当前位置： SCI文献检索 > ACS Chemical Biology期刊下所有文献 > Botryllamides: natural product inhibitors of ABCG2.

Botryllamides: natural product inhibitors of ABCG2.

Abstract：

:ABCG2 is a membrane-localized, human transporter protein that has been demonstrated to reduce the intracellular accumulation of substrates through ATP-dependent efflux. Highly expressed in placental syncytiotrophoblasts, brain microvasculature, and the gastrointestinal tract, ABCG2 has been shown to mediate normal tissue protection as well as limit oral bioavailability of substrate compounds. Development of ABCG2 inhibitors for clinical use may allow increased penetration of therapeutic agents into sanctuary sites and increased gastrointestinal absorption. Previously identified inhibitors have lacked potency or specificity or were toxic at concentrations needed to inhibit ABCG2; none are in clinical development. A previously developed high-throughput assay measuring inhibition of ABCG2-mediated pheophorbide a transport was applied to natural product extract libraries. Among the active samples were extracts from the marine ascidian Botryllus tyreus. Bioassay-guided fractionation resulted in purification of a series of botryllamides. Ten botryllamides were obtained, two of which (designated I and J) were novel. Activity against ABCG2 was confirmed by assessing the ability of the compounds to inhibit ABCG2-mediated BODIPY-prazosin transport in ABCG2-transfected HEK293 cells, compete with [(125)I]-iodoarylazidoprazosin (IAAP) labeling of ABCG2, stimulate ABCG2-associated ATPase activity, and reverse ABCG2-mediated resistance.

journal_name

ACS Chem Biol

journal_title

ACS chemical biology

authors

Henrich CJ,Robey RW,Takada K,Bokesch HR,Bates SE,Shukla S,Ambudkar SV,McMahon JB,Gustafson KR

doi

10.1021/cb900134c

subject

Has Abstract

pub_date

2009-08-21 00:00:00

pages

637-47

issue

8

eissn

1554-8929

issn

1554-8937

journal_volume

4

pub_type

杂志文章

相关文献

ACS Chemical Biology文献大全
  • Unleashing biocatalysis/chemical catalysis synergies for efficient biomass conversion.

    abstract：:The goal of incorporating renewable carbon into the fuel and chemical enterprise will most likely be successful when combined systems of biocatalysts and chemical catalysts are exploited. Significant efforts in the biocatalytic release of sugars from biomass are being pursued for subsequent use in fermentation. Two re...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb7001522

    authors： Shanks BH

    更新日期：2007-08-17 00:00:00

  • Advances in the Chemical Biology of Desferrioxamine B.

    abstract：:Desferrioxamine B (DFOB) was discovered in the late 1950s as a hydroxamic acid metabolite of the soil bacterium Streptomyces pilosus. The exquisite affinity of DFOB for Fe(III) identified its potential for removing excess iron from patients with transfusion-dependent hemoglobin disorders. Many studies have used semisy...

    journal_title：ACS chemical biology

    pub_type： 杂志文章,评审

    doi：10.1021/acschembio.7b00851

    authors： Codd R,Richardson-Sanchez T,Telfer TJ,Gotsbacher MP

    更新日期：2018-01-19 00:00:00

  • A chemical biological strategy to facilitate diabetic wound healing.

    abstract：:A complication of diabetes is the inability of wounds to heal in diabetic patients. Diabetic wounds are refractory to healing due to the involvement of activated matrix metalloproteinases (MMPs), which remodel the tissue resulting in apoptosis. There are no readily available methods that identify active unregulated MM...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb4005468

    authors： Gooyit M,Peng Z,Wolter WR,Pi H,Ding D,Hesek D,Lee M,Boggess B,Champion MM,Suckow MA,Mobashery S,Chang M

    更新日期：2014-01-17 00:00:00

  • RNA Phosphorothioate Modification in Prokaryotes and Eukaryotes.

