- Nanomechanics of Anion-πInteraction in Aqueous Solution
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Noncovalent interactions play a constitutive role in numerous biological processes, including biomolecular adhesion, recognition, and transport. Unlike π-πand cation-πinteractions, anion-πinteraction was only recently and computationally recognized to par
- Zhang, Jiawen,Xiang, Li,Yan, Bin,Zeng, Hongbo
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- CONJUGATES AND CONJUGATES FOR USE IN PREVENTING OR TREATING OF BRAIN DAMAGE AND NEURODEGENERATIVE DISEASES
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The present invention relates to conjugates comprising one or more compounds selected from of (i) an anti-inflammatory compound, and/or (ii) an antioxidant compound, and/or (iii) and antibiotic compound and/or, (iv) a metal chelating compound and at least
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- Synthetic Mimics of Native Siderophores Disrupt Iron Trafficking in Acinetobacter baumannii
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Many pathogenic bacteria biosynthesize and excrete small molecule metallophores, known as siderophores, that are used to extract ferric iron from host sources to satisfy nutritional need. Native siderophores are often structurally complex multidentate chelators that selectively form high-affinity octahedral ferric iron complexes with defined chirality recognizable by cognate protein receptors displayed on the bacterial cell surface. Simplified achiral analogues can serve as synthetically tractable siderophore mimics with potential utility as chemical probes and therapeutic agents to better understand and treat bacterial infections, respectively. Here, we demonstrate that synthetic spermidine-derived mixed ligand bis-catecholate monohydroxamate siderophores (compounds 1-3) are versatile structural and biomimetic analogues of two native siderophores, acinetobactin and fimsbactin, produced by Acinetobacter baumannii, a multidrug-resistant Gram-negative human pathogen. The metal-free and ferric iron complexes of the synthetic siderophores are growth-promoting agents of A. baumannii, while the Ga(III)-complexes are potent growth inhibitors of A. baumannii with MIC values 1 μM. The synthetic siderophores compete with native siderophores for uptake in A. baumannii and maintain comparable apparent binding affinities for ferric iron (KFe) and the siderophore-binding protein BauB (Kd). Our findings provide new insight to guide the structural fine-tuning of these compounds as siderophore-based therapeutics targeting pathogenic strains of A. baumannii.
- Banas, Victoria S.,Bohac, Tabbetha J.,Fang, Luting,Giblin, Daryl E.,Wencewicz, Timothy A.
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p. 2138 - 2151
(2021/07/07)
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- PEPTOID-BASED CHELATING LIGANDS FOR SELECTIVE METAL CHELATION
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The present disclosure provides peptoid-based chelating ligands, corresponding cyclic peptoids, and methods of making thereof. Functional groups may be tailored for high metal binding affinity and selectivity. The side chains of a cyclic peptoid according to the present disclosure may be selected based on, for example, high affinity for actinide or other metal ions, selectivity for actinide or other metal ions, the ability to recover a metal once it is bound to the peptoid, and whether the overall peptoid should be hydrophobic or hydrophilic. Unlike siderophores, peptoid-based chelating ligands of the present disclosure are not readily hydrolyzed under physiological conditions. Therefore, peptoid-based chelating ligands may be, for example, used to treat actinide (e.g., iron and lead) poisoning in vivo. Moreover, peptoid-based chelating ligands of the present disclosure may be used for medical imaging, chelation therapy, drug delivery, and separation technologies, for example.
