine ring were efficiently synthesized. Furthermore, 3’-fluorine analogs of natural products nebularine and 6-methylpurine riboside were constructed via our convergent synthetic strategy. Synthesized nucleosides were tested against HT116 (colon cancer) and 143B (osteosarcoma cancer) tumor cell lines. We have demonstrated 3’-fluorine purine nucleoside analogues display potent tumor cell growth inhibition activity at sub- or low micromolar concentration.
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2

Pogosian, L. H., L. S. Nersesova, M. G. Gazariants, Z. S. Mkrtchian, and J. I. Akopian. "Some inhibitors of purine nucleoside phosphorylase." Biomeditsinskaya Khimiya 57, no. 5 (2011): 526–34. http://dx.doi.org/10.18097/pbmc20115705526.

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Purine nucleoside phosphorylase (PNP) catalyzes reversible phosphorolysis of purine deoxy- and ribonucleosides with formation (d)Rib-1-P and corresponding bases. PNP plays a leading role in the cell metabolism of nucleosides and nucleotides, as well as in maintaining the immune status of an organism. The major aim of the majority of studies on the PNP is the detection of highly effective inhibitors of this enzyme, derivatives of purine nucleosides used in medicine as immunosuppressors, which are essential for creating selective T-cell immunodeficiency in a human body for organ and tissue transplantation.The present work is devoted to the study of the effects of some synthetic derivatives of purine nucleosides on activity of highly purified PNP from rabbit spleen and also from human healthy and tumor tissues of lung and kidneys. Purine nucleoside analogues modified at various positions of both the heterocyclic base and carbohydrate residues have been investigated. Several compounds, including 8-mercapto-acyclovir, 8-bromo-9-(3,4-hydroxy-butyl)guanine, which demonstrated potent PNP inhibition, could be offered for subsequent study as immunosuppressors during organ and tissue transplantation.
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3

Robins, Morris J., Ruiming Zou, Fritz Hansske, and Stanislaw F. Wnuk. "Synthesis of sugar-modified 2,6-diaminopurine and guanine nucleosides from guanosine via transformations of 2-aminoadenosine and enzymatic deamination with adenosine deaminase." Canadian Journal of Chemistry 75, no. 6 (June 1, 1997): 762–67. http://dx.doi.org/10.1139/v97-092.

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Treatment of 2,6-diaminopurine riboside (2-aminoadenosine) with α-acetoxyisobutyryl bromide in acetonitrile gave mixtures of the trans 2′,3′-bromohydrin acetates 2. Treatment of 2 with zinc–copper couple effected reductive elimination, and deprotection gave 2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl)purine (3a). Treatment of 2 with Dowex 1 × 2 (OH−) resin in methanol gave the 2′,3′-anhydro derivative 4. Stannyl radical-mediated hydrogenolysis of 2 and deprotection gave the 2′-deoxy 6a and 3′-deoxy 7a nucleosides. Treatment of the 3′,5′-O-(tetraisopropyldisiloxanyl) derivative (5a) with trifluoromethanesulfonyl chloride – 4-(dimethylamino)pyridine gave 2′-triflate 5c. Displacement with lithium azide–dimethylformamide and deprotection gave the arabino 2′-azido derivative 8a, which was reduced to give 2,6-diamino-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purine (8b). Sugar-modified 2,6-diaminopurine nucleosides were treated with adenosine deaminase to give the corresponding guanine analogues. Keywords: adenosine deaminase, 2,6-diaminopurine nucleosides, deoxygenation, guanine nucleosides, nucleosides.
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4

Karwowski, Bolesław. "Consequence of hydrogen atom abstraction from 5’-hydroxyl group of 2’-deoxyadenosine. Theoretical quantum mechanics study." Open Chemistry 6, no. 3 (September 1, 2008): 450–55. http://dx.doi.org/10.2478/s11532-008-0038-z.

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AbstractReactive oxygen species (ROS) may generate different nucleoside/nucleotide radicals in a cell environment. In this study, the possibility of cyclic-2’-deoxyadenosines formation by a rearrangement of their free radicals was investigated. It seems that for cyclic-nucleosides formation, adoption of an O4’-exo conformation by the sugar moiety is necessary. However, this is the energetically unfavoured form of the 2-deoxyribose ring. Moreover, the creation of a O5’, C8 bond in purine deoxy-nucleosides/nucleotides leads to the termination of the DNA elongation process.
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5

Fateev, Ilja V., Konstantin V. Antonov, Irina D. Konstantinova, Tatyana I. Muravyova, Frank Seela, Roman S. Esipov, Anatoly I. Miroshnikov, and Igor A. Mikhailopulo. "The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases." Beilstein Journal of Organic Chemistry 10 (July 22, 2014): 1657–69. http://dx.doi.org/10.3762/bjoc.10.173.

