Synthesis and radiolabeling of (64)Cu-labeled 2-nitroimidazole derivative (64)Cu-BMS2P2 for hypoxia imaging.

Abstract:

:The objective of this study was to develop a positron emission tomography (PET) probe with hypoxia targeting specificity and a relatively long half-life. The synthesis, (64)Cu-labeling in vitro and in vivo study of the novel 2-nitroimidazole complex (64)Cu-BMS2P2 is presented in this study. The hypoxia targeting capacity of (64)Cu-BMS2P2 in vitro was evaluated and compared with the (64)Cu-BMS181321, and confirmed by PET imaging in vivo and immunohistochemistry for carbonic anhydrase 9 (CA9) in a tumor mouse model. These results suggest that (64)Cu-BMS2P2 is a promising candidate for PET hypoxia imaging and worthy of further investigations in dynamic hypoxia imaging.

journal_name

Bioorg Med Chem Lett

authors

Luo Z,Zhu H,Lin X,Chu T,Luo R,Wang Y,Yang Z

doi

10.1016/j.bmcl.2016.01.077

subject

Has Abstract

pub_date

2016-03-01 00:00:00

pages

1397-400

issue

5

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(16)30074-9

journal_volume

26

pub_type

杂志文章
  • Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: capturing interactions with Asp48.

    abstract::A series of monocyclic thiophenes was designed and synthesized as PTP1B inhibitors. Guided by X-ray co-crystal structural information and computational modeling, rational design led to key interactions with Asp48 and improved inhibitory potency against PTP1B. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.06.051

    authors: Wan ZK,Lee J,Xu W,Erbe DV,Joseph-McCarthy D,Follows BC,Zhang YL

    更新日期:2006-09-15 00:00:00

  • 2-Cycloalkyl phenoxyacetic acid CRTh2 receptor antagonists.

    abstract::High throughput screening identified a phenoxyacetic acid scaffold as a novel CRTh2 receptor antagonist chemotype, which could be optimised to furnish a compound with functional potency for inhibition of human eosinophil shape change and oral bioavailability in the rat. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.05.019

    authors: Sandham DA,Aldcroft C,Baettig U,Barker L,Beer D,Bhalay G,Brown Z,Dubois G,Budd D,Bidlake L,Campbell E,Cox B,Everatt B,Harrison D,Leblanc CJ,Manini J,Profit R,Stringer R,Thompson KS,Turner KL,Tweed MF,Walker C,

    更新日期:2007-08-01 00:00:00

  • Non-peptide alphavbeta3 antagonists. Part 6: design and synthesis of alphavbeta3 antagonists containing a pyridone or pyrazinone central scaffold.

    abstract::Two novel series of small-molecule RGD mimetics containing either a substituted pyridone or pyrazinone central constraint were prepared. Modification of the beta-alanine 3-substituent produced compounds that are potent and selective alpha(v)beta(3) antagonists and exhibit a range of physicochemical properties. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00254-3

    authors: Breslin MJ,Duggan ME,Halczenko W,Fernandez-Metzler C,Hunt CA,Leu CT,Merkle KM,Naylor-Olsen AM,Prueksaritanont T,Stump G,Wallace A,Rodan SB,Hutchinson JH

    更新日期:2003-05-19 00:00:00

  • An efficient synthesis of [1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel thiazapodophyllotoxin analogues with potential anticancer activity.

    abstract::A catalyst-free synthesis of 6,9-dihydro-[1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel analogues of podophyllotoxins was developed by a three-component reaction of aldehydes, ethyl 2,4-dioxotetrahydrothiophene-3-carboxylate and 3,4-(methylenedioxy)aniline. This methodology not only provides new chemical...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.02.047

    authors: Li T,Lu T,Yu C,Yao C

    更新日期:2015-04-01 00:00:00

  • Synthesis and biological evaluation of indomethacin analogs possessing a N-difluoromethyl-1,2-dihydropyrid-2-one ring system: a search for novel cyclooxygenase and lipoxygenase inhibitors.

