Preparation of alkyne-labeled 2-nitroimidazoles for identification of tumor hypoxia by Raman spectroscopy.

Abstract:

:Hypoxia is a characteristic feature of solid tumors. Herein, we have developed novel hypoxia-sensitive probes (IM-ACs) for Raman spectroscopic analysis, consisting of nitroimidazole as a hypoxia-targeting unit and acetylene group as the signal-emitting unit. Among IM-ACs synthesized in this study, IM-AC possessing a diacetylene group (IM-AC 3), showed suitable properties as a hypoxia indicator. When administered to A549 cells, we observed a strong signal of IM-AC 3 around 2200cm-1 in the Raman spectra from hypoxic cells. Ex vivo experiments suggest that IM-AC 3 remained in hypoxic tumor tissue and emitted a strong signal.

journal_name

Bioorg Med Chem Lett

authors

Kurihara R,Ikemura Y,Tanabe K

doi

10.1016/j.bmcl.2016.09.024

subject

Has Abstract

pub_date

2016-10-15 00:00:00

pages

4892-4894

issue

20

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(16)30964-7

journal_volume

26

pub_type

杂志文章
  • Optimization of alpha-acylaminoketone ecdysone agonists for control of gene expression.

    abstract::Fifteen new alpha-acylaminoketones were prepared by four different routes in an initial effort to optimize the potency of these compounds as ecdysone agonists. The compounds were assayed in mammalian cells expressing the ecdysone receptors from Bombyx mori (BmEcR) and Choristoneura fumiferana (CfEcR) for their ability...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00315-9

    authors: Tice CM,Hormann RE,Thompson CS,Friz JL,Cavanaugh CK,Saggers JA

    更新日期:2003-06-02 00:00:00

  • Eicosapentaenoic-acid-derived isoprostanes: synthesis and discovery of two major isoprostanes.

    abstract::The stereospecific synthesis of two all-syn-EPA-derived isoprostanes (iPs), 5-epi-8,12-iso-iPF(3alpha)-VI 17 and 8,12-iso-iPF(3alpha)-VI 18, has been accomplished. These two synthetic probes have been used to discover and identify their presence in human urine. The eventual quantitative measurement of these two iPs ma...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.09.008

    authors: Chang CT,Patel P,Kang N,Lawson JA,Song WL,Powell WS,FitzGerald GA,Rokach J

    更新日期:2008-10-15 00:00:00

  • A new class of selective and potent inhibitors of neuronal nitric oxide synthase.

    abstract::The synthesis and SAR of a series of 6-(4-(substituted)phenyl)-2-aminopyridines as inhibitors of nitric oxide synthase are described. Compound 3a from this series shows potent and selective inhibition of the human nNOS isoform, with pharmacokinetics sufficient to provide in vivo inhibition of nNOS activity. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00432-1

    authors: Lowe JA 3rd,Qian W,Volkmann RA,Heck S,Nowakowski J,Nelson R,Nolan C,Liston D,Ward K,Zorn S,Johnson C,Vanase M,Faraci WS,Verdries KA,Baxter J,Doran S,Sanders M,Ashton M,Whittle P,Stefaniak M

    更新日期:1999-09-06 00:00:00

  • Structure based medicinal chemistry approach to develop 4-methyl-7-deazaadenine carbocyclic nucleosides as anti-HCV agent.

    abstract::The structure-based approaches were implemented to design and rationally select the molecules for synthesis and anti-HCV activity evaluation. The systematic structure-activity relationships of previously discovered molecules (types I, II, III) were analyzed to design new molecules (type IV) by bioisosteric replacement...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.09.072

    authors: Thiyagarajan A,Salim MT,Balaraju T,Bal C,Baba M,Sharon A

    更新日期:2012-12-15 00:00:00

  • Targeting prostate cancer cells with a multivalent PSMA inhibitor-guided streptavidin conjugate.

