Synthesis of chondroitin sulfate CC and DD tetrasaccharides and interactions with 2H6 and LY111.

Abstract:

:We synthesized the biotinylated chondroitin sulfate tetrasaccharides CS-CC [-3)βGalNAc6S(1-4)βGlcA(1-]2 and CS-DD [-3)βGalNAc6S(1-4)βGlcA2S(1-]2 which possess sulfate groups at O-6 of GalNAc and an additional sulfate group at O-2 of GlcA, respectively. We also analyzed interactions among CS-CC and CS-DD and the antibodies 2H6 and LY111, both of which are known to bind with CS-A, while CS-DD was shown for the first time to bind with both antibodies.

journal_name

Bioorg Med Chem

authors

Matsushita K,Nakata T,Takeda-Okuda N,Nadanaka S,Kitagawa H,Tamura JI

doi

10.1016/j.bmc.2018.01.011

subject

Has Abstract

pub_date

2018-03-01 00:00:00

pages

1016-1025

issue

5

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(17)32396-9

journal_volume

26

pub_type

杂志文章
  • Chemical synthesis and biological activity of novel brominated 7-deazaadenosine-3',5'-cyclic monophosphate derivatives.

    abstract::Synthetic derivatives of cyclic adenosine monophosphate, such as halogenated or other more hydrophobic analogs, are widely used compounds, to investigate diverse signal transduction pathways of eukaryotic cells. This inspired us to develop cyclic nucleotides, which exhibit chemical structures composed of brominated 7-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.03.024

    authors: Lelle M,Otte M,Thon S,Bertinetti D,Herberg FW,Benndorf K

    更新日期:2019-04-15 00:00:00

  • Synthesis of (+)-crocacin D and simplified bioactive analogues.

    abstract::The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.01.008

    authors: Pasqua AE,Ferrari FD,Crawford JJ,Whittingham WG,Marquez R

    更新日期:2015-03-01 00:00:00

  • Novel 5-HT7R antagonists, arylsulfonamide derivatives of (aryloxy)propyl piperidines: Add-on effect to the antidepressant activity of SSRI and DRI, and pro-cognitive profile.

    abstract::A novel series of arylsulfonamide derivatives of (aryloxy)propyl piperidines was designed to obtain potent 5-HT7R antagonists. Among the compounds evaluated herein, 3-chloro-N-{1-[3-(1,1-biphenyl-2-yloxy)2-hydroxypropyl]piperidin-4-yl}benzenesulfonamide (25) exhibited antagonistic properties at 5-HT7R and showed selec...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.03.057

    authors: Canale V,Partyka A,Kurczab R,Krawczyk M,Kos T,Satała G,Kubica B,Jastrzębska-Więsek M,Wesołowska A,Bojarski AJ,Popik P,Zajdel P

    更新日期:2017-05-15 00:00:00

  • Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH.

    abstract::The boronic acid group is widely used in chemosensor design due to its ability to reversibly bind diol-containing compounds. The thermodynamic properties of the boronic acid-diol binding process have been investigated extensively. However, there are few studies of the kinetic properties of such binding processes. In t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.03.014

    authors: Ni N,Laughlin S,Wang Y,Feng Y,Zheng Y,Wang B

    更新日期:2012-05-01 00:00:00

  • 2-(2-Bromophenyl)-formononetin and 2-heptyl-formononetin are PPARγ partial agonists and reduce lipid accumulation in 3T3-L1 adipocytes.

    abstract::Isoflavones are bioactive compounds that have been shown to decrease lipid accumulation in vitro. However, the knowledge of the isoflavone formononetin is limited. The aim of the study was to assess the effects of formononetin and its two synthetic analogues, 2-(2-bromophenyl)-formononetin and 2-heptyl-formononetin, o...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.037

    authors: Andersen C,Kotowska D,Tortzen CG,Kristiansen K,Nielsen J,Petersen RK

    更新日期:2014-11-01 00:00:00

  • The conformation and activity relationship of fused analogs of DuP753.

    abstract::We have prepared three conformationally restricted analogs of DuP753 in which one of the phenyl rings in the biphenyl moiety is fused to the imidazole ring, and have investigated the conformation-biological activity relationship of these compounds. Conformational analysis on DuP753 and these compounds confirms that a ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(95)00002-x

    authors: Yoo SE,Shin YA,Lee SH,Kim NJ

    更新日期:1995-03-01 00:00:00

  • Inhibitory effect of beta-diketones and their metal complexes on TNF-alpha induced expression of ICAM-1 on human endothelial cells.