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- DOUBLE-HEADED PROTEASE INHIBITOR
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The present invention provides a compound that is highly safe and useful in the prevention, alleviation, and/or treatment of various diseases involving enteropeptidase inhibition and/or trypsin inhibition, a pharmaceutical composition containing the compo
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- Hexadentate β-Dicarbonyl(bis-catecholamine) Ligands for Efficient Uranyl Cation Decorporation: Thermodynamic and Antioxidant Activity Studies
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The special linear dioxo cation structure of the uranyl cation, which relegates ligand coordination to an equatorial plane perpendicular to the O=U=O vector, poses an unusual challenge for the rational design of efficient chelating agents. Therefore, the
- Zhang, Qingchun,Jin, Bo,Zheng, Tian,Tang, Xingyan,Guo, Zhicheng,Peng, Rufang
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supporting information
p. 14626 - 14634
(2019/11/03)
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- Impact of Molecular Architecture and Adsorption Density on Adhesion of Mussel-Inspired Surface Primers with Catechol-Cation Synergy
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Marine mussels secrete proteins rich in residues containing catechols and cationic amines that displace hydration layers and adhere to charged surfaces under water via a cooperative binding effect known as catechol-cation synergy. Mussel-inspired adhesives containing paired catechol and cationic functionalities are a promising class of materials for biomedical applications, but few studies address the molecular adhesion mechanism(s) of these materials. To determine whether intramolecular adjacency of these functionalities is necessary for robust adhesion, a suite of siderophore analog surface primers was synthesized with systematic variations in intramolecular spacing between catechol and cationic functionalities. Adhesion measurements conducted with a surface forces apparatus (SFA) allow adhesive failure to be distinguished from cohesive failure and show that the failure mode depends critically on the siderophore analog adsorption density. The adhesion of these molecules to muscovite mica in an aqueous electrolyte solution demonstrates that direct intramolecular adjacency of catechol and cationic functionalities is not necessary for synergistic binding. However, we show that increasing the catechol-cation spacing by incorporating nonbinding domains results in decreased adhesion, which we attribute to a decrease in the density of catechol functionalities. A mechanism for catechol-cation synergy is proposed based on electrostatically driven adsorption and subsequent binding of catechol functionalities. This work should guide the design of new adhesives for binding to charged surfaces in saline environments.
- Degen, George D.,Stow, Parker R.,Lewis, Robert B.,Andresen Eguiluz, Roberto C.,Valois, Eric,Kristiansen, Kai,Butler, Alison,Israelachvili, Jacob N.
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supporting information
p. 18673 - 18681
(2019/11/28)
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- Mimicking salmochelin S1 and the interactions of its Fe(III) complex with periplasmic iron siderophore binding proteins CeuE and VctP
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A mimic of the tetradentate stealth siderophore salmochelin S1, was synthesised, characterised and shown to form Fe(III) complexes with ligand-to-metal ratios of 1:1 and 3:2. Circular dichroism spectroscopy confirmed that the periplasmic binding proteins
- Wilde, Ellis J.,Blagova, Elena V.,Sanderson, Thomas J.,Raines, Daniel J.,Thomas, Ross P.,Routledge, Anne,Duhme-Klair, Anne-Kathrin,Wilson, Keith S.
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- Catechol-Based Ligands as Potential Metal Chelators Inhibiting Redox Activity in Alzheimer's Disease
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The loss of homeostasis of redox metal ions, namely, copper and iron, has been considered to be an important contributing factor in neuronal death observed in the brain of patients affected by Alzheimer's disease (AD). Specific ligands able to regulate the homeostasis of copper and, to a lesser extent, iron ions in the brain have therefore been considered to be potential drugs for the treatment of AD. Herein, the synthesis and metal coordination properties of a series of ligands based on a bis(2,3-dihydroxyalkylbenzamide) scaffold, which are potentially able to regulate the homeostasis of redox metal ions, are reported. These catechol-based ligands exhibit high specific affinities for CuII and FeIII, and a lower affinity for ZnII, which indicates that they may interact with redox metal ions without disturbing the structural and dynamic role of zinc chelation in many proteins. These ligands inhibit the reduction of dioxygen induced by CuII–Aβ1–16, and this suggests that they may be able to efficiently reduce the oxidative stress induced by metal-loaded amyloids in the AD brain.
