- Small Molecule Inhibitors of the Bacterioferritin (BfrB)-Ferredoxin (Bfd) Complex Kill Biofilm-Embedded Pseudomonas aeruginosa Cells
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Bacteria depend on a well-regulated iron homeostasis to survive adverse environments. A key component of the iron homeostasis machinery is the compartmentalization of Fe3+ in bacterioferritin and its subsequent mobilization as Fe2+ to satisfy metabolic requirements. In Pseudomonas aeruginosa Fe3+ is compartmentalized in bacterioferritin (BfrB), and its mobilization to the cytosol requires binding of a ferredoxin (Bfd) to reduce the stored Fe3+ and release the soluble Fe2+. Blocking the BfrB-Bfd complex in P. aeruginosa by deletion of the bfd gene triggers an irreversible accumulation of Fe3+ in BfrB, concomitant cytosolic iron deficiency and significant impairment of biofilm development. Herein we report that small molecules developed to bind BfrB at the Bfd binding site block the BfrB-Bfd complex, inhibit the mobilization of iron from BfrB in P. aeruginosa cells, elicit a bacteriostatic effect on planktonic cells, and are bactericidal to cells embedded in mature biofilms.
- Soldano, Anabel,Yao, Huili,Punchi Hewage, Achala N. D.,Meraz, Kevin,Annor-Gyamfi, Joel K.,Bunce, Richard A.,Battaile, Kevin P.,Lovell, Scott,Rivera, Mario
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p. 123 - 140
(2020/12/21)
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- Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy
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Scalable syntheses of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki.Heck reaction to render the desired coupled products in high overall yield.
- Chen, Lei,Li, Jianfeng,Wang, Xiaoting,Zhang, Rong-Ping
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- Synthesis and antimicrobial activity of δ-viniferin analogues and isosteres
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The natural stilbenoid dehydro-δ-viniferin, containing a benzofuran core, has been recently identified as a promising antimicrobial agent. To define the structural elements relevant to its activity, we modified the styryl moiety, appended at C5 of the ben
- Catinella, Giorgia,Dallavalle, Sabrina,Krogfelt, Karen Angeliki,Mattio, Luce Micaela,Musso, Loana,Pedersen, Kasandra Juliet,Pinna, Cecilia,Pinto, Andrea
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supporting information
(2021/12/24)
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- XYLOSIDE DERIVATIVES OF RESVERATROL FOR USE THEREOF IN COSMETICS
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The present invention relates to the use of a compound of formula (I): in which R1, R2 and R3 independently denote: -a group of formula (II), or -a hydrogen atom H, it being understood that at least one of the radicals R1, R2, R3 denotes a group of formul
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Page/Page column 22; 23
(2019/07/13)
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- Total Synthesis of Two Glycosylated Stilbenes, Oxyresveratrol 2-O-β- d -Glucopyranoside and 2,3,5,4′-Tetrahydroxystilbene 2-O-β- d -Glucopyranoside
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Glycosylated stilbenes are biologically active secondary metabolites of plants and have the potential to alleviate a broad range of human diseases. However, some of these compounds are not naturally abundant, and thus the synthesis of such molecules is de
- Kumar, Sunil,Lee, Hsueh-Yun,Liou, Jing-Ping
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p. 1294 - 1301
(2017/05/31)
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- Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression
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A series of benzothiazol-2-one containing α-ethoxyphenylpropionic acid derivatives incorporating resveratrol or butein scaffolds were designed as fused full PPARγ agonist ligands and SIRT1-activating compounds for the treatment of type 2 diabetes (T2D) an
- Pirat, Celine,Dacquet, Catherine,Leclerc, Veronique,Hennuyer, Nathalie,Beucher-Gaudin, Monique,Zanirato, Ghislaine,Géant, Anne,Staels, Bart,Ktorza, Alain,Farce, Amaury,Caignard, Daniel-Henri,Berthelot, Pascal,Lebegue, Nicolas
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p. 310 - 326
(2017/06/14)
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- Resveratrol derivative containing fluorine group, and preparation method and application
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The invention belongs to the technical field of medicines and discloses a resveratrol derivative containing a fluorine group, and a preparation method and an application. The resveratrol derivative has the structural characteristics as shown in a general
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Paragraph 0068; 0073; 0074
(2017/09/01)
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- Identification of human T2R receptors that respond to bitter compounds that elicit the bitter taste in compositions, and the use thereof in assays to identify compounds that inhibit (block) bitter taste in compositions and use thereof
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The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.
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Page/Page column 360; 362; 363
(2016/02/26)
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- Synthesis of a tetrasubstituted tetrahydronaphthalene scaffold for α-helix mimicry via a MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation
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α-Helices are ubiquitous protein recognition elements that bind diverse biomolecular targets. The synthesis of a small molecule scaffold to present the side chains of an α-helix is described. The 1,3,5,7-tetrasubstituted 1,2,3,4-tetrahydronaphthalene scaf
- Naduthambi, Devan,Bhor, Santosh,Elbaum, Michael B.,Zondlo, Neal J.
