Biochemical and antitumor activity of tiazofurin and its selenium analog (2-beta-D-ribofuranosyl-4-selenazolecarboxamide).

@article{Boritzki1985BiochemicalAA,
  title={Biochemical and antitumor activity of tiazofurin and its selenium analog (2-beta-D-ribofuranosyl-4-selenazolecarboxamide).},
  author={Theodore J. Boritzki and David A. Berry and Judith A. Besserer and Philip Dan Cook and David W. Fry and Wilbur R. Leopold and Robert C. Jackson},
  journal={Biochemical pharmacology},
  year={1985},
  volume={34 7},
  pages={
          1109-14
        }
}
2-beta-D-Ribofuranosyl-4-selenazolecarboxamide (selenazofurin, CI-935), the selenium analog of tiazofurin (CI-909), was 3- to 10-fold more cytotoxic to murine or human tumor cells in vitro than tiazofurin and was also more active against P388 mouse leukemia in vivo. In vitro cytotoxicity could be reversed by guanosine or guanine but not by other purine nucleosides or bases. Three human tumor cell lines selected for selenazofurin or tiazofurin resistance showed cross resistance between… Expand
Antiviral activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4- carboxamide and related compounds
TLDR
5-Ethynyl-1-beta-D-ribofuranosylimidazole-4- carboxamide (EICAR), the most potent congener of the group, showed antiviral potency about 10- to 100-fold greater than that of ribavirin. Expand
Implications of selective type II IMP dehydrogenase (IMPDH) inhibition by the 6-ethoxycarbonyl-3,3-disubstituted-1,5-diazabicyclo[3.1.0]hexane-2,4-diones on tumor cell death.
TLDR
Results from in vitro studies suggest that the 6-ethoxycarbonyl-3,3-disubstituted-1,5-diazabicyclo[3.1.0]hexane-2,4-diones may be used as effective isozyme-selective chemotherapeutic agents. Expand
Induction of HL60 cell differentiation by tiazofurin and its analogues: characterization and efficacy.
TLDR
Tiazofurin was found to induce expression of a phosphatidylinositol-specific phospholipase C-sensitive Fc gamma-receptor III (FcRIII) on HL60 cells, a feature consistent with neutrophilic, but not monocytic, differentiation. Expand
Tiazofurin metabolism in human lymphoblastoid cells: evidence for phosphorylation by adenosine kinase and 5'-nucleotidase.
TLDR
Results indicate that two enzymes, adenosine kinase and a cytoplasmic 5'-nucleotidase, are functionally important anabolizing enzymes for tiazofurin in human cells. Expand
Crystallographic studies of two alcohol dehydrogenase-bound analogues of thiazole-4-carboxamide adenine dinucleotide (TAD), the active anabolite of the antitumor agent tiazofurin.
TLDR
Close intramolecular S-O and Se-O contacts observed in the parent nucleoside analogues are maintained in both LADH-bound beta-TAD and beta-SAD, respectively, which may influence the binding specificity of the inhibitors. Expand
Therapeutic synergism of tiazofurin and selected antitumor drugs against sensitive and resistant P388 leukemia in mice.
TLDR
The observed therapeutic synergism of these drugs with tiazofurin in animal models suggests the possibility that treatment with tiafurin combinations may yield clinical results superior to those obtained with the single agents alone. Expand
NAD-analogues as potential anticancer agents: conformational restrictions as basis for selectivity.
TLDR
NAD-analogues containing such conformationally restricted nicotinamide nucleoside moiety are expected to be selective inhibitors of B-specific (IMPDH) or A-specific dehydrogenases, respectively. Expand
Crystal structure of human type II inosine monophosphate dehydrogenase: implications for ligand binding and drug design.
