Synthesis and restriction enzyme analysis of oligodeoxyribonucleotides containing the anti-cancer drug 2',2'-difluoro-2'-deoxycytidine.

Abstract:

:The anti-cancer drug 2',2'-difluoro-2'-deoxycytidine (dFdC) is internally incorporated into DNA in vitro. To determine the effects of this incorporation on DNA structure and function, the beta-cyanoethyl phosphoramidite of dFdC was synthesized and oligodeoxyribonucleotides containing dFdC were made using automated solid phase DNA synthesis techniques. Extension of the coupling time was required to achieve high coupling efficiency, suggesting a significant reduction in the rate of phosphotriester formation. Insertion of dFdC 5' into the recognition sequence of restriction enzymes HpaII and KpnI reduced the rate of cutting by 4% and 14% over 60 minutes. This reduction is similar to the effects seen with arabinofuranosylcytidine (ara-C) but small compared to the reductions caused by base analogues and phosphothioates. Insertion of dFdC into the BamHI recognition sequence, but not 5' to the cut site, did not alter the rate of cutting/recognition. The presence of a single dFdC reduced the Tm's of oligomers by 2-4 degrees C, depending on sequence and location. These results demonstrate that, once incorporated into DNA, dFdC does not greatly alter recognition between DNA and restriction enzymes; however, it does significantly alter duplex stability.

journal_name

Nucleic Acids Res

journal_title

Nucleic acids research

authors

Richardson FC,Richardson KK,Kroin JS,Hertel LW

doi

10.1093/nar/20.7.1763

keywords:

subject

Has Abstract

pub_date

1992-04-11 00:00:00

pages

1763-8

issue

7

eissn

0305-1048

issn

1362-4962

journal_volume

20

pub_type

杂志文章
  • Multi-omic analysis of gametogenesis reveals a novel signature at the promoters and distal enhancers of active genes.

    abstract::Epigenetic regulation of gene expression is tightly controlled by the dynamic modification of histones by chemical groups, the diversity of which has largely expanded over the past decade with the discovery of lysine acylations, catalyzed from acyl-coenzymes A. We investigated the dynamics of lysine acetylation and cr...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkaa163

    authors: Crespo M,Damont A,Blanco M,Lastrucci E,Kennani SE,Ialy-Radio C,Khattabi LE,Terrier S,Louwagie M,Kieffer-Jaquinod S,Hesse AM,Bruley C,Chantalat S,Govin J,Fenaille F,Battail C,Cocquet J,Pflieger D

    更新日期:2020-05-07 00:00:00

  • A comparative genomic method for computational identification of prokaryotic translation initiation sites.

    abstract::The ever growing number of completely sequenced prokaryotic genomes facilitates cross-species comparisons by genomic annotation algorithms. This paper introduces a new probabilistic framework for comparative genomic analysis and demonstrates its utility in the context of improving the accuracy of prokaryotic gene star...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkf423

    authors: Walker M,Pavlovic V,Kasif S

    更新日期:2002-07-15 00:00:00

  • Primer specific and mispair extension analysis (PSMEA) as a simple approach to fast genotyping.

    abstract::A simple method, primer specific and mispair extension analysis (PSMEA) with pfu DNA polymerase was developed for genotyping. PSMEA is based on the unique properties of 3'-->5' exonuclease proofreading activity. In the presence of an incomplete set of dNTPs, pfu was found to be extremely discriminative in nucleotide i...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/26.21.5013

    authors: Hu YW,Balaskas E,Kessler G,Issid C,Scully LJ,Murphy DG,Rinfret A,Giulivi A,Scalia V,Gill P

    更新日期:1998-11-01 00:00:00

  • Roles of yeast eIF2α and eIF2β subunits in the binding of the initiator methionyl-tRNA.

    abstract::Heterotrimeric eukaryotic/archaeal translation initiation factor 2 (e/aIF2) binds initiator methionyl-tRNA and plays a key role in the selection of the start codon on messenger RNA. tRNA binding was extensively studied in the archaeal system. The γ subunit is able to bind tRNA, but the α subunit is required to reach h...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gks1180

    authors: Naveau M,Lazennec-Schurdevin C,Panvert M,Dubiez E,Mechulam Y,Schmitt E

    更新日期:2013-01-01 00:00:00

  • Inter-individual variation of DNA methylation and its implications for large-scale epigenome mapping.

    abstract::Genomic DNA methylation profiles exhibit substantial variation within the human population, with important functional implications for gene regulation. So far little is known about the characteristics and determinants of DNA methylation variation among healthy individuals. We performed bioinformatic analysis of high-r...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkn122

    authors: Bock C,Walter J,Paulsen M,Lengauer T

    更新日期:2008-06-01 00:00:00

  • Transcriptional repression of BRCA1 by aberrant cytosine methylation, histone hypoacetylation and chromatin condensation of the BRCA1 promoter.

