Tyrosine specific sequential labeling of proteins.

Abstract:

:We report (a) on the synthesis of a long-wavelength fluorescent coumarin containing an allyloxy acetate moiety, (b) the synthesis of two linkers containing an allyloxy acetate and an alkyne or azide function, respectively, and (c) the selective modification human serum albumin by a sequential method involving Pd(II) catalyzed modification of the phenolic side chain of tyrosine residues with an alkyne bearing linker and a subsequent azide-alkyne click reaction with an azide functionalized long-wavelength emitting coumarin dye. The method is likely to be applicable to various kinds of azido-modified fluorophores, and the Pd(II)-catalyzed modification of the tyrosines may also be used to introduce other kinds of tags. With these reagents, tyrosine specific modulation of proteins and peptides becomes possible either directly or in a sequential manner.

journal_name

Bioorg Med Chem Lett

authors

Cserép GB,Herner A,Wolfbeis OS,Kele P

doi

10.1016/j.bmcl.2013.09.002

subject

Has Abstract

pub_date

2013-11-01 00:00:00

pages

5776-8

issue

21

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(13)01065-2

journal_volume

23

pub_type

杂志文章
  • Substituted indoles as selective protease activated receptor 4 (PAR-4) antagonists: Discovery and SAR of ML354.

    abstract::Herein we report the discovery and SAR of an indole-based protease activated receptor-4 (PAR-4) antagonist scaffold derived from a similarity search of the Vanderbilt HTS collection, leading to MLPCN probe ML354 (VU0099704). Using a novel PAC-1 fluorescent αIIbβ3 activation assay this probe molecule antagonist was fou...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.08.021

    authors: Wen W,Young SE,Duvernay MT,Schulte ML,Nance KD,Melancon BJ,Engers J,Locuson CW 2nd,Wood MR,Daniels JS,Wu W,Lindsley CW,Hamm HE,Stauffer SR

    更新日期:2014-10-01 00:00:00

  • 2-Anilino-4-aryl-1,3-thiazole inhibitors of valosin-containing protein (VCP or p97).

    abstract::Valosin-containing protein (VCP; also known as p97) is a member of the AAA ATPase family with a central role in the ubiquitin-degradation of misfolded proteins. VCP also exhibits antiapoptotic function and metastasis via activation of nuclear factor kappa-B signaling pathway. We have discovered that 2-anilino-4-aryl-1...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.01.058

    authors: Bursavich MG,Parker DP,Willardsen JA,Gao ZH,Davis T,Ostanin K,Robinson R,Peterson A,Cimbora DM,Zhu JF,Richards B

    更新日期:2010-03-01 00:00:00

  • Trityl radicals in perfluorocarbon emulsions as stable, sensitive, and biocompatible oximetry probes.

    abstract::EPR oximetry with the use of trityl radicals can enable sensitive O2 measurement in biological cells and tissues. However, in vitro cellular and in vivo biological applications are limited by rapid trityl probe degradation or biological clearance and the need to enhance probe O2 sensitivity. We synthesized novel perfl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.10.066

    authors: Dhimitruka I,Alzarie YA,Hemann C,Samouilov A,Zweier JL

    更新日期:2016-12-01 00:00:00

  • Kinetic investigation of human 5-lipoxygenase with arachidonic acid.

    abstract::Human 5-lipoxygenase (5-LOX) is responsible for the formation of leukotriene (LT)A4, a pivotal intermediate in the biosynthesis of the leukotrienes, a family of proinflammatory lipid mediators. 5-LOX has thus gained attention as a potential drug target. However, details of the kinetic mechanism of 5-LOX are still obsc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.06.025

    authors: Mittal M,Kumar RB,Balagunaseelan N,Hamberg M,Jegerschöld C,Rådmark O,Haeggström JZ,Rinaldo-Matthis A

    更新日期:2016-08-01 00:00:00

  • Synthesis and SAR of novel, potent and orally bioavailable benzimidazole inhibitors of poly(ADP-ribose) polymerase (PARP) with a quaternary methylene-amino substituent.

