Synthesis of 6-N-(benzothiazol-2-yl)deoxyadenosine and its exciton-coupled circular dichroism.

Abstract:

:6-N-(Benzothiazol-2-yl)deoxyadenosine (A(BT)) was synthesized and incorporated into DNAs. Although, the multipoint benzothiazole (BT) modification of oligodeoxynucleotides reduced the stability of duplexes with their complementary strands, it induced the strong exciton coupling between BT moieties. The circular dichroism (CD) spectra of this exciton coupling interaction were observed at wavelengths above 300nm and overlapping with the UV absorption bands of nucleotides could be avoided. The shapes of the CD spectra due to this interaction were strongly influenced by the helicity of two BT groups.

journal_name

Bioorg Med Chem

authors

Masaki Y,Ohkubo A,Seio K,Sekine M

doi

10.1016/j.bmc.2009.12.009

subject

Has Abstract

pub_date

2010-01-15 00:00:00

pages

567-72

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)01093-1

journal_volume

18

pub_type

杂志文章
  • Ratiometric nanoprobe for circulating tumor cell detection and intracellular hydrogen peroxide evaluation in colorectal cancer patients.

    abstract::The application of intensity-based H2O2-responsive fluorescence nanoprobe for circulating tumor cell detection was limited by the complex background and the nanoprobe uptake in each CTC. In this context, we developed a ratiometric fluorescence nanoprobe, on which a H2O2-responsive subunit and a stable subunit grafted ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115930

    authors: Pan R,Lu X,Ju J,Guan Q,Su Y,Li C,Li P

    更新日期:2021-01-15 00:00:00

  • Synthesis and evaluation of the 2,4-diaminoquinazoline series as anti-tubercular agents.

    abstract::The 2,4-diaminoquinazoline class of compounds has previously been identified as an effective inhibitor of Mycobacterium tuberculosis growth. We conducted an extensive evaluation of the series for its potential as a lead candidate for tuberculosis drug discovery. Three segments of the representative molecule N-(4-fluor...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.10.007

    authors: Odingo J,O'Malley T,Kesicki EA,Alling T,Bailey MA,Early J,Ollinger J,Dalai S,Kumar N,Singh RV,Hipskind PA,Cramer JW,Ioerger T,Sacchettini J,Vickers R,Parish T

    更新日期:2014-12-15 00:00:00

  • Study on synthesis, characterization and biological activity of some new nitrogen heterocycle porphyrins.

    abstract::Seven new nitrogen heterocycle porphyrins, 5,10,15,20-tetra[4-(N-pyrrolidinyl)phenyl]porphine (TBPPH(2)), 5,10,15,20-tetra[4-(4'-ethylpiperazinyl)phenyl]porphine (TEPPH(2)), 5,10,15,20-tetra [4-(4'-butylpiperazinyl)phenyl]porphine (TUPPH(2)), 5,10,15,20-tetra[4-(4'-heptylpiperazinyl) phenyl]porphine (THPPH(2)), 5-[4-(...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00027-0

    authors: Guo CC,Li HP,Zhang XB

    更新日期:2003-04-17 00:00:00

  • 2-(2-Bromophenyl)-formononetin and 2-heptyl-formononetin are PPARγ partial agonists and reduce lipid accumulation in 3T3-L1 adipocytes.

    abstract::Isoflavones are bioactive compounds that have been shown to decrease lipid accumulation in vitro. However, the knowledge of the isoflavone formononetin is limited. The aim of the study was to assess the effects of formononetin and its two synthetic analogues, 2-(2-bromophenyl)-formononetin and 2-heptyl-formononetin, o...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.037

    authors: Andersen C,Kotowska D,Tortzen CG,Kristiansen K,Nielsen J,Petersen RK

    更新日期:2014-11-01 00:00:00

  • 5-demethylovalicin, as a methionine aminopeptidase-2 inhibitor produced by Chrysosporium.

    abstract::5-Demethylovalicin was isolated from the fermentation broth Chrysosporium lucknowense and the structure was identified by spectroscopic methods. 5-Demethylovalicin inhibited the recombinant human MetAP-2 (IC(50)=17.7 nM) and the growth of human umbilical vein endothelial cells (HUVEC; IC(50)=100 nM) in cell proliferat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00268-1

    authors: Son KH,Kwon JY,Jeong HW,Kim HK,Kim CJ,Chang YH,Choi JD,Kwon BM

    更新日期:2002-01-01 00:00:00

  • Synthesis and biological activities of quinazoline derivatives with ortho-phenol-quaternary ammonium salt groups.

