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Open AccessArticle Synthesis of a Cytokinin Linked by a Spacer to Dexamethasone and Biotin: Conjugates to Detect Cytokinin-Binding Proteins
Molecules 2016, 21(5), 576; doi:10.3390/molecules21050576
Received: 19 February 2016 / Revised: 25 April 2016 / Accepted: 25 April 2016 / Published: 30 April 2016
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Abstract
Yeast cells expressing cDNA libraries have provided two new approaches to facilitate further identification of cytokinin-binding proteins and receptors. These are the yeast three hybrid (Y3H) system and fluorescence activated cell sorting (FACS). The Y3H system requires a synthetic hybrid ligand comprising an
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Yeast cells expressing cDNA libraries have provided two new approaches to facilitate further identification of cytokinin-binding proteins and receptors. These are the yeast three hybrid (Y3H) system and fluorescence activated cell sorting (FACS). The Y3H system requires a synthetic hybrid ligand comprising an “anchor” moiety (e.g., dexamethasone) linked to a cytokinin via a spacer. In the yeast nucleus, this ligand by binding connects two fusion proteins leading to a reporter gene activation and detection and characterisation of cytokinin binding proteins. Herein is reported the first synthesis of dexamethasone-cytokinin ligands with a spacer linkage. This was attached to the purine ring of 6-benzylaminopurine (BAP) at positions 2, 8 or 9. To achieve this, dexamethasone was modified by periodate oxidation yielding a carboxylic group used for conjugation to the spacer by amide formation. Biotinyl derivatives of cytokinins for FACS included those synthesised by reaction of an activated ester of biotin with 8-(10-amino-decylamino) derivatives of BAP and BAP 9-riboside. Properties of the conjugates and some biological situations where they could be applicable are discussed briefly. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessArticle Site-Selective Ribosylation of Fluorescent Nucleobase Analogs Using Purine-Nucleoside Phosphorylase as a Catalyst: Effects of Point Mutations
Molecules 2016, 21(1), 44; doi:10.3390/molecules21010044
Received: 13 November 2015 / Revised: 7 December 2015 / Accepted: 9 December 2015 / Published: 28 December 2015
Cited by 2 | Viewed by 935 | PDF Full-text (870 KB) | HTML Full-text | XML Full-text
Abstract
Enzymatic ribosylation of fluorescent 8-azapurine derivatives, like 8-azaguanine and 2,6-diamino-8-azapurine, with purine-nucleoside phosphorylase (PNP) as a catalyst, leads to N9, N8, and N7-ribosides. The final proportion of the products may be modulated by point mutations in the enzyme active site. As an example,
[...] Read more.
Enzymatic ribosylation of fluorescent 8-azapurine derivatives, like 8-azaguanine and 2,6-diamino-8-azapurine, with purine-nucleoside phosphorylase (PNP) as a catalyst, leads to N9, N8, and N7-ribosides. The final proportion of the products may be modulated by point mutations in the enzyme active site. As an example, ribosylation of the latter substrate by wild-type calf PNP gives N7- and N8-ribosides, while the N243D mutant directs the ribosyl substitution at N9- and N7-positions. The same mutant allows synthesis of the fluorescent N7-β-d-ribosyl-8-azaguanine. The mutated form of the E. coli PNP, D204N, can be utilized to obtain non-typical ribosides of 8-azaadenine and 2,6-diamino-8-azapurine as well. The N7- and N8-ribosides of the 8-azapurines can be analytically useful, as illustrated by N7-β-d-ribosyl-2,6-diamino-8-azapurine, which is a good fluorogenic substrate for mammalian forms of PNP, including human blood PNP, while the N8-riboside is selective to the E. coli enzyme. Full article
(This article belongs to the Special Issue Nucleoside Modifications) Printed Edition available
Open AccessArticle Cladribine Analogues via O6-(Benzotriazolyl) Derivatives of Guanine Nucleosides
Molecules 2015, 20(10), 18437-18463; doi:10.3390/molecules201018437
Received: 17 August 2015 / Revised: 20 September 2015 / Accepted: 22 September 2015 / Published: 9 October 2015
Cited by 2 | Viewed by 1347 | PDF Full-text (1310 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Cladribine, 2-chloro-2′-deoxyadenosine, is a highly efficacious, clinically used nucleoside for the treatment of hairy cell leukemia. It is also being evaluated against other lymphoid malignancies and has been a molecule of interest for well over half a century. In continuation of our interest
[...] Read more.