    abstract::Prostate-specific membrane antigen (PSMA), a type II membrane glycoprotein, its high expression is associated with prostate cancer progression, and has been becoming an active target for imaging or therapeutic applications for prostate cancer. On the other hand, streptavidin-biotin system has been successfully employe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.04.110

    authors: Liu T,Nedrow-Byers JR,Hopkins MR,Wu LY,Lee J,Reilly PT,Berkman CE

    更新日期:2012-06-15 00:00:00

  • Synthesis and antimicrobial activity of some new pyrazole derivatives containing a ferrocene unit.

    abstract::A series of new imines and amines have been synthesized by condensation of 1H-3-ferrocenyl-1-phenylpyrazole-4-carboxaldehyde with the corresponding amines, followed by reduction with sodium borohydride. The synthesized compounds have been screened for their in vitro antimicrobial activity against 11 bacteria and three...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.01.006

    authors: Damljanović I,Vukićević M,Radulović N,Palić R,Ellmerer E,Ratković Z,Joksović MD,Vukićević RD

    更新日期:2009-02-15 00:00:00

  • Macrocyclic factor XIa inhibitors.

    abstract::A series of macrocyclic factor XIa (FXIa) inhibitors was designed based on an analysis of the crystal structures of the acyclic phenylimidazole compounds. Further optimization using structure-based design led to inhibitors with pM affinity for FXIa, excellent selectivity against a panel of relevant serine proteases, a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.07.048

    authors: Wang C,Corte JR,Rossi KA,Bozarth JM,Wu Y,Sheriff S,Myers JE Jr,Luettgen JM,Seiffert DA,Wexler RR,Quan ML

    更新日期:2017-09-01 00:00:00

  • Pyrimidine benzamide-based thrombopoietin receptor agonists.

    abstract::A series of pyrimidine benzamide-based thrombopoietin receptor agonists is described. The lead molecule contains a 2-amino-5-unsubstituted thiazole, a group that has been associated with idiosyncratic toxicity. The potential for metabolic oxidation at C-5 of the thiazole, the likely source of toxic metabolites, was re...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.07.038

    authors: Reiter LA,Subramanyam C,Mangual EJ,Jones CS,Smeets MI,Brissette WH,McCurdy SP,Lira PD,Linde RG,Li Q,Zhang F,Antipas AS,Blumberg LC,Doty JL,Driscoll JP,Munchhof MJ,Ripp SL,Shavnya A,Shepard RM,Sperger D,Thomasco LM

    更新日期:2007-10-01 00:00:00

  • Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.

    abstract::Millettia pachycarpa Benth, a widely used anthelminthic drug in folk, is rich in flavonoids with various bioactivities. This study aimed to identify active flavonoids with anti-Alzheimer's disease (AD) effect from its seeds by a bioassay-guided isolation. A novel rotenoid with unusual oxidative ring-opening skeleton (...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.03.024

    authors: Tu Y,Wu C,Kang Y,Li Q,Zhu C,Li Y

    更新日期:2019-05-15 00:00:00

  • Carbon analogs of antifungal dioxane-triazole derivatives: synthesis and in vitro activities.

    abstract::A new series of triazole compounds possessing a carbon atom in place of a sulfur atom were efficiently synthesized and their in vitro antifungal activities were investigated. The carbon analogs showed excellent in vitro activity against Candida, Cryptococcus, and Aspergillus species. The MICs of compound 1c against C....

