3056-33-5Relevant academic research and scientific papers
Voltammetric study of the affinity of divalent heavy metals for guanine-functionalized iron oxide nanoparticles
Sawan, Simona,Hamze, Khalil,Youssef, Ali,Boukarroum, Rayyan,Bouhadir, Kamal,Errachid, Abdelhamid,Maalouf, Rita,Jaffrezic-Renault, Nicole
, p. 229 - 240 (2021/02/12)
In this study, a novel nanobiomaterial based on (3-aminopropyl)triethoxysilane (APTES)-coated iron oxide (Fe3O4) nanoparticles functionalized with newly synthesized guanine hydrazide (GH) was elaborated. A boron-doped diamond electrode coated with GH-APTES–Fe3O4 nanoparticles was used to assess the interaction of heavy metal ions with guanine hydrazide. The adsorption isotherms were electrochemically investigated and it was shown that the adsorption capacity of the nanoparticles towards heavy metals decreased in the following order: Cu2+ > Pb2+ > Cd2+. From the calibration curves, the sensitivities of detection were as follows: 171.6 μA/μM for Cu(II), 156 μA/μM for Pb(II), and 101.4 μA/μM for Cd(II). Graphic abstract: [Figure not available: see fulltext.].
Preparation method of N2,9-diacetylguanine
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Paragraph 0027; 0028; 0029; 0030; 0031; 0032, (2017/06/02)
The invention belongs to the technical field of chemistry, and in particular, relates to a preparation method of N2,9-diacetylguanine. The method comprises the steps: A, dissolving guanine in pyridine under the condition of stirring, then adding a 4-dimethylamino pyridine DMAP catalyst into a guanine pyridine solution, cooling to -5+/-1 DEG C, slowly dropping an acylating agent acetyl chloride, and in the dropping process, controlling the temperature to be lower than 10 DEG C; and after dropping is finished, carrying out a reaction for 2-4 h at room temperature, to obtain an X1-containing reaction liquid; B, heating the X1 reaction liquid, carrying out reduced pressure distillation to remove substances X2 and X3, and separating out an X1-containing solid; C, washing the X1-containing solid obtained in the step B with distilled water, and filtering to remove X4 and X5; and D, dissolving the X1-containing solid obtained in the step C in an acetic acid solution through stirring, and filtering to remove an undissolved substance X6, to obtain an X1-containing filtrate. The total yield of N2,9-diacetylguanine reaches 90.2%, and the purity of the product reaches 99.5%.
Small Molecules in the Cone Snail Arsenal
Neves, Jorge L. B.,Lin, Zhenjian,Imperial, Julita S.,Antunes, Agostinho,Vasconcelos, Vitor,Olivera, Baldomero M.,Schmidt, Eric W.
supporting information, p. 4933 - 4935 (2015/11/03)
Cone snails are renowned for producing peptide-based venom, containing conopeptides and conotoxins, to capture their prey. A novel small-molecule guanine derivative with unprecedented features, genuanine, was isolated from the venom of two cone snail species. Genuanine causes paralysis in mice, indicating that small molecules and not just polypeptides may contribute to the activity of cone snail venom.
Synthesis of some biologically active halogenopurines
Hu, Yu Lin,Liu, Xiang,Lu, Ming,Ge, Qiang,Liu, Xiao Bin
experimental part, p. 429 - 436 (2010/12/29)
A series of some biologically active halogenopurines were synthesized from commercially available guanine (1). The reaction of guanine with acetic anhydride yielded 2,9-diacetylguanine (2-1) by acetylation reaction. Further treatment of 2-1 with POCl3 by PEG-2000 phase transfer catalysis furnished the important compound 3a, then 2-amino-6-halogenopurines (3b-d) were obtained through chlorine-exchange halogenations between KX and 3a by TPPB phase transfer catalyst. Further, 2-halogenopurines (2-2a-d, 4-2a-d, 5a-d) were efficiently prepared from 2-amino-6-substituted purines (1, 3a, 4-1) via a diazotization catalyzed by their corresponding CuX, and some new compounds 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c and 5d have been discovered. The structures of synthesized compounds were mainly established on the basis of their elemental analysis, 1H NMR, as well as their mass spectral data. All the title compounds were screened for their antifungal activities, and some of the compounds showed promising activity.