    abstract::A novel class of indomethacin analogs were synthesized wherein a N-difluoromethyl-1,2-dihydropyrid-2-one moiety (5-LOX pharmacophore) was attached at its C-4 or C-5 position via either a CO (14a-b) or CH(2) (19a-b) linker to the indole N(1)-position. In this regard, replacement of the 4-chlorobenzoyl group present in ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.07.132

    authors: Chowdhury MA,Huang Z,Abdellatif KR,Dong Y,Yu G,Velázquez CA,Knaus EE

    更新日期:2010-10-01 00:00:00

  • Sequence selective naked-eye detection of DNA harnessing extension of oligonucleotide-modified nucleotides.

    abstract::DNA polymerases can efficiently and sequence selectively incorporate oligonucleotide (ODN)-modified nucleotides and the incorporated oligonucleotide strand can be employed as primer in rolling circle amplification (RCA). The effective amplification of the DNA primer by Φ29 DNA polymerase allows the sequence-selective ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.12.082

    authors: Verga D,Welter M,Marx A

    更新日期:2016-02-01 00:00:00

  • Opsin shift in an aldolase antibody.

    abstract::An antibody-retinal assembly that mimics the opsin shift (OS) of the naturally occurring visual pigments is reported. Both experiments and calculations show that the aldolase antibody 33F12 covalently binds all-trans retinal via a protonated Schiff base with a lysine residue. This chromophore, which exhibits a remarka...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00406-0

    authors: Grynszpan F,Keinan E

    更新日期:1999-08-16 00:00:00

  • The discovery of potent, selective, and orally bioavailable PDE9 inhibitors as potential hypoglycemic agents.

    abstract::Starting from a non-selective pyrazolo-pyrimidone lead, the sequential use of parallel medicinal chemistry and directed synthesis led to the discovery of potent, highly selective, and orally bioavailable PDE9 inhibitors. The availability of these tools allowed for a thorough evaluation of the therapeutic potential of ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.03.024

    authors: Deninno MP,Andrews M,Bell AS,Chen Y,Eller-Zarbo C,Eshelby N,Etienne JB,Moore DE,Palmer MJ,Visser MS,Yu LJ,Zavadoski WJ,Michael Gibbs E

    更新日期:2009-05-01 00:00:00

  • N-Alkyl-N-arylmethylpiperidin-4-amines: novel dual inhibitors of serotonin and norepinephrine reuptake.

    abstract::A series of N-alkyl-N-arylmethylpiperidin-4-amines have been prepared and are demonstrated to be inhibitors of both serotonin and norepinephrine reuptake. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.02.008

    authors: Boot JR,Boulet SL,Clark BP,Cases-Thomas MJ,Delhaye L,Diker K,Fairhurst J,Findlay J,Gallagher PT,Gilmore J,Harris JR,Masters JJ,Mitchell SN,Naik M,Simmonds RG,Smith SM,Richards SJ,Timms GH,Whatton MA,Wolfe CN,Wood

    更新日期:2006-05-15 00:00:00

  • Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives.

    abstract::Ionic liquid ethyl ammonium nitrate is used as an excellent catalyst and solvent for three-component one-pot reaction of an aldehydes, amines and diethylphosphite to form novel α-aminophosphonates at room temperature. Among the various catalysts, the preparation of ethyl ammonium nitrate is an environmental friendly, ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.02.039

    authors: Dake SA,Raut DS,Kharat KR,Mhaske RS,Deshmukh SU,Pawar RP

    更新日期:2011-04-15 00:00:00

  • Conformationally-restricted cyclic sulfones as potent and selective mTOR kinase inhibitors.