    abstract::Poly(ADP-ribose) polymerases (PARPs) play significant roles in various cellular functions including DNA repair and control of RNA transcription. PARP inhibitors have been demonstrated to potentiate the effect of cytotoxic agents or radiation in a number of animal tumor models. Utilizing a benzimidazole carboxamide sca...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.06.023

    authors: Zhu GD,Gandhi VB,Gong J,Thomas S,Luo Y,Liu X,Shi Y,Klinghofer V,Johnson EF,Frost D,Donawho C,Jarvis K,Bouska J,Marsh KC,Rosenberg SH,Giranda VL,Penning TD

    更新日期:2008-07-15 00:00:00

  • Bioisosteric modification of PETT-HIV-1 RT-inhibitors: synthesis and biological evaluation.

    abstract::Bioisosteric substitution of the thiourea (3, 5, 7, 9) and urea (10) moiety of PETT compounds with sulfamide (1), cyanoguanidine (2, 4) and guanidine (6, 8) functionalities, and replacement of the phenethyl group with benzoylethyl group (compounds 11-20) have been studied. Synthesis and antiviral activities are descri...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00675-7

    authors: Högberg M,Engelhardt P,Vrang L,Zhang H

    更新日期:2000-02-07 00:00:00

  • Effective molarity in a nucleic acid-controlled reaction.

    abstract::Positioning of reactive functional groups within a DNA duplex can enable chemical reactions that otherwise would not occur to an appreciable extent. However, few studies have quantitatively defined the extent to which the enforced proximity of reaction partners in duplex DNA can favor chemical processes. Here, we meas...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.04.022

    authors: Catalano MJ,Price NE,Gates KS

    更新日期:2016-06-01 00:00:00

  • Synthesis and antitumor activities of 5-methyl-1- and 2-[[2-dimethylaminoethyl]amino]-aza-thiopyranoindazoles.

    abstract::The synthesis of 1- and 2-substituted aza-benzothiopyranoindazoles has been accomplished. The comparisons of the in vitro antitumor activities of the 2-substituted analogues with the benzothiopyranoindazole chemotypes indicate that the positioning of the nitrogen atom at C-9 (9-aza analogue 4d) leads to a substrate wi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00689-7

    authors: Krapcho AP,Haydar SN,Truong-Chiott S,Hacker MP,Menta E,Beggiolin G

    更新日期:2000-02-07 00:00:00

  • Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I.

    abstract::To elucidate the role of the hydrophobic alkyl tail of acetogenins in the inhibitory action, we synthesized an acetogenin derivative possessing the shortest tail (i.e., methyl group) and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicated that the alkyl tail, which is o...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00374-8

    authors: Motoyama T,Yabunaka H,Miyoshi H

    更新日期:2002-08-19 00:00:00

  • Regioselective synthesis and cytotoxicities of camptothecin derivatives modified at the 7-, 10- and 20-positions.

    abstract::A series of 7-acyloxymethylcamptothecin and 20-O-acyl-7-acyloxymethylcamptothecin derivatives were regioselectively prepared on different solvents. 7-Acyloxymethylcamptothecins possess more efficacy than 20-O-acyl-7-acyloxymethylcamptothecins against six human cancer cell lines in vitro. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.08.012

    authors: Pan XD,Han R,Sun PY

    更新日期:2003-11-03 00:00:00

  • Pharmacokinetics and metabolism studies on (3-tert-butyl-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-1,2,4-triazol-5-ylmethoxy) pyrazolo[1,5-d][1,2,4]triazine, a functionally selective GABA(A) alpha5 inverse agonist for cognitive dysfunction.

    abstract::(3-tert-Butyl-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-1,2,4-triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine (1) was recently identified as a functionally selective, inverse agonist at the benzodiazepine site of GABA(A) alpha5 receptors and enhances performance in animal models of cognition. The routes of metabolis...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.11.012

    authors: Jones P,Atack JR,Braun MP,Cato BP,Chambers MS,O'Connor D,Cook SM,Hobbs SC,Maxey R,Szekeres HJ,Szeto N,Wafford KA,MacLeod AM