- Nguyen, Michel,Meunier, Bernard,Robert, Anne
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p. 3198 - 3204
(2017/07/22)
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- CONDENSED HETEROCYCLIC COMPOUND
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The present invention relates to a condensed heterocyclic compound that has an enteropeptidase inhibitory effect and is useful in the treatment or prevention of obesity, diabetes mellitus, or the like, and a medicament containing the same. Specifically, t
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- Identification of the Ferric-Acinetobactin Outer Membrane Receptor in Aeromonas salmonicida subsp. salmonicida and Structure-Activity Relationships of Synthetic Acinetobactin Analogues
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Aeromonas salmonicida subsp. salmonicida, the causative agent of furunculosis in several fish species, produces acinetobactin and amonabactin as siderophores. In a previous study, we chemically characterized these siderophores and proposed a biosynthetic
- Balado, Miguel,Segade, Yuri,Rey, Diego,Osorio, Carlos R.,Rodríguez, Jaime,Lemos, Manuel L.,Jiménez, Carlos
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p. 479 - 493
(2017/03/01)
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- ANTIBACTERIAL SIDEROMYCINS
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A compound, comprising: an Fe(III)-binding and/or Fe(III)-bound siderophore; one or more optional linker covalently bound to the siderophore; and daptomycin covalently bound to the linker, or, if no linker is present, then to the siderophore; or pharmaceu
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- Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection
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Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.
- Lee, Albert A.,Chen, Yi -Chen S.,Ekalestari, Elisa,Ho, Sheng -Yang,Hsu, Nai -Shu,Kuo, Tang -Feng,Wang, Tsung -Shing Andrew
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p. 12338 - 12342
(2016/10/13)
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- DENDRITIC COMPOUNDS INCLUDING A CHELATING, FLUOROCHROME OR RECOGNITION AGENT, COMPOSITIONS INCLUDING SAME AND USES THEREOF
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The invention relates to dendritic compounds comprising a chelating, fluorochrome or recognition agent of formula (I), to compositions comprising same, and to uses thereof, wherein in said formula (I): T, L1, D, R, L2, V and n are as defined in the description.
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- Benzoic hydroxamate-based iron complexes as model compounds for humic substances: Synthesis, characterization and algal growth experiments
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A series of monomeric and dimeric FeIII complexes bearing benzoic hydroxamates as O,O-chelates has been prepared and characterized by elemental analysis, IR spectroscopy, UV-Vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), cyclic voltammetry, EPR spectroscopy and for some examples by X-ray diffraction analysis. The stability of the synthesized complexes in pure water and seawater was monitored over 24 h by means of UV-Vis spectrometry. The ability to release iron from the synthesized model complexes has been investigated with algae growth experiments.
- Orlowska, Ewelina,Roller, Alexander,Wiesinger, Hubert,Pignitter, Marc,Jirsa, Franz,Krachler, Regina,Kandioller, Wolfgang,Keppler, Bernhard K.
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p. 40238 - 40249
(2016/05/24)
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- Synthesis of bifunctional biscatecholamine chelators for uranium decorporation
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New 1,3-dicarbonyl biscatecholamide ligands were synthesized to decorporate uranium for nuclear contamination. The derivatives were characterized via1H NMR spectroscopy,13C NMR spectroscopy, FTIR spectroscopy and mass spectrometry. The complexation abilities of ligands 8a–8d with UO22+, Cu2+and Zn2+were determined through spectrophotometric and potentiometric titrations technology. The antioxidant capacities of the ligands were assessed through DPPH antioxidant assay. Results indicated that ligands 8a–8d are potential decorporating agents for uranyl ion (pUO2up to 22.41) and copper(II) ion (pCu up to 17.71) without depletion of the essential element zinc (pZn lower than 7.48).
