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New Cytosine Derivatives As Inhibitors of DNA Methylation

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New Cytosine Derivatives As Inhibitors of DNA Methylation BioTechnologia vol. 94(1) C pp. 66-113 C 2013 SHORT CONTRIBUTIONS New cytosine derivatives as inhibitors of DNA methylation EWELINA ADAMSKA, BEATA PLITTA, MAŁGORZATA GIEL-PIETRASZUK, AGNIESZKA FEDORUK-WYSZOMIRSKA, MIROSŁAWA NASKRĘT-BARCISZEWSKA, WOJCIECH T. MARKIEWICZ, JAN BARCISZEWSKI Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland Neoplastic transformation is associated with alter- thyltransferase from Spiroplazma. Cytosine derivatives ation in DNA methylation, includes both global hypo- were divided into three groups according to modification methylation and gene specific hypermethylation. Great at exocyclic amino group. 4-N-furfurylcytosine (I) and effort has been directed on towards development of 4-N-benzylcytosine (II) (Ki 70 and 10 μM, respectively) novel strategies that can change the inappropriate gene were further modified. methylation pattern in cells and thus, to redirect cell fate HN HN in human cancers. O It is believed that the creation of conditions for re- N N storation of the pattern of epigenetic modification that N O N O is proper for every organism is an opportunity to reverse H H cancerogenesis. III DNA cytosine methylation catalyzed by DNA methyl- The best obtained inhibitors were 4-N-furfuryl-5-aza- transferase 1 (DNMT1) is an epigenetic route to gene cytosine, 4-N-benzyl-5-methylcytosine, 4-N-furfuryl-5-me- expression regulation and development. Changes in me- thylcytosine with Ki 0.7, 3.6 and 15 μM, respectively. thylation pattern lead to carcinogenesis. Inhibition of These compounds cause a much greater reduction in the DNMT1 activity could be a good strategy of safe and effi- level of DNA methylation in cancer (HeLa) than in nor- cient epigenetic therapy. mal (HEK293) cells. Derivatives substituted with alipha- We present a novel group of cytosine analogs as inhi- tic chains at 4-N acted as uncompetitive inhibitors. bitors of DNA methylation, new methods of their synthe- Almost all of analyzed compounds inhibit DNA me- sis and their effect on in vitro reaction of DNA methyla- thyltransferase activity in the competitive manner. tion. The results covered by patent co-financed by the Inhibitory activity of each compound was analyzed in European Regional Development Fund under the Opera- in vitro DNA methylation reaction catalyzed by DNA me- tional Programme Innovative Economy. Short contributions 67 SERRATE and CBC: two important factors involved in pre-mRNA splicing and microRNA biogenesis MATEUSZ BAJCZYK, AGATA STĘPIEŃ, KATARZYNA SKORUPA, DAWID BIELEWICZ, JAKUB DOLATA, ZOFIA SZWEYKOWSKA-KULINSKA, ARTUR JARMOŁOWSKI Faculty of Biology, Adam Mickiewicz University, Poznań, Poland MicroRNAs (miRNAs) are small non-coding RNAs of and se-1 mutants with the level observed in wt Arabidop- about 21 nt in length, which take part in a wide variety sis plants. The results showed that the expression level of physiological and cellular processes. In plants, primary of more than 50% A. thaliana pri-miRNAs was changed transcripts of miRNA genes, called pri-miRNAs, are synthe- in the se-1 and cbc mutants, and 40% in hyl1-2. In the sized by RNA polymerase II (RNAPII), and contain charac- case of the se-1 and cbc mutants, we observe changes teristic hairpin-like secondary structures in which sequen- in the same pri-miRNAs, and in the hyl1-2 mutant, the ces of mature miRNAs are embedded. These pri-miRNAs changes appear also in other precursors. In order to are processed by DCL1 into pre-miRNAs that consist only understand the processes in which the SERRATE pro- of miRNA-containing stem/loop structures which are then tein is involved, we have decided to search for RNAs and processed into miRNA/miRNA* duplexes. The duplexes proteins that interact with SERRATE. To this end, we are exported from the nucleus to the cytoplasm, where have constructed the Arabidopsis thaliana transgenic mature miRNAs are loaded into RNA silencing com- plant, in which in the genetic background of the se-1 plexes (RISC) that induce mRNA cleavage or translatio- mutant the FLAG-tagged version of the SE gene is inte- nal inhibition. Although the conversion of pri-miRNAs grated into the genome. We chose two stable lines with into mature miRNAs is catalyzed in the plant nucleus by the highest expression level of FLAG-SE. Next, we carry one enzyme, DCL1, other proteins are also involved in out immunoprecipitation against the FLAG epitop of the the process. These are: CBC (a nuclear cap-binding com- fusion protein to find interactions between SERRATE plex, which is composed of two subunits, CBP20 and and proteins and RNAs. Using Western blot, we confir- CBP80), a dsRNA binding protein HYL1 (HYPONASTIC med the interaction of SE with CBP80 and HYL1. The LEAVES1) and a zinc-finger containing protein SERRATE interaction between CBP80 and SE has been previously (SE). It has been reported that these DCL1 partners are detected by us in transfected Arabidopsis protoplasts required for the efficient and correct excision of miRNA using the BiFC method. Identification of novel protein from pri-miRNA. Moreover, SERRATE and CBC have dual partners of SE will be performed by mass spectrometry. roles: in miRNA biogenesis and pre-mRNA splicing. There- In addition, we will also sequence RNA molecules pre- fore, we compared the level of pri-miRNAs in cbc, hyl1-2 sent in the complexes precipitated with SERRATE. 