    abstract：:RNA modifications play important roles in RNA structures and regulation of gene expression and translation. We report the first RNA modification on the phosphate, the RNA phosphorothioate (PS) modification, discovered in both prokaryotes and eukaryotes. The PS modification is also first reported on nucleic acids of eu...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.0c00163

    authors： Wu Y,Tang Y,Dong X,Zheng YY,Haruehanroengra P,Mao S,Lin Q,Sheng J

    更新日期：2020-06-19 00:00:00

  • A derivatized scorpion toxin reveals the functional output of heteromeric KCNQ1-KCNE K+ channel complexes.

    abstract：:KCNE transmembrane peptides are a family of modulatory beta-subunits that assemble with voltage-gated K+ channels, producing the diversity of potassium currents needed for proper function in a variety of tissues. Although all five KCNE transcripts have been found in cardiac and other tissues, it is unclear whether two...

    journal_title：ACS chemical biology

    pub_type： 信件

    doi：10.1021/cb700089s

    authors： Morin TJ,Kobertz WR

    更新日期：2007-07-20 00:00:00

  • 2D NMR-based metabolomics uncovers interactions between conserved biochemical pathways in the model organism Caenorhabditis elegans.

    abstract：:Ascarosides are small-molecule signals that play a central role in C. elegans biology, including dauer formation, aging, and social behaviors, but many aspects of their biosynthesis remain unknown. Using automated 2D NMR-based comparative metabolomics, we identified ascaroside ethanolamides as shunt metabolites in C. ...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb3004644

    authors： Izrayelit Y,Robinette SL,Bose N,von Reuss SH,Schroeder FC

    更新日期：2013-02-15 00:00:00

  • Directed Evolution Reveals the Functional Sequence Space of an Adenylation Domain Specificity Code.

    abstract：:Nonribosomal peptides are important natural products biosynthesized by nonribosomal peptide synthetases (NRPSs). Adenylation (A) domains of NRPSs are highly specific for the substrate they recognize. This recognition is determined by 10 residues in the substrate-binding pocket, termed the specificity code. This findin...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.9b00532

    authors： Throckmorton K,Vinnik V,Chowdhury R,Cook T,Chevrette MG,Maranas C,Pfleger B,Thomas MG

    更新日期：2019-09-20 00:00:00

  • Enzymatic Plasticity Inspired by the Diterpene Cyclase CotB2.

    abstract：:Enzymatic plasticity, as a modern term referring to the functional conversion of an enzyme, is significant for enzymatic activity redesign. The bacterial diterpene cyclase CotB2 is a typical plastic enzyme by which its native form precisely conducts a chemical reaction while its mutants diversify the catalytic functio...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.0c00645

    authors： Tang X,Zhang F,Zeng T,Li W,Yin S,Wu R

    更新日期：2020-10-16 00:00:00

  • Evaluation of analogues of GalNAc as substrates for enzymes of the mammalian GalNAc salvage pathway.

    abstract：:Changes in glycosylation are correlated to disease and associated with differentiation processes. Experimental tools are needed to investigate the physiological implications of these changes either by labeling of the modified glycans or by blocking their biosynthesis. N-Acetylgalactosamine (GalNAc) is a monosaccharide...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb200511t

    authors： Pouilly S,Bourgeaux V,Piller F,Piller V

    更新日期：2012-04-20 00:00:00

  • Role of stoichiometry in the dimer-stabilizing effect of AMPA receptor allosteric modulators.

    abstract：:Protein dimerization provides a mechanism for the modulation of cellular signaling events. In α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors, the rapidly desensitizing, activated state has been correlated with a weakly dimeric, glutamate-binding domain conformation. Allosteric modulators can fo...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb4007166

    authors： Ptak CP,Hsieh CL,Weiland GA,Oswald RE

    更新日期：2014-01-17 00:00:00

  • Short pathways to complexity generation: fungal peptidyl alkaloid multicyclic scaffolds from anthranilate building blocks.

    abstract：:Complexity generation in naturally occurring peptide scaffolds can occur either by posttranslational modifications of nascent ribosomal proteins or through post assembly line tailoring of nonribosomal peptides. Short enzymatic pathways utilizing bimodular and trimodular nonribosomal peptide synthetase (NRPS) assembly ...

