Nucleosides Nucleotides &amp Nucleic Acids (Nucleos Nucleot Nucleic Acids )


This all-inclusive journal features research articles; short notices; and concise, critical reviews of related topics in the organic and medicinal chemistry and biochemistry of nucleosides and nucleotides. Presenting the latest original research papers with complete experimental details, Nucleosides & Nucleotides emphasizes the synthesis, biological activities, new and improved synthetic methods, and significant observations related to new compounds.

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Publications in this journal

  • [Show abstract] [Hide abstract]
    ABSTRACT: The present article describes the synthesis of new 4H-1,4-benzothiazines via condensation and oxidative cyclization of substituted 2-aminobenzenethiols with compounds containing active methylene groups. It is believed that the reaction proceeds via intermediary of the enaminoketone system. The sulfone derivatives were synthesized by oxidation of 4H-1,4-benzothiazines using 30% hydrogen peroxide in glacial acetic acid. Benzothiazines were used as bases to prepare ribofuranosides by treatment with a sugar derivative (β-D-ribofuranosyl-1-acetate-2,3,5-tribenzoate). The pharmacological importance of the synthesized compounds was evaluated by their, antimicrobial properties against various bacterial strains and fungal species. The structures of the compounds have been confirmed by spectral and chemical analysis.
    Nucleosides Nucleotides &amp Nucleic Acids 01/2015; 34(1):40-55.
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    ABSTRACT: The interaction between [Pd(But-dtc)(phen)]NO3 (where But-dtc = butyldithiocarbamate and phen = 1,10-phenanthroline) with HSA (Human Serum Albumin) was investigated by applying fluorescence, UV-Vis and circular dichroism techniques under physiological conditions. The results of fluorescence spectra indicated that the Pd(II) complex could effectively quench the fluorescence intensity of HSA molecules via static mechanism. The number of binding sites and binding constant of HSA-Pd(II) complex were calculated. Analysis of absorption titration data on the interaction between Pd(II) complex and HSA revealed the formation of HSA-Pd(II) complex with high-binding affinity. Thermodynamic parameters indicated that hydrophobic forces play a major role in this interaction. Furthermore, CD measurements were taken to explore changes in HSA secondary structure induced by the Pd(II) complex.
    Nucleosides Nucleotides &amp Nucleic Acids 01/2015; 34(1):16-32.
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    ABSTRACT: We describe concise and efficient synthesis of biologically very important 3'-O-tetraphosphates namely 2'-deoxyadenosine-3'-O-tetraphosphate (2'-d-3'-A4P) and 2'-deoxycytidine-3'-O-tetra-phosphate (2'-d-3'-C4P). N(6)-benzoyl-5'-O-levulinoyl-2'-deoxyadenosine was converted into N(6)-benzoyl-5'-O-levulinoyl-2'-deoxyadenosine-3'-O-tetraphosphate in 87% yield using a one-pot synthetic methodology. One-step concurrent deprotection of N(6)-benzoyl and 5'-O-levulinoyl groups using concentrated aqueous ammonia resulted 2'-d-3'-A4P in 74% yield. The same synthetic strategy was successfully employed to convert N(4)-benzoyl-5'-O-levulinoyl-2'-deoxycytidine into 2'-d-3'-C4P in 68% yield.
    Nucleosides Nucleotides &amp Nucleic Acids 01/2015; 34(1):33-9.
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    ABSTRACT: Hydroquinoline acyclonucleosides 2, 4, 6a,b, 8a,b, 9a,b, and their corresponding N-alkyl derivatives (10-12) were obtained by the reaction of 1a,b with acetoxybutylbromide, (2-acetoxyethoxy)methyl bromide, 3-chloropropanol, 1,3-dichloro-2-propanol, epichlorohydrin, propargyl/allyl bromides in the presence of K2CO3 in dry dimethylformamide (DMF). In a similar manner, reaction of 1a,b with glycosyl/galactosyl and lactosyl bromide afforded the corresponding N-nucloside derivatives 13a,b, 15a,b, and 17, respectively. Deacetylation of the N-nucleosides derivatives in the presence of Et3N/MeOH and few drops of water gave the deprotected derivatives 3, 5, 7a,b, 14a,b, 16a,b, and 18 in good yields, respectively. All the newly synthesized compounds are elucidated by infrared, (1)H, (13)C NMR and elemental analyses. Some of these compounds were screened for antimicrobial activities.
    Nucleosides Nucleotides &amp Nucleic Acids 04/2014; 33(3):111-28.
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    ABSTRACT: A series of quinoxaline azido reverse nucleosides 3a-c and their O-regioisomers 4a-c was prepared by reaction of quinoxaline 1a-c with 3-azido-3-deoxy-1,2-O-isopropylidene-5-p-toluenesulfonyl-D-ribofuranose (2) in the presence of sodium hydride. Structure modification of these interesting structures includes reduction and the subsequent acetylation reactions to give quinoxaline amino and acetyl amino reverse nucleosides and their O-regioisomers.