    更新日期:2006-02-15 00:00:00

  • 3-Substituted-(5-arylfuran-2-ylcarbonyl)guanidines as NHE-1 inhibitors.

    abstract::The C-3 substituents effect on NHE-1 inhibitory activity of (5-arylfuran-2-ylcarbonyl)guanidines, previously identified as potent NHE-1 inhibitors, was investigated. The introduction of amine or alkyl groups at the 3-position of the furan ring, next to the acylguanidine moiety, remarkably improves NHE-1 inhibitory pot...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.12.012

    authors: Lee S,Kim T,Lee BH,Yoo SE,Lee K,Yi KY

    更新日期:2007-03-01 00:00:00

  • Discovery, SAR, and X-ray structure of novel biaryl-based dipeptidyl peptidase IV inhibitors.

    abstract::The discovery, SAR, and X-ray crystal structure of novel biarylaminoacyl-(S)-2-cyano-pyrrolidines and biarylaminoacylthiazolidines as potent inhibitors of dipeptidyl peptidase IV (DPP IV) are reported. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.09.037

    authors: Qiao L,Baumann CA,Crysler CS,Ninan NS,Abad MC,Spurlino JC,Desjarlais RL,Kervinen J,Neeper MP,Bayoumy SS,Williams R,Deckman IC,Dasgupta M,Reed RL,Huebert ND,Tomczuk BE,Moriarty KJ

    更新日期:2006-01-01 00:00:00

  • The synthesis of amino-acid functionalized beta-carbolines as topoisomerase II inhibitors.

    abstract::The synthesis and biological activity of amino acid functionalized beta-carboline derivatives, which are structurally related to azatoxin and the tryprostatins, are reported. These compounds were assayed for their growth inhibition properties in H520 and PC3 cell lines and were examined for their abilities to inhibit ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00136-6

    authors: Deveau AM,Labroli MA,Dieckhaus CM,Barthen MT,Smith KS,Macdonald TL

    更新日期:2001-05-21 00:00:00

  • Synthesis and biological evaluation of triazolothienopyrimidine derivatives as novel HIV-1 replication inhibitors.

    abstract::We identified a novel class of triazolothienopyrimidine (TTPM) compounds as potent HIV-1 replication inhibitors during a high-throughput screening campaign that evaluated more than 200,000 compounds using a cell-based full replication assay. Herein, we report the optimization of the antiviral activity in a cell-based ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.10.134

    authors: Kim J,Kwon J,Lee D,Jo S,Park DS,Choi J,Park E,Hwang JY,Ko Y,Choi I,Ju MK,Ahn J,Kim J,Han SJ,Kim TH,Cechetto J,Nam J,Ahn S,Sommer P,Liuzzi M,No Z,Lee J

    更新日期:2013-01-01 00:00:00

  • The discovery of potent glycine transporter type-2 inhibitors: design and synthesis of phenoxymethylbenzamide derivatives.

    abstract::We describe the discovery of phenoxymethylbenzamide derivatives as a novel class of glycine transporter type-2 (GlyT-2) inhibitors. We found hit compound 1 (human GlyT-2, IC50=4040 nM) in our library and converted its 1-(1-(naphthalen-2-ylmethyl)piperidin-4-yl)pyrrolidin-3-yl group to an 1-(N,N-dimethylaminopropyl)pip...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.06.059

    authors: Takahashi E,Arai T,Akahira M,Nakajima M,Nishimura K,Omori Y,Kumagai H,Suzuki T,Hayashi R

    更新日期:2014-09-15 00:00:00

  • Quality by design (QbD) of amide isosteres: 5,5-Disubstituted isoxazolines as potent CRTh2 antagonists with favorable pharmacokinetic and drug-like properties.