    abstract::Recent reports show that the natural beta-diketone curcumin displays important biological properties regarding the intercellular adhesion molecule-1 (ICAM-1), which plays a critical role in the immune responses and inflammation. In this study the ICAM-1 inhibitory activity of beta-diketone compounds, which are curcumi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.07.064

    authors: Caruso F,Pettinari C,Marchetti F,Rossi M,Opazo C,Kumar S,Balwani S,Ghosh B

    更新日期:2009-09-01 00:00:00

  • Design and synthesis of 1,2-annulated adamantane piperidines with anti-influenza virus activity.

    abstract::1-2 Annulated adamantane piperidines 4, 6, 16, 17, 19, 23 and 25 were synthesized and evaluated for anti-influenza A virus activity. The stereoelectronic requirements for optimal antiviral potency were investigated. Piperidine 23 proved to be the most active of the compounds tested against influenza A virus, being 3.5...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.01.009

    authors: Zoidis G,Kolocouris N,Naesens L,De Clercq E

    更新日期:2009-02-15 00:00:00

  • Synthesis, structure, molecular docking, and structure-activity relationship analysis of enamines: 3-aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials.

    abstract::Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.01.051

    authors: Xiao ZP,He XB,Peng ZY,Xiong TJ,Peng J,Chen LH,Zhu HL

    更新日期:2011-03-01 00:00:00

  • Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis.

    abstract::Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacter...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.09.012

    authors: Samala G,Brindha Devi P,Saxena S,Gunda S,Yogeeswari P,Sriram D

    更新日期:2016-11-01 00:00:00

  • Protein linear indices of the 'macromolecular pseudograph alpha-carbon atom adjacency matrix' in bioinformatics. Part 1: prediction of protein stability effects of a complete set of alanine substitutions in Arc repressor.

    abstract::A novel approach to bio-macromolecular design from a linear algebra point of view is introduced. A protein's total (whole protein) and local (one or more amino acid) linear indices are a new set of bio-macromolecular descriptors of relevance to protein QSAR/QSPR studies. These amino-acid level biochemical descriptors ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.01.062

    authors: Marrero-Ponce Y,Medina-Marrero R,Castillo-Garit JA,Romero-Zaldivar V,Torrens F,Castro EA

    更新日期:2005-04-15 00:00:00

  • Synthesis and evaluation of imidazole-dioxolane compounds as selective heme oxygenase inhibitors: effect of substituents at the 4-position of the dioxolane ring.

    abstract::Several imidazole-dioxolane compounds were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). These compounds, which include a series of substituted thiophenol and substituted phenol derivatives of (2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(phenylsulfanyl)methyl]-1,3-dioxol...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.01.078

    authors: Vlahakis JZ,Hum M,Rahman MN,Jia Z,Nakatsu K,Szarek WA

    更新日期:2009-03-15 00:00:00

  • Development of a platform for activatable fluorescent substrates of glucose transporters (GLUTs).

    abstract::We have developed a platform for activatable fluorescent substrates of glucose transporters (GLUTs). We firstly conjugated fluorescein to glucosamine via an amide or methylene linker at the C-2 position of d-glucosamine, but the resulting compounds, FLG1 and FLG2, showed no uptake into MIN6 cells. So, we changed the f...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.02.055

    authors: Takasugi T,Hanaoka K,Sasaki A,Ikeno T,Komatsu T,Ueno T,Yamada K,Urano Y

    更新日期:2019-05-15 00:00:00

  • Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure-anti-mycobacterial activities.

    abstract::The preparation of novel 5-aryl-2-thio-1,3,4-oxadiazoles 4a-41 and the computer-aided study of their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv (ATCC 27294) are reported. The average accuracy of the electronic-topological method and neural network methods applied to the activity predict...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.05.011

    authors: Macaev F,Rusu G,Pogrebnoi S,Gudima A,Stingaci E,Vlad L,Shvets N,Kandemirli F,Dimoglo A,Reynolds R

    更新日期:2005-08-15 00:00:00

  • The design and synthesis of a novel compound of berberine and baicalein that inhibits the efficacy of lipid accumulation in 3T3-L1 adipocytes.

    abstract::The combination of berberine and baicalein may have a better therapeutic effect against disease. To explore the combined effect of baicalein and berberine in the treatment of obesity, we designed and synthesized a hybrid compound, and its biological activities were evaluated in 3T3-L1 adipocytes. The structures of the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.08.013

    authors: Hao M,Li Y,Liu L,Yuan X,Gao Y,Guan Z,Li W

    更新日期:2017-10-15 00:00:00

  • New highly active taxoids from 9beta-dihydrobaccatin-9,10-acetals. Part 4.