    abstract::Novel conformationally-restricted mTOR kinase inhibitors with cyclic sulfone scaffold were designed. Synthesis and structure-activity relationship (SAR) studies are described with emphasis on optimization of the mTOR potency and selectivity against class I PI3Kα kinase. PF-05139962 was identified with excellent mTOR b...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.05.104

    authors: Liu KK,Bailey S,Dinh DM,Lam H,Li C,Wells PA,Yin MJ,Zou A

    更新日期:2012-08-01 00:00:00

  • Synthesis and properties of 2'-O-methyl-2-thiouridine and oligoribonucleotides containing 2'-O-methyl-2-thiouridine.

    abstract::A new method for the synthesis of 2'-O-methyl-2-thiouridine (s2Um) found in thermophilic bacterial tRNA was developed. Structural properties of s2Um and s2Um(p)U were studied by using 1H NMR spectroscopy. A modified nonaribonucleotide (RNA*: 5'-CGUUs2UmUUGC-3') was synthesized to study the base-recognition ability of ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00342-5

    authors: Shohda K,Okamoto I,Wada T,Seio K,Sekine M

    更新日期:2000-08-21 00:00:00

  • Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties.

    abstract::A series of aromatic sulfonamides incorporating indane moieties were prepared starting from commercially available 1- and 2-indanamine, and their activity as inhibitors of two carbonic anhydrase (CA, EC 4.2.1.1) isozymes, hCA I and II was studied. The new sulfonamides incorporating acetamido, 4-chloro-benzoyl, valproy...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.09.061

    authors: Chazalette C,Masereel B,Rolin S,Thiry A,Scozzafava A,Innocenti A,Supuran CT

    更新日期:2004-12-06 00:00:00

  • Structure-activity and in vivo evaluation of a novel lipoprotein lipase (LPL) activator.

    abstract::Elevated triglycerides (TG) contribute towards increased risk for cardiovascular disease. Lipoprotein lipase (LPL) is an enzyme that is responsible for the metabolism of core triglycerides of very-low density lipoproteins (VLDL) and chylomicrons in the vasculature. In this study, we explored the structure-activity rel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.11.053

    authors: Geldenhuys WJ,Caporoso J,Leeper TC,Lee YK,Lin L,Darvesh AS,Sadana P

    更新日期:2017-01-15 00:00:00

  • Investigation of the PDZ domain ligand binding site using chemically modified peptides.

    abstract::Several chemically modified analogues to a tightly binding ligand for the second PDZ domain of MAGI-3 were synthesized and evaluated for their ability to compete with native peptide ligands. N-methyl scanning of the ligand backbone amides revealed the energetically important hydrogen bonds between the ligand backbone ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00345-1

    authors: Novak KA,Fujii N,Guy RK

    更新日期:2002-09-02 00:00:00

  • Silanediol-based inhibitor of thermolysin.

    abstract::The first silanediol inhibitor of thermolysin is reported, prepared by analogy with the Grobelny/Bartlett phosphinate inhibitor. A Cbz group on nitrogen proved to be unstable to the triflic acid mediated silanediol deprotection and was replaced with a dihydrocinnamoyl group. The silanediol was prepared in high purity ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00804-1

    authors: Kim J,Glekas A,McN Sieburth S

    更新日期:2002-12-16 00:00:00

  • Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide.

    abstract::The X-ray crystal structure for the adduct of human carbonic anhydrase (hCA) II with a topically acting antiglaucoma sulfonamide (the 2-N,N-diethylaminoethylamide of 5-(4-carboxybenzenesulfonamido-1,3,4-thiadiazole-2-sulfonamide), has been resolved at a resolution of 1.6A. This compound is a very potent inhibitor of t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.01.096

    authors: Abbate F,Casini A,Scozzafava A,Supuran CT

    更新日期:2004-05-03 00:00:00

  • Synthesis of novel 2-pyrazoline analogues with potent anti-inflammatory effect mediated by inhibition of phospholipase A2: Crystallographic, in silico docking and QSAR analysis.

