当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > The use of aminoglycoside derivatives to study the mechanism of aminoglycoside 6'-N-acetyltransferase and the role of 6'-NH2 in antibacterial activity.

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')-Ii and aminoglycoside-RNA complexes. Our results emphasize the central role of N-6' nucleophilicity for transformation by AAC(6')-Ii and the importance of hydrogen bonding between 6'-NH(2) and 16S rRNA for antibacterial activity.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

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

doi

10.1016/j.bmc.2007.02.009

subject

Has Abstract

pub_date

2007-04-15 00:00:00

pages

2944-51

issue

8

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)00124-1

journal_volume

15

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • 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

  • Palladium(II) saccharinate complexes with bis(2-pyridylmethyl)amine induce cell death by apoptosis in human breast cancer cells in vitro.

    abstract：:The outcomes of breast cancer patients are still poor although new compounds have recently been introduced into the clinic. Therefore, novel chemical approaches are required. In the present study, palladium(II) and corresponding platinum(II) complexes containing bis(2-pyridylmethyl)amine (bpma) and saccharine were syn...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.03.073

    authors： Ari F,Ulukaya E,Sarimahmut M,Yilmaz VT

    更新日期：2013-06-01 00:00:00

  • Reaction of thymidine and ascorbic acid induced by UV in the presence of salicylic acid.

    abstract：:When a neutral solution of thymidine and ascorbic acid was irradiated with UV light of wavelength longer than 300 nm in the presence of salicylic acid as a photosensitizer, six product peaks appeared in an HPLC chromatogram in addition to small amounts of thymidine dimers. The six products were identified as three pai...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.115046

    authors： Suzuki T,Kishida Y

    更新日期：2019-10-01 00:00:00

  • Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.

    abstract：:A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of beta-phenethylamines. Fair agreement was observed with data obtained for aryl and ethylene chain substituted analogs in an AV12-664 cell line in which hemag...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.06.009

    authors： Lewin AH,Navarro HA,Mascarella SW

    更新日期：2008-08-01 00:00:00

  • Comparison of the dark and light-induced toxicity of thio and seleno analogues of the thiopyrylium dye AA1.

    abstract：:2,6-Bis(4-anilino)-4-(4-N,N-dimethylanilino)thiopyrylium chloride (AA1) and -selenopyrylium chloride (AA1-Se) and 2,6-bis(4-anilino)-4-(4-N-morpholinophenyl)thiopyrylium chloride (1) and -selenopyrylium chloride (2) were prepared via the addition of 4-N,N-dimethylanilino magnesium bromide and 4-N-morpholinophenyl magn...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.03.025

    authors： Detty MR,Gibson SL,Hilf R

    更新日期：2004-05-15 00:00:00

  • Mutation of active site residues Asn67 to Ile, Gln92 to Val and Leu204 to Ser in human carbonic anhydrase II: influences on the catalytic activity and affinity for inhibitors.

    abstract：:Site-directed mutagenesis has been used to change three amino acid residues involved in the binding of inhibitors (Asn67Ile; Gln92Val and Leu204Ser) within the active site of human carbonic anhydrase (CA, EC 4.2.1.1) II (hCA II). Residues 67, 92 and 204 were changed from hydrophobic to hydrophilic ones, and vice versa...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.02.029

    authors： Turkoglu S,Maresca A,Alper M,Kockar F,Işık S,Sinan S,Ozensoy O,Arslan O,Supuran CT

    更新日期：2012-04-01 00:00:00

  • Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors.

    abstract：:Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase (complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.03.070

    authors： Leiris SJ,Khdour OM,Segerman ZJ,Tsosie KS,Chapuis JC,Hecht SM

    更新日期：2010-05-15 00:00:00

  • Synthesis, biological evaluation and molecular modelling studies of methyleneimidazole substituted biaryls as inhibitors of human 17alpha-hydroxylase-17,20-lyase (CYP17). Part I: Heterocyclic modifications of the core structure.