- Lei, Shan,Jin, Bo,Zhang, Qingchun,Zhang, Zhichao,Wang, Xiaofang,Peng, Rufang,Chu, Shijin
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p. 387 - 395
(2016/10/13)
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- Symmetrical 1,3-dicarbonyl biscatecholamide ligands as sequestering agents for uranyl decorporation
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The synthesis of a series of new symmetrical 1,3-dicarbonyl biscatecholamide ligands CH2[COX(CH2)nCAM; X = O, NH; n = 2, 3, 4]2 [CAM = 2,3-Ph(OH)2CONH] is presented. 1H NMR, 13C
- Zhang, Qingchun,Jin, Bo,Peng, Rufang,Lei, Shan,Chu, Shijin
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p. 417 - 423
(2015/02/05)
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- Total synthesis and structure revision of mirubactin, and its iron binding activity
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Dechloro-chlorocatechelin A (3), a deschloro-derivative of a microbial siderophore chlorocatechelin A (2), was synthesized from 2,3-dihydroxybenzoic acid, D-arginine, and 1-benzyl Dglutamate. The spectral data were unambiguously identical with those of mi
- Kishimoto, Shinji,Nishimura, Shinichi,Kakeya, Hideaki
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p. 1303 - 1305
(2015/11/23)
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- NOVEL BIOACTIVE SUBSTANCE
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PROBLEM TO BE SOLVED: To provide a novel compound useful as an aminopeptidase A inhibitor. SOLUTION: This invention provides a compound represented by formula (I) or salt thereof, and a pharmaceutical composition comprising the same, wherein R1
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Paragraph 0091-0092
(2018/02/08)
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- Synthesis and characterization of a potential bifunctional C60-Ih fullerene-based catechol amide ligand
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The new C60-Ih fullerene-based catechol amide derivatives C60{C[COO(CH2)nCAM]2} [n = 2, 3 or 4; CAM = 2,3-Ph(OH)2CONH] were prepared using a modified Bingel-type reaction of Csu
- Zhang, Qingchun,Jin, Bo,Peng, Rufang,Lei, Shan,Chu, Shijin
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p. 204 - 206
(2015/06/17)
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- Synthesis and antibacterial activity of catecholate-ciprofloxacin conjugates
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The development of an efficient route to obtain artificial siderophore-antibiotic conjugates active against Gram-negative bacteria is crucial. Herein, a practical access to triscatecholate enterobactin analogues linked to the ciprofloxacin along with their antibacterial evaluation are described. Two series of conjugates were obtained with and without a piperazine linker which is known to improve the pharmacokinetics profile of a drug. A monocatecholate-ciprofloxacin conjugate was also synthesized and evaluated. The antibacterial activities against Pseudomonas aeruginosa for some conjugates are related to the iron concentration in the culture medium and seem to depend on the bacterial iron uptake systems.
- Fardeau, Sylvain,Dassonville-Klimpt, Alexandra,Audic, Nicolas,Sasaki, Andre,Pillon, Marine,Baudrin, Emmanuel,Mullie, Catherine,Sonnet, Pascal
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p. 4049 - 4060
(2014/08/18)
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- Synthesis and structural characterization of hexacoordinate silicon, germanium, and titanium complexes of the E. coli siderophore enterobactin
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The E. coli siderophore enterobactin, one of the strongest FeIII chelators known to date, is also capable of binding SiIV under physiological conditions. We report on the synthesis and structural characterization of the tris(catecholate) SiIV-enterobactin complex and its GeIV and TiIV analogues. Comparative structural analysis, supported by quantum-chemical calculations, reveals the correlation between the ionic radius and the structural changes in enterobactin upon complexation. Copyright
- Baramov, Todor,Keijzer, Karlijn,Irran, Elisabeth,Moesker, Eva,Baik, Mu-Hyun,Suessmuth, Roderich
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supporting information
p. 10536 - 10542
(2013/08/23)
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- HIV INTEGRASE INHIBITORS
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Provided herein, inter alia, are novel compounds for the inhibition of HIV integrase. The compounds disclosed herein are useful for methods of treating HIV infection in a subject in need thereof.
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- EDTA and DTPA modified ligands as sequestering agents for uranyl decorporation
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Synthesis of modified EDTA and DTPA ligands and determination of their binding affinities for the uranyl cation are described. Thanks to a screening method, based on a chromophoric complex displacement procedure, chelating properties were studied in aqueous media under various pH conditions for evaluation of their in vivo uranyl-removal efficacy. Each ligand showed a more or less pronounced affinity for uranium. Specific ligands based on EDTA or DTPA analogues containing sulfocatecholamide (CAMS) were found to exhibit a significant affinity towards uranyl ion in acidic, neutral or basic conditions.
