13389-03-2Relevant academic research and scientific papers
Preparation of pyrenyl-modified nucleosides via Suzuki-Miyaura cross-coupling reactions
Amann, Nicole,Wagenknecht, Hans-Achim
, p. 687 - 691 (2002)
The modified nucleosides 5-pyrenyl-2′-deoxyuridine (1) and 8-pyrenyl-2′-deoxyguanosine (2) were synthesized via palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of pyren-1-yl boronic acid (3) to either 5-iodo-2′-deoxyuridine (4), or 8-bromo-2′-deoxyguanosine (7), respectively. No protecting groups for the hydroxy and amino functions of the nucleoside are needed during the preparation. Both pyrene derivatives are suitable nucleoside models for the spectrosopic investigation of reductive electron transfer (in 1), or oxidative hole transfer (in 2).
DNA-polyamine cross-links generated upon one electron oxidation of DNA
Silerme, Stéphanie,Bobyk, Laure,Taverna-Porro, Marisa,Cuier, Camille,Saint-Pierre, Christine,Ravanat, Jean-Luc
, p. 1011 - 1018 (2014)
The possibility to induce the formation of covalent cross-links between polyamines and guanine following one electron oxidation of double stranded DNA has been evaluated. For such a purpose, a strategy has been developed to chemically synthesize the polyamine-C8-guanine adducts, and efforts have been made to characterize them. Then, an analytical method, based on HPLC separation coupled through electrospray ionization to tandem mass spectrometry, has been setup for their detection and quantification. Using such a sensitive approach, we have demonstrated that polyamine-C8-guanine adducts could be produced with significant yields in double stranded DNA following a one-electron oxidation reaction induced by photosensitization. These adducts, involving either putrescine, spermine, or spermidine, are generated by the nucleophilic addition of primary amino groups of polyamines onto the C8 position of the guanine radical cation. Our data demonstrate that such a nucleophilic addition of polyamines is much more efficient than the addition of a water molecule that leads to 8-oxo-7,8-dihydroguanine formation.
8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells
Lin,Cheng,Ishiguro,Sartorelli
, p. 1194 - 1198 (1985)
A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted -N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.
An improved synthesis of 8-bromo-2'-deoxyguanosine
Gannett,Sura
, p. 1611 - 1615 (1993)
A new synthesis of 8-bromo-2'-deoxyguanosine, a key intermediate in the synthesis of the mutagenic DNA adduct 8-oxo-2'-deoxyguanosine is described. The advantage of this method are significantly improved yields and ease of isolation.
Selective C8-Metalation of Purine Nucleosides via Oxidative Addition
Kampert, Florian,Brackemeyer, Dirk,Tan, Tristan Tsai Yuan,Ekkehardt Hahn
, p. 4181 - 4185 (2018)
8-Bromo-2′-deoxy-3′,5′-di-O-acetylguanosine (1), 8-bromo-2′,3′,5′-tri-O-acetylguanosine (2), 8-bromo-2′-deoxy-3′,5′-di-O-acetyladenosine (3), and 8-bromo-2′,3′,5′-tri-O-acetyladenosine (4) react with [Pd(PPh3)4] via a C8-Br oxidative addition to give the C8-palladated azolato complexes [5]-[8] featuring an unprotonated N7 ring nitrogen atom. The complexes feature diastereotopic trans-disposed triphenylphosphine ligands, which allowed the determination of 2JPP for complexes of the type trans-[PdL2(PPh3)2] (2JPP = 442 Hz for [7]). In addition, two complex molecules of [7] form a trans-Watson-Crick/Hoogsteen AA base pair in the solid state. N7-protonation of the guanosine-derived complexes [5] and [6] with HBF4·Et2O and of adenosine-derived complexes [7] and [8] using lutidinium triflate yields complexes [9]BF4 and [10]BF4 and complexes [11]OTf and [12]OTf bearing protic NH,NR-NHC ligands derived from guanosine and adenosine, respectively.
Synthesis and optical properties of the C-8 adduct of benzo[a]pyrene and deoxyguanosine
Valis, Linda,Wagenknecht, Hans-Achim
, p. 2281 - 2284 (2005)
8-(Benzo[a]pyren-6-yl)-2′-deoxyguanosine (Bp-dG) was prepared via a palladium-catalyzed Suzuki-Miyaura-type cross-coupling reaction from the pinacol ester of 6-benzo[a]pyrenyl boronic acid and the corresponding brominated deoxyguanosine precursor. The absorption and steady-state fluorescence properties of Bp-dG were characterized and compared with that of 6-benzo[a]pyrene. The modified nucleoside Bp-dG exhibits an unexpected high stability towards nucleosidic hydrolysis even under irradiation with UV light. Georg Thieme Verlag Stuttgart.
Synthesis of oligonucleotides bearing an arylamine modification in the C8-position of 2′-deoxyguanosine
Meier,Graesl,Detmer,Marx
, p. 691 - 694 (2005)
C8-Arylamine-dG adducts were converted into their corresponding 5′-0-DMTr-3′-0-phosphoramidite-C8-arylamine-dG derivatives. These compounds were used for the automated synthesis of site-specifically modified oligonucleotides. The oligonucleotides were stu
Expanding the hoogsteen edge of 2′-deoxyguanosine: Consequences for G-quadruplex formation
Gubala, Vladimir,Betancourt, Jose E.,Rivera, Jose M.
, p. 4735 - 4738 (2004)
(Chemical Equation Presented) The synthesis and self-assembling properties of 8-aryl-2′-deoxyguanosine derivatives are described. Our studies suggest that a properly placed acetyl group can increase the stability and specificity of the resulting G-quadrup
An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing
Schlitt, Katherine M.,Millen, Andrea L.,Wetmore, Stacey D.,Manderville, Richard A.
, p. 1565 - 1571 (2011)
Pyrrole- and indole-linked C8-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson-Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ～ 10-fold brighter and shows promise as a fluorescent reporter of Hoogsteen base pairing. The Royal Society of Chemistry 2011.
Synthesis of 8-oxo-dGTP and its β,γ-CH2-, β,γ-CHF-, and β,γ-CF2- analogues
Zheng, Yiying,Haratipour, Pouya,Kashemirov, Boris A.,McKenna, Charles E.
supporting information, (2021/02/22)
Three novel bisphosphonate analogues of 8-oxo-dGTP 3 in which the bridging β,γ-oxygen is replaced by a methylene, fluoromethylene or difluoromethylene group (4–6, respectively) have been synthesized from 8-oxo-dGMP 2 by reaction of its morpholine 5′-phosphoramidate 14 or preferably, its N-methylimidazole 5′-phosphoramidate 15 with tri-n-butylammonium salts of the appropriate bisphosphonic acids, 11–13. The latter method also provides a convenient new route to 3. Analogues 4–6 may be useful as mechanistic probes for the role of 3 in abnormal DNA replication and repair.