    abstract：:Novel chemical entities were prepared via Suzuki and S(N) reaction as AC-ring substrate mimetics of CYP17. The synthesised compounds 1-31 were tested for activity using human CYP17 expressed in Escherichia coli. Promising compounds were tested for selectivity against hepatic CYP enzymes (3A4, 2D6, 1A2, 2C9, 2C19, 2B6)...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.10.094

    authors： Jagusch C,Negri M,Hille UE,Hu Q,Bartels M,Jahn-Hoffmann K,Pinto-Bazurco Mendieta MA,Rodenwaldt B,Müller-Vieira U,Schmidt D,Lauterbach T,Recanatini M,Cavalli A,Hartmann RW

    更新日期：2008-02-15 00:00:00

  • Design, synthesis, and evaluation of alpha-ketoheterocycles as class C beta-lactamase inhibitors.

    abstract：:A series of specific alpha-ketoheterocycles (benzoxazole, thiazole, imidazole, tetrazole, and thiazole-4-carboxylate) has been synthesized in order to assess their potential as beta-lactamase inhibitors. The syntheses were achieved either by construction of the heterocycle (benzoxazole) from an appropriate alpha-hydro...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00107-9

    authors： Kumar S,Pearson AL,Pratt RF

    更新日期：2001-08-01 00:00:00

  • 3D-chiral quadratic indices of the 'molecular pseudograph's atom adjacency matrix' and their application to central chirality codification: classification of ACE inhibitors and prediction of sigma-receptor antagonist activities.

    abstract：:Quadratic indices of the 'molecular pseudograph's atom adjacency matrix' have been generalized to codify chemical structure information for chiral drugs. These 3D-chiral quadratic indices make use of a trigonometric 3D-chirality correction factor. These indices are nonsymmetric and reduced to classical (2D) descriptor...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.07.051

    authors： Ponce YM,Diaz HG,Zaldivar VR,Torrens F,Castro EA

    更新日期：2004-10-15 00:00:00

  • Cyclic MOG35-55 ameliorates clinical and neuropathological features of experimental autoimmune encephalomyelitis.

    abstract：:EAE is induced to susceptible mice using linear peptides of myelin proteins of the central nervous system. Specific peptide motifs within the peptide-binding groove of the MHC peptide-complex determines the affinity of the peptide in each animal and the consequent T-cell receptor recognition and activation of the cell...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.06.005

    authors： Lourbopoulos A,Deraos G,Matsoukas MT,Touloumi O,Giannakopoulou A,Kalbacher H,Grigoriadis N,Apostolopoulos V,Matsoukas J

    更新日期：2017-08-01 00:00:00

  • Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties.

    abstract：:Previously, we reported 2-N-carbamoylguanine (cmG) as a guanine analog. We further studied the synthetic protocol and hybridization properties of oligodeoxynucleotides (ODNs) incorporating cmG. These ODNs were synthesized using the phosphoramidite of cmG without protection of the 6-O position. However, the isolated pr...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.11.042

    authors： Sasami T,Odawara Y,Ohkubo A,Sekine M,Seio K

    更新日期：2009-02-01 00:00:00

  • Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.

    abstract：:Bioactivity-guided fractionation of the extract from a Fijian red alga Peyssonnelia sp. led to the isolation of two novel sterol glycosides 19-O-β-d-glucopyranosyl-19-hydroxy-cholest-4-en-3-one (1) and 19-O-β-d-N-acetyl-2-aminoglucopyranosyl-19-hydroxy-cholest-4-en-3-one (2), and two known alkaloids indole-3-carboxald...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.10.010

    authors： Lin AS,Engel S,Smith BA,Fairchild CR,Aalbersberg W,Hay ME,Kubanek J

    更新日期：2010-12-01 00:00:00

  • The chemoenzymatic synthesis of neoglycolipids and lipid-linked oligosaccharides using glycosyltransferases.

    abstract：:The application of glycosyltransferases to the chemoenzymatic synthesis of neoglycosphingolipids and lipid-linked oligosaccharides allows the regio- and stereoselective formation of glycosidic bonds. In our laboratory galactosyl-, sialyl-, and fucosyltransferases have been used to assemble oligosaccharide headgroups d...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)82075-1

    authors： Flitsch SL,Goodridge DM,Guilbert B,Revers L,Webberley MC,Wilson IB

    更新日期：1994-11-01 00:00:00

  • Modeling and synthesis of novel tight-binding inhibitors of cytochrome P450 2C9.