- Leydier, Antoine,Lin, Yi,Arrachart, Guilhem,Turgis, Rapha?l,Lecerclé, Delphine,Favre-Reguillon, Alain,Taran, Frédéric,Lemaire, Marc,Pellet-Rostaing, Stéphane
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experimental part
p. 1163 - 1170
(2012/02/15)
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- Synthesis and evaluation of C-ring aromatized analogues of phenanthridone alkaloids
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Phenanthridone alkaloids are envisaged as an attractive lead for the development of anticancer agents. We have prepared a series of aromatized analogues on the basis of the structure of this class of alkaloids with the hope of finding the simplified compounds with comparable activities. The obtained analogues were evaluated for their cytotoxic effect against several cancer cell lines and found to be virtually inactive. These observations together with molecular modeling studies strongly suggest that the stereochemistries of hydroxyl groups in C-ring of phenanthridone alkaloids are crucial to biological effects.
- Lee, Seokwoo,Hwang, Soonho,Yu, Shuai,Jang, Wonyoung,Lee, Yun Mi,Kim, Sanghee
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p. 1065 - 1070
(2012/07/14)
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- Chemical synthesis and biological evaluation of gallidermin-siderophore conjugates
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The lantibiotic gallidermin was modified at lysine residues by regioselective attachment of derivatives of pyochelin, agrobactin and desferrioxamine B with the objective of having siderophore receptors of Gram-negative bacteria transport the antibiotic-iron chelator conjugate through the outer membrane. All of the conjugates retained activity against the Gram-positive indicator strain, Lactococcus lactis subsp. cremoris HP. However, testing of the conjugates against several Gram-negative strains yielded unexpected results. Bacteria treated with 100 μM of the conjugates complexed with Fe3+ grew better than bacteria grown in iron-free media but worse than bacteria grown in the same media supplemented with 10 μM FeCl 3. Although these findings indicate that the conjugates are unable to inhibit the growth of Gram-negative bacteria, they indicate penetration of the outer membrane and provide structure-activity information for design of other lantibiotic conjugates. The synthetic strategy is applicable for linking biomarkers or fluorescence probes to gallidermin for studies on its localization and mode of action. As there are many lantibiotics that operate with unknown mechanisms of action, this chemical approach provides a means to modify such peptides with biomarkers for biological investigations.
- Yoganathan, Sabesan,Sit, Clarissa S.,Vederas, John C.
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p. 2133 - 2141
(2011/05/14)
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- Identification of novel matrix metalloproteinase inhibitors by screening of phenol fragments library
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In the last 20 years, a great variety of synthetic, low molecular weight MMP inhibitors (MMPIs) have been synthesized and tested, although none has reached clinical utility. Exploration of novel ZBGs and development of non-hydroxamate MMPI has become a focus in current research. It's well-known that polyphenols can produce beneficial effects on human health by their antioxidant properties as well as they have the ability to block gelatinase activity. In this work we tested a series of selected phenols as MMP inhibitors. The most interesting hit (B6) shows sub-micromolar activity against MMP-2 (IC50 0.59 ± 0.05 μM, LE = 1.07) and a fairly good selectivity spectrum. A screening of selected phenols against four matrix metalloproteinases is reported. Eight phenols showed a very interesting activity and selective profile. The most interesting hit (B6) presents a sub-micromolar activity against MMP-2 (IC50 0.59±0.05μM). Copyright
- Rubino, Maria Teresa,Maggi, Dariana,Laghezza, Antonio,Loiodice, Fulvio,Tortorella, Paolo
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p. 557 - 563
(2012/06/30)
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- Synthesis and biological activity of analogues of vanchrobactin, a siderophore from Vibrio anguillarum serotype O2
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Several analogues of vanchrobactin, a catechol siderophore isolated from the bacterial fish pathogen Vibrio anguillarum serotype O2 strain RV22, have been synthesized. The biological evaluation of these novel compounds showed that most of them are active as siderophores, as determined by growth promotion assays using the producer strain, as well as V. anguillarum serotype O1, Salmonella enterica, and Erwinia chrysanthemi. These compounds also gave a positive chrome azurol-S (CAS) test. On the basis of these results, we were able to deduce some structure-activity relationships. Furthermore, we found an analogue with siderophore activity that has appropriate functionality (an amino group) for use as an antibiotic vector to be employed in a "Trojan horse strategy". This journal is The Royal Society of Chemistry.