    abstract::Isoxazoles are frequently used amide isosteres, as shown in the context of discovery of CRTh2 antagonists from amide 1 to isoxazole 2. However, persistent agonism and poor solubility in isoxazole series presented challenges to its further development. Based on the concept of quality by design (QbD), 5,5-disubstituted ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.01.043

    authors: Xiao D,Zhu X,Yu Y,Shao N,Wu J,McCormick KD,Dhondi P,Qin J,Mazzola R,Tang H,Rao A,Siliphaivanh P,Qiu H,Yang X,Rivelli M,Garlisi CG,Eckel S,Mukhopadhyay G,Correll C,Rindgen D,Aslanian R,Palani A

    更新日期:2014-03-15 00:00:00

  • Diaminopyrimidine and diaminopyridine 5-HT7 ligands.

    abstract::The present studies have identified a series of diaminopyrimidines and diaminopyridines as novel 5-HT(7) receptor ligands. Three regiosiomeric classes of pyrimidines and four regioisomeric classes of pyridines were synthesized and analyzed for binding to the 5-HT(7) receptor. The 5-HT(7) binding affinities of differen...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.06.007

    authors: Denhart DJ,Purandare AV,Catt JD,King HD,Gao A,Deskus JA,Poss MA,Stark AD,Torrente JR,Johnson G,Mattson RJ

    更新日期:2004-08-16 00:00:00

  • A chemically stable fluorescent marker of the ureter.

    abstract::Surgical methods guided by exogenous fluorescent markers have the potential to define tissue types in real time. Small molecule dyes with efficient and selective renal clearance could enable visualization of the ureter during surgical procedures involving the abdomen and pelvis. These studies report the design and syn...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.02.040

    authors: Cha J,Nani RR,Luciano MP,Kline G,Broch A,Kim K,Namgoong JM,Kulkarni RA,Meier JL,Kim P,Schnermann MJ

    更新日期:2018-09-01 00:00:00

  • Activation of mitogen activated protein kinase (MAPK) during D-galactosamine intoxication in the rat liver.

    abstract::A significant increase in plasma glutamate-oxaloacetate transaminase and glutamate-pyruvate transaminase was observed 6 h after intraperitoneal administration of D-galactosamine (D-Galn). Three hours after administration of D-Galn, the vitamin C concentration in the liver decreased significantly compared to that in a ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.02.057

    authors: Nishioka H,Kishioka T,Iida C,Fujii K,Ichi I,Kojo S

    更新日期:2006-06-01 00:00:00

  • Antihypertensive activity of substituted 2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridinedicarboxylate enantiomers.

    abstract::The synthesis and antihypertensive activity of racemates and enantiomers of substituted 2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridinedicarboxylates have been reported. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00691-5

    authors: Martín E,Morán A,Martín ML,San Román L,Puebla P,Medarde M,Caballero E,San Feliciano A

    更新日期:2000-02-21 00:00:00

  • Enzymatic synthesis of monocyclic beta-lactams.

    abstract::An Mg2+ and ATP dependent beta-lactam synthetase (BLS) catalyses formation of a beta-lactam ring during the biosynthesis of clavulanic acid, an important beta-lactamase inhibitor. An epimeric mixture of a 2-methylated derivative of the natural BLS substrate N2-(2-carboxyethyl)-L-arginine was synthesised and found to b...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00806-x

    authors: Sleeman MC,MacKinnon CH,Hewitson KS,Schofield CJ

    更新日期:2002-02-25 00:00:00

  • Synthesis of novel chromeno-annulated cis-fused pyrano[3,4-c]benzopyran and naphtho pyran derivatives via domino aldol-type/hetero Diels-Alder reaction and their cytotoxicity evaluation.

    abstract::New chromeno-annulated cis-fused pyrano[3,4-c]benzopyran and naphtho pyran derivatives have been synthesized by domino aldol-type reaction/hetero Diels-Alder reaction generated from o-quinone methide in situ from 7-O-prenyl derivatives of 8-formyl-2,3-disubstituted chromenones with resorcinols/naphthols in the presenc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.08.005

    authors: Madda J,Venkatesham A,Naveen Kumar B,Nagaiah K,Sujitha P,Ganesh Kumar C,Rao TP,Jagadeesh Babu N

    更新日期:2014-09-15 00:00:00

  • Synthesis and antiviral activity of novel D- and L-2'-azido-2',3'-dideoxyribofuranosyl-4'-thiopyrimidines and purines.