    abstract：:Cytochrome P450 2C9 (2C9) is one of the three major drug metabolizing cytochrome P450 enzymes in human liver. Although the crystal structure of 2C9 has been solved, the important physicochemical properties of substrate-enzyme interactions remain difficult to be determined. This is due in part to the conformational fle...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.01.021

    authors： Peng CC,Rushmore T,Crouch GJ,Jones JP

    更新日期：2008-04-01 00:00:00

  • Selective inhibition of methoxyflavonoids on human CYP1B1 activity.

    abstract：:Cytochrome P450 (CYP) 1B1 catalyzes 17beta-estradiol (E(2)) to predominantly carcinogenic 4-hydroxy-E(2), whereas CYP1A1 and 1A2 convert E(2) to non-carcinogenic 2-hydroxy-E(2). Hence, selective inhibition of CYP1B1 is recognized to be beneficial for the prevention of E(2) related breast cancer. In this study, we firs...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.07.020

    authors： Takemura H,Itoh T,Yamamoto K,Sakakibara H,Shimoi K

    更新日期：2010-09-01 00:00:00

  • Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.

    abstract：:Caffeic acid esters, one of the components of propolis, are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities. Although, the anti-inflammatory activities of caffeic acid esters have been studied by analyzing their structure, the detailed mechanisms of thei...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.07.006

    authors： Uwai K,Osanai Y,Imaizumi T,Kanno S,Takeshita M,Ishikawa M

    更新日期：2008-08-15 00:00:00

  • Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit.

    abstract：:Grapefruit juice has been shown to increase the oral bioavailability of several clinically important drugs by inhibiting first pass metabolism. Several compounds in grapefruit juice have shown different biological activities. Unique among them are furocoumarins with potent inhibitory activity against cytochrome P450 e...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.03.047

    authors： Girennavar B,Jayaprakasha GK,Jadegoud Y,Nagana Gowda GA,Patil BS

    更新日期：2007-06-01 00:00:00

  • In vitro antitumor activities of 2,6-di-[2-(heteroaryl)vinyl]pyridines and pyridiniums.

    abstract：:The in vitro antitumor activities of 2,6-di-[2-(heteroaryl)vinyl]pyridines versus the standard National Cancer Institute 60 cell lines panel and of 2,6-di-[2-(heteroaryl)vinyl] pyridinium cations versus MCF7 (human mammary carcinoma) and LNCap (prostate carcinoma) cell lines are reported. Antiproliferative effects in ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00142-6

    authors： Barresi V,Condorelli DF,Fortuna CG,Musumarra G,Scirè S

    更新日期：2002-09-01 00:00:00

  • Design, synthesis and QSAR studies on N-aryl heteroarylisopropanolamines, a new class of non-peptidic HIV-1 protease inhibitors.

    abstract：:A series of N-aryl heteroarylisopropanolamines in which an indole or a 3-arylpyrrole moiety was linked to an aryl group through an isopropanolamine linker, were designed and synthesized as potential anti-HIV-1-PR agents. Series was tested for their ability in blocking PR activity. As a rule, indole derivatives of clas...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00119-0

    authors： Di Santo R,Costi R,Artico M,Massa S,Ragno R,Marshall GR,La Colla P

    更新日期：2002-08-01 00:00:00

  • The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step.

    abstract：:2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-delta 3-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (-)-(5) was converted into ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(96)00234-9

    authors： Adger B,Bes MT,Grogan G,McCague R,Pedragosa-Moreau S,Roberts SM,Villa R,Wan PW,Willetts AJ

    更新日期：1997-02-01 00:00:00

  • 1,2,3,4-tetrahydroisoquinoline derivatives: a new class of 5-HT1A receptor ligands.

    abstract：:Three series of new N-substituted 1,2,3,4-tetrahydroisoquinolines with 2-, 3-, and 4-membered alkyl chains (a, b, and c, respectively) were synthesized, and the effect of some structural modifications on their 5-HT1A receptor affinities and functional properties was discussed. It was found that the volume of the termi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00238-7

    authors： Mokrosz MJ,Bojarski AJ,Duszyńska B,Tatarczyńska E,Kłodzińska A,Dereń-Wesołek A,Charakchieva-Minol S,Chojnacka-Wójcik E