- Soengas, Raquel G.,Larrosa, Marta,Balado, Miguel,Rodriguez, Jaime,Lemos, Manuel L.,Jimenez, Carlos
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scheme or table
p. 1278 - 1287
(2008/10/09)
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- Synthesis and investigation of a chiral enterobactin analogue based on a macrocyclic peptide scaffold
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A chiral C3-symmetric enterobactin analogue (1) has been synthesized by attachment of three 2,3-dihydroxybenzoyl units to a chiral oxazole-containing macrocyclic peptide scaffold. Complex formation kinetics and stoichiometry with various metal ions were investigated by spectrophotometric methods. In the cases of AlIII, InIII and FeIII complexes, UV absorption and CD kinetics showed nonlinearity, which results from slow conformational changes of the octahedral complexes. Virtual binding constants were determined from UV absorption data and showed selective binding of GaIII in preference to FeIII, by two orders of magnitude. CD spectroscopy revealed highly diastereoselective binding of Al III, GaIII, InIII, FeIII and Ge IV ions at room temperature, corresponding to the helical chirality opposite to that of the analogous enterobactin complexes. Ab initio calculations confirmed the energetic stabilization of the A isomers relative to the A isomers.
- Pinter, Aron,Haberhauer, Gebhard
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experimental part
p. 11061 - 11068
(2009/11/30)
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- Vanchrobactin: absolute configuration and total synthesis
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The stereochemistry of vanchrobactin, a siderophore produced by the bacterial fish pathogenVibrio anguillarum serotype O2, was elucidated by chiral capillary electrophoresis analysis and total synthesis as N-[N′-(2,3-dihydroxybenzoyl)-d-arginyl]-l-serine.
- Soengas, Raquel G.,Anta, Cristina,Espada, Alfonso,Nieto, Rosa M.,Larrosa, Marta,Rodríguez, Jaime,Jiménez, Carlos
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p. 3021 - 3024
(2008/02/06)
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- Ortho-substituted catechol derivatives: The effect of intramolecular hydrogen-bonding pathways on chloride anion recognition
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(Chemical Equation Presented) This paper reports a series of chloride anion receptors containing two catechol head groups connected through their ortho-positions via a spacer chain. The linking group chosen to attach the spacer chain to the catechol units has a major impact on the anion-binding potential of the receptor. Linking groups that are capable of forming stable six-membered intramolecular hydrogen-bonded rings with the catechol O-H groups significantly inhibit the ability of the catechol units to hydrogen bond to chloride anions. However, where the linking groups are only capable of forming five- or seven-membered intramolecular hydrogen-bonded rings, then anion binding via hydrogen bonding through the catechol O-H groups becomes a possibility. This process is solvent dependent; the presence of competitive solvent (e.g., DMSO-d6) disrupts the intramolecular hydrogen-bonding pattern and enhances anion binding relative to simple unfunctionalized catechol. The most effective receptor is that in which the hydrogen-bonding linker (-CH 2CONH-) is most distant from the catechol units and can only form a seven-membered intramolecular hydrogen-bonded ring. In this case, the receptor, which contains two catechol units, is a more effective chloride anion binder than simple unfunctionalized catechol, demonstrating that the two head groups, in combination with the N-H groups in the linker, act cooperatively and enhance the degree of anion binding. In summary, this paper provides insight into the hydrogen-bonding patterns in orthofunctionalized catechols and the impact these have on the potential of the catechol O-H groups to hydrogen bond to a chloride anion.
- Winstanley, Keith J.,Smith, David K.
