STD NMR and molecular modelling insights into interaction of novel mannose-based ligands with DC-SIGN

被引：10

作者：

Kotar, Anita ^{[1
]}

Tomasic, Tihomir ^{[2
]}

Zivkovic, Martina Lenarcic ^{[1
]}

Jug, Gregor ^{[2
]}

Plavec, Janez ^{[1
,3
,4
]}

Anderluh, Marko ^{[2
]}

机构：

[1] Natl Inst Chem, Slovenian NMR Ctr, Hajdrihova 19, Ljubljana 1000, Slovenia

[2] Univ Ljubljana, Fac Pharm, Askerceva 7, Ljubljana 1000, Slovenia

[3] EN FIST Ctr Excellence, Trg OF 13, Ljubljana 1000, Slovenia

[4] Univ Ljubljana, Fac Chem & Chem Technol, Vecna Pot 113, Ljubljana 1000, Slovenia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 03期

关键词：

GENERAL FORCE-FIELD; C-TYPE LECTINS; CARBOHYDRATE-RECOGNITION; BINDING; DYNAMICS; HIV; ORGANIZATION; ANTAGONISTS; AUTOMATION; INHIBITORS;

D O I：

10.1039/c5ob01916h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Study of interaction of mannose-based ligands with receptor DC-SIGN using high resolution NMR in combination with molecular modelling showed that four alpha-D-mannoside ligands interact with the binding site predominantly through the mannose moiety. The other two aromatic groups that are bound to alpha-D-mannose through a glycerol linker demonstrate interaction that can be related to their substitution pattern. Ligand with naphthyl and meta-substituted phenyl ring exhibited the most favourable binding characteristics. In addition to the predicted hydrophobic interactions of aromatic moieties our results propose new contacts of substituted phenyl moiety in the more polar area of the flat binding site of DC-SIGN and thus offer new possibilities in further designing of novel, more potent DC-SIGN antagonists.

引用

页码：862 / 875

页数：14

共 46 条

[1] DCs and NK cells: critical effectors in the immune response to HIV-1 [J].

Altfeld, Marcus ;

Fadda, Lena ;

Frleta, Davor ;

Bhardwaj, Nina .

NATURE REVIEWS IMMUNOLOGY, 2011, 11 (03) :176-186

[2] DC-SIGN Antagonists, a Potential New Class of Anti-Infectives [J].

Anderluh, M. ;

Jug, G. ;

Svajger, U. ;

Obermajer, N. .

CURRENT MEDICINAL CHEMISTRY, 2012, 19 (07) :992-1007

[3] Saturation Transfer Difference (STD) NMR Spectroscopy Characterization of Dual Binding Mode of a Mannose Disaccharide to DC-SIGN [J].

Angulo, Jesus ;

Diaz, Irene ;

Reina, Jose J. ;

Tabarani, Georges ;

Fieschi, Franck ;

Rojo, Javier ;

Nieto, Pedro M. .

CHEMBIOCHEM, 2008, 9 (14) :2225-2227

[4] Internalization and Accumulation in Dendritic Cells of a Small pH-Activatable Glycomimetic Fluorescent Probe as Revealed by Spectral Detection [J].

Arsov, Zoran ;

Svajger, Urban ;

Mravljak, Janez ;

Pajk, Stane ;

Kotar, Anita ;

Urbancic, Iztok ;

Strancar, Janez ;

Anderluh, Marko .

CHEMBIOCHEM, 2015, 16 (18) :2660-2667

[5] High-Affinity Glycopolymer Binding to Human DC-SIGN and Disruption of DC-SIGN Interactions with HIV Envelope Glycoprotein [J].

Becer, C. Remzi ;

Gibson, Matthew I. ;

Geng, Jin ;

Ilyas, Rebecca ;

Wallis, Russell ;

Mitchell, Daniel A. ;

Haddleton, David M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15130-15132

[6]

BioSolve IT (GmbH), LEADIT VERS 2 1 3

[7] Non-carbo hydrate inhibitors of the lectin DC-SIGN [J].

Borrok, M. Jack ;

Kiessling, Laura L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12780-12785

[8] Role of DC-SIGN and L-SIGN receptors in HIV-1 vertical transmission [J].

da Silva, Ronald Celerino ;

Segat, Ludovica ;

Crovella, Sergio .

HUMAN IMMUNOLOGY, 2011, 72 (04) :305-311

[9] Polymeric Anti-HIV Therapeutics [J].

Danial, Maarten ;

Klok, Harm-Anton .

MACROMOLECULAR BIOSCIENCE, 2015, 15 (01) :9-35

[10] PARTICLE MESH EWALD - AN N.LOG(N) METHOD FOR EWALD SUMS IN LARGE SYSTEMS [J].

DARDEN, T ;

YORK, D ;

PEDERSEN, L .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (12) :10089-10092

← 1 2 3 4 5 →