    更新日期：1999-02-01 00:00:00

  • Synthesis and glycogen phosphorylase inhibitor activity of 2,3-dihydrobenzo[1,4]dioxin derivatives.

    abstract：:Novel 5-benzyl and 5-benzylidene-thiazolidine-2,4-diones carrying 2,3-dihydrobenzo[1,4]dioxin pharmacophore were synthesized and their glycogen phosphorylase inhibitor activity was also studied. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.03.084

    authors： Juhász L,Docsa T,Brunyászki A,Gergely P,Antus S

    更新日期：2007-06-15 00:00:00

  • Replacement of benzylic hydroxy group by vinyl or hydroxymethyl moiety at the 3-benzazepine scaffold retaining GluN2B affinity.

    abstract：:Since overactivation of NMDA receptors is associated with neurodegenerative disorders, the design and development of subunit-selective NMDA receptor antagonists are of great interest. In order to avoid the formation of quinone-like intermediates as starting point for degradation the benzylic OH group of the lead compo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.07.059

    authors： Rath S,Schepmann D,Wünsch B

    更新日期：2017-10-15 00:00:00

  • Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors.

    abstract：:We have synthesized three categories of α,β-unsaturated carbonyl derivatives and evaluated their MAO-A and MAO-B inhibitory activities. Among them, compound 10b including α,β-unsaturated ketone group showed the most potent and selective MAO-B inhibitory activity (IC₅₀ human MAO-B 16 nM, >6000-fold selective vs MAO-A) ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.08.012

    authors： Choi JW,Jang BK,Cho NC,Park JH,Yeon SK,Ju EJ,Lee YS,Han G,Pae AN,Kim DJ,Park KD

    更新日期：2015-10-01 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

  • Synthesis and biological evaluation of BMS-986120 and its deuterated derivatives as PAR4 antagonists.

    abstract：:BMS-986120 is a PAR4 antagonist that is being investigated as an antiplatelet agent in phase I clinical trial. An improved synthesis of BMS-986120 has been developed. Based on the novel synthetic approach to BMS-986120, a series of deuterated derivatives of BMS-986120 have been synthesized and biologically evaluated t...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.11.024

    authors： Chen P,Ren S,Song H,Chen C,Chen F,Xu Q,Kong Y,Sun H

    更新日期：2019-01-01 00:00:00

  • Selective angiotensin II AT(2) receptor agonists devoid of the imidazole ring system.

    abstract：:A versatile parallel synthetic method to obtain three series of non-cyclic analogues of the first drug-like selective angiotensin II AT(2) receptor agonist (1) has been developed. In analogy with the transformation of losartan to valsartan it was demonstrated that a non-cyclic moiety could be employed as an imidazole ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.07.026

    authors： Murugaiah AM,Wallinder C,Mahalingam AK,Wu X,Wan Y,Plouffe B,Botros M,Karlén A,Hallberg M,Gallo-Payet N,Alterman M

    更新日期：2007-11-15 00:00:00

  • Photodynamic inactivation of Candida albicans using bridged polysilsesquioxane films doped with porphyrin.

    abstract：:Novel photoactive bridged polysilsesquioxane films were prepared by doped with a porphyrin derivative. The films were formed by acid-catalyzed polycondensation reaction of a precursor of a bridged silsesquioxane, based on the reaction product of (glycidoxypropyl)trimethoxysilane with n-dodecylamine in the presence of ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.05.012

    authors： Alvarez MG,Gómez ML,Mora SJ,Milanesio ME,Durantini EN

    更新日期：2012-07-01 00:00:00

  • Synthesis, kinetic mechanism and docking studies of vanillin derivatives as inhibitors of mushroom tyrosinase.

    abstract：:The purpose of the present study was to discover the extent of contribution to antityrosinase activity by adding hydroxy substituted benzoic acid, cinnamic acid and piperazine residues to vanillin. The study showed the transformation of vanillin into esters as shown in (4a-4d), (6a-6b), and (8a-8b). In addition, the r...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.06.068

    authors： Ashraf Z,Rafiq M,Seo SY,Babar MM,Zaidi NU

    更新日期：2015-09-01 00:00:00