Cladribine, 2-chloro-2′-deoxyadenosine, is a highly efficacious, clinically used nucleoside for the treatment of hairy cell leukemia. It is also being evaluated against other lymphoid malignancies and has been a molecule of interest for well over half a century. In continuation of our interest in the amide bond-activation in purine nucleosides via the use of (benzotriazol-1yl-oxy)tris(dimethylamino)phosphonium hexafluorophosphate, we have evaluated the use of O6-(benzotriazol-1-yl)-2′-deoxyguanosine as a potential precursor to cladribine and its analogues. These compounds, after appropriate deprotection, were assessed for their biological activities, and the data are presented herein. Against hairy cell leukemia (HCL), T-cell lymphoma (TCL) and chronic lymphocytic leukemia (CLL), cladribine was the most active against all. The bromo analogue of cladribine showed comparable activity to the ribose analogue of cladribine against HCL, but was more active against TCL and CLL. The bromo ribose analogue of cladribine showed activity, but was the least active among the C6-NH2-containing compounds. Substitution with alkyl groups at the exocyclic amino group appears detrimental to activity, and only the C6 piperidinyl cladribine analogue demonstrated any activity. Against adenocarcinoma MDA-MB-231 cells, cladribine and its ribose analogue were most active. Full article
(This article belongs to the Special Issue Nucleoside Modifications) Printed Edition available
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Open AccessArticle Synthesis and Pharmacophore Modelling of 2,6,9-Trisubstituted Purine Derivatives and Their Potential Role as Apoptosis-Inducing Agents in Cancer Cell Lines
Molecules 2015, 20(4), 6808-6826; doi:10.3390/molecules20046808
Received: 4 March 2015 / Revised: 9 April 2015 / Accepted: 10 April 2015 / Published: 15 April 2015
Cited by 4 | Viewed by 1548 | PDF Full-text (978 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A series of 2,6,9-trisubstituted purine derivatives have been synthesized and investigated for their potential role as antitumor agents. Twelve compounds were obtained by a three step synthetic procedure using microwave irradiation in a pivotal step. All compounds were evaluated in vitro to determine
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A series of 2,6,9-trisubstituted purine derivatives have been synthesized and investigated for their potential role as antitumor agents. Twelve compounds were obtained by a three step synthetic procedure using microwave irradiation in a pivotal step. All compounds were evaluated in vitro to determine their potential effect on cell toxicity by the MTT method and flow cytometry analysis on four cancer cells lines and Vero cells. Three out of twelve compounds were found to be promising agents compared to a known and effective anticancer drug, etoposide, in three out of four cancer cell lines assayed with considerable selectivity. Preliminary flow cytometry data suggests that compounds mentioned above induce apoptosis on these cells. The main structural requirements for their activity for each cancer cell line were characterized with a preliminary pharmacophore model, which identified aromatic centers, hydrogen acceptor/donor center and a hydrophobic area. These features were consistent with the cytotoxic activity of the assayed compounds. Full article
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Open AccessReview Functionalized Solid Electrodes for Electrochemical Biosensing of Purine Nucleobases and Their Analogues: A Review
Sensors 2015, 15(1), 1564-1600; doi:10.3390/s150101564
Received: 27 November 2014 / Accepted: 4 January 2015 / Published: 14 January 2015
Cited by 14 | Viewed by 1493 | PDF Full-text (1997 KB) | HTML Full-text | XML Full-text
Abstract
Interest in electrochemical analysis of purine nucleobases and few other important purine derivatives has been growing rapidly. Over the period of the past decade, the design of electrochemical biosensors has been focused on achieving high sensitivity and efficiency. The range of existing electrochemical
[...] Read more.
Interest in electrochemical analysis of purine nucleobases and few other important purine derivatives has been growing rapidly. Over the period of the past decade, the design of electrochemical biosensors has been focused on achieving high sensitivity and efficiency. The range of existing electrochemical methods with carbon electrode displays the highest rate in the development of biosensors. Moreover, modification of electrode surfaces based on nanomaterials is frequently used due to their extraordinary conductivity and surface to volume ratio. Different strategies for modifying electrode surfaces facilitate electron transport between the electrode surface and biomolecules, including DNA, oligonucleotides and their components. This review aims to summarize recent developments in the electrochemical analysis of purine derivatives, as well as discuss different applications. Full article
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Open AccessArticle Formation of Mixed-Ligand Complexes of Pd2+ with Nucleoside 5'-Monophosphates and Some Metal-Ion-Binding Nucleoside Surrogates
Molecules 2014, 19(10), 16976-16986; doi:10.3390/molecules191016976
Received: 16 September 2014 / Revised: 8 October 2014 / Accepted: 17 October 2014 / Published: 22 October 2014
Cited by 6 | Viewed by 1290 | PDF Full-text (449 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Formation of mixed-ligand Pd2+ complexes between canonical nucleoside 5'-monophosphates and five metal-ion-binding nucleoside analogs has been studied by 1H-NMR spectroscopy to test the ability of these nucleoside surrogates to discriminate between unmodified nucleobases by Pd2+-mediated base pairing. The nucleoside
[...] Read more.