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p. 2803 - 2815
(2008/02/01)
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- Synthesis and studies of catechol-containing mycobactin S and T analogs
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The syntheses of catechol-containing mycobactin S and T analogs are described. These analogs incorporate a catechol-glycine moiety in place of the phenol-oxazoline of the naturally occurring mycobactins S and T. Studies indicated that the new siderophore
- Walz, Andrew J.,Moellmann, Ute,Miller, Marvin J.
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p. 1621 - 1628
(2008/02/07)
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- Conjugates of methyl 6-aminopenicillanate with biscatechol-hydroxamate chelators: synthesis and siderophoric activity
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A synthesis of biscatechol-hydroxamate and triscatechol chelators and of conjugates of the former with methyl 6-aminopenicillanate is described. It is based on the multiple use of the ylide Ph3PCCO as a C2 building block in one-pot c
- Schobert, Rainer,Stangl, Andreas,Hannemann, Kerstin
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p. 7799 - 7808
(2007/10/03)
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- Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter hydrocarbonoclasticus, an Oil-Degrading Bacteria
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A modular synthesis was developed to access petrobactin, a catechol-containing siderophore isolated from Marinobacter hydrocarbonoclasticus. A range of petrobactin homologues with differing dihydroxybenzamide motifs and in one case an increased number of
- Gardner, Richard Andrew,Kinkade, Rebecca,Wang, Chaojie,Phanstiel IV, Otto
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p. 3530 - 3537
(2007/10/03)
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- Formal total synthesis of the PKC inhibitor, balanol: Preparation of the fully protected benzophenone fragment
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The synthesis of a perbenzylated derivative of balanol's highly functionalized benzophenone fragment is reported employing a regioselective Heck reaction as the key step for the connection of the two aromatic rings. The intermediate 7-membered lactone obt
- Laursen, Bolette,Denieul, Marie-Pierre,Skrydstrup, Troels
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p. 2231 - 2238
(2007/10/03)
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- Deuterium labelled borocryptands: Synthesis, structural analysis and binding studies
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High yield syntheses of two new deuterium labelled compound 2 and 3 based on the [22] macrocyclic backbone bearing two catechol units was achieved. The solid state structure of the tetradeuterated compound 3 was elucidated by X-ray diffraction methods. Th
- Graf, Ernest,Hosseini, Mir Wais,De Cian, Andre,Fischer, Jean
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p. 3501 - 3504
(2007/10/03)
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- An efficient synthesis of alterobactin A; a super siderophore of marine origin
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Alterobactin A (1), a cyclic depsipeptide and a super siderophore isolated from an open-ocean bacterium, was efficiently synthesized for the first time by a convergent manner with the maximum protection of various functional groups.
- Deng,Hamada,Shioiri
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p. 627 - 638
(2007/10/03)
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- Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives
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This paper describes the discovery of a new non-peptide endothelin A (ET(A)) selective ligand, 2,4-dibenzyloxybenzoic acid 3, which inhibits the binding of [125I]ET-1 to ET(A) receptors with an IC50 of 9 μM (ET-1 = endothelin-1). Optimisation of 3 resulted in compound 52 which had an IC50 of 1 μM. One of the analogues of 3, compound 15, was examined in a functional assay and shown to antagonise ET-1-induced contraction of rat aorta. The identification of 3 was made through the application of ChemDBS-3D searching of our corporate database. The 3D query, using an aromatic ring to a carboxylic acid group separated by 10.2 ± 1.1 A, was derived from an examination of common pharmacophoric distances found in the low energy conformations of two known ET(A) antagonists, the cyclic pentapeptide BQ 123 1 and myriceron caffeoyl ester 2.