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.10.055

    authors: Uchida T,Somada A,Kagoshima Y,Konosu T,Oida S

    更新日期:2008-12-15 00:00:00

  • Design and synthesis of phosphotyrosine mimetics.

    abstract::Selective inhibitors of protein tyrosine phosphatases (PTPases) are of great interest as therapeutic agents and research tools. Several phenylalanine derivatives (1, 2) designed as phosphotyrosine mimetics or irreversible active site inhibitors were successfully synthesized, then incorporated into a combinatorial libr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00253-1

    authors: Yan Z,Kahn M,Qabar M,Urban J,Kim HO,Blaskovich MA

    更新日期:2003-06-16 00:00:00

  • Discovery of a novel olefin derivative as a highly potent and selective acetyl-CoA carboxylase 2 inhibitor with in vivo efficacy.

    abstract::Novel acetyl-CoA carboxylase 2 (ACC2) selective inhibitors were identified by the conversion of the alkyne unit of A-908292 to the olefin linker. Modification of the center and left part of the lead compound 1b improved the ACC2 inhibitory activity and CYP450 inhibition profile, and afforded a highly selective ACC2 in...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.05.055

    authors: Nishiura Y,Matsumura A,Kobayashi N,Shimazaki A,Sakamoto S,Kitade N,Tonomura Y,Ino A,Okuno T

    更新日期:2018-08-01 00:00:00

  • Novel dual inhibitors of calpain and lipid peroxidation.

    abstract::A series of molecules with dual inhibitory activities on calpain and lipid peroxidation were synthesized. These hybrid compounds were built on the calpain pharmacophore 2-hydroxytetrahydrofuran linked to a set of antioxidants via a l-leucine linker. Compound 7, the most potent in cellular calpain and lipid peroxidatio...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.04.105

    authors: Auvin S,Pignol B,Navet E,Pons D,Marin JG,Bigg D,Chabrier PE

    更新日期:2004-07-16 00:00:00

  • P2-P3 conformationally constrained ketoamide-based inhibitors of cathepsin K.

    abstract::An orally bioavailable series of ketoamide-based cathepsin K inhibitors with good pharmacokinetic properties has been identified. Starting from a potent inhibitor endowed with poor drug properties, conformational constraint of the P(2)-P(3) linker and modifications to P(1') elements led to an enhancement in potency, s...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.05.062

    authors: Barrett DG,Boncek VM,Catalano JG,Deaton DN,Hassell AM,Jurgensen CH,Long ST,McFadyen RB,Miller AB,Miller LR,Payne JA,Ray JA,Samano V,Shewchuk LM,Tavares FX,Wells-Knecht KJ,Willard DH Jr,Wright LL,Zhou HQ

    更新日期:2005-08-01 00:00:00

  • A comparison of the alpha-helix forming propensities and hydrogen bonding properties of serine phosphate and alpha-amino-gamma-phosphonobutyric acid.

    abstract::The ability of serine phosphate (SerP) or alpha-amino-gamma-phosphonobutyric acid (AbuP) and arginine to form a salt bridge between their side chains appears to be much greater when they are spaced i/i+4 than when they are spaced i/i+3. The side chain-side chain interaction between SerP/Arg and AbuP/Arg, positioned i/...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00469-2

    authors: Liehr S,Chenault HK

    更新日期:1999-09-20 00:00:00

  • Sugar Chips immobilized with synthetic sulfated disaccharides of heparin/heparan sulfate partial structure.

    abstract::Carbohydrate chip technology has a great potential for the high-throughput evaluation of carbohydrate-protein interactions. Herein, we report syntheses of novel sulfated oligosaccharides possessing heparin and heparan sulfate partial disaccharide structures, their immobilization on gold-coated chips to prepare array-t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.01.069

    authors: Wakao M,Saito A,Ohishi K,Kishimoto Y,Nishimura T,Sobel M,Suda Y

    更新日期:2008-04-01 00:00:00

  • Discovery of novel benzylidene-1,3-thiazolidine-2,4-diones as potent and selective inhibitors of the PIM-1, PIM-2, and PIM-3 protein kinases.

    abstract::Novel substituted benzylidene-1,3-thiazolidine-2,4-diones (TZDs) have been identified as potent and highly selective inhibitors of the PIM kinases. The synthesis and SAR of these compounds are described, along with X-ray crystallographic, anti-proliferative, and selectivity data. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.05.098

    authors: Dakin LA,Block MH,Chen H,Code E,Dowling JE,Feng X,Ferguson AD,Green I,Hird AW,Howard T,Keeton EK,Lamb ML,Lyne PD,Pollard H,Read J,Wu AJ,Zhang T,Zheng X