    abstract::One phenol-quaternary ammonium salt derivative with a flexible linker and three derivatives with a quinazoline moiety are present. Their binding affinities for DNA are discussed and it is clearly demonstrated that this class of phenol-quaternary ammonium salt derivatives could inhibit DNA transcription effectively. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.07.053

    authors: Zhang L,Ren L,Bai M,Weng L,Huang J,Wu L,Deng M,Zhou X

    更新日期:2007-11-15 00:00:00

  • The use of aminoglycoside derivatives to study the mechanism of aminoglycoside 6'-N-acetyltransferase and the role of 6'-NH2 in antibacterial activity.

    abstract::Aminoglycoside antibiotics act by binding to 16S rRNA. Resistance to these antibiotics occurs via drug modifications by enzymes such as aminoglycoside 6'-N-acetyltransferases (AAC(6')s). We report here the regioselective and efficient synthesis of N-6'-acylated aminoglycosides and their use as probes to study AAC(6')-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.02.009

    authors: Yan X,Gao F,Yotphan S,Bakirtzian P,Auclair K

    更新日期:2007-04-15 00:00:00

  • Synthesis and biological activity of a fluorescent schweinfurthin analogue.

    abstract::Most of the natural schweinfurthins are potent and selective inhibitors of cell growth as measured by the National Cancer Institute's 60-cell line screen. Due to the limited supply of these natural products, we have initiated a program aimed at their synthesis. To date, this effort has led to the preparation of three ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.04.071

    authors: Kuder CH,Neighbors JD,Hohl RJ,Wiemer DF

    更新日期:2009-07-01 00:00:00

  • Molecular structure and stereoelectronic properties of herbicide sulphonylureas.

    abstract::MO theoretical calculations were used with the aim to investigate the electronic properties of a number of sulphonylureas 1-8 which are employed as antifeedants. Quantum chemical descriptors [electron density, molecular electrostatic potential (MEP), the topology of frontier orbitals and reactivity index] were determi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00357-1

    authors: Galeazzi R,Marucchini C,Orena M,Zadra C

    更新日期:2002-04-01 00:00:00

  • Synthesis and biological evaluation of 18F-labled 2-phenylindole derivatives as PET imaging probes for β-amyloid plaques.

    abstract::A novel series of fluorinated 2-phenylindole derivatives were synthesized and evaluated as β-amyloid imaging probes for PET. The in vitro inhibition assay demonstrated that their binding affinities for Aβ(1-42) aggregates ranged from 28.4 to 1097.8 nM. One ligand was labeled with (18)F ([(18)F]1a) for its high affinit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.04.028

    authors: Fu H,Yu L,Cui M,Zhang J,Zhang X,Li Z,Wang X,Jia J,Yang Y,Yu P,Jia H,Liu B

    更新日期:2013-07-01 00:00:00

  • Search for alpha-helical propensity in the receptor-bound conformation of glucagon-like peptide-1.

    abstract::To elucidate the receptor-bound conformation of glucagon-like peptide-1 (GLP-1), a series of conformationally constrained GLP-1 analogues were synthesized by introducing lactam bridges between Lys(i) and Glu(i)(+4) to form alpha-helices at various positions. The activity and affinity of these analogues to GLP-1 recept...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.006

    authors: Murage EN,Schroeder JC,Beinborn M,Ahn JM

    更新日期:2008-12-01 00:00:00

  • Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products.

    abstract::The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in approximately 9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows act...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.10.016

    authors: Labarbera DV,Skibo EB

    更新日期:2005-01-17 00:00:00

  • Benzhydrylquinazolinediones: novel cytosolic phospholipase A2alpha inhibitors with improved physicochemical properties.

    abstract::The synthesis and optimization of a class of trisubstituted quinazoline-2,4(1H,3H)-dione cPLA(2)alpha inhibitors are described. Utilizing pharmacophores that were found to be important in our indole series, we discovered inhibitors with reduced lipophilicity and improved aqueous solubility. These compounds are active ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.05.027

    authors: Kirincich SJ,Xiang J,Green N,Tam S,Yang HY,Shim J,Shen MW,Clark JD,McKew JC

    更新日期:2009-07-01 00:00:00

  • Design, synthesis, and docking studies of quinazoline analogues bearing aryl semicarbazone scaffolds as potent EGFR inhibitors.

