Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine.

Abstract:

:2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

journal_name

Bioorg Med Chem

authors

Lou C,Xiao Q,Brennan L,Light ME,Vergara-Irigaray N,Atkinson EM,Holden-Dye LM,Fox KR,Brown T

doi

10.1016/j.bmc.2010.07.005

subject

Has Abstract

pub_date

2010-09-01 00:00:00

pages

6389-97

issue

17

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00648-6

journal_volume

18

pub_type

杂志文章
  • Activation of lysine-specific demethylase 1 inhibitor peptide by redox-controlled cleavage of a traceless linker.

    abstract::We have previously employed cyclization of a linear peptide as a strategy to modulate peptide function and properties, but cleavage to regenerate the linear peptide left parts of the linker structure on the peptide, interfering with its activity. Here, we focused on cyclization of a linear peptide via a "traceless" di...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.12.033

    authors: Amano Y,Umezawa N,Sato S,Watanabe H,Umehara T,Higuchi T

    更新日期:2017-02-01 00:00:00

  • Discovery of novel phenoxazinone derivatives as DKK1/LRP6 interaction inhibitors: Synthesis, biological evaluation and structure-activity relationships.

    abstract::Amino derivatives of NCI8642 were synthesized and evaluated as inhibitors of DKK1/LRP6 interactions. The new inhibitors were able to activate the Wnt signaling pathway as indicated by the increased levels of β-catenin, and decrease the DKK1-induced Tau phosphorylation at serine 396. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.01.025

    authors: Thysiadis S,Mpousis S,Avramidis N,Katsamakas S,Balomenos A,Remelli R,Efthimiopoulos S,Sarli V

    更新日期:2016-03-01 00:00:00

  • 3-Phenyl substituted 6,7-dimethoxyisoquinoline derivatives as FtsZ-targeting antibacterial agents.

    abstract::The emergence of multidrug-resistant bacteria has created an urgent need for antibiotics with a novel mechanism of action. The bacterial cell division protein FtsZ is an attractive target for the development of novel antibiotics. The benzo[c]phenanthridinium sanguinarine and the dibenzo[a,g]quinolizin-7-ium berberine ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.10.009

    authors: Kelley C,Zhang Y,Parhi A,Kaul M,Pilch DS,LaVoie EJ

    更新日期:2012-12-15 00:00:00

  • HSP90-like artificial chaperone activity based on indole beta-cyclodextrin.

    abstract::Indole beta-cyclodextrin (beta-1) was found to be able to prevent aggregation of citrate synthase (CS) on heating condition. As a result, beta-1 showed anti-CS aggregation in this system by regulating in early stage. The depression mechanism of beta-1 for aggregation of CS is as follows: the beta-1 formed a complex wi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.12.040

    authors: Toda M,Itoh H,Kondo Y,Hamada F

    更新日期:2007-03-01 00:00:00

  • Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration.

    abstract::Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Acc...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.10.001

    authors: Matralis AN,Xanthopoulos D,Huot G,Lopes-Paciencia S,Cole C,de Vries H,Ferbeyre G,Tsantrizos YS

    更新日期:2018-11-01 00:00:00

  • Structure-activity relationship study of pyrimido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent anti-HIV agents.

    abstract::3,4-Dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182) is an antiretroviral agent with submicromolar inhibitory activity against human immunodeficiency virus-1 (HIV-1) and HIV-2 infection. In the current study, the structure-activity relationships of accessory groups at the 3- and 9-positions of pyrimi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.08.030

    authors: Mizuhara T,Oishi S,Ohno H,Shimura K,Matsuoka M,Fujii N

    更新日期:2012-11-01 00:00:00

  • Solution structure of endothelin B receptor selective antagonist RES-701-1 determined by 1H NMR spectroscopy.

    abstract::The three-dimensional structure of the endothelin B receptor (ETB) selective antagonist RES-701-1 has been determined by 1H NMR in deuterated dimethyl sulphoxide. RES-701-1 consists of 16 amino acid residues with a novel internal linkage between the beta-carboxyl group of Asp9 and the alpha-amino group of Gly1. The st...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(95)00122-w

    authors: Katahira R,Shibata K,Yamasaki M,Matsuda Y,Yoshida M

    更新日期:1995-09-01 00:00:00

  • Synthesis of novel 5-amino-thiazolo[4,5-d]pyrimidines as E. coli and S. aureus SecA inhibitors.