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Two approaches to the synthesis of 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (1, clofarabine) were studied. The first approach consists in the chemical synthesis of 2-deoxy-2-fluoro-α-D-arabinofuranose-1-phosphate (12a, 2FAra-1P) via three step conversion of 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (9) into the phosphate 12a without isolation of intermediary products. Condensation of 12a with 2-chloroadenine catalyzed by the recombinant E. coli purine nucleoside phosphorylase (PNP) resulted in the formation of clofarabine in 67% yield. The reaction was also studied with a number of purine bases (2-aminoadenine and hypoxanthine), their analogues (5-aza-7-deazaguanine and 8-aza-7-deazahypoxanthine) and thymine. The results were compared with those of a similar reaction with α-D-arabinofuranose-1-phosphate (13a, Ara-1P). Differences of the reactivity of various substrates were analyzed by ab initio calculations in terms of the electronic structure (natural purines vs analogues) and stereochemical features (2FAra-1P vs Ara-1P) of the studied compounds to determine the substrate recognition by E. coli nucleoside phosphorylases. The second approach starts with the cascade one-pot enzymatic transformation of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a, followed by its condensation with 2-chloroadenine thereby affording clofarabine in ca. 48% yield in 24 h. The following recombinant E. coli enzymes catalyze the sequential conversion of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a: ribokinase (2-deoxy-2-fluoro-D-arabinofuranose-5-phosphate), phosphopentomutase (PPN; no 1,6-diphosphates of D-hexoses as co-factors required) (12a), and finally PNP. The substrate activities of D-arabinose, D-ribose and D-xylose in the similar cascade syntheses of the relevant 2-chloroadenine nucleosides were studied and compared with the activities of 2-deoxy-2-fluoro-D-arabinose. As expected, D-ribose exhibited the best substrate activity [90% yield of 2-chloroadenosine (8) in 30 min], D-arabinose reached an equilibrium at a concentration of ca. 1:1 of a starting base and the formed 2-chloro-9-(β-D-arabinofuranosyl)adenine (6) in 45 min, the formation of 2-chloro-9-(β-D-xylofuranosyl)adenine (7) proceeded very slowly attaining ca. 8% yield in 48 h.
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6

Ting, Jing-Wen, Min-Feng Wu, Chih-Tung Tsai, Ching-Chun Lin, Ing-Cherng Guo, and Chi-Yao Chang. "Identification and characterization of a novel gene of grouper iridovirus encoding a purine nucleoside phosphorylase." Journal of General Virology 85, no. 10 (October 1, 2004): 2883–92. http://dx.doi.org/10.1099/vir.0.80249-0.

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Purine nucleoside phosphorylase (PNP) is a key enzyme in the purine salvage pathway. It catalyses the reversible phosphorolysis of purine (2′-deoxy)ribonucleosides to free bases and (2′-deoxy)ribose 1-phosphates. Here, a novel piscine viral PNP gene that was identified from grouper iridovirus (GIV), a causative agent of an epizootic fish disease, is reported. This putative GIV PNP gene encodes a protein of 285 aa with a predicted molecular mass of 30 332 Da and shows high similarity to the human PNP gene. Northern and Western blot analyses of GIV-infected grouper kidney (GK) cells revealed that PNP expression increased in cells with time from 6 h post-infection. Immunocytochemistry localized GIV PNP in the cytoplasm of GIV-infected host cells. PNP–EGFP fusion protein was also observed in the cytoplasm of PNP–EGFP reporter construct-transfected GK and HeLa cells. From HPLC analysis, the recombinant GIV PNP protein was shown to catalyse the reversible phosphorolysis of purine nucleosides and could accept guanosine, inosine and adenosine as substrates. In conclusion, this is the first report of a viral PNP with enzymic activity.
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7

Il’icheva, Irina A., Konstantin M. Polyakov, and Sergey N. Mikhailov. "Strained Conformations of Nucleosides in Active Sites of Nucleoside Phosphorylases." Biomolecules 10, no. 4 (April 5, 2020): 552. http://dx.doi.org/10.3390/biom10040552.