    abstract::Two series of quinazoline derivatives bearing aryl semicarbazone scaffolds (9a-o and 10a-o) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, HepG2, MCF-7 and PC-3). The selected compound 9o was further evaluated for the inhibitory activity against EGFR kinases. Four of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.04.001

    authors: Tu Y,Wang C,Xu S,Lan Z,Li W,Han J,Zhou Y,Zheng P,Zhu W

    更新日期:2017-06-15 00:00:00

  • Design and synthesis of novel benzimidazole derivatives as inhibitors of hepatitis B virus.

    abstract::A series of novel benzimidazole derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. The preliminary SAR was discussed. Compound 12a, with IC50<0.41 microM and SI>81.2, was the most promising compound and selected as the benchmark comp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.05.076

    authors: Luo Y,Yao JP,Yang L,Feng CL,Tang W,Wang GF,Zuo JP,Lu W

    更新日期:2010-07-15 00:00:00

  • Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents.

    abstract::A series of 1,3,4-oxadiazole derivatives derived from 4-methoxysalicylic acid or 4-methylsalicylic acid (6a-6z) have been first synthesized for their potential immunosuppressive activity. Among them, compound 6z displayed the most potent biological activity against lymph node cells (inhibition=38.76% for lymph node ce...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.03.064

    authors: Zhang ZM,Zhang XW,Zhao ZZ,Yan R,Xu R,Gong HB,Zhu HL

    更新日期:2012-05-15 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

  • Multivalent presentation of a hydrolytically stable GM(3) lactone mimetic as modulator of melanoma cells motility and adhesion.

    abstract::A hydrolytically stable mimetic of the tumour antigen GM(3) lactone is used to decorate multivalent scaffolds. Two of them positively interfere on melanoma cell adhesion, migration and resistance to apoptosis (anoikis). Notably, their ability to hamper melanoma-cells adhesion and reduce the metastatic potential is enh...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.03.021

    authors: Richichi B,Comito G,Cerofolini L,Gabrielli G,Marra A,Moni L,Pace A,Pasquato L,Chiarugi P,Dondoni A,Toma L,Nativi C

    更新日期:2013-05-15 00:00:00

  • Benzoic acid derivatives with improved antifungal activity: Design, synthesis, structure-activity relationship (SAR) and CYP53 docking studies.

    abstract::Previously, we identified CYP53 as a fungal-specific target of natural phenolic antifungal compounds and discovered several inhibitors with antifungal properties. In this study, we performed similarity-based virtual screening and synthesis to obtain benzoic acid-derived compounds and assessed their antifungal activity...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.06.042

    authors: Berne S,Kovačič L,Sova M,Kraševec N,Gobec S,Križaj I,Komel R

    更新日期:2015-08-01 00:00:00

  • Synthesis of 3-acyloxyxanthone derivatives as α-glucosidase inhibitors: A further insight into the 3-substituents' effect.

    abstract::Considerable interest has been attracted in xanthone and its derivatives because of their important biological activities. In this paper, a series of novel 3-arylacyloxyxanthone derivatives 2a-p were synthesized and evaluated for their biological activities toward α-glucosidase. In comparison to the parent 1,3-dihydro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.01.022

    authors: Li GL,Cai CY,He JY,Rao L,Ma L,Liu Y,Wang B

    更新日期:2016-04-01 00:00:00

  • 2-Methylene 19-nor-25-dehydro-1alpha-hydroxyvitamin D3 26,23-lactones: synthesis, biological activities and molecular basis of passive antagonism.

    abstract::To investigate the molecular mechanism of vitamin D receptor (VDR) antagonists having no structurally bulky group interfering with helix 12 of the ligand-binding domain of the VDR, we have synthesized four diastereomers at C(20) and C(23) of 19-nor-1alpha-hydroxyvitamin D(3) 25-methylene-26,23-lactone bearing a 2MD-ty...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.09.017

    authors: Yoshimoto N,Inaba Y,Yamada S,Makishima M,Shimizu M,Yamamoto K

    更新日期:2008-01-01 00:00:00

  • Norbornyllactone-substituted xanthines as adenosine A(1) receptor antagonists.

    abstract::During the search for second-generation adenosine A(1) receptor antagonist alternatives to the clinical candidate 8-(3-oxa-tricyclo[3.2.1.0(2,4)]oct-6-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (BG9719), we developed a series of novel xanthines substituted with norbornyl-lactones that possessed high binding affinit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.01.021

    authors: Kiesman WF,Zhao J,Conlon PR,Petter RC,Jin X,Smits G,Lutterodt F,Sullivan GW,Linden J