    abstract::BRCA1 expression is repressed by aberrant cytosine methylation in sporadic breast cancer. We hypothesized that aberrant cytosine methylation of the BRCA1 promoter was associated with the transcriptionally repressive effects of histone hypoacetylation and chromatin condensation. To address this question, we developed a...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/28.17.3233

    authors: Rice JC,Futscher BW

    更新日期:2000-09-01 00:00:00

  • Unidirectional translocation from recognition site and a necessary interaction with DNA end for cleavage by Type III restriction enzyme.

    abstract::Type III restriction enzymes have been demonstrated to require two unmethylated asymmetric recognition sites oriented head-to-head to elicit double-strand break 25-27 bp downstream of one of the two sites. The proposed DNA cleavage mechanism involves ATP-dependent DNA translocation. The sequence context of the recogni...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkh899

    authors: Raghavendra NK,Rao DN

    更新日期:2004-10-22 00:00:00

  • Adenovirus 12-mediated down-regulation of the major histocompatibility complex (MHC) class I promoter: identification of a negative regulatory element responsive to Ad12 E1A.

    abstract::In highly oncogenic adenovirus (Ad) 12-transformed cells, major histocompatibility complex (MHC) class I gene expression is down-regulated by the products of the viral E1A oncogene at the level of initiation of transcription. However, class I gene expression is unaltered or elevated in non-oncogenic Ad2- or Ad5-transf...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/22.22.4779

    authors: Proffitt JL,Sharma E,Blair GE

    更新日期:1994-11-11 00:00:00

  • Allele frequency net: a database and online repository for immune gene frequencies in worldwide populations.

    abstract::The allele frequency net database (http://www.allelefrequencies.net) is an online repository that contains information on the frequencies of immune genes and their corresponding alleles in different populations. The extensive variability observed in genes and alleles related to the immune system response and its signi...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkq1128

    authors: Gonzalez-Galarza FF,Christmas S,Middleton D,Jones AR

    更新日期:2011-01-01 00:00:00

  • DNA-like duplexes with repetitions. I. Properties of concatemer duplexes formed by d(T-G-C-A-C-A-T-G).

    abstract::A new class of synthetic DNA duplexes containing repeating oligonucleotide sequences, double-helical concatemers, is characterized. The UV-absorption and circular dichroism of a concatemer formed in self-association of d(T-G-C-A-C-A-T-G) have been studied. The thermodynamical parameters of complex formation are the fo...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/8.11.2413

    authors: Shabarova ZA,Dolinnaya NG,Turkin SI,Gromova ES

    更新日期:1980-06-11 00:00:00

  • Involvement of Schizosaccharomyces pombe rrp1+ and rrp2+ in the Srs2- and Swi5/Sfr1-dependent pathway in response to DNA damage and replication inhibition.

    abstract::Previously we identified Rrp1 and Rrp2 as two proteins required for the Sfr1/Swi5-dependent branch of homologous recombination (HR) in Schizosaccharomyces pombe. Here we use a yeast two-hybrid approach to demonstrate that Rrp1 and Rrp2 can interact with each other and with Swi5, an HR mediator protein. Rrp1 and Rrp2 f...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkt564

    authors: Dziadkowiec D,Kramarz K,Kanik K,Wisniewski P,Carr AM

    更新日期:2013-09-01 00:00:00

  • Differential roles for Fos and Jun in DNA-binding: redox-dependent and independent functions.

    abstract::The Fos and Jun family of transcription factors contain an invariant sequence motif lysine-cysteine-arginine (KCR) in the highly conserved DNA-binding region. Reduction of the cysteine residue is necessary to facilitate DNA-binding. Here, we examined the potential dual roles of the flanking lysine and arginine residue...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/21.25.5831

    authors: Ng L,Forrest D,Curran T

    更新日期:1993-12-25 00:00:00

  • In vitro transcription analysis of the region of Saccharomyces cerevisiae mitochondrial DNA containing the tRNA(fMet) gene.

    abstract::Prior work has indicated that an octanucleotide [5'TATAAGTA(+1)3'] sequence is used as a promoter in yeast mitochondria. Two such sequences (FP1 and FP2) are present upstream of the tRNA(fMet)-RNAse P RNA -tRNA(Pro) gene cluster but only the FP1 promoter but not the FP2 appears to be active in vivo and in vitro. The r...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/19.21.5937

    authors: Biswas TK

    更新日期:1991-11-11 00:00:00

  • 3' processing of pre-mRNA plays a major role in proliferation-dependent regulation of histone gene expression.