    journal_title：ACS chemical biology

    pub_type： 杂志文章,评审

    doi：10.1021/cb4001684

    authors： Walsh CT,Haynes SW,Ames BD,Gao X,Tang Y

    更新日期：2013-07-19 00:00:00

  • Topology specific stabilization of promoter over telomeric G-quadruplex DNAs by bisbenzimidazole carboxamide derivatives.

    abstract：:Various potential G-quadruplex forming sequences present in the genome offer a platform to modulate their function by means of stabilizing molecules. Though G-quadruplex structures exhibit diverse structural topologies, the presence of G-quartets as a common structural element makes the design of topology specific lig...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb5008597

    authors： Dhamodharan V,Harikrishna S,Bhasikuttan AC,Pradeepkumar PI

    更新日期：2015-03-20 00:00:00

  • Surprising Non-Additivity of Methyl Groups in Drug-Kinase Interaction.

    abstract：:Drug optimization is guided by biophysical methods with increasing popularity. In the context of lead structure modifications, the introduction of methyl groups is a simple but potentially powerful approach. Hence, it is crucial to systematically investigate the influence of ligand methylation on biophysical character...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.9b00476

    authors： Wienen-Schmidt B,Schmidt D,Gerber HD,Heine A,Gohlke H,Klebe G

    更新日期：2019-12-20 00:00:00

  • High Throughput Screen Identifies Small Molecule Effectors That Modulate Thin Filament Activation in Cardiac Muscle.

    abstract：:Current therapeutic interventions for both heart disease and heart failure are largely insufficient and associated with undesired side effects. Biomedical research has emphasized the role of sarcomeric protein function for the normal performance and energy efficiency of the heart, suggesting that directly targeting th...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.0c00908

    authors： Parijat P,Kondacs L,Alexandrovich A,Gautel M,Cobb AJA,Kampourakis T

    更新日期：2021-01-15 00:00:00

  • Mutations of Triad Determinants Changes the Substrate Alignment at the Catalytic Center of Human ALOX5.

    abstract：:For the specificity of ALOX15 orthologs of different mammals, the geometry of the amino acids Phe353, Ile418, Met419, and Ile593 ("triad determinants") is important, and mutagenesis of these residues altered the reaction specificity of these enzymes. Here we expressed wild-type human ALOX5 and its F359W/A424I/N425M/A6...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.9b00674

    authors： Ivanov I,Golovanov AB,Ferretti C,Canyelles-Niño M,Heydeck D,Stehling S,Lluch JM,González-Lafont À,Kühn H

    更新日期：2019-12-20 00:00:00

  • Price for Opening the Transient Specificity Pocket in Human Aldose Reductase upon Ligand Binding: Structural, Thermodynamic, Kinetic, and Computational Analysis.

    abstract：:Insights into the thermodynamic and kinetic signature of the transient opening of a protein-binding pocket resulting from accommodation of suitable substituents attached to a given parent ligand scaffold are presented. As a target, we selected human aldose reductase, an enzyme involved in the development of late-stage...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.7b00062

    authors： Rechlin C,Scheer F,Terwesten F,Wulsdorf T,Pol E,Fridh V,Toth P,Diederich WE,Heine A,Klebe G

    更新日期：2017-05-19 00:00:00

  • Chemical Probe To Monitor the Parkinsonism-Associated Protein DJ-1 in Live Cells.

    abstract：:Reactive oxygen species (ROS) play an important role in the onset of Parkinson's disease (PD), and deciphering protective mechanisms is a major goal for therapeutic development. Here, DJ-1 (PARK7) gained major attention when a conserved cysteine residue with a putative role in oxidative stress sensing/protection was l...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.8b00633

    authors： Drechsel J,Mandl FA,Sieber SA

    更新日期：2018-08-17 00:00:00

  • 3-Oxo-β-sultam as a Sulfonylating Chemotype for Inhibition of Serine Hydrolases and Activity-Based Protein Profiling.