    abstract::An efficient synthesis of a library of 5-amino-thiazolo[4,5-d]pyrimidines is reported. Regioselective displacements of chlorines, as well as regioselective diazotation reactions are described, which allow the introduction of structural diversity on the scaffold by consecutive reactions. Screening of this focused libra...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.10.027

    authors: Jang MY,De Jonghe S,Segers K,Anné J,Herdewijn P

    更新日期:2011-01-01 00:00:00

  • Heteroarylamide smoothened inhibitors: Discovery of N-[2,4-dimethyl-5-(1-methylimidazol-4-yl)phenyl]-4-(2-pyridylmethoxy)benzamide (AZD8542) and N-[5-(1H-imidazol-2-yl)-2,4-dimethyl-phenyl]-4-(2- pyridylmethoxy)benzamide (AZD7254).

    abstract::Aberrant hedgehog (Hh) pathway signaling is implicated in multiple cancer types and targeting the Smoothened (SMO) receptor, a key protein of the Hh pathway, has proven effective in treating metastasized basal cell carcinoma. Our lead optimization effort focused on a series of heteroarylamides. We observed that a meth...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.115227

    authors: Yang B,Hird AW,Bodnarchuk MS,Zheng X,Dakin L,Su Q,Daly K,Godin R,Hattersley MM,Brassil P,Redmond S,John Russell D,Janetka JW

    更新日期:2020-01-15 00:00:00

  • Novel pyrazolo[1,5-a]pyrimidines as c-Src kinase inhibitors that reduce IKr channel blockade.

    abstract::To improve the in vitro potency of the c-Src inhibitor 1a and to address its hERG liability, a structure-activity study was carried out, focusing on two regions of the lead compound. The blockade of the delayed cardiac current rectifier K(+) (I(Kr)) channel was overcome by replacing the ethylenediamino group with an a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.10.068

    authors: Mukaiyama H,Nishimura T,Kobayashi S,Komatsu Y,Kikuchi S,Ozawa T,Kamada N,Ohnota H

    更新日期:2008-01-15 00:00:00

  • Dihydrofolate reductase and cell growth activity inhibition by the beta-carboline-benzoquinolizidine plant alkaloid deoxytubulosine from Alangium lamarckii: its potential as an antimicrobial and anticancer agent.

    abstract::Beta-carboline-benzoquinolizidine plant alkaloid deoxytubulosine (DTB) was evaluated and assessed for the first time for its biochemical and biological activity employing the biomarker dihydrofolate reductase (DHFR) (5,6,7,8-tetrahydrofolate: NADP+ oxidoreductase, EC 1.5.1.3) as the probe enzyme, a key target in cance...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00262-4

    authors: Rao KN,Venkatachalam SR

    更新日期:1999-06-01 00:00:00

  • ortho-Halogen naphthaleins as specific inhibitors of Lactobacillus casei thymidylate synthase. Conformational properties and biological activity.

    abstract::Thymidylate synthase (TS) (EC 2.1.1.45), an enzyme involved in the DNA synthesis of both prokaryotic and eukaryotic cells, is a potential target for the development of anticancer and antinfective agents. Recently, we described a series of phthalein and naphthalein derivatives as TS inhibitors. These compounds have str...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00541-2

    authors: Ghelli S,Rinaldi M,Barlocco D,Gelain A,Pecorari P,Tondi D,Rastelli G,Costi MP

    更新日期:2003-03-20 00:00:00

  • Lipase-catalysed selective deacetylation of phenolic/enolic acetoxy groups in peracetylated benzyl phenyl ketones.

    abstract::Highly chemo- and regioselective de-esterification has been observed in the deacetylation of peracetylated enolic forms of polyphenolic benzyl phenyl ketones by lipase from porcine pancreas (PPL) suspended in tetrahydrofuran (THF). The enzyme selectively deacetylates the enolic acetoxy over the phenolic acetoxy group(...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(97)10010-4

    authors: Parmar VS,Pati HN,Azim A,Kumar R,Himanshu,Bisht KS,Prasad AK,Errington W

    更新日期:1998-01-01 00:00:00

  • Design and synthesis of novel HDAC8 inhibitory 2,5-disubstituted-1,3,4-oxadiazoles containing glycine and alanine hybrids with anti cancer activity.