    abstract::Oxidative-stress induces inflammatory diseases. Further, infections caused by drug-resistant microbial strains are on the rise. This necessitates the discovery of novel small-molecules for intervention therapy. A series of 3-(2,3-dichlorophenyl)-1-(aryl)prop-2-en-1-ones are synthesized as intermediates via Claisen-Sch...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.06.063

    authors: Lokeshwari DM,Achutha DK,Srinivasan B,Shivalingegowda N,Krishnappagowda LN,Kariyappa AK

    更新日期:2017-08-15 00:00:00

  • Discovery, synthesis and biochemical profiling of purine-2,6-dione derivatives as inhibitors of the human poly(A)-selective ribonuclease Caf1.

    abstract::Eukaryotic mRNA contains a 3' poly(A) tail, which plays important roles in the regulation of mRNA stability and translation. Well-characterized enzymes involved in the shortening of the poly(A) tail include the multi-subunit Ccr4-Not deadenylase, which contains the Caf1 (Pop2) and Ccr4 catalytic components, and poly(A...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.07.095

    authors: Jadhav GP,Kaur I,Maryati M,Airhihen B,Fischer PM,Winkler GS

    更新日期:2015-10-01 00:00:00

  • A new insight on the hypochlorous acid scavenging mechanism of tryptamine and tryptophan derivatives.

    abstract::The reaction mechanisms of hypochlorous acid (HOCl) with several tryptophan and tryptamine derivatives, previously reported to scavenge this powerful oxidant, was investigated to determine whether ionic or radical pathways were involved. For this purpose, the reaction of tryptamine and tryptophan derivatives with HOCl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.09.067

    authors: Carvalho LC,Estevão MS,Ferreira LM,Fernandes E,Marques MM

    更新日期:2010-11-15 00:00:00

  • Synthesis of [¹¹C]uric acid, using [¹¹C]phosgene, as a possible biomarker in PET imaging for diagnosis of gout.

    abstract::The synthesis and in vivo evaluation of (11)C -labeled uric acid ([(11)C]1), a potential imaging agent for the diagnosis of urate-related life-style diseases, was performed using positron emission tomography (PET) image analysis. First, the synthesis of [(11)C]1 was achieved by reacting 5,6-diaminouracil (2) with (11)...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.11.055

    authors: Yashio K,Katayama Y,Takashima T,Ishiguro N,Doi H,Suzuki M,Wada Y,Tamai I,Watanabe Y

    更新日期:2012-01-01 00:00:00

  • Analogues of dealanylalahopcin are inhibitors of human HIF prolyl hydroxylases.

    abstract::Analogues of the naturally occurring cyclic hydroxamate dealanylalahopcin, which is an inhibitor of procollagen prolyl-4-hydroxylase, were synthesised and shown to be inhibitors of the human hypoxia-inducible factor prolyl hydroxylases. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00149-5

    authors: Schlemminger I,Mole DR,McNeill LA,Dhanda A,Hewitson KS,Tian YM,Ratcliffe PJ,Pugh CW,Schofield CJ

    更新日期:2003-04-17 00:00:00

  • Venezuelines A-G, new phenoxazine-based alkaloids and aminophenols from Streptomyces venezuelae and the regulation of gene target Nur77.

    abstract::Five new phenoxazine-based alkaloids venezuelines A-E (1-5) and two new aminophenols venezuelines F-G (6-7), as well as three known analogues exfoliazone, chandrananimycin D and carboxyexfoliazone were isolated from the fermentation broth of the marine-derived bacterium Streptomyces venezuelae. The structures of new c...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.10.096

    authors: Ren J,Liu D,Tian L,Wei Y,Proksch P,Zeng J,Lin W

    更新日期:2013-01-01 00:00:00

  • N-heterocyclic dicarboxylic acids: broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria.