    abstract：:3-Oxo-β-sultams are four-membered ring ambident electrophiles that can react with nucleophiles either at the carbonyl carbon or at the sulfonyl sulfur atoms, and that have been reported to inhibit serine hydrolases via acylation of the active-site serine residue. We have developed a panel of 3-oxo-β-sultam inhibitors ...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.0c00090

    authors： Carvalho LAR,Almeida VT,Brito JA,Lum KM,Oliveira TF,Guedes RC,Gonçalves LM,Lucas SD,Cravatt BF,Archer M,Moreira R

    更新日期：2020-04-17 00:00:00

  • Boron dipyrromethene as a fluorescent caging group for single-photon uncaging with long-wavelength visible light.

    abstract：:Caged compounds are useful tools for precise spatiotemporal modulation of cell functions, but in most cases uncaging requires ultraviolet (UV) light, which is cytotoxic and has limited tissue penetration. Therefore, caged compounds that can be activated by longer-wavelength light are required. Here we describe a novel...

    journal_title：ACS chemical biology

    pub_type： 信件

    doi：10.1021/cb500525p

    authors： Umeda N,Takahashi H,Kamiya M,Ueno T,Komatsu T,Terai T,Hanaoka K,Nagano T,Urano Y

    更新日期：2014-10-17 00:00:00

  • Rational Design of Hybrid Natural Products by Utilizing the Promiscuity of an Amide Synthetase.

    abstract：:WS9326A and annimycin are produced by Streptomyces asterosporus DSM 41452. WS9326A is a nonribosomal peptide synthetase-(NRPS-) derived depsipeptide containing a cinnamoyl moiety, while annimycin is a linear polyketide bearing a 2-amino-3-hydroxycyclopent-2-enone (C5N) group. Both gene clusters have been sequenced and...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.9b00351

    authors： Zhu J,Zhang S,Zechel DL,Paululat T,Bechthold A

    更新日期：2019-08-16 00:00:00

  • Biochemical and biophysical analysis of a chiral PqsD inhibitor revealing tight-binding behavior and enantiomers with contrary thermodynamic signatures.

    abstract：:Antivirulence strategies addressing bacterial pathogenicity without exhibiting growth inhibition effects represent a novel approach to overcome today's crisis in antibiotic development. In recent studies, we examined various inhibitors of PqsD, an enzyme involved in formation of Pseudomonas aeruginosa cell-to-cell sig...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb400530d

    authors： Storz MP,Brengel C,Weidel E,Hoffmann M,Hollemeyer K,Steinbach A,Müller R,Empting M,Hartmann RW

    更新日期：2013-12-20 00:00:00

  • Crystal Structures of Fumarate Hydratases from Leishmania major in a Complex with Inhibitor 2-Thiomalate.

    abstract：:Leishmaniases affect the poorest people on earth and have no effective drug therapy. Here, we present the crystal structure of the mitochondrial isoform of class I fumarate hydratase (FH) from Leishmania major and compare it to the previously determined cytosolic Leishmania major isoform. We further describe the mecha...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.8b00972

    authors： Feliciano PR,Drennan CL,Nonato MC

    更新日期：2019-02-15 00:00:00

  • Stepwise Loop Insertion Strategy for Active Site Remodeling to Generate Novel Enzyme Functions.

    abstract：:The remodeling of active sites to generate novel biocatalysts is an attractive and challenging task. We developed a stepwise loop insertion strategy (StLois), in which randomized residue pairs are inserted into active site loops. The phosphotriesterase-like lactonase from Geobacillus kaustophilus (GkaP-PLL) was used t...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.7b00018

    authors： Hoque MA,Zhang Y,Chen L,Yang G,Khatun MA,Chen H,Hao L,Feng Y

    更新日期：2017-05-19 00:00:00

  • Cell-penetrating bisubstrate-based protein kinase C inhibitors.

    abstract：:Although protein kinase inhibitors present excellent pharmaceutical opportunities, lack of selectivity and associated therapeutic side effects are common. Bisubstrate-based inhibitors targeting both the high-selectivity peptide substrate binding groove and the high-affinity ATP pocket address this. However, they are t...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb300709g

    authors： van Wandelen LT,van Ameijde J,Ismail-Ali AF,van Ufford HC,Vijftigschild LA,Beekman JM,Martin NI,Ruijtenbeek R,Liskamp RM