    更新日期:2012-07-15 00:00:00

  • Slow generation of hydrogen sulfide from sulfane sulfurs and NADH models.

    abstract::Here we report the model studies of the reactions between NADH models (using HEH and BNAH) and sulfane sulfurs (using polysulfides). Such reactions could lead to the oxidation of NADH models and the production of hydrogen sulfide (H2S). Kinetics of the reaction between BNAH and elemental sulfur S8 were determined in e...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.12.023

    authors: Peng B,Liu C,Li Z,Day JJ,Lu Y,Lefer DJ,Xian M

    更新日期:2017-02-01 00:00:00

  • Diaryl piperidines as CB1 receptor antagonists.

    abstract::The syntheses and SAR investigations of novel CB(1) receptor antagonists based on a 1,2-diaryl piperidine core have been described. Optimization of this core afforded a compound with robust in vivo potency by reducing food intake in a mouse DIO model. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.11.075

    authors: Scott JD,Li SW,Wang H,Xia Y,Jayne CL,Miller MW,Duffy RA,Boykow GC,Kowalski TJ,Spar BD,Stamford AW,Chackalamannil S,Lachowicz JE,Greenlee WJ

    更新日期:2010-02-01 00:00:00

  • Synthesis and evaluation of 2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione derivatives as Mnk inhibitors.

    abstract::Post-translational modulation of eIF4E through phosphorylation by Mnks is highly integral to the pathogenesis of different cancers. Therefore, inhibition of Mnks offers a strategy for cancer treatment. Herein, a series of 2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione derivatives is presented as Mnk in...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.07.043

    authors: Abdelaziz AM,Basnet SKC,Islam S,Li M,Tadesse S,Albrecht H,Gerber C,Yu M,Wang S

    更新日期:2019-09-15 00:00:00

  • A computational docking study for prediction of binding mode of diospyrin and derivatives: Inhibitors of human and leishmanial DNA topoisomerase-I.

    abstract::A computational approach was utilized to study the relative binding modes of diospyrin (bisnaphthoquinonoid) with the crystal structure of human DNA-TopoI and the recently reported Leishmania donavani DNA-TopoI. Additionally, the binding site interactions of amino derivatives of diospyrin with human TopoI were studied...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,收录出版

    doi:10.1016/j.bmcl.2007.05.082

    authors: Chhabra S,Sharma P,Ghoshal N

    更新日期:2007-08-15 00:00:00

  • Syntheses of prodrug-type phosphotriester oligonucleotides responsive to intracellular reducing environment for improvement of cell membrane permeability and nuclease resistance.

    abstract::We synthesized prodrug-type phosphotriester (PTE) oligonucleotides containing the six-membered cyclic disulfide moiety by using phosphoramidite chemistry. Prodrug-type oligonucleotides named "Reducing-Environment-Dependent Uncatalyzed Chemical Transforming (REDUCT) PTE oligonucleotides" were converted into natural oli...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.05.031

    authors: Hayashi J,Samezawa Y,Ochi Y,Wada SI,Urata H

    更新日期:2017-07-15 00:00:00

  • 3D-QSAR models on clinically relevant K103N mutant HIV-1 reverse transcriptase obtained from two strategic considerations.

    abstract::Clinically relevant Lys103Asn (K103N) mutant frequently observed in HIV-1 reverse transcriptase (RT) confers drug resistance. To obtain useful structural information necessary for targeted-inhibitor design, molecular docking combined with 3D-QSAR CoMFA and CoMSIA was applied to a set of 53 structurally diverse HIV-RT ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.11.134

    authors: San Juan AA

    更新日期:2008-02-01 00:00:00

  • New synthetic route to ethynyl-dUTP: A means to avoid formation of acetyl and chloro vinyl base-modified triphosphates that could poison SELEX experiments.