    更新日期:2006-06-01 00:00:00

  • Synthesis and biological activity of previtamin D(3) analogues with A-ring modifications.

    abstract::Synthesis of two novel 6-s-cis analogues of 1alpha,25-dihydroxyvitamin D3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2beta-(3'-hydroxypropoxy) moiety or a 2beta,3beta-epoxy group into 1alpha,25-OH(2)-19-nor-pre-D3. The synthesized analogue...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.053

    authors: Sánchez-Abella L,Fernández S,Verstuyf A,Verlinden L,Gotor V,Ferrero M

    更新日期:2008-12-15 00:00:00

  • SRC2-3 binds to vitamin D receptor with high sensitivity and strong affinity.

    abstract::Vitamin D receptor (VDR) is a member of the nuclear receptor superfamily and regulates the expression of target genes through ligand binding. To express the target gene, coactivator binding to the VDR/ligand complex is essential. Although there are many coactivators in living cells, precise interactions between coacti...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.11.020

    authors: Egawa D,Itoh T,Kato A,Kataoka S,Anami Y,Yamamoto K

    更新日期:2017-01-15 00:00:00

  • New, stronger nucleophiles for nucleic acid-templated chemistry: Synthesis and application in fluorescence detection of cellular RNA.

    abstract::Nucleic acid-templated chemistry is a promising strategy for imaging genetic sequences in living cells. Here we describe the synthesis of two new nucleophiles for use in templated nucleophilic displacements with DNA probes. The nucleophilic groups are phosphorodithioate and phosphorotrithioate; we report on synthetic ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.04.051

    authors: Miller GP,Silverman AP,Kool ET

    更新日期:2008-01-01 00:00:00

  • The phytoalexins brassilexin and camalexin inhibit cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola.

    abstract::Alternaria brassicicola is a fungal pathogen of many agriculturally important cruciferous crops. Cyclobrassinin hydrolase (CH) is an enzyme produced by A. brassicicola that catalyzes the transformation of the cruciferous phytoalexin cyclobrassinin into S-methyl[(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate. The purif...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.11.005

    authors: Pedras MS,Minic Z

    更新日期:2014-01-01 00:00:00

  • Analgesic agents without gastric damage: design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors.

    abstract::In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the an...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.10.029

    authors: Zheng X,Oda H,Takamatsu K,Sugimoto Y,Tai A,Akaho E,Ali HI,Oshiki T,Kakuta H,Sasaki K

    更新日期:2007-01-15 00:00:00

  • Simple molecular engineering of glycol nucleic acid: progression from self-pairing to cross-pairing with cDNA and RNA.

    abstract::The acyclic chiral nucleic acid analogue, Glycol Nucleic Acid (GNA), displayed exceptional structural simplicity and atom economy while forming self-paired duplexes, using canonical Watson-Crick base pairing. We disclose here that the replacement of phosphodiester linker in GNA with somewhat rigid and shorter carbamat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.022

    authors: Bose T,Kumar VA

    更新日期:2014-11-01 00:00:00

  • Identification of N-ethylmethylamine as a novel scaffold for inhibitors of soluble epoxide hydrolase by crystallographic fragment screening.

    abstract::Soluble epoxide hydrolase (sEH) is a potential target for the treatment of inflammation and hypertension. X-ray crystallographic fragment screening was used to identify fragment hits and their binding modes. Eight fragment hits were identified via soaking of sEH crystals with fragment cocktails, and the co-crystal str...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.03.083

    authors: Amano Y,Tanabe E,Yamaguchi T

    更新日期:2015-05-15 00:00:00

  • Alkyl deoxy-arabino-hexopyranosides: synthesis, surface properties, and biological activities.

    abstract::Octyl and dodecyl glycosides possessing 2-deoxy-arabino-hexopyranoside moieties belonging to the D- and L-series in their alpha- and beta-forms were synthesized by reaction of an acetyl protected glycal with octanol or dodecanol, catalyzed by triphenylphosphine hydrobromide, followed by deprotection. Their surface pro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.01.020

    authors: Silva FV,Goulart M,Justino J,Neves A,Santos F,Caio J,Lucas S,Newton A,Sacoto D,Barbosa E,Santos MS,Rauter AP

    更新日期:2008-04-01 00:00:00