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Nucleoside phosphorylases catalyze the reversible phosphorolysis of nucleosides to heterocyclic bases, giving α-d-ribose-1-phosphate or α-d-2-deoxyribose-1-phosphate. These enzymes are involved in salvage pathways of nucleoside biosynthesis. The level of these enzymes is often elevated in tumors, which can be used as a marker for cancer diagnosis. This review presents the analysis of conformations of nucleosides and their analogues in complexes with nucleoside phosphorylases of the first (NP-1) family, which includes hexameric and trimeric purine nucleoside phosphorylases (EC 2.4.2.1), hexameric and trimeric 5′-deoxy-5′-methylthioadenosine phosphorylases (EC 2.4.2.28), and uridine phosphorylases (EC 2.4.2.3). Nucleosides adopt similar conformations in complexes, with these conformations being significantly different from those of free nucleosides. In complexes, pentofuranose rings of all nucleosides are at the W region of the pseudorotation cycle that corresponds to the energy barrier to the N↔S interconversion. In most of the complexes, the orientation of the bases with respect to the ribose is in the high-syn region in the immediate vicinity of the barrier to syn ↔ anti transitions. Such conformations of nucleosides in complexes are unfavorable when compared to free nucleosides and they are stabilized by interactions with the enzyme. The sulfate (or phosphate) ion in the active site of the complexes influences the conformation of the furanose ring. The binding of nucleosides in strained conformations is a characteristic feature of the enzyme–substrate complex formation for this enzyme group.
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8

Shibata, Hirofumi, Noriaki Ohnishi, Keiko Takeda, Hideko Fukunaga, Kanako Shimamura, Emiko Yasunobu, Isamu Tani, and Tadayo Hashimoto. "Germination of Bacillus cereus spores induced by purine ribosides and their analogs: effects of modification of base and sugar moieties of purine nucleosides on germination-inducing activity." Canadian Journal of Microbiology 32, no. 2 (February 1, 1986): 186–89. http://dx.doi.org/10.1139/m86-038.

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Purine riboside and some of its analogs were tested for their ability to induce germination of Bacillus cereus T spores. Hypoxanthine and adenine showed no germination-inducing activity either in the present or absence of D-ribose or its phosphorylated derivatives. Purine riboside and 18 analogs with modified purine base were all able to induce germination of the spores to various extents. In contrast to this, the requirement for the sugar moiety in the purine riboside appeared to be more stringent. Only those nucleosides that contained either D-ribose or deoxy-D-ribose, and certain species of azole derivatives such as 5-aminoimidazole-4-carboxamide covalently linked to the C(1′) of the sugar actively induced germination.
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9

Van Draanen, Nanine A., George A. Freeman, Steven A. Short, Robert Harvey, Robert Jansen, George Szczech, and George W. Koszalka. "Synthesis and Antiviral Activity of 2‘-Deoxy-4‘-thio Purine Nucleosides." Journal of Medicinal Chemistry 39, no. 2 (January 1996): 538–42. http://dx.doi.org/10.1021/jm950701k.

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10

Messini, Lea, Kamal N. Tiwari, John A. Montgomery, and John A. Secrist. "Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides." Nucleosides and Nucleotides 18, no. 4-5 (April 1999): 683–85. http://dx.doi.org/10.1080/15257779908041540.

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Dissertations / Theses on the topic "'-deoxy purine nucleosides"

1

Zhong, Minghong. "N9 Alkylation and Glycosylation of Purines; A Practical Synthesis of 2-Chloro-2'-deoxyadenosine." Diss., CLICK HERE for online access, 2004. http://contentdm.lib.byu.edu/ETD/image/etd433.pdf.

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2

Raoul, Sébastien. "Réactions d'oxydation des bases puriques des acides nucléiques." Université Joseph Fourier (Grenoble), 1995. http://www.theses.fr/1995GRE10178.