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p. 4892 - 4895
(2013/10/08)
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- Synthesis of the spiroketal core of integramycin
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A concise synthetic strategy towards the spiroketal core of the HIV-integrase inhibitor integramycin (1) was developed. The required ketone precursor was efficiently constructed from two simple and easily accessible subunits by means of a hydrozirconation/copper catalyzed acylation reaction. The effects of different protecting groups on the spiroketalization step were also investigated.
- Prusov, Evgeny V.
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p. 2446 - 2450
(2014/01/06)
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- Molecular docking studies of (1E,3E,5E )-1,6-bis(substituted phenyl)-hexa-1,3,5-triene and 1,4-bis(substituted trans-styryl)benzene analogs as novel tyrosinase inhibitors
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We simulated the docking of the tertiary structure of mushroom tyrosinase with our compounds. From the structure-tyrosinase inhibitory activity relationship, it is notable that compounds 4, 8 and 11 showed similar or better activity rates than kojic acid which was used as a positive control. Compounds 17, 21, and 23 among benzene analogs that possess the same substituent showed significantly lower tyrosinase inhibitory effects. Therefore, we have confirmed that among the compounds showing better tyrosinase inhibitory effects than kojic acid, the compounds with triene analogs have better tyrosinase inhibitory effect than the compounds with benzene analogs. Docking simulation suggested the mechanism of compounds by several key residues which had possible hydrogen bonding interactions. The pharmacophore model underlined the features of active compounds, 4,4′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)diphenol, 5,5′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxy-phenol), and 5,5′-((1 E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol among triene derivatives which had several hydrogen bond groups on both terminal rings. The soundness of the docking results and the agreement with the pharmacophores suggest that it can be conveniently exploited to design inhibitors with an improved affinity for tyrosinase.
- Ha, Young Mi,Lee, Hye Jin,Park, Daeui,Jeong, Hyoung Oh,Park, Ji Young,Park, Yun Jung,Lee, Kyung Jin,Lee, Ji Yeon,Moon, Hyung Ryong,Chung, Hae Young
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- Unexpected O-alkylation and ester migration in phenolic 2,3-diaryl-2,3-dihydrobenzo[b]furans
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O-alkylation of 2-(4-methoxyphenyl)-5-hydroxy-3-[1,3-phenylene-bis(4- nitrobenzoate)]-2,3-dihydrobenzo[b]furan results in the unexpected hydrolysis of the nitrobenzoate esters, transfer of a 4-nitrobenzoic acid group to the 5-hydroxyl group and double alkylation of the newly formed 3,5-diphenol moiety. A range of alkyl halides can be used and give access to O-alkyl analogues of -viniferin.
- Tran, Henry,Dickson, Benjamin D.,Barker, David
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p. 2093 - 2096
(2013/04/23)
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- MOLECULARLY IMPRINTED POLYMERS
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The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
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- Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction
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A series of monophenols and diphenols containing the ferrocene-C triazolyl and ferrocene-Ntriazolyl bond were prepared in a cycloaddition reaction of ethynylferrocene with aryl and benzyl azides and in a reaction of azidoferrocene with phenylacetylenes, respectively. The anticancer activity of the prepared compounds against hormone-dependent (MCF-7) and hormone-independent (HCC38) breast cancer cell lines was studied. The investigated compounds exhibited moderate anticancer activity against hormone-independent (IC50 ~ 15-48 μM) cancer cell line and low activity against hormone-dependent cancer cell line (IC50 ~ 84-98 μM).
- Plazuk, Damian,Rychlik, B?azej,B?auz, Andrzej,Domaga?a, S?awomir
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scheme or table
p. 102 - 112
(2012/09/07)
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- HYDROXYL GROUP-CONTAINING METHYLSTYRENE AND POLYMERS INCORPORATING SAME
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Vulcanizates with desirable properties can be obtained from compounds incorporating polymers that include hydroxyl group-containing α-methylstyrene functionalities. The functionalities can be incorporated by using any or all of appropriate initiators, mon
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Page/Page column 21
(2011/12/14)
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- Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites
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Five resveratrol sulfate metabolites were synthesized and assessed for activities known to be mediated by resveratrol: inhibition of tumor necrosis factor (TNF) α induced NFkB activity, cylcooxygenases (COX-1 and COX-2), aromatase, nitric oxide
- Hoshino, Juma,Park, Eun-Jung,Kondratyuk, Tamara P.,Marler, Laura,Pezzuto, John M.,Van Breemen, Richard B.,Mo, Shunyan,Li, Yongchao,Cushman, Mark
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experimental part
p. 5033 - 5043
(2010/09/16)
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- Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer
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A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 μM) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 μM. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC 50 1.7 μM and 0.27 μM, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer.