TLDR
The 2.9-A structure of a ternary complex of the human type II isoform of IMPDH is presented, suggesting strategies for the design of isoform-specific agents in antitumor and immunosuppressive drug design. Expand
Novel Mechanism for Induction of Tumor Cell Apoptosis Nicotinamide Phosphoribosyltransferase , Represents a FK 866 , a Highly Specific Noncompetitive Inhibitor of Updated
Deregulation of apoptosis, the physiological form of cell death, is closely associated with immunological diseases and cancer. Apoptosis is activated either by death receptor-driven or mitochondrialExpand
FK866, a highly specific noncompetitive inhibitor of nicotinamide phosphoribosyltransferase, represents a novel mechanism for induction of tumor cell apoptosis.
TLDR
This work has identified the first low molecular weight compound, designated FK866, which induces apoptosis by highly specific, noncompetitive inhibition of nicotinamide phosphoribosyltransferase (NAPRT), a key enzyme in the regulation of NAD+ biosynthesis from the natural precursor Nicotinamide. Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 25 REFERENCES
Comparative in vitro studies of Tiazofurin and a selenazole analog.
TLDR
The dose-dependency for this inhibition correlates with the relative cytotoxicities of both drugs, indicating that a more potent inhibition of IMP dehydrogenase by the selenazole analog is primarily responsible for its increased cytotoxicity. Expand
Activity and metabolism of 2-beta-D-ribofuranosylthiazole-4-carboxamide in human lymphoid tumor cells in culture.
TLDR
The results suggest that the antitumor effects of TR in human tumor cell lines may relate to guanine nucleotide depletion. Expand
New antitumor imidazole derivative, 5-carbamoyl-1H-imidazol-4-yl piperonylate, as an inhibitor of purine synthesis and its activation by adenine phosphoribosyltransferase.
TLDR
Results strongly suggest that SL-1250 is, after being converted to SM-108, activated to its nucleotide form by adenine phosphoribosyltransferase and that thisSM-108 nucleotide blocks de novo synthesis of guanosine 5'-monophosphate by inhibiting IMP dehydrogenase. Expand
Synthesis and antiviral activity of certain thiazole C-nucleosides.
TLDR
Thiazole nucleosides were tested for in vitro activity against type 1 herpes virus, type 3 parainfluenza virus, and type 13 rhinovirus and they were evaluated as potential inhibitors of purine nucleotide biosynthesis. Expand
Synthesis and antitumor activity of 2-beta-D-ribofuranosylselenazole-4- carboxamide and related derivatives.
Treatment of 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl-1-carbonitrile with hydrogen selenide provided 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonselenoamide (3). Compound 3 was treated with ethylExpand
Toxicity and anticancer activity of a new triazine antifolate (NSC 127755).
TLDR
A new triazine folate antagonist was highly active against four transplantable colon adenocarcinomas and the Dunning murine ovarian tumor M5076 and treatment schedule studies indicated that a prolonged time of exposure provided optimum antitumor activity for the compound. Expand
Metabolism and biochemistry of mycophenolic acid.
TLDR
There is a correlation between the sensitivity of experimental tumors to mycophenolic acid and the relative activities of β-glucuronidase and hypoxanthine-guanine phosphoribosyltransferase, which may indicate the potential effectiveness of mycopenolic acid in humans. Expand
Biochemical and pharmacological effects of the fermentation-derived antitumor agent, (alphaS,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125).
TLDR
Support for such a hypothesis was provided when it was observed that a combination of cytosine and guanosine ribonucleosides acted synergistically in reversing the growth-inhibitory activity of AT-125 towards L1210 cells in culture. Expand
Anticancer activity of the structurally novel antibiotic Cl-920 and its analogues.
TLDR
Cl-920 failed to show confirmed activity against the following tumors in mice: M5076 sarcoma, B16 melanoma, and Ridgway osteogenic sarcomA, which may be caused by a transport deficiency similar to that found with methotrexate. Expand
Contributions of the depletions of guanine and adenine nucleotides to the toxicity of purine starvation in the mouse T lymphoma cell line.
TLDR
It is suggested that guanine ribonucleotides, probably in DNA synthesis, is the cellular process most sensitive to the inhibition of early de novo purine biosynthesis, and the biological consequences of purine starvation are primarily mediated by the depletion of Guanine nucleotides rather than that of adenine nucleOTides. Expand
...
1
2
3
...