    更新日期：2013-07-19 00:00:00

  • First-in-class small molecule inhibitors of the single-strand DNA cytosine deaminase APOBEC3G.

    abstract：:APOBEC3G is a single-stranded DNA cytosine deaminase that comprises part of the innate immune response to viruses and transposons. Although APOBEC3G is the prototype for understanding the larger mammalian polynucleotide deaminase family, no specific chemical inhibitors exist to modulate its activity. High-throughput s...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb200440y

    authors： Li M,Shandilya SM,Carpenter MA,Rathore A,Brown WL,Perkins AL,Harki DA,Solberg J,Hook DJ,Pandey KK,Parniak MA,Johnson JR,Krogan NJ,Somasundaran M,Ali A,Schiffer CA,Harris RS

    更新日期：2012-03-16 00:00:00

  • HIV-1 Env-Dependent Cell Killing by Bifunctional Small-Molecule/Peptide Conjugates.

    abstract：:A strategy has been established for the synthesis of a family of bifunctional HIV-1 inhibitor covalent conjugates with the potential to bind simultaneously to both the gp120 and gp41 subunits of the HIV-1 envelope glycoprotein trimeric complex (Env). One component of the conjugates is derived from BNM-III-170, a small...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.0c00888

    authors： Gaffney A,Nangarlia A,Ang CG,Gossert S,Rashad Ahmed AA,Hossain MA,Abrams CF,Smith AB 3rd,Chaiken I

    更新日期：2021-01-15 00:00:00

  • Mechanism-Based Post-Translational Modification and Inactivation in Terpene Synthases.

    abstract：:Terpenes are ubiquitous natural chemicals with diverse biological functions spanning all three domains of life. In specialized metabolism, the active sites of terpene synthases (TPSs) evolve in shape and reactivity to direct the biosynthesis of a myriad of chemotypes for organismal fitness. As most terpene biosynthesi...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.5b00539

    authors： Kersten RD,Diedrich JK,Yates JR 3rd,Noel JP

    更新日期：2015-11-20 00:00:00

  • Harnessing Fluorine-Sulfur Contacts and Multipolar Interactions for the Design of p53 Mutant Y220C Rescue Drugs.

    abstract：:Many oncogenic mutants of the tumor suppressor p53 are conformationally unstable, including the frequently occurring Y220C mutant. We have previously developed several small-molecule stabilizers of this mutant. One of these molecules, PhiKan083, 1-(9-ethyl-9H-carbazole-3-yl)-N-methylmethanamine, binds to a mutation-in...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.6b00315

    authors： Bauer MR,Jones RN,Baud MG,Wilcken R,Boeckler FM,Fersht AR,Joerger AC,Spencer J

    更新日期：2016-08-19 00:00:00

  • ATP-mediated kinome selectivity: the missing link in understanding the contribution of individual JAK Kinase isoforms to cellular signaling.

    abstract：:Kinases constitute an important class of therapeutic targets being explored both by academia and the pharmaceutical industry. The major focus of this effort was directed toward the identification of ATP competitive inhibitors. Although it has long been recognized that the intracellular concentration of ATP is very dif...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/cb5002125

    authors： Thorarensen A,Banker ME,Fensome A,Telliez JB,Juba B,Vincent F,Czerwinski RM,Casimiro-Garcia A

    更新日期：2014-07-18 00:00:00

  • EcoSynther: A Customized Platform To Explore the Biosynthetic Potential in E. coli.

    abstract：:Developing computational tools for a chassis-centered biosynthetic pathway design is very important for a productive heterologous biosynthesis system by considering enormous foreign biosynthetic reactions. For many cases, a pathway to produce a target molecule consists of both native and heterologous reactions when ut...

    journal_title：ACS chemical biology

    pub_type： 杂志文章

    doi：10.1021/acschembio.7b00605

    authors： Ding S,Liao X,Tu W,Wu L,Tian Y,Sun Q,Chen J,Hu QN

    更新日期：2017-11-17 00:00:00