Formation of mixed-ligand Pd2+ complexes between canonical nucleoside 5'-monophosphates and five metal-ion-binding nucleoside analogs has been studied by 1H-NMR spectroscopy to test the ability of these nucleoside surrogates to discriminate between unmodified nucleobases by Pd2+-mediated base pairing. The nucleoside analogs studied included 2,6-bis(3,5-dimethylpyrazol-1-yl)-, 2,6-bis(1-methylhydrazinyl)- and 6-(3,5-dimethylpyrazol-1-yl)-substituted 9-(β-d-ribofuranosyl)purines 13, and 2,4-bis(3,5-dimethylpyrazol-1-yl)- and 2,4-bis(1-methylhydrazinyl)-substituted 5-(β-d-ribofuranosyl)-pyrimidines 45. Among these, the purine derivatives 1-3 bound Pd2+ much more tightly than the pyrimidine derivatives 4, 5 despite apparently similar structures of the potential coordination sites. Compounds 1 and 2 formed markedly stable mixed-ligand Pd2+ complexes with UMP and GMP, UMP binding favored by 1 and GMP by 2. With 3, formation of mixed-ligand complexes was retarded by binding of two molecules of 3 to Pd2+. Full article
(This article belongs to the Special Issue Nucleoside Modifications) Printed Edition available
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Open AccessArticle Platinum(II) Oxalato Complexes Involving Adenosine-Based N-Donor Ligands: Synthesis, Characterization and Cytotoxicity Evaluation
Molecules 2014, 19(3), 3832-3847; doi:10.3390/molecules19033832
Received: 31 January 2014 / Revised: 11 March 2014 / Accepted: 21 March 2014 / Published: 24 March 2014
Cited by 7 | Viewed by 1819 | PDF Full-text (643 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A one-step synthetic procedure using the reaction of potassium bis(oxalato)platinate(II) with the corresponding N6-benzyladenosine derivative (nL) provided the [Pt(ox)(nL)2]∙1.5H2O oxalato (ox) complexes 15, involving the nL molecules as monodentate coordinated
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A one-step synthetic procedure using the reaction of potassium bis(oxalato)platinate(II) with the corresponding N6-benzyladenosine derivative (nL) provided the [Pt(ox)(nL)2]∙1.5H2O oxalato (ox) complexes 15, involving the nL molecules as monodentate coordinated N-donor ligands. The complexes were thoroughly characterized by elemental analysis, multinuclear (1H, 13C, 15N, 195Pt) and two dimensional NMR, infrared and Raman spectroscopy, and mass spectrometry, proving their composition and purity as well as coordination of nL through the N7 atom of the purine moiety. Geometry of [Pt(ox)(4FL)2] (5) was optimized at the B3LYP/LANLTZ/6-311G** level of theory. The complexes were screened for their in vitro cytotoxicity against two human cancer cell lines (HOS osteosarcoma and MCF7 breast adenocarcinoma), but they did not show any effect up to the concentration of 50.0 µM (compounds 1, 2) or 20.0 µM (compounds 35). Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessReview Metabolic Interactions of Purine Derivatives with Human ABC Transporter ABCG2: Genetic Testing to Assess Gout Risk
Pharmaceuticals 2013, 6(11), 1347-1360; doi:10.3390/ph6111347
Received: 30 September 2013 / Revised: 22 October 2013 / Accepted: 27 October 2013 / Published: 4 November 2013
Cited by 9 | Viewed by 2941 | PDF Full-text (317 KB) | HTML Full-text | XML Full-text
Abstract
In mammals, excess purine nucleosides are removed from the body by breakdown in the liver and excretion from the kidneys. Uric acid is the end product of purine metabolism in humans. Two-thirds of uric acid in the human body is normally excreted through
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In mammals, excess purine nucleosides are removed from the body by breakdown in the liver and excretion from the kidneys. Uric acid is the end product of purine metabolism in humans. Two-thirds of uric acid in the human body is normally excreted through the kidney, whereas one-third undergoes uricolysis (decomposition of uric acid) in the gut. Elevated serum uric acid levels result in gout and could be a risk factor for cardiovascular disease and diabetes. Recent studies have shown that human ATP-binding cassette transporter ABCG2 plays a role of renal excretion of uric acid. Two non-synonymous single nucleotide polymorphisms (SNPs), i.e., 421C>A (major) and 376C>T (minor), in the ABCG2 gene result in impaired transport activity, owing to ubiquitination-mediated proteosomal degradation and truncation of ABCG2, respectively. These genetic polymorphisms are associated with hyperuricemia and gout. Allele frequencies of those SNPs are significantly higher in Asian populations than they are in African and Caucasian populations. A rapid and isothermal genotyping method has been developed to detect the SNP 421C>A, where one drop of peripheral blood is sufficient for the detection. Development of simple genotyping methods would serve to improve prevention and early therapeutic intervention for high-risk individuals in personalized healthcare. Full article
