Nucleic acids components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine

Pískala, A.; Šorm, F.

doi:10.1135/cccc19642060

Cited by 163 publications

(61 citation statements)

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“…The chemical synthesis of 5-aza-2Ј-deoxycytidine (5azaCdR) was originally aimed at generating a chemotherapeutic drug (1). Since that time, it also has been exploited by molecular biologists to manipulate genomic methylation both in tissue culture cells and in vivo to demonstrate the inverse relationship between DNA methylation and gene expression and to reactivate epigenetically silenced genes (2).…”

mentioning

confidence: 99%

Mutagenicity of 5-aza-2′-deoxycytidine is mediated by the mammalian DNA methyltransferase

Jackson-Grusby

Laird

Magge

et al. 1997

Proc. Natl. Acad. Sci. U.S.A.

191

146

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The cytosine analog 5-aza-2-deoxycytidine has been used clinically to reactivate genes silenced by DNA methylation. In particular, patients with ␤-thalassemia show fetal globin expression after administration of this hypomethylating drug. In addition, silencing of tumor suppressor gene expression by aberrant DNA methylation in tumor cells may potentially be reversed by a similar regimen. Consistent with its function in maintaining tumor suppressor gene expression, 5-aza-2-deoxycytidine significantly reduces intestinal tumor multiplicity in the predisposed Min mouse strain. Despite its utility as an anti-cancer agent, the drug is highly mutagenic by an unknown mechanism. To gain insight into how 5-aza-2-deoxycytidine induces mutations in vivo, we examined the mutational spectrum in an Escherichia coli lac I transgene in colonic DNA from 5-aza-2-deoxycytidinetreated mice. Mutations induced by 5-aza-2-deoxycytidine were predominantly at CpG dinucleotides, which implicates DNA methyltransferase in the mutagenic mechanism. C:G3G:C transversions were the predominant class of mutations observed. We suggest a model for how the mammalian DNA methyltransferase may be involved in facilitating these mutations. The observation that 5-aza-2-deoxycytidineinduced mutations are mediated by the enzyme suggests that novel inhibitors of DNA methyltransferase, which can inactivate the enzyme before its interaction with DNA, are needed for chemoprevention or long term therapy.

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confidence: 99%

Mutagenicity of 5-aza-2′-deoxycytidine is mediated by the mammalian DNA methyltransferase

Jackson-Grusby

Laird

Magge

et al. 1997

Proc. Natl. Acad. Sci. U.S.A.

191

146

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“…5-Azacytidine (5Az) is a cytidine analogue, synthesized in 1964 as a cancer therapeutic agent (22). This drug also has antibacterial properties (2) and medical application against sickle cell anemia and thalassemia (1,16).…”

Section: Introductionmentioning

confidence: 99%

Apoptosis in the Central Nervous System of Developing Mouse Fetuses from 5-Azacytidine-Administered Dams

1995

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pan.To determine the effect of 5-azacytidine (5Az), a cytidine analogue, on the developing fetus, different strains of mice were injected with various doses of the agent, ip, at 11 days of gestation. Light microscopically, severely pyknotic cell death profiles were observed in different layers of the developing brain and spinal cord (central nervous system) on the day after the injection. Electron microscopy of the pyknotic cells revealed the shrinkage of the cell body, to various degrees margination of the nuclear chromatin, condensation of nuclear materials, fragmentation of the affected cells, and, finally, neat "bite-size" bodies engulfed by surrounding normal neuroepithelial cells and macrophage-like cells. DNA fragmentation was detected in the nuclei of the pyknotic cells by an in situ detection method for fragmented DNA ends. These changes were consistent with the criteria of apoptosis.

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“…El papel de la metilación del ADN en relación a la expresión sexual de las plantas ha sido estudiado mediante el empleo del compuesto 5-azacitidina (5-azaC). Este compuesto es un análogo del nucleó-sido citidina que actúa como agente demetilante de las citosinas en las regiones hipermetiladas del ADN inhibiendo la acción del enzima ADN citosina c5-metiltranferasas, que fue sintetizado por primera vez por Piskala & Sorm (1964). Li et al (2015) constataron la existencia de un importante incremento en el porcentaje de individuos monoicos en espinaca (Spinacia oleracea L.) al ser sometido a este agente hipometilante.…”

Section: Introductionunclassified

¿Las plantas pueden revertir su sexo?

Iglesias-Andreu¹,

Romero²,

Martínez³

2016

cdbio

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The sex determination is an event of great relevance in the life cycle of those plants that reproduce sexually. In recent years we have obtained substantial advances in elucidating the mechanisms involved, and in particular the role of epigenetic factors, in plant sex determination. Taking into account the relevance of this topic especially for dioecious species threatened as Cycads studies have been underwent to determine the basis of epigenetics of sex and to test whether compounds such as the de-metilating agent 5-azacytidine may be involved in sexual expression. This paper reviews the main progress made within this context obtained in Z. furfuraceae as well as cases of reversal of sex in cycads and different plant species.

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Nucleic acids components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine

Cited by 163 publications

References 0 publications

Mutagenicity of 5-aza-2′-deoxycytidine is mediated by the mammalian DNA methyltransferase

Mutagenicity of 5-aza-2′-deoxycytidine is mediated by the mammalian DNA methyltransferase

Apoptosis in the Central Nervous System of Developing Mouse Fetuses from 5-Azacytidine-Administered Dams

¿Las plantas pueden revertir su sexo?

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