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Les modifications des bases de l'adn, support de l'information genetique, sont une des causes possibles de la mutagenese et la cancerogenese. Bien souvent ces modifications sont de type oxydatives. Elles sont induites par les especes reactives de l'oxygene, formees lors du metabolisme cellulaire et/ou par l'action de divers rayonnements (ionisants, uv, visible). Les mecanismes d'oxydation des deux bases puriques de l'adn, l'adenine et la guanine, ont ete etudies en identifiant et caracterisant les produits finals resultant de l'oxydation des nucleosides correspondants, pris comme systemes modeles. Les produits principaux de modification radio-induite de la 2'-desoxyadenosine en solution aqueuse ainsi que ceux provenant de l'oxydation photosensibilisee ont ete isoles par clhp puis caracterises par diverses methodes spectroscopiques dont notamment la rmn mono- et bi-dimensionnelle heteronucleaire #1h-#1#3c et #1h-#1#5n. L'analyse quantitative de la formation de ces produits dans differentes conditions a permis de proposer un schema de mecanismes coherent. La caracterisation du produit majoritaire de l'oxydation photosensibilisee de la 2'-desoxyguanosine, forme par un mecanisme radicalaire (type i), a ete realisee par les techniques pre-citees. La mise au point d'une methode de detection sensible et specifique de ce nucleoside oxyde, basee sur ses proprietes physico-chimiques, a permis de le rechercher dans un adn irradie. En outre, un schema du mecanisme rendant compte de sa formation est propose. La detection de ce produit, alliee a l'identification et la detection des produits formes par l'intermediaire de l'oxygene singulet (type ii) ont permis l'etude du mode d'action de divers photosensibilisateurs et de determiner pour chacun d'eux la contribution relative du mecanisme de desexcitation (type i/type ii). Enfin, nous avons etudie l'oxydation photosensibilisee de la 8-oxo-7,8-dihydro-2'-desoxyguanosine en identifiant les produits d'oxydation. En effet, ce nucleoside oxyde est un meilleur substrat que la 2'-desoxyguanosine pour l'oxygene singulet
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3

Bourdat, Anne-Gaëlle. "Lésions tandem radio-induites de l'ADN : formation, insertion dans des oligonucléotides et réparation." Université Joseph Fourier (Grenoble), 2000. http://www.theses.fr/2000GRE10100.

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La formation de lesions simples de l'adn generees par des photosensibilisateurs excites, les radiations ionisantes, les agents chimiques ne peut expliquer a elle seule la forte letalite cellulaire. Aussi, des modifications multiples sont supposees avoir un fort impact biologique. Parmi ces lesions complexes, la n-(2-desoxy, d-erythro-pentofuranosyl)-formylamine (df)/8-oxo-7,8-dihydro-2-desoxyguanosine (8-oxodguo) a ete observee dans de courts fragments d'adn apres exposition a un rayonnement x en solution aqueuse aeree. Afin d'evaluer les consequences biologiques liees a la presence de telles lesions, les residus 8-oxodguo et df ont ete introduits dans des oligonucleotides synthetiques en position vicinale. La chimie des phosphoramidites pac sur support solide a permis de preparer les oligonucleotides modifies. La purete des fragments d'adn synthetiques et l'integrite des bases modifiees inserees ont ete confirmees par differentes techniques analytiques : clhp, page, sm ies, sm malditof et electrophorese capillaire. Ces modeles synthetiques ont ete utilises pour determiner les specificites de substrats et les mecanismes d'excision de trois adn n-glycosylases impliquees dans la reparation par excision de base : endo iii et fpg of e. Coli ainsi que yogg1 of s. Cerevisiae. Les oligonucleotides sont incises par chacune des trois enzymes etudiees. Pourtant, les lesions tandem ne sont pas completement excisees par ces enzymes. L'efficacite d'excision, determinee par le rapport des constantes cinetiques de michaelis vm/km, n'est que peu modifiee par la presence des dommages multiples. La sm maldi-tof apporte des informations interessantes quand au mecanisme d'action des enzymes. Des experiences de replication in vitro ont montre que la progression des trois polymerases taq pol, pol et le fragment de klenow exo, est arretee par la presence des lesions tandem. Enfin, nous avons mesure par lc-ms/ms le taux de lesion tandem genere dans de l'adn expose a un rayonnement. Les lesions df-8-oxodguo et 8-oxodguo-df se forme significativement dans ces conditions. Il est interessant de noter que le dommage 8-oxodguo-df est produit en plus grande quantite que la lesion de sequence inverse. De plus, les resultats de ces experiences indiquent indirectement qu'il se forme d'autres dommages multiples comportant une lesion 8-oxodguo.
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