    abstract::In an effort to identify novel, broad-spectrum inhibitors against the metallo-β-lactamases (MβLs), several N-heterocyclic derivatives were tested as inhibitors of MβLs CcrA, ImiS, and L1, which are representative enzymes from the distinct MβL subclasses. Three N-heterocyclic dicarboxylic acid derivatives were competit...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.06.074

    authors: Feng L,Yang KW,Zhou LS,Xiao JM,Yang X,Zhai L,Zhang YL,Crowder MW

    更新日期:2012-08-15 00:00:00

  • Design and efficient synthesis of new stable 1alpha,25-dihydroxy-19-norvitamin D3 analogues containing amide bond.

    abstract::The design and synthesis of new 1alpha,25-dihydroxy-19-norvitamin D(3) analogues 3a-c, which have an amide bond in the molecule instead of the diene, are described. The A-ring moiety was constructed by a (3S,5S)-3,5-dihydroxypiperidine derivative (9, 11, or 13) prepared from D-mannose, and a CD-ring carboxylic acid 16...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00800-4

    authors: Suhara Y,Kittaka A,Ono K,Kurihara M,Fujishima T,Yoshida A,Takayama H

    更新日期:2002-12-16 00:00:00

  • Austalides V and W, new meroterpenoids from the fungus Aspergillus ustus and their antitumor activities.

    abstract::Two new austalide meroterpenoids, named austalides V and W (1 and 2), were isolated from the fungus Aspergillus ustus VKM F-4692. Their structures were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. The main structural feature of both compounds is a tetrahydrofuranyl rin...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.126708

    authors: Antipova TV,Zaitsev KV,Oprunenko YF,Ya Zherebker A,Rystsov GK,Zemskova MY,Zhelifonova VP,Ivanushkina NE,Kozlovsky AG

    更新日期:2019-11-15 00:00:00

  • Design and synthesis of AX4697, a bisindolylmaleimide exo-affinity probe that labels protein kinase C alpha and beta.

    abstract::The synthesis and biochemical characterization of AX4697, a fluorescent, bisindolylmaleimide-derived probe for PKCalpha and beta, is described. AX4697 was able to quantify changes in PKC expression in drug-treated Jurkat cells and was shown to covalently label PKCalpha on C619, a residue that sits just outside the act...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.08.045

    authors: Liu Y,Wu J,Weissig H,Betancort JM,Gai WZ,Leventhal PS,Patricelli MP,Samii B,Szardenings AK,Shreder KR,Kozarich JW

    更新日期:2008-11-15 00:00:00

  • Evaluation of series of isobenzofuranone dimers as PKCalpha ligands: implication for the distance between the two ligand binding sites.

    abstract::Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. To examine the distance between the two ligand binding sites (C1A and C1B) of PKC, we designed and synthesized two series of isobenzofuranone dimers. Peak binding activities were observed for the C3-acyl cha...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.02.098

    authors: Baba Y,Mayumi S,Hirai G,Kawasaki H,Ogoshi Y,Yanagisawa T,Hashimoto Y,Sodeoka M

    更新日期:2004-06-07 00:00:00

  • DNA-templated click chemistry for creation of novel DNA binding molecules.

    abstract::We have developed a new methodology for producing new molecules that bind to dsDNA using DNA-templated click chemistry. The click reactions between the minor groove binding peptide and acridine intercalators were accelerated by the addition of dsDNA. Furthermore, the resulting peptide-acridine conjugate showed a sligh...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.08.074

    authors: Imoto S,Hirohama T,Nagatsugi F

    更新日期:2008-10-15 00:00:00

  • Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D2 and 5-hydroxytryptamine 5HT(1A) receptors.

    abstract::It is suggested that the ratio of dopamine D(2) to 5-hydroxytryptamine 5-HT(1A) activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.04.098

    authors: Sukalovic V,Ignjatovic D,Tovilovic G,Andric D,Shakib K,Kostic-Rajacic S,Soskic V

    更新日期:2012-06-15 00:00:00