68 Short contributions Medicago ABCG10 transports (iso)liquiritigenin WANDA BIAŁA 1,2, JOANNA BANASIAK 2, MICHAŁ JASIŃSKI 1, 2 1 Departament of Biochemistry and Biotechnology, Poznan University of Life Sciences, Poznań, Poland 2 Institute of Bioorganic Chemistry, Polish Academy of Science, Poznań, Poland [email protected] Full size ABC proteins belonging to the ABCG sub- (IFS). Silencing of MtABCG10 in Medicago hairy roots family were identified mainly in plants and fungi. They resulted in lower accumulation of phenolic compounds, are influencing different physiological processes, and among them were precursors of Medicago phytoalexin play a particular role in defense response to biotic and medicarpin. abiotic stresses. There is growing number of evidence Interestingly exogenous application of such precur- that ABCG transporters could be responsible for trans- sors as liquiritigenin and isoliquiritigenin resulted in the port of antifungal, antimicrobial secondary metabolites induction of MtABCG10 expression. Loading/transport and signaling molecules (Goossens et al., 2003). experiment performed with liquiritigenin and isoliquiri- The ABCG10 from Medicago truncatula was propo- tigenin in MtABCG10 silenced hairy roots has shown sed as a modulator of isoflavonoid levels during the de- a significant differences in the transport efficiency of fense response associated with de novo synthesis of these compounds between wild type and MtABCG10 si- medicarpin (Banasiak et al., 2013). Expression analyses lenced lines. We postulate that MtABCG10 is a transpor- revealed that MtABCG10 transcript is present in the ter of liquiritigenin and isoliquiritgenin free aglycones. vascular tissue of different organs and the corresponding protein has been found in the plasma membrane. References Treatment of roots with fungal cell wall oligosac- Banasiak J., Biała W., Staszków A., Swarcewicz B., Kępczyńska charides (general elicitor) resulted in a strong induction E., Figlerowicz M., Jasiński M. (2013) J. Exp. Bot. 64(4): of MtABCG10 expression together with genes coding 1005-1015. Goossens A., Hakkinen S.T., Laakso I., Oksman-Caldentey enzymes from phenylpropanoid pathway namely: phenyl- K.M., Inze D. (2003) Plant Physiol. 131: 1161-1164. alanine ammonia – lyase (PAL) and isoflavone synthase Short contributions 69 High-resolution crystal structures of complexes of plant AdoHcy hydrolase KRZYSZTOF BRZEZINSKI 1, ZBIGNIEW DAUTER 2, MARIUSZ JASKOLSKI 3, 4 1 Institute of Chemistry, University of Bialystok, Bialystok, Poland 2 Synchrotron Radiation Research Section, MCL, National Cancer Institute, Argonne National Laboratory, Argonne, USA 3 Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland 4 Faculty of Chemistry, Adam Mickiewicz University, Poznań, Poland S -Adenosyl-L-methionine (AdoMet) is the most com- We present the first crystal structure of AdoHcy mon donor of methyl group in cellular methylation of hydrolase of plant origin, from the legume yellow lupine a wide range of substrates, from small-molecule com- (Lupinus luteus). The structures have been determined pounds, such as norepinephrine, catecholamines or for three complexes of the enzyme, with a reaction phospholipids, to macromolecules, including proteins, byproduct/substrate (adenosine), its nonoxidizable ana- nucleic acids and polysaccharides. AdoMet-Dependent log (cordycepin), and a product of inhibitor cleavage methylation generates equimolar amounts of S-adenosyl- (adenine). In all three complexes, the enzyme has a clo- L-homocysteine (AdoHcy), which is a strong inhibitor of sed conformation. In addition to the adenosine, adenine AdoMet-dependent methylases. By removal of AdoHcy, or cordycepin ligands found in the substrate-binding S-adenosyl-L-homocysteine hydrolases serve as an im- domain, each subunit contains a tightly bound NAD+ mo- portant regulator of AdoMet-dependent methylation re- lecule in the cofactor-binding domain. A sodium cation is actions. The enzyme controls the AdoMet:AdoHcy ratio, found near the active site, coordinated by residues from which is perceived as an indicator of transmethylation a conserved loop that hinges domain movement upon
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