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Chemical Compound Review:

AdThd 1-[(2R,4S,5R)-5- (aminomethyl)-4-hydroxy...

Synonyms: SureCN51992, CHEMBL319447, CHEBI:269782, KB-41633, FT-0638498, ...

Kinsella, T.J. et al., Kunugi, K.A. et al., Vazquez-Padua, M.A. et al., Zucker, M.L. et al., Chawla, R.R. et al., et al.

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of AIDS-000915

Preferential inhibition of 5-trifluoromethyl-2'-deoxyuridine phosphorylation by 5'-amino-5'-deoxythymidine in uninfected versus herpes simplex virus-infected cells [1].
In vivo modulation of iododeoxyuridine metabolism and incorporation into cellular DNA by 5'-amino-5'-deoxythymidine in normal mouse tissues and two human colon cancer xenografts [2].
5'-amino-5'-deoxythymidine: topical therapeutic efficacy in ocular herpes and systemic teratogenic and toxicity studies [3].
As part of our studies on the molecular basis for the antiherpes activity of 5'-AdThd (5'-amino-5'-deoxythymidine), a study of the HSV-1 DNA synthesized in infected Vero cells exposed to 5'-AdThd was undertaken [4].

High impact information on AIDS-000915

We have studied the effect of pH on the interactions between thymidine kinase, thymidine triphosphate, and 5'-amino-2',5'-dideoxythymidine (5'-AdThd) in purified preparations of the enzyme and in intact 647V cells, a human bladder cancer cell line [5].
Template- directed ligation of the extended donor and an acceptor ODN, followed by acid hydrolysis, yields the acceptor ODN extended by a single 5'-amino-5'-deoxythymidine residue at its 5'terminus [6].
In HeLa and Vero cells the antiproliferative effects of iododeoxyuridine (IdUrd) were modulated in a biphasic manner by 5'-amino-5'-deoxythymidine (5'-AdThd) [7].
Mouse L fibroblasts were grown in vitro in the presence of 1 mM 5'-amino-5'-deoxythymidine, which was found to suppress greater than 99% of cellular thymidine kinase activity while inhibiting the rate of cell division by only 30% [8].
We report that coincubation of 647V cells for one cell cycle with low concentrations (30 microM) of 5'-amino-5'-deoxythymidine increased IdUrd DNA incorporation and radiosensitivity at low extracellular pH (pHe 6.8) in a fashion similar to treatment at normal pHe [9].

Chemical compound and disease context of AIDS-000915

This in vivo study examines the ability of 5'-amino-5'-deoxythymidine (5'-AdThd) to modulate 5-iododeoxyuridine (IdUrd) cellular metabolism in two human colon cancer xenografts (HT 29 and HCT-116), two actively proliferating normal mouse tissues (bone marrow and intestine), and a quiescent normal mouse tissue (liver) [2].

Biological context of AIDS-000915

A series of 3'-O-acyl derivatives of 5'-amino-5'-deoxythymidine (5'-NH2-TdR) (IIIa-j) was synthesized by acylation of 5'-azido-5'-deoxythymidine (I) [10].
The effect of 5'-amino-5'-deoxythymidine on the pattern of polyadenylation of herpes simplex virus type 1 ribonucleic acid [11].

Associations of AIDS-000915 with other chemical compounds

Comparative effects of 5'-amino-5'-deoxythymidine, a new antiviral agent, and 5-iodo-2'-deoxyuridine on the immune response of mice. No immunosuppression with 5'-amino-5'-deoxythymidine [12].

Gene context of AIDS-000915

Whereas the thymidine analogue 5'-amino-5'-deoxythymidine (AdThd) caused an increase in HSV-1 tk synthesis and activity in wild type Vero and BHK cells, 5-iodo-2'-deoxyuridine (IdUrd) caused a similar increase only in tk- cells (LMtk-, BHKtk-) [13].

References

Preferential inhibition of 5-trifluoromethyl-2'-deoxyuridine phosphorylation by 5'-amino-5'-deoxythymidine in uninfected versus herpes simplex virus-infected cells. Fischer, P.H., Murphy, D.G., Kawahara, R. Mol. Pharmacol. (1983) [Pubmed]
In vivo modulation of iododeoxyuridine metabolism and incorporation into cellular DNA by 5'-amino-5'-deoxythymidine in normal mouse tissues and two human colon cancer xenografts. Kinsella, T.J., Glennon, M.C., Kunugi, K.A., Lindstrom, M.J. Clin. Cancer Res. (1996) [Pubmed]
5'-amino-5'-deoxythymidine: topical therapeutic efficacy in ocular herpes and systemic teratogenic and toxicity studies. Pavan-Langston, D., Park, N.H., Lass, J., Papale, J., Albert, D.M., Lin, T., Prusoff, W.H., Percy, D.H. Proc. Soc. Exp. Biol. Med. (1982) [Pubmed]
The relationship between the antiviral activity of 5'-amino-5'-deoxythymidine and its incorporation into herpes simplex virus type 1 DNA. Otto, M.J., Prusoff, W.H. Antiviral Res. (1984) [Pubmed]
Modulation of the feedback regulation of thymidine kinase activity by pH in 647V cells. Vazquez-Padua, M.A., Kunugi, K., Risueno, C., Fischer, P.H. Cancer Res. (1989) [Pubmed]
A simple procedure for constructing 5'-amino-terminated oligodeoxynucleotides in aqueous solution. Bruick, R.K., Koppitz, M., Joyce, G.F., Orgel, L.E. Nucleic Acids Res. (1997) [Pubmed]
Modulation of the metabolism and cytotoxicity of iododeoxyuridine by 5'-amino-5'-deoxythymidine. Fischer, P.H., Weddle, M.A., Mossie, R.D. Mol. Pharmacol. (1983) [Pubmed]
Bis(m-nitrophenyl) and bis(p-nitrophenyl) esters and the phosphorodiamidate of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in mouse cells in culture. Chawla, R.R., Freed, J.J., Hampton, A. J. Med. Chem. (1984) [Pubmed]
Low pH does not affect the dose response for 5'-amino-5'-deoxythymidine modulation of IdUrd DNA incorporation and radiosensitization in a human bladder cancer cell line. Kunugi, K.A., Miller, E.M., Vazquez-Padua, M.A., Kinsella, T.J. Radiat. Res. (1992) [Pubmed]
Synthesis and in vitro antiviral activity of 3'-O-acyl derivatives of 5'-amino-5'-deoxythymidine: potential prodrugs for topical application. Lin, T.S. Journal of pharmaceutical sciences. (1984) [Pubmed]
The effect of 5'-amino-5'-deoxythymidine on the pattern of polyadenylation of herpes simplex virus type 1 ribonucleic acid. Zucker, M.L., Dube, S., Prusoff, W.H. Virus Res. (1988) [Pubmed]
Comparative effects of 5'-amino-5'-deoxythymidine, a new antiviral agent, and 5-iodo-2'-deoxyuridine on the immune response of mice. No immunosuppression with 5'-amino-5'-deoxythymidine. Bennett, J.A., Savoca, P.E., Lin, T.S., Prusoff, W.H. Int. J. Immunopharmacol. (1982) [Pubmed]
Production of herpes simplex virus type 1 thymidine kinase in the presence of thymidine analogues. Zucker, M.L., Mancini, W.R., Otto, M.J., Lee, J.J., Prusoff, W.H. Antiviral Res. (1986) [Pubmed]

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