    abstract::It was shown that a new taxane analogue 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both i.v. and p.o. administration, was prone to be metabolized by human liver microsomes. We identified a major metabolite, M-1, generated by human liver microsomes as 20a, a hydroxylated compound at the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00454-1

    authors: Takeda Y,Uoto K,Chiba J,Horiuchi T,Iwahana M,Atsumi R,Ono C,Terasawa H,Soga T

    更新日期:2003-10-01 00:00:00

  • Facile synthesis and characterization of novel pyrazole-sulfonamides and their inhibition effects on human carbonic anhydrase isoenzymes.

    abstract::In the current study, a series of pyrazole-sulfonamide derivatives (2-14) were synthesized, characterized, and the inhibition effects of the derivatives on human carbonic anhydrases (hCA I and hCA II) were investigated as in vitro. Structures of these sulfonamides were confirmed by FT-IR, (1)H NMR, (13)C NMR and LC-MS...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.11.012

    authors: Balseven H,Mustafa İşgör M,Mert S,Alım Z,Beydemir S,Ok S,Kasımoğulları R

    更新日期:2013-01-01 00:00:00

  • Selection of genomic target RNAs by iterative screening.

    abstract::A growing number of proteins are known to exert their regulatory or biological functions via RNA binding. In some cases genetic interactions allow us to infer candidate targets for RNA directed regulation, but in many other cases identification of potential regulatory targets is problematic. We have developed an in vi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00029-3

    authors: Brunel C,Ehresmann B,Ehresmann C,McKeown M

    更新日期:2001-10-01 00:00:00

  • Discovery of 1H-benzo[d][1,2,3]triazol-1-yl 3,4,5-trimethoxybenzoate as a potential antiproliferative agent by inhibiting histone deacetylase.

    abstract::Twenty-one benzotriazoles (3-16 and 18-24) were synthesized and half of them (5, 8-16, 20, and 21) were reported for the first time. Their antiproliferative activities against three human cancer cells were assayed. It revealed that 1H-benzo[d][1,2,3]triazol-1-yl 3,4,5-trimethoxybenzoate (9) showed considerable activit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.10.049

    authors: Fu J,Yang Y,Zhang XW,Mao WJ,Zhang ZM,Zhu HL

    更新日期:2010-12-15 00:00:00

  • Screening helix-threading peptides for RNA binding using a thiazole orange displacement assay.

    abstract::The fluorescent intercalator displacement assay using thiazole orange has been adapted to the study of RNA-binding helix-threading peptides (HTPs). This assay is highly sensitive with HTP-binding RNAs and provides binding affinity data in good agreement with quantitative ribonuclease footprinting without the need for ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.08.066

    authors: Krishnamurthy M,Schirle NT,Beal PA

    更新日期:2008-10-01 00:00:00

  • Structure-activity relationships in glycosylated 2-phenyl-indoles, 2-phenyl-benzo[b]thiophenes and 2-phenyl-benzo[b]furans as DNA binding and potential antitumor agents.

    abstract::In earlier investigations we have described the synthesis and biological evaluation of a panel of novel glycosylated heteroaromatics (1-12). It was found that these compounds can bind to DNA in vitro and are cytotoxic against several cancer cell lines at low micromolar concentration. We report here structure-activity ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.01.014

    authors: Shi W,Lowary TL

    更新日期:2011-03-01 00:00:00

  • Protective effect of ε-viniferin on β-amyloid peptide aggregation investigated by electrospray ionization mass spectrometry.

    abstract::Abnormal β-amyloid peptide accumulation and aggregation is considered to be responsible for the formation and cerebral deposition of senile plaques in the brains of patients with Alzheimer's disease (AD). Inhibition of the formation of β-amyloid (Aβ) fibrils would be an attractive therapeutic target for the treatment ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.04.001

    authors: Richard T,Poupard P,Nassra M,Papastamoulis Y,Iglésias ML,Krisa S,Waffo-Teguo P,Mérillon JM,Monti JP

    更新日期:2011-05-15 00:00:00

  • Recent progress in discovery of small-molecule CCR5 chemokine receptor ligands as HIV-1 inhibitors.