(This article belongs to the Special Issue Purine and Its Derivatives)
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Open AccessArticle Novel Coumarin Derivatives Containing 1,2,4-Triazole, 4,5-Dicyanoimidazole and Purine Moieties: Synthesis and Evaluation of Their Cytostatic Activity
Molecules 2012, 17(9), 11010-11025; doi:10.3390/molecules170911010
Received: 16 July 2012 / Revised: 23 August 2012 / Accepted: 3 September 2012 / Published: 12 September 2012
Cited by 16 | Viewed by 2452 | PDF Full-text (271 KB)
Abstract
We report here on the synthesis and in vitro anti-tumor effects of a series of novel 1,2,4-triazole (compounds 36), 4,5-dicyanoimidazole (compound 7), and purine (compounds 813) coumarin derivatives and their acyclic nucleoside analogues 1418
[...] Read more.
We report here on the synthesis and in vitro anti-tumor effects of a series of novel 1,2,4-triazole (compounds 36), 4,5-dicyanoimidazole (compound 7), and purine (compounds 813) coumarin derivatives and their acyclic nucleoside analogues 1418. Structures of novel compounds 318 were deduced from their 1H- and 13C-NMR and corresponding mass spectra. Results of anti-proliferative assays performed on a panel of selected human tumor cell lines revealed that compound 6 had moderate cytostatic activity against the HeLa cell line (IC50 = 35 µM), whereas compound 10 showed moderate activity against the HeLa (IC50 = 33 µM), HepG2 (IC50 = 25 µM) and SW620 (IC50 = 35 µM) cell lines. These compounds showed no cytotoxic effects on normal (diploid) human fibroblasts. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessReview Terpenyl-Purines from the Sea
Mar. Drugs 2009, 7(4), 833-849; doi:10.3390/md7040833
Received: 12 November 2009 / Revised: 26 November 2009 / Accepted: 22 December 2009 / Published: 23 December 2009
Cited by 21 | Viewed by 8673 | PDF Full-text (175 KB) | HTML Full-text | XML Full-text
Abstract
Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity
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Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity against a variety of species, including Mycobacterium tuberculosis, and also an important cytotoxic activity against several cancer cell lines, including multidrug-resistant ones. Of particular interest in this context are the asmarines (tetrahydro[1,4]diazepino[1,2,3-g,h]purines), which have shown potent antiproliferative activity against several types of human cancer cell lines. This review summarizes the sources of isolation, chemistry and bioactivity of marine alkylpurines and their bioactive derivatives. Full article
(This article belongs to the Special Issue Alkaloid Analogs)
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Open AccessArticle Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids
Molecules 2009, 14(12), 5124-5143; doi:10.3390/molecules14125124
Received: 13 November 2009 / Revised: 26 November 2009 / Accepted: 7 December 2009 / Published: 9 December 2009
Cited by 7 | Viewed by 8452 | PDF Full-text (240 KB)
Abstract
A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols
[...] Read more.
A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols and methyl propiolate and subsequent ester aminolysis with primary and secondary amines furnished the target compounds, which were obtained in excellent yields with no racemization. Docking of selected target compounds shows that the chiral 1,4-disubstituted-1,2,3-triazoles derivatives has the potential of mimicking the binding mode of known purine analogues. Full article
Open AccessArticle Study of Copper and Purine-Copper Complexes on Modified Carbon Electrodes by Cyclic and Elimination Voltammetry
Sensors 2008, 8(1), 429-444; doi:10.3390/s8010429
Received: 30 December 2007 / Accepted: 15 January 2008 / Published: 24 January 2008
Cited by 19 | Viewed by 4701 | PDF Full-text (515 KB) | HTML Full-text | XML Full-text
Abstract
Using a paraffin impregnated graphite electrode (PIGE) and mercury-modifiedpyrolytic graphite electrode with basal orientation (Hg-PGEb) copper(II) and Cu(II)-DNApurine base solutions have been studied by cyclic (CV) and linear sweep voltammetry(LSV) in connection with elimination voltammetry with linear scan (EVLS). In chlorideand bromide solutions
[...] Read more.