    abstract::Oxadiazole is a heterocyclic compound containing an oxygen atom and two nitrogen atoms in a five-membered ring. Of the four oxadiazoles known, 1,3,4-oxadiazole has become an important structural motif for the development of new drugs and the compounds containing 1,3,4-oxadiazole cores have a broad spectrum of biologic...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.09.022

    authors: Pidugu VR,Yarla NS,Pedada SR,Kalle AM,Satya AK

    更新日期:2016-11-01 00:00:00

  • Directed evolution of N-acetylneuraminic acid aldolase to catalyze enantiomeric aldol reactions.

    abstract::Expanding the scope of substrate specificity and stereoselectivity is of current interest in enzyme catalysis. Using error-prone PCR for in vitro directed evolution, the Neu5Ac aldolase from Escherichia coli has been altered to improve its catalytic activity toward enantiomeric substrates including N-acetyl-L-mannosam...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00052-x

    authors: Wada M,Hsu CC,Franke D,Mitchell M,Heine A,Wilson I,Wong CH

    更新日期:2003-05-01 00:00:00

  • 2,3-Disubstituted quinuclidines as a novel class of dopamine transporter inhibitors.

    abstract::There is considerable interest in developing dopamine transporter (DAT) inhibitors as potential therapies for the treatment of cocaine abuse. We report herein our pharmacophore-based discovery and molecular modeling-assisted rational design of 2,3-disubstituted quinuclidines as potent DAT inhibitors with a novel chemi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00450-9

    authors: Sakamuri S,Enyedy IJ,Zaman WA,Tella SR,Kozikowski AP,Flippen-Anderson JL,Farkas T,Johnson KM,Wang S

    更新日期:2003-03-20 00:00:00

  • Synthesis and biology of bis-xylosylated dihydroxynaphthalenes.

    abstract::The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-x...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.02.020

    authors: Johnsson R,Mani K,Ellervik U

    更新日期:2007-04-15 00:00:00

  • Synergistic reduction of HIV-1 infectivity by 5-azacytidine and inhibitors of ribonucleotide reductase.

    abstract::Although many compounds have been approved for the treatment of human immunodeficiency type-1 (HIV-1) infection, additional anti-HIV-1 drugs (particularly those belonging to new drug classes) are still needed due to issues such as long-term drug-associated toxicities, transmission of drug-resistant variants, and devel...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.03.052

    authors: Rawson JM,Roth ME,Xie J,Daly MB,Clouser CL,Landman SR,Reilly CS,Bonnac L,Kim B,Patterson SE,Mansky LM

    更新日期:2016-06-01 00:00:00

  • Synthesis and evaluation of N-aryl and N-alkenyl CBI derivatives.

    abstract::The preparation of a novel series of N-aryl CBI derivatives in which an aryl substituent could be used to predictably modulate the reactivity of the resulting CC-1065/duocarmycin alkylation subunit analogue is detailed and its extension to a unique series of N-alkenyl derivatives is reported. The N-aryl derivatives we...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.08.032

    authors: Parrish JP,Trzupek JD,Hughes TV,Hwang I,Boger DL

    更新日期:2004-11-15 00:00:00

  • Impact of stereochemistry on the biological activity of novel oleandomycin derivatives.

    abstract::A set of 8-methylene-, 8-methyl-, and 8-methyl-9-dihydro-oleandomycin derivatives having different combinations of stereochemistries at positions C-8 and/or C-9 have been prepared in a chemoselective and stereoselective manner and tested in vitro for antibacterial activity and inhibition of IL-6 production. Configurat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.02.013

    authors: Bauer J,Vine M,Corić I,Bosnar M,Pašalić I,Turkalj G,Lazarevski G,Culić O,Kragol G

    更新日期:2012-04-01 00:00:00

  • Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group.

    abstract::In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhib...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.05.016

    authors: Carrión MD,Chayah M,Entrena A,López A,Gallo MA,Acuña-Castroviejo D,Camacho ME

    更新日期:2013-07-15 00:00:00

  • Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.

    abstract::Members of the GATA family of transcription factors are zinc finger proteins that were shown to play evolutionary conserved roles in cell differentiation and proliferation in different organisms. We hypothesized that by finding new molecules that inhibit their function to be crucial in future therapeutical interventio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.01.022

    authors: El-Hachem N,Nemer G

    更新日期:2011-03-01 00:00:00

  • Kolavenic acid analog restores growth in HSET-overproducing fission yeast cells and multipolar mitosis in MDA-MB-231 human cells.