    abstract::This review addresses key pharmacology and virology issues relevant in discovery and development of CCR5 antagonists as anti-HIV drugs, such as target validation, receptor internalization, allosterism, viral resistance and tropism. Recent progress in the discovery and development of CCR5 antagonists, SAR and clinical ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0968-0896(03)00161-5

    authors: Kazmierski W,Bifulco N,Yang H,Boone L,DeAnda F,Watson C,Kenakin T

    更新日期:2003-07-03 00:00:00

  • Synthesis, molecular docking and biological evaluation of N,N-disubstituted 2-aminothiazolines as a new class of butyrylcholinesterase and carboxylesterase inhibitors.

    abstract::A series of 31 N,N-disubstituted 2-amino-5-halomethyl-2-thiazolines was designed, synthesized, and evaluated for inhibitory potential against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and carboxylesterase (CaE). The compounds did not inhibit AChE; the most active compounds inhibited BChE and CaE with I...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.01.031

    authors: Makhaeva GF,Boltneva NP,Lushchekina SV,Serebryakova OG,Stupina TS,Terentiev AA,Serkov IV,Proshin AN,Bachurin SO,Richardson RJ

    更新日期:2016-03-01 00:00:00

  • Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects.

    abstract::Glyoxalase I (GLO I) is the rate-limiting enzyme for detoxification of methylglyoxal (MG), a side product of glycolysis, which is able to induce apoptosis. Since GLO I is known to be highly expressed in the most tumor cells and little in normal cells, specific inhibitors of this enzyme have been expected as effective ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.01.031

    authors: Takasawa R,Takahashi S,Saeki K,Sunaga S,Yoshimori A,Tanuma S

    更新日期:2008-04-01 00:00:00

  • Synthesis, biological evaluation and molecular modeling study of 2-amino-3,5-disubstituted-pyrazines as Aurora kinases inhibitors.

    abstract::Serine/threonine protein kinases Aurora A, B, and C play essential roles in cell mitosis and cytokinesis, and a number of Aurora kinase inhibitors have been evaluated in the clinic. Herein we report the synthesis and their antiproliferation of 3,5-disubstituted-2-aminopyrazines as kinases inhibitors. Amongst, 4-((3-am...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115351

    authors: Bo YX,Xiang R,Xu Y,Hao SY,Wang XR,Chen SW

    更新日期:2020-03-01 00:00:00

  • Antimitotic and antivascular activity of heteroaroyl-2-hydroxy-3,4,5-trimethoxybenzenes.

    abstract::This study reports the synthesis of a series of heteroaroyl-2-hydroxy-3,4,5-trimethoxybenzenes, which are potent antitubulin agents. Compound 13, (2-hydroxy-3,4,5-trimethoxyphenyl)-(6-methoxy-1H-indol-3-yl)-methanone exhibits marked antiproliferative activity against KB and MKN45 cells with IC50 values of 8.8 and 10.5...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.06.043

    authors: Lee HY,Chang CY,Lai MJ,Chuang HY,Kuo CC,Chang CY,Chang JY,Liou JP

    更新日期:2015-08-01 00:00:00

  • Synthesis and biological relationships of 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents.

    abstract::As part of a continuing search for potential anticancer drug candidates in the 2-phenyl-4-quinolone series, 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized and evaluated. Preliminary screening showed that carboxylic acid analogs containing a m-fluoro substituted 2-p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.09.041

    authors: Lai YY,Huang LJ,Lee KH,Xiao Z,Bastow KF,Yamori T,Kuo SC

    更新日期:2005-01-03 00:00:00

  • Phosphoenolpyruvate as a dual purpose reagent for integrated nucleotide/nicotinamide cofactor recycling.

    abstract::An efficient technique is presented which integrates cofactor dependent enzymic phosphorylation and dehydrogenation into a single, closed-loop system by employing phosphoenolpyruvate as the sacrificial reagent for sequential ATP and NAD+ recycling steps. Exemplary applications are developed for the synthesis of 6-phos...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(94)85012-7

    authors: Fessner WD,Sinerius G

    更新日期:1994-07-01 00:00:00

  • Synthesis, biological evaluation, and molecular modeling of cinnamic acyl sulfonamide derivatives as novel antitubulin agents.

    abstract::A series of novel cinnamic acyl sulfonamide derivatives (9a-16e) have been designed and synthesized and their biological activities were also evaluated as potential tubulin polymerization inhibitors. Among all the compounds, 10c showed the most potent growth inhibitory activity against B16-F10 cancer cell line in vitr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.088

    authors: Luo Y,Qiu KM,Lu X,Liu K,Fu J,Zhu HL

    更新日期:2011-08-15 00:00:00