    Nucleosides Nucleotides &amp Nucleic Acids 04/2014; 33(3):129-40.
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    ABSTRACT: A series of purine 5'-deoxyphosphonate analogues were designed and synthesized to mimic naturally occurring purine monophosphate from 1,3-dihydroxyacetone as starting material. The discovery of threosyl phosphonate nucleoside (PMDTA, EC50 = 2.53 μM) as a potent anti-HIV agent has led to the synthesis and biological evaluation of 2',3'-modified 5'-deoxyversions of the threosyl phosphonate nucleosides. The synthesized 2'-fluoro-3'-hydroxymethyl 5'-deoxythreosyl phosphonic acid nucleoside analogues 14, 18, 23, and 27 were tested for anti-HIV activity as well as cytotoxicity. The adenine analogue 18 exhibits weak in vitro anti-HIV-1 activity (EC50 = 19.2 μM).
    Nucleosides Nucleotides &amp Nucleic Acids 03/2014; 33(2):92-109.
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    ABSTRACT: The preparation of a series of novel chromone-fused cytosine analogues, i.e., chromeno[2,3-d]pyrimidines has been carried out from substituted 2-amino-4-oxo-4H-chromene-3-carbonitriles with urea, thiourea, and guanidine under different reaction conditions. These chromone-fused cytosine analogues were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv strain and different microbial pathogenic strains in cell culture for their structure-activity relationships, respectively. Among the synthesized compounds, 2d, 3a, and 4e showed better results against Mycobacterium tuberculosis H37Rv. The compounds 2a, 2b, and 3a showed potential antibacterial activity against E. coli and P. aeruginosa, while the majority of compounds were found to be active against S. aureus as compared to ampicillin. The synthesized cytosine analogues having an imine (-C&dbnd;NH) have been less sensitive to the bacterial and fungal strains but have a more beneficial effect on Mycobacterium tuberculosis H37Rv.
    Nucleosides Nucleotides &amp Nucleic Acids 03/2014; 33(2):80-91.
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    ABSTRACT: A small library of peptidyl adenosine antibiotic analogs was synthesized, under the Pilot Scale Library Program of the NIH Roadmap initiative, from 2',3'-O-isoproylideneadenosine-5'-carboxylic acid 2 in excellent yield. The coupling of the amino terminus of L-2-aminophenylbutyric methyl ester to a free 5'-carboxylic acid moiety of 2 followed by sodium hydroxide treatment led to carboxylic acid analog 4. Hydrolysis of this latter gave unprotected nucleoside analog 5. Intermediate 4 served as the precursor for the preparation of novel peptidyl adenosine analogs 6-18 in good yields and high purity through peptide coupling reactions to diverse amine derivatives. No marked anticancer and antimalaria activity was noted on preliminary cellular testing; however these analogs should be useful candidates for other types of biological activity.
    Nucleosides Nucleotides &amp Nucleic Acids 03/2014; 33(2):53-63.
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    ABSTRACT: A series of 4-amino-5-((4-chlorophenyl)diazenyl)-6-(alkylamino)-1-methylpyrimidin-2-one deri- vatives 7-16 were prepared by nucleophilic displacement of 6-chloro-pyrimidine 6 by various amines. 4-Amino-5-((aryl-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one analogs 19-27, as well as 4-amino-5-((aryl-[1,1'-biphenyl]-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one 29-31 and 4-amino-6-aryl-1-methylpyrimidin-2-one 34-34, were synthesized via Suzuki cross-coupling reaction, using Pd(PPh3)4 as a catalyst and arylboronic acids as reagents. All compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4. Compounds 6, 16, 27, and 29 showed a 50% effective concentration of >2.15, >3.03, >2.29, and >1.63 μM, respectively, but no selectivity was observed (selectivity index < 1). Two of the newly synthesized pyrimidines 12 and 29 exhibited moderate kinesin Eg5 inhibition.
    Nucleosides Nucleotides &amp Nucleic Acids 03/2014; 33(3):141-61.
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    ABSTRACT: We report a new method for synthesis of capped RNA or 2'-OMe RNA that uses a N(2-)4,4'-dimethoxytrityl (DMT) group as a lipophilic purification handle to allow convenient isolation and purification of the capped RNA. The DMT group is easily removed under mild conditions without degradation of the cap. We have used this approach to prepare capped 10- and 20-mers. This method is compatible with the many condensation reactions that have been reported for preparation of capped RNA or cap analogues.
    Nucleosides Nucleotides &amp Nucleic Acids 03/2014; 33(1):40-52.