    abstract::A short histone-like fusion RNA, generated when the RNA 3' processing signal from a mouse histone H4 gene is inserted into a heterologous transcription unit, becomes correctly down-regulated in G1-arrested cells of a temperature-sensitive mouse mastocytoma cell cycle mutant (21-Tb; Stauber et al., EMBO J. 5, 3297-3303...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/16.20.9399

    authors: Stauber C,Schümperli D

    更新日期:1988-10-25 00:00:00

  • Tetracycline-inducible gene regulation in mycobacteria.

    abstract::A system for the tetracycline-inducible regulation of gene expression in mycobacteria has been developed. We have sub-cloned the tetRO region from the Corynebacterium glutamicum TetZ locus into a mycobacterial shuttle plasmid, making expression of genes cloned downstream of tetRO responsive to tetracycline. Using the ...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gni023

    authors: Blokpoel MC,Murphy HN,O'Toole R,Wiles S,Runn ES,Stewart GR,Young DB,Robertson BD

    更新日期:2005-02-01 00:00:00

  • The telomere resolvase of the Lyme disease spirochete, Borrelia burgdorferi, promotes DNA single-strand annealing and strand exchange.

    abstract::Spirochetes of the genus Borrelia include the tick-transmitted causative agents of Lyme disease and relapsing fever. They possess unusual genomes composed mainly of linear replicons terminated by closed DNA hairpin telomeres. Hairpin telomeres present an uninterrupted DNA chain to the replication machinery overcoming ...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkt832

    authors: Mir T,Huang SH,Kobryn K

    更新日期:2013-12-01 00:00:00

  • EENdb: a database and knowledge base of ZFNs and TALENs for endonuclease engineering.

    abstract::We report here the construction of engineered endonuclease database (EENdb) (http://eendb.zfgenetics.org/), a searchable database and knowledge base for customizable engineered endonucleases (EENs), including zinc finger nucleases (ZFNs) and transcription activator-like effector nucleases (TALENs). EENs are artificial...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gks1144

    authors: Xiao A,Wu Y,Yang Z,Hu Y,Wang W,Zhang Y,Kong L,Gao G,Zhu Z,Lin S,Zhang B

    更新日期:2013-01-01 00:00:00

  • Carbon nanotubes selective destabilization of duplex and triplex DNA and inducing B-A transition in solution.

    abstract::Single-walled carbon nanotubes (SWNTs) have been considered as the leading candidate for nanodevice applications ranging from gene therapy and novel drug delivery to membrane separations. The miniaturization of DNA-nanotube devices for biological applications requires fully understanding DNA-nanotube interaction mecha...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkl513

    authors: Li X,Peng Y,Qu X

    更新日期:2006-08-02 00:00:00

  • TcruziDB: an integrated Trypanosoma cruzi genome resource.

    abstract::TcruziDB (http://TcruziDB.org) is an integrated genome database for the parasitic organism Trypanosoma cruzi, the causative agent of Chagas' disease. The database currently incorporates all available sequence data (Genomic, BAC, EST) in a single user-friendly location. The database contains a variety of tools specific...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkh049

    authors: Luchtan M,Warade C,Weatherly DB,Degrave WM,Tarleton RL,Kissinger JC

    更新日期:2004-01-01 00:00:00

  • The thy pol-2 intein of Thermococcus hydrothermalis is an isoschizomer of PI-TliI and PI-TfuII endonucleases.

    abstract::THY Pol-2 intein, from Thermococcus hydrothermalis, belongs to the same allelic family as TLI Pol-2 (PI-TLII), Tfu Pol-2 (PI-TFUII) and TspTY Pol-3 mini-intein, all inserted at the pol-c site of archaeal DNA polymerase genes. This new intein was cloned, expressed in Escherichia coli and purified. The intein is a speci...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/28.21.4391

    authors: Saves I,Eleaume H,Dietrich J,Masson JM

    更新日期:2000-11-01 00:00:00

  • Structures of m-iodo Hoechst-DNA complexes in crystals with reduced solvent content: implications for minor groove binder drug design.

    abstract::The DNA photosensitisers m-iodo Hoechst and m-iodo, p-methoxy Hoechst have been co-crystallised with the oligonucleotide d(CGCGAATTCGCG)(2)and their crystal structures determined. The crystals were then subjected to slow dehydration, which reduced their solvent contents from 40 (normal) to 30 (partially dehydrated) an...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/28.5.1252

    authors: Squire CJ,Baker LJ,Clark GR,Martin RF,White J

    更新日期:2000-03-01 00:00:00

  • Transactivation and growth suppression by the gut-enriched Krüppel-like factor (Krüppel-like factor 4) are dependent on acidic amino acid residues and protein-protein interaction.

    abstract::Gut-enriched Krüppel-like factor (GKLF or KLF4) is a pleiotropic (activating and repressive) transcription factor. This study characterizes the mechanisms of transactivation by GKLF. Using a GAL4 fusion assay, the activating domain of murine GKLF was localized to the 109 amino acid residues in the N-terminus. Site-dir...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/28.5.1106

    authors: Geiman DE,Ton-That H,Johnson JM,Yang VW

    更新日期:2000-03-01 00:00:00

  • A novel CRISPR-engineered prostate cancer cell line defines the AR-V transcriptome and identifies PARP inhibitor sensitivities.

