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PubMed1999

Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'alpha-C-branched-chain sugar pyrimidine nucleosides.

A series of 4'alpha-C-branched-chain pyrimidine nucleosides was synthesized from 2'-deoxycytidine or uridine. In the 2'-deoxycytidine series, the substituent at the 4'alpha-position affected cytotoxicity against L1210 mouse leukemic cells in vitro in the order Me (23) > CN (22) > C(symbol)CH (21) > CH=CH(2) (19) > Et (24) > CH=CHCl (20). However, uridine and cytidine derivatives with ethynyl and cyano groups at the 4'alpha-position did not show any cytotoxicity. The antiviral activities of these nucleosides against HSV-1, HSV-2, and HIV-1 in vitro were also examined. Compounds 22 and 23 showed antiviral activities against HSV-1 and HSV-2 without showing significant toxicity to the host cells (MRC-5 cells). Although almost all of the nucleosides showed anti-HIV-1 activities, they were also cytotoxic to the host cells (MT-4).

Animals↗
PubMed1996

Iontophoresis of bases, nucleosides, and nucleotides.

PURPOSE: To investigate whether transdermal iontophoresis may be potentially useful for delivery of oligonucleotide drugs, the electrotransport of representative bases (uracil and adenine), nucleosides (uridine and adenosine) and nucleotides (AMP, ATP, GTP and imido-GTP) across mammalian skin in vitro has been considered. METHODS: While the passive permeability of all compounds investigated (from 1 mM solutions at pH 7.4) was very low, the application of constant current iontophoresis (0.55 mA/cm2) significantly enhanced the transport of both charged and uncharged species. RESULTS: The efficiency of delivery depended only weakly upon lipophilicity, varied quite linearly with concentration (for AMP and ATP), was inversely sensitive to molecular weight, and was strongly influenced by charge. Neutral solutes were delivered better from the anode than the cathode, as expected; post-iontophoresis, passive permeabilities were greater than those of the untreated controls, suggesting that iontophoretically-induced changes in barrier function cannot be completely repaired in in vitro model systems. The triphosphate nucleotides, ATP and GTP, were essentially completely metabolized (presumably to their corresponding mono-phosphates) during their iontophoretic delivery, while imido-GTP was apparently resistant to enzymatic attack; however, comparison of the transport data from AMP and ATP suggested that ATP metabolism occurred primarily after the rate-limiting step of iontophoresis. CONCLUSIONS: The results obtained are consistent with the general patterns of behavior previously observed in investigations of amino acid and peptide electrotransport. It remains to be seen whether extension of the research described here to larger oligonucleotide species is a feasible long-term objective.

Adenine↗
PubMed1985

Microbore packed-column anion-exchange liquid chromatography of nucleobases, nucleosides and nucleotides.

Low-capacity anion-exchange resin was packed into a 45 cm X 0.19 mm I.D. fused-silica tubing and applied to micro-column liquid chromatography of nucleobases, nucleosides and isomers of nucleotides. The effects of the chromatographic conditions on the elution behaviour of these compounds were studied. The efficiency of the microbore packed column was comparable with that of the conventional size column.

Anion Exchange Resins↗
PubMed1992

A mixture of nucleosides and a nucleotide alters hepatic energy metabolism 24 hours after hepatectomy in rabbits.

The effect of administering a nucleoside-nucleotide mixture on hepatic energy metabolism was evaluated at 24 h after hepatectomy in rabbits that had had 70% of their livers removed. After hepatectomy, animals were administered continuous intravenous infusion of 2 mL/(kg body wt-h) of 9 g/L NaCl (Group S), 5.99 mmol/L nucleoside-nucleotide mixture (Group N1) or 11.98 mmol/L nucleoside-nucleotide mixture (Group N2). At 24 h after hepatectomy, the hepatic adenylate energy charge in Group S (0.83 +/- 0.01, mean +/- SEM) was significantly lower than that before hepatectomy (0.90 +/- 0.01). By contrast, the values in Groups N1 and N2 after hepatectomy (0.74 +/- 0.04 and 0.73 +/- 0.04, respectively) were significantly lower than that in Group S. The hepatic mitochondrial phosphorylation rate before hepatectomy was 46.40 +/- 4.88 nmol ATP/(mg mitochondrial protein-min). After hepatectomy, significantly greater values were observed in Groups N1 and N2 (69.53 +/- 7.20 and 63.31 +/- 6.11, respectively), yet those values were less than observed in Group S (109.14 +/- 4.80). These results suggest that the nucleoside-nucleotide mixture suppressed the enhancement of hepatic mitochondrial phosphorylative activity at a time when hepatic adenylate energy charge is compromised. Such enhancement is needed to compensate for the increased energy expenditure due to surgical intervention.

Adenosine Diphosphate↗
PubMedDate not supplied

Purine nucleosides and nucleotides stimulate proliferation of a wide range of cell types.

Presumptive astrocytes isolated from 10-day white Leghorn chick embryos, Factor VIII-positive human brain capillary endothelial cells, meningeal fibroblasts from 10-day chick embryos, Swiss mouse 3T3 cells, and human astrocytoma cell lines, SKMG-1 and U373, were rendered quiescent when placed in culture medium that contained 0 or 0.2% serum for 48 h; their proliferation was markedly reduced and they incorporated [3H]thymidine at a low rate. [3H]Thymidine incorporation and cell proliferation were induced in all types of cells by addition of guanosine, GMP, GDP, GTP, and to a lesser extent, adenosine, AMP, ADP or ATP to the culture medium. The stimulation of proliferation by adenosine and guanosine was abolished by 1,3-dipropyl-7-methylxanthine (DPMX), an adenosine A2 receptor antagonist, but not by 1,3-dipropyl-8-(2-amino-4-chorophenyl)xanthine (PACPX), an A1 antagonist. Stimulation of proliferation by the nucleotides was not abolished by either DPMX or PACPX. The P2 receptor agonists, alpha, beta-methyleneATP and 2-methylthioATP, also stimulated [3H]thymidine incorporation into the cells with peak activity at approximately 3.5 and 0.03 nM, respectively. These data imply that adenosine and guanosine stimulate proliferation of these cell types through activation of an adenosine A2 receptor, and the stimulation of cell proliferation by the nucleotides may be due to the activation of purinergic P2y receptors. As the primary cultures grew older their growth rate slowed. The capacity of the purine nucleosides and nucleotides to stimulate their growth diminished concomitantly. The 3T3 cells showed neither decreased growth with increased passages nor reduced response to the purines. In contrast, although the doubling time of the immortalized human astrocytoma cell lines SKMG-1 and U373 remained constant, the responsiveness to purinergic stimulation of the U373 cells decreased but that of the SKMG-1 did not. These data are compatible with a decrease in the number, or the ligand-binding affinity of the purinergic receptors, or a decreased coupling of purinergic receptors to intracellular mediators in primary cells aged in tissue culture.

Adenine Nucleotides↗