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    ABSTRACT: The cDNA fragments of hnRNPA2/B1 were cloned from the giant panda and black bear using RT-PCR method, which were, respectively, 1029bp and 1026bp in length encoding 343 and 341 amino acids. Analysis indicated the cDNA cloned from the giant panda encoded variant B1 while the cDNA cloned from black bear encoded variant A2. Analyzing the hnRNPA2B1 peptide of the giant panda and black bear, 76 glycine residues and 86 glycine residues were, respectively, found, and moreover, most glycine are concentrated in the latter halves of the hnRNPA2B1 peptides. Functional sites prediction also showed many N-myristoylation sites existed in the glycine-rich domain, which is probably related to the role of telomere maintenance. From base bias and substitution analysis, we can conclude that the ORF of hnRNPA2/B1 biased G while hated C, and transition of the third site did not achieve the level of saturation. Orthology analysis indicated that both the nucleotide sequence and the deduced amino acid sequence showed high identity to other 26 hnRNPA2/B1 sequences from mammals and nonmammals reported. These sequences were used to construct phylogenetic trees employing the NJ method with 1000 bootstrap, and the obtained tree demonstrated similar topology with the classical systematics, which suggested the potential value of hnRNPA2/B1 in phylogenetic analysis. This report will be the first step to the study function of hnRNPA2/B1 in the giant panda and black bear, and will provide a scientific basis to disease surveillance, captive breeding, and conservation of the endangered species.
    Nucleosides Nucleotides &amp Nucleic Acids 01/2014; 33(1):18-30.
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    ABSTRACT: Atomic force microscopy (AFM) can dynamically detect the adhesion or affinity force between a sample surface and a cantilever. This feature could be used to analyze bio-molecular interactions between a DNA aptamer and a target molecule. In this study, the binding force between adenosine triphosphate (ATP) and the anti-ATP DNA aptamer DH25.42, based on structural changes was measured using AFM. In addition, the relationship between the cations in the binding buffer, and the affinity and structure formation of the DNA aptamer was also evaluated using AFM and circular dichroism (CD) spectrum analysis. As a result, the specific force between DH25.42 and ATP could be measured by AFM. Moreover, it was suggested that Mg(2+) in the binding buffer was critical to the binding function of DH25.42 to ATP.
    Nucleosides Nucleotides &amp Nucleic Acids 01/2014; 33(1):31-9.
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    ABSTRACT: 5-Aryl-2-methylisoxazolidin-3-yl-3-phosphonates have been synthesised from N-methyl-C-diethoxyphosphorylnitrone and vinyl aryls in good yields. Isoxazolidine phosphonates obtained herein were evaluated for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity nor cytostatic activity at 100 to 250 μM concentrations.
    Nucleosides Nucleotides &amp Nucleic Acids 12/2013; 32(12):682-699.
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    ABSTRACT: The interaction of an anti-HIV drug, stavudine (STV) with calf thymus deoxyribonucleic acid (DNA) was investigated employing acridine orange (AO) as a fluorescence probe. Spectroscopic investigations revealed the intercalative mode of binding of STV to DNA. The analysis of fluorescence data indicated the presence of static quenching mechanism between STV and DNA. Thermodynamic parameters indicated the presence of van der Waals forces in addition to intercalative mode of binding. CD data revealed the partial B→A conformational transition of DNA upon intercalative mode of binding with STV.
    Nucleosides Nucleotides &amp Nucleic Acids 12/2013; 32(12):660-669.
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    ABSTRACT: β-Ureidopropionase is the third enzyme of the pyrimidine degradation pathway and it catalyzes the conversion of N-carbamyl-β-alanine and N-carbamyl-β-aminoisobutyric acid to β-alanine and β-aminoisobutyric acid, respectively, and ammonia and CO2. To date, only 16 genetically confirmed patients with a complete ß-ureidopropionase deficiency have been reported. Here, we report the clinical, biochemical, and molecular analysis of a newly identified patient with β-ureidopropionase deficiency. Mutation analysis of the UPB1 gene showed that the patient was compound heterozygous for a novel synonymous mutation c.93C >T (p.Gly31Gly) in exon 1 and a previously described missense mutation c.977G >A (p.Arg326Gln) in exon 9. The in silico predicted effect of the synonymous mutation p.Gly31Gly on pre-mRNA splicing was investigated using a minigene approach. Wild-type and the mutated minigene constructs, containing the entire exon 1, intron 1, and exon 2 of UPB1, yielded different splicing products after expression in HEK293 cells. The c.93C >T (p.Gly31Gly) mutation resulted in altered pre-mRNA splicing of the UPB1 minigene construct and a deletion of the last 13 nucleotides of exon 1. This deletion (r.92_104delGCAAGGAACTCAG) results in a frame shift and the generation of a premature stop codon (p.Lys32SerfsX31). Using a minigene approach, we have thus identified the first synonymous mutation in the UPB1 gene, creating a cryptic splice-donor site affecting pre-mRNA splicing.
    Nucleosides Nucleotides &amp Nucleic Acids 12/2013; 32(12):639-645.