    abstract::Novel D- and L-2'-azido-2',3'-dideoxyribofuranosyl-4'-thiopyrimidines and purines have been synthesized starting from L-xylose and D-xylose, respectively. Among synthesized compounds tested against several viruses such as HIV-1, HSV-1, HSV-2, and HCMV, D-beta-N6-methyladenine (ent-22a) and D-alpha-N6-methyladenine (en...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00006-3

    authors: Kim HO,Kim YH,Suh H,Jeong LS

    更新日期:2001-02-26 00:00:00

  • Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution.

    abstract::A series of 19 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro whole cell antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two types of Mycobacterium avium. The series consisted of 3-(benzylamino)-5-cyan...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.11.052

    authors: Zitko J,Paterová P,Kubíček V,Mandíková J,Trejtnar F,Kuneš J,Doležal M

    更新日期:2013-01-15 00:00:00

  • Synthesis and in vivo antihyperglycemic activity of 5-(1H-pyrazol-3-yl)methyl-1H-tetrazoles.

    abstract::A series of 5-[(5-aryl-1H-pyrazol-3-yl)methyl]-1H-tetrazoles 3a-h have been synthesized and evaluated for their in vivo antihyperglycemic activity. Some of the synthesized compounds have shown significant glucose lowering activity in male Sprague-Dawley rats in sucrose loaded model. These compounds were also evaluated...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.02.060

    authors: Sharon A,Pratap R,Tiwari P,Srivastava A,Maulik PR,Ram VJ

    更新日期:2005-04-15 00:00:00

  • Pyrazole NNRTIs 1: design and initial optimisation of a novel template.

    abstract::The design and synthesis of a novel series of non-nucleoside HIV reverse transcriptase inhibitors (NNRTIs) based on a pyrazole template is described. These compounds are active against wild type reverse transcriptase (RT) and retain activity against clinically important mutants. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.08.039

    authors: Mowbray CE,Burt C,Corbau R,Perros M,Tran I,Stupple PA,Webster R,Wood A

    更新日期:2009-10-01 00:00:00

  • New chemotypes for cathepsin K inhibitors.

    abstract::Cyano pyrimidine acetylene and cyano pyrimidine t-amine, which belong to a new chemical class, were prepared and tested for inhibitory activities against cathepsin K and the highly homologous cathepsins L and S. The use of novel chemotypes in the development of cathepsin K inhibitors has been demonstrated by derivativ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.03.036

    authors: Teno N,Irie O,Miyake T,Gohda K,Horiuchi M,Tada S,Nonomura K,Kometani M,Iwasaki G,Betschart C

    更新日期:2008-04-15 00:00:00

  • Discovery of benzamides as potent human β3 adrenergic receptor agonists.

    abstract::The paper will describe the synthesis and SAR studies that led to the discovery of benzamide (reverse amide) as potent and selective human β3-adrenergic receptor agonist. Based on conformationally restricted pyrrolidine scaffold we discovered earlier, pyrrolidine benzoic acid intermediate 22 was synthesized. From libr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.11.030

    authors: Zhu C,Kar NF,Li B,Costa M,Dingley KH,Di Salvo J,Ha SN,Hurley AL,Li X,Miller RR,Salituro GM,Struthers M,Weber AE,Hale JJ,Edmondson SD

    更新日期:2016-01-01 00:00:00

  • Synthesis and thrombolytic activity of fibrinogen fragment related cyclopeptides.

    abstract::In the modification of the fibrinogen fragment related sequences ARPAK, QRPAK GRPAK and KRPAK, the corresponding cyclo-ARPAK, cyclo-QRPAK, cyclo-GRPAK, and cyclo-KRPAK were prepared in the diluted solution. The bioassay in vivo indicated that the thrombolytic potencies of cyclo-ARPAK, cyclo-GRPAK, cyclo-QRPAK, and cyc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)01072-7

    authors: Zhao M,Lin N,Wang C,Peng S

    更新日期:2003-03-10 00:00:00