Synthesis and biological activities of O6-alkylguanine derivatives
Hu, Yu Lin,Ge, Qiang,Lu, Ming,Lu, Hong Fei
experimental part, p. 425 - 432 (2012/01/13)
The synthesis of some biologically active O6-alkylguanine derivatives was achieved by alkoxylation of 2-amino-6-chloropurine with sodium alkoxides in polar aprotic solvent (DMSO) conditions. The starting material 2-amino-6-chloropurine was prepared by chlorination of 2,9-diacetylguanine (obtained from acetylation of commercially available guanine) by PEG-2000 phase transfer catalysis. The structures of the products were deduced from elemental analysis and spectral data (IR, 1H NMR, and mass spectra). All the title compounds were screened for their antifungal activities, and some of the compounds showed promising activities.
Guanine-Containing DNA Minor-Groove binders
Pulido, Daniel,Sanchez, Albert,Robles, Jordi,Pedroso, Enrique,Grandas, Anna
experimental part, p. 1398 - 1406 (2009/08/07)
Solid-phase procedures have been used to prepare six di-pyrrole-containing DNA ligands that combine (guanin-9-yl)-acetyl, (guanin-7-yl)acetyl or acetyl moieties at the N-terminal end and two lysines or a (dimethylamino)propyl group at the C terminus. Inspection of their DNA-stabilizing properties by UV-monitored thermal denaturation experiments showed that the ligand incorporating the (guanin-9-yl)acetyl group and the (dimethylamino)propyl tail had the highest duplex-stabilizing effects. Wiley-VCH Verlag GmbH & Co, KGaA.
Engineering a selective small-molecule substrate binding site into a deoxyribozyme
Hoebartner, Claudia,Silverman, Scott K.
, p. 7420 - 7424 (2008/09/18)
A small goal: An RNA ligase deoxyribozyme is engineered to accept a small-molecule NTP substrate in a multiple-turnover fashion. Selective binding is enforced by hydrogen bonding, and structural preorganization within the NTP itself is important for its efficient utilization as a substrate. This study points the way toward a broader use of small-molecule substrates with nucleic acid enzymes. (Figure Presented)
Positively-charged peptide nucleic acid analogs with improved properties
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Page/Page column 8-9, (2008/06/13)
The present invention relates to novel types of peptide nucleic acids (PNAS) with improved properties. In particular, it relates to positively charged PNA units having an ethylene linker between the backbone and the nucleobase, to oligonucleotide analogs comprising these units, to oligomers comprising these units, and to the use of positively charged PNAs as novel delivery agents with therapeutic and diagnostic applications including for antisense therapy.
A novel approach to the synthesis of the purine anti-viral agent gancyclovir
Sariri, Reyhaneh,Khalili, Gholamhosein
, p. 651 - 654 (2007/10/03)
The aim of this research is to synthesize gancyclovir, a purine anti-viral drug in large scale via simple intermediates. Reaction of guanine 1 with acetic anhydride followed by the attachment of the 2-O-acetoxymethyl-1,3-di-O-benzyl glycerol 3 as a side chain, subsequently lead to the production of N2acetyl-9-(1,3dibenzyloxy-2-propoxymethyl)guanine 6 and N2, acetyl-9-(1,3-dihydroxy-2-propoxymethyl)guanine 7 and finally synthesizing gancyclovir 8. Among many pathways to the synthesis of purine derivatives, our four step procedure results in good yield and is proved to be an economic way of large scale synthesis.