    abstract::Resistance to androgen receptor (AR)-targeted therapies in prostate cancer (PC) is a major clinical problem. A key mechanism of treatment resistance in advanced PC is the generation of alternatively spliced forms of the AR termed AR variants (AR-Vs) that are refractory to targeted agents and drive tumour progression. ...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkz286

    authors: Kounatidou E,Nakjang S,McCracken SRC,Dehm SM,Robson CN,Jones D,Gaughan L

    更新日期:2019-06-20 00:00:00

  • TRAP150 interacts with the RNA-binding domain of PSF and antagonizes splicing of numerous PSF-target genes in T cells.

    abstract::PSF (a.k.a. SFPQ) is a ubiquitously expressed, essential nuclear protein with important roles in DNA damage repair and RNA biogenesis. In stimulated T cells, PSF binds to and suppresses the inclusion of CD45 exon 4 in the final mRNA; however, in resting cells, TRAP150 binds PSF and prevents access to the CD45 RNA, tho...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkv816

    authors: Yarosh CA,Tapescu I,Thompson MG,Qiu J,Mallory MJ,Fu XD,Lynch KW

    更新日期:2015-10-15 00:00:00

  • BYKdb: the Bacterial protein tYrosine Kinase database.

    abstract::Bacterial tyrosine-kinases share no resemblance with their eukaryotic counterparts and they have been unified in a new protein family named BY-kinases. These enzymes have been shown to control several biological functions in the bacterial cells. In recent years biochemical studies, sequence analyses and structure reso...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkr915

    authors: Jadeau F,Grangeasse C,Shi L,Mijakovic I,Deléage G,Combet C

    更新日期:2012-01-01 00:00:00

  • A method for generating subtractive cDNA libraries retaining clones containing repetitive elements.

    abstract::Here we describe a two-stepped photobiotin-based procedure to enrich a target (canine retinal) cDNA library for tissue specific clones without removing those containing repetitive ( SINE ) elements, despite the presence of these elements in the driver population. In a first hybridization excess SINE elements were hybr...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/25.21.4427

    authors: Lin CT,Sargan DR

    更新日期:1997-11-01 00:00:00

  • Transcription factor decoy oligonucleotides modified with locked nucleic acids: an in vitro study to reconcile biostability with binding affinity.

    abstract::Double-stranded oligonucleotides (ODNs) containing the consensus binding sequence of a transcription factor provide a rationally designed tool to manipulate gene expression at the transcriptional level by the decoy approach. However, modifications introduced into oligonucleotides to increase stability quite often do n...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkh503

    authors: Crinelli R,Bianchi M,Gentilini L,Palma L,Sørensen MD,Bryld T,Babu RB,Arar K,Wengel J,Magnani M

    更新日期:2004-03-29 00:00:00

  • Oestrogen regulates cathepsin D mRNA levels in oestrogen responsive human breast cancer cells.

    abstract::A cDNA library was constructed from the mRNA of the ZR-75 oestrogen responsive human breast cancer cell line and screened for oestrogen regulated mRNA sequences. Of the recombinants isolated, 30 contained cDNA that corresponded to a single mRNA species of 2.1 kb that was induced between 10 and 15 fold by oestradiol tr...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/15.9.3773

    authors: Westley BR,May FE

    更新日期:1987-05-11 00:00:00

  • Evolutionary changes in the Leishmania eIF4F complex involve variations in the eIF4E-eIF4G interactions.

    abstract::Translation initiation in eukaryotes is mediated by assembly of the eIF4F complex over the m(7)GTP cap structure at the 5'-end of mRNAs. This requires an interaction between eIF4E and eIF4G, two eIF4F subunits. The Leishmania orthologs of eIF4E are structurally diverged from their higher eukaryote counterparts, since ...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/gkp190

    authors: Yoffe Y,Léger M,Zinoviev A,Zuberek J,Darzynkiewicz E,Wagner G,Shapira M

    更新日期:2009-06-01 00:00:00

  • The putative promoter of a Xenopus laevis ribosomal gene is reduplicated.

    abstract::With the aid of a novel poly-dA tailing-partial restriction technique and S1-protection mapping, the 5' terminal coding sequence for the 40S precursor ribosomal RNA of Xenopus laevis has been exactly identified. Since the promoter sequence for the 40S RNA should lie close to its 5' terminal coding sequence, we are abl...

    journal_title:Nucleic acids research

    pub_type: 杂志文章

    doi:10.1093/nar/6.12.3733

    authors: Moss T,Birnstiel ML

    更新日期:1979-08-24 00:00:00