    abstract::5-Ethynyl-2'-deoxyuridine is a common base-modified nucleoside analogue that has served in various applications including selection experiments for potent aptamers and in biosensing. The synthesis of the corresponding triphosphates involves a mild acidic deprotection step. Herein, we show that this deprotection leads ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.01.009

    authors: Röthlisberger P,Levi-Acobas F,Hollenstein M

    更新日期:2017-02-15 00:00:00

  • Discovery and in vitro evaluation of potent TrkA kinase inhibitors: oxindole and aza-oxindoles.

    abstract::The discovery, synthesis, potential binding mode, and in vitro kinase profile of 3-(3-bromo-4-hydroxy-5-(2'-methoxyphenyl)-benzylidene)-5-bromo-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one, 3-[(1-methyl-1H-indol-3-yl)methylene]-1,3-dihydro-2H-pyrrolo[3,2-b]-pyridin-2-one as potent TrkA inhibitors are discussed. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.12.002

    authors: Wood ER,Kuyper L,Petrov KG,Hunter RN 3rd,Harris PA,Lackey K

    更新日期:2004-02-23 00:00:00

  • HIV-1 integrase pharmacophore model derived from diverse classes of inhibitors.

    abstract::A three-dimensional pharmacophore model has been generated for HIV-1 integrase (HIV-1 IN) from known inhibitors. A dataset consisting of 26 inhibitors was selected on the basis of the information content of the structures and activity data as required by the catalyst/HypoGen program. Our model was able to predict the ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.01.027

    authors: Mustata GI,Brigo A,Briggs JM

    更新日期:2004-03-22 00:00:00

  • Progress in discovery of small-molecule modulators of protein-protein interactions via fragment screening.

    abstract::Protein-protein interactions (PPIs) present a formidable challenge to medicinal chemistry. The extended and open nature of many binding sites at protein interfaces has made it difficult to find useful chemical matter by traditional screening methods using standard screening libraries. This Digest focuses on the progre...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmcl.2015.04.089

    authors: Magee TV

    更新日期:2015-06-15 00:00:00

  • Montmorillonite K-10 catalyzed cyclization of N-ethoxycarbonyl-N'-arylguanidines: access to pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole derivatives.

    abstract::Two new heterocycles, pyrimido[4,5-c]carbazole and pyrimido[5,4-b]indole, were prepared in three steps from 3-aminocarbazole and 3-aminoindole, respectively. The key Friedel-Crafts intramolecular cyclization was realized under microwave irradiation using montmorillonite K-10 clay as a catalyst. The pyrimido[4,5-c]carb...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.05.028

    authors: Debray J,Zeghida W,Baldeyrou B,Mahieu C,Lansiaux A,Demeunynck M

    更新日期:2010-07-15 00:00:00

  • N-(pyrimidin-4-yl) and N-(pyridin-2-yl) phenylalanine derivatives as VLA-4 integrin antagonists.

    abstract::The SAR studies to optimise both potency and rate of clearance in the rat for a series of pyrimidine and pyridine based VLA-4 antagonists are described. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00241-x

    authors: Porter JR,Archibald SC,Brown JA,Childs K,Critchley D,Head JC,Hutchinson B,Parton TA,Robinson MK,Shock A,Warrellow GJ,Zomaya A

    更新日期:2002-06-17 00:00:00

  • The binding of cocaine to cyclodextrins.

    abstract::Cocaine binds into beta-cyclodextrin, but not detectably into alpha- or gamma-cyclodextrin, in water solution. NMR studies indicate the geometry of the complex, which is confirmed by molecular mechanics calculations and binding studies on cocaine analogues and cyclodextrin dimers. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00371-1

    authors: Nesna N,Lou J,Breslow R

    更新日期:2000-09-04 00:00:00