Using a paraffin impregnated graphite electrode (PIGE) and mercury-modifiedpyrolytic graphite electrode with basal orientation (Hg-PGEb) copper(II) and Cu(II)-DNApurine base solutions have been studied by cyclic (CV) and linear sweep voltammetry(LSV) in connection with elimination voltammetry with linear scan (EVLS). In chlorideand bromide solutions (pH 6), the redox process of Cu(II) proceeded on PIGE with twocathodic and two anodic potentially separated signals. According to the eliminationfunction E4, the first cathodic peak corresponds to the reduction Cu(II) e- → Cu(I) withthe possibility of fast disproportionation 2Cu(I) → Cu(II) Cu(0). The E4 of the secondcathodic peak signalized an electrode process controlled by a surface reaction. Theelectrode system of Cu(II) on Hg-PGEb in borate buffer (pH 9.2) was characterized by onecathodic and one anodic peak. Anodic stripping voltammetry (ASV) on PIGE and cathodicstripping voltammetry (CSV) on Hg-PGEb were carried out at potentials where thereduction of copper ions took place and Cu(I)-purine complexes were formed. By usingASV and CSV in combination with EVLS, the sensitivity of Cu(I)-purine complexdetection was enhanced relative to either ASV or CSV alone, resulting in higher peakcurrents of more than one order of magnitude. The statistical treatment of CE data wasused to determine the reproducibility of measurements. Our results show that EVLS inconnection with the stripping procedure is useful for both qualitative and quantitativemicroanalysis of purine derivatives and can also reveal details of studied electrodeprocesses. Full article
Open AccessArticle Pyrazolo[4,3-e][1,2,4]triazines: Purine Analogues with Electronic Absorption in the Visible Region
Molecules 2005, 10(10), 1298-1306; doi:10.3390/10101298
Received: 12 April 2005 / Accepted: 10 July 2005 / Published: 31 October 2005
Cited by 10 | Viewed by 4398 | PDF Full-text (139 KB) | HTML Full-text | XML Full-text
Abstract
Synthesis of several pryrazolo[4,3-e][1,2,4]-triazines is described. Theabsorption spectrum of some 5-substituted derivatives was found to extend to the visibleregion. These compounds were found to inhibit some enzymes of purine metabolism, likexanthine oxidase or bacterial purine-nucleoside phosphorylase with Ki values in the 10-3
[...] Read more.
Synthesis of several pryrazolo[4,3-e][1,2,4]-triazines is described. Theabsorption spectrum of some 5-substituted derivatives was found to extend to the visibleregion. These compounds were found to inhibit some enzymes of purine metabolism, likexanthine oxidase or bacterial purine-nucleoside phosphorylase with Ki values in the 10-3 –10-5 M range. Full article
Open AccessArticle Synthesis of N-7-Substituted Purines from Imidazole Precursors
Molecules 1999, 4(10), 287-309; doi:10.3390/41000287
Received: 23 February 1999 / Accepted: 4 June 1999 / Published: 25 September 1999
Cited by 8 | Viewed by 3469 | PDF Full-text (136 KB) | HTML Full-text | XML Full-text
Abstract
Synthesis of purines and purine mono-1-oxides from the respective 5-substituted 4-nitroimidazole derivatives is described. The commercially available 4-nitroimidazole, in a few simple steps (including Vicarious Nucleophilic Substitution of Hydrogen), was transformed into: 4-aminoimidazoyl-5-carboximes, N-[1-(4-amino-1H-imidazol-5-yl)methylidene]-N-(aryl)amine derivatives or into 4-amino-5-aminomethyl-imidazole.
[...] Read more.
Synthesis of purines and purine mono-1-oxides from the respective 5-substituted 4-nitroimidazole derivatives is described. The commercially available 4-nitroimidazole, in a few simple steps (including Vicarious Nucleophilic Substitution of Hydrogen), was transformed into: 4-aminoimidazoyl-5-carboximes, N-[1-(4-amino-1H-imidazol-5-yl)methylidene]-N-(aryl)amine derivatives or into 4-amino-5-aminomethyl-imidazole. These intermediates were cyclized to the final products. Full article
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