    abstract::Although cancer cells often harbor supernumerary centrosomes, they form pseudo-bipolar spindles via centrosome clustering, instead of lethal multipolar spindles, and thus avoid cell death. Kinesin-14 HSET/KIFC1 is a crucial protein involved in centrosome clustering. Accordingly, a compound that targets HSET could pote...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.115154

    authors: Kurisawa N,Yukawa M,Koshino H,Onodera T,Toda T,Kimura KI

    更新日期:2020-01-01 00:00:00

  • Synthesis of indomethacin analogues for evaluation as modulators of MRP activity.

    abstract::Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00292-3

    authors: Maguire AR,Plunkett SJ,Papot S,Clynes M,O'Connor R,Touhey S

    更新日期:2001-03-01 00:00:00

  • Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells.

    abstract::A series of benzyloxybenzaldehyde derivatives were prepared and tested against the HL-60 cell line for anticancer activity. Preliminary structure-activity relationships were established. It was discovered that 2-(benzyloxy)benzaldehyde (17), 2-(benzyloxy)-4-methoxybenzaldehyde (26), 2-(benzyloxy)-5-methoxybenzaldehyde...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.12.026

    authors: Lin CF,Yang JS,Chang CY,Kuo SC,Lee MR,Huang LJ

    更新日期:2005-03-01 00:00:00

  • Novel benzimidazol-2-ylidene carbene precursors and their silver(I) complexes: Potential antimicrobial agents.

    abstract::Novel benzimidazolium salts were synthesized as N-heterocyclic carbene (NHC) precursors, these NHC precursors were metallated with Ag2O in dichloromethane at room temperature to give novel silver(I)-NHC complexes. Structures of these benzimidazolium salts and silver(I)-NHC complexes were characterized on the basis of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.06.004

    authors: Kaloğlu M,Kaloğlu N,Özdemir İ,Günal S,Özdemir İ

    更新日期:2016-08-15 00:00:00

  • Stereostructure-based differences in the interactions of cardiotoxic local anesthetics with cholesterol-containing biomimetic membranes.

    abstract::Amide-type pipecoloxylidide local anesthetics, bupivacaine, and ropivacaine, show cardiotoxic effects with the potency depending on stereostructures. Cardiotoxic drugs not only bind to cardiomyocyte membrane channels to block them but also modify the physicochemical property of membrane lipid bilayers in which channel...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.04.030

    authors: Tsuchiya H,Ueno T,Mizogami M

    更新日期:2011-06-01 00:00:00

  • Design, synthesis and biological assessment of novel N-substituted 3-(phthalimidin-2-yl)-2,6-dioxopiperidines and 3-substituted 2,6-dioxopiperidines for TNF-α inhibitory activity.

    abstract::Eight novel 2-(2,6-dioxopiperidin-3-yl)phthalimidine EM-12 dithiocarbamates 9 and 10, N-substituted 3-(phthalimidin-2-yl)-2,6-dioxopiperidines 11-14 and 3-substituted 2,6-dioxopiperidines 16 and 18 were synthesized as tumor necrosis factor-α (TNF-α) synthesis inhibitors. Synthesis involved utilization of a novel conde...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.05.029

    authors: Luo W,Yu QS,Salcedo I,Holloway HW,Lahiri DK,Brossi A,Tweedie D,Greig NH

    更新日期:2011-07-01 00:00:00

  • Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties.

    abstract::Combretastatin A-4 (CA-4) is a highly cytotoxic natural product and several derivatives have been prepared which underwent clinical trial. These investigations revealed that the cis-stilbene moiety of the natural product is prone to undergo cis/trans isomerization under physiological conditions, reducing the overall a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.07.048

    authors: Nowikow C,Fuerst R,Kauderer M,Dank C,Schmid W,Hajduch M,Rehulka J,Gurska S,Mokshyna O,Polishchuk P,Zupkó I,Dzubak P,Rinner U

    更新日期:2019-10-01 00:00:00

  • A combination of in silico and SAR studies to identify binding hot spots of Bcl-xL inhibitors.

    abstract::Inhibition of Bcl-2 family protein-protein interactions (PPI) is a very promising direction in cancer chemotherapy. Hence over the last decade, many medicinal chemistry studies endeavoured to discover drug candidates, and a wealth of chemical scaffolds with striking chemical diversity was reported as Bcl-xL inhibitors...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.02.060

    authors: Levoin N,Vo DD,Gautier F,Barillé-Nion S,Juin P,Tasseau O,Grée R

    更新日期:2015-04-15 00:00:00