- Sun, Bin,Hoshino, Juma,Jermihov, Katie,Marler, Laura,Pezzuto, John M.,Mesecar, Andrew D.,Cushman, Mark
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experimental part
p. 5352 - 5366
(2010/09/05)
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- A novel competitive class of α-glucosidase inhibitors: (E)-1-phenyl-3-(4-styrylphenyl)urea derivatives
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Competitive glycosidase inhibitors are generally sugar mimics that are costly and tedious to obtain because they require challenging and elongated chemical synthesis, which must be stereo-and regiocontrolled. Here, we show that readily accessible achiral
- Kim, Jun Young,Lee, Ji Won,Kim, Young Soo,Lee, Yuno,Ryu, Young Bae,Kim, Songmi,Ryu, Hyung Won,Curtis-Long, Marcus J.,Lee, Keun Woo,Lee, Woo Song,Park, Ki Hun
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body text
p. 2125 - 2131
(2011/12/05)
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- Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARα
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Pterostilbene, a naturally occurring analog of resveratrol, has previously shown PPARα activation in H4IIEC3 cells and was found to decrease cholesterol levels in animals. In this study, analogs of pterostilbene were synthesized and their ability to activ
- Mizuno, Cassia S.,Ma, Guoyi,Khan, Shabana,Patny, Akshay,Avery, Mitchell A.,Rimando, Agnes M.
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p. 3800 - 3808
(2008/09/21)
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- Quinone reductase induction activity of methoxylated analogues of resveratrol
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Agents that induce the activity of phase II enzymes play an important role in intervening with the carcinogenic process at the initiation stage. Resveratrol is well known for its chemopreventive activity against major stages of carcinogenesis. In this study, several methoxylated analogues of resveratrol were synthesized and evaluated for their ability to induce the activity of the phase II enzyme quinone reductase (QR). Methoxy groups serve to increase lipophilicity and improve metabolic stability. Compared to resveratrol, analogues with ortho-methoxy substituents were found to be more potent inducers of QR and to exert their activity in a qualitatively different manner. The greater induction activities associated with these stilbenoids serve as a useful starting point for the design of improved chemopreventive agents.
- Zhang,Go
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p. 841 - 850
(2008/02/12)
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- Antineoplastic agents. 465. Structural modification of resveratrol: Sodium resverastatin phosphate
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As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI50 = 0.01-0.001 μg/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.
- Pettit, George R.,Grealish, Matthew P.,Jung, M. Katherine,Hamel, Ernest,Pettit, Robin K.,Chapuis, J.-Charles,Schmidt, Jean M.
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p. 2534 - 2542
(2007/10/03)
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- End-cap stabilized oligoynes: Model compounds for the linear sp carbon allotrope carbyne
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Three series of differently 3,5-disubstituted α,ω-diphenylpolyynes Ar-(C≡C)n-Ar (n=2, 4, 6, 8, 10) were synthesized under optimized Cadiot - Chodkiewicz conditions, isolated and completely characterized. These compounds can be considered as mod
- Gibtner, Thomas,Hampel, Frank,Gisselbrecht, Jean-Paul,Hirsch, Andreas
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p. 408 - 432
(2007/10/03)
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- A new efficient resveratrol synthesis
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The (E)-3,4′,5-trihydroxystilbene (resveratrol) was synthesised via Heck reaction in few steps and with an overall 70% yield.
- Guiso, Marcella,Marra, Carolina,Farina, Angela
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p. 597 - 598
(2007/10/03)
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- Climacostol, a defense toxin of the heterotrich ciliate Climacostomum virens against predators
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A toxic substance (climacostol) of the protozoan ciliate Climacostomum virens against the predatory ciliate Dileptus margaritifer was established as 1,3-dihydoxy-5-[(Z)-2'-nonenyl]benzene. The structure was rigorously confirmed by the total synthesis.
- Masaki, Miyuki Eiraku,Harumoto, Terue,Terazima, Masayo Noda,Miyake, Akio,Usuki, Yoshinosuke,Iio, Hideo
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p. 8227 - 8229
(2007/10/03)
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- Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)
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(E)-3-(β-D-Glucopyranosyloxy)-4',5-dihydroxystilbene (resveratrol 3-β-D-glucoside, piceid), (Z)-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin A-1), (Z)-3'-hydroxy-3,4,4', 5-tetramethoxystilbene (combretastatin A-4), (Z)-2'-hydroxy-3,4,4',5-tetramethoxystilbene (combretastatin iso-A-4), α,β-dihydro-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin B-1), the corresponding glucosides, and related compounds have been synthesized via Wittig reactions followed by,glucosylation under phase-transfer catalysis. Most of the compounds synthesized have been tested with respect to biological activity (cytostatic, cytotoxic, antimitotic, neurotoxic, antiplatelet aggregation activity).
- Orsini, Fulvia,Pelizzoni, Francesca,Bellini, Barbara,Miglierini, Giuliana
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- Desilylation Reactions of Polys
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Poly and poly (R)-2-phenylpropionate> were desilylated with Bu4NF in THF.The solution changed its color depending on the structure of the aromatic pe
- Yamaguchi, Masahiko,Omata, Kenji,Hirama, Masahiro
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p. 2261 - 2262
(2007/10/02)
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