- Astles,Brown,Handscombe,Harper,Harris,Lewis,Lockey,McCarthy,McLay,Porter,Roach,Smith,Walsh
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p. 409 - 423
(2007/10/03)
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- Synthesis of an exo-ditopic receptor based on calix[4]arene and catechol
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The synthesis of a calix[4]arene derivative immobilised in 1,3- alternate conformation by alkylation at the lower rim and bearing four catechoylamide units at the upper rim was achieved. The chelating coordination sites were by construction oriented, in a
- Mislin, Gilles,Graf, Ernest,Hosseini, Mir Wais
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p. 4503 - 4506
(2007/10/03)
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- Synthesis of C3-cyclotriveratrylene ligands for iron(II) and iron(III) coordination
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The design and synthesis of a new family of siderophores based on cyclotriveratrylene is described. The ligands consist of a C3-cyclotriveratrylene unit provided with three arms (spacers) ending with hydroxamate, catecholate, bipyridine, or iminopyridine units suitable for the octahedral coordination of transition metals and particularly for the complexation of iron(II) and iron(III).
- Veriot, Gilles,Dutasta, Jean-Pierre,Matouzenko, Galina,Collet, Andre
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p. 389 - 400
(2007/10/02)
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- Synthesis of macrocyclic ditopic receptors designed for simulataneous binding of alkaline and transition metal cations
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The synthesis of diazatetraoxacyclooctadecane derivatives bearing two catechol groups was achieved in good yield. The binucleating ligands were designed to bind both soft and hard cations simultaneously.
- Graf, Ernest,Hosseini, Mir Wais,Ruppert, Romain
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p. 7779 - 7782
(2007/10/02)
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- Conformationally Rigid Tricyclic Tripods: Synthesis and Application to Preparation of Enterobactin Analogs
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The syntheses of the conformationally rigid triol 2 and triamine 3 are described.One of the key features of these syntheses was that each of the intermediates involved contained a symmetry element, which made their structure elucidation facile and conclus
- Tse, Bruno,Kishi, Yoshito
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p. 7807 - 7814
(2007/10/02)
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- Spermexatin and Spermexatol: New Synthetic Spermidine-Based Siderophore Analogues
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Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described.Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate.These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine.Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized.Thereagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine.The ability of these iron chelators to stimulate microbial growth is also described.
- Sharma, Sushil K.,Miller, Marvin J.,Payne, Shelley M.
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p. 357 - 367
(2007/10/02)
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- Peptide derivatives having an inhibitory action on hydroxylating enzymes, a process for their preparation, agents containing them, and their use
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The invention relates to peptide derivatives of the formula STR1 in which STR2 represents an acyl radical, B represents the radical of a dipeptide composed of a Nω -acylated basic α-amino acid and another α-amino acid, and W represents hydroxyl or optionally substituted amino, to a process for their preparation, to agents containing them, and to their use.
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- Synthesis of Parabactin Analogues and Formation of Transition Metal Complexes of Parabactin and Related Compounds
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Transition metal complexes of parabactin and its related synthetic spermidine catecholamides which lack the central o-hydroxyphenyloxazoline were studied by the potentiometric titration method, e.s.r. spectroscopy, and fast atom bombardment mass spectrometry (FAB-MS).Direct mass spectral sampling of the parabactin-Fe(III) complex in glycerol solution was first achieved by FAB-MS spectrometry, confirming that the composition of the parabactin-Fe(III) complex is (2-)*2Na(1+) and that the iron(III) ion binds with two catechols and an o-hydroxyphenyl-Δ2-oxazoline moiety in NaOH solution.The e.s.r. g value (4.5) of the parabactin-Fe(III) complex differed from those (4.3) of the 3:1 catechol-Fe(III) complex and other parabactin-related catecholamide-Fe(III) complexes.These results suggest that the structure of the parabactin-Fe(III) complex differs considerably from the regular octahedral structure of the 3:1 catechol-Fe(III) complex and may have a structure similar to the ferrimycobactin P-Fe(III) complex, in which the iron(III) lies exposed in a splayed V-shaped cleft and binds with five oxygens and one nitrogen in a very strained octahedron.
- Miyasaka, Tadayo,Nagao, Yoshimitsu,Fujita, Eiichi,Sakurai, Hiromu,Ishizu, Kazuhiko
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p. 1542 - 1550
(2007/10/02)
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