Thiourea-based spacers in potent divalent inhibitors of Pseudomonas aeruginosa virulence lectin LecA

被引：7
作者：
Pukin, Aliaksei V. [1 ]
Brouwer, Arwin J. [1 ]
Koomen, Leonie [1 ]
van Ufford, H. C. Quarles [1 ]
Kemmink, Johan [1 ]
de Mol, Nico J. [1 ]
Pieters, Roland J. [1 ]
机构：
[1] Univ Utrecht, Utrecht Inst Pharmaceut Sci, Dept Med Chem & Chem Biol, NL-3508 TB Utrecht, Netherlands
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 44期
关键词：
DRUG; GLYCOCLUSTERS; DERIVATIVES; DESIGN; ISOTHIOCYANATES; CYTOTOXICITY; MULTIVALENCY; RECOGNITION; BACTERIAL; AFFINITY;
D O I：
10.1039/c5ob01452b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new divalent highly potent inhibitor of the Pseudomonas aeruginosa lectin and virulence factor LecA was prepared. It contains two thiourea linkages which were found to be in the Z,Z isomeric form. This brings the spacer into an elongated conformation required to bridge the two binding sites, which results in the chelating binding mode responsible for the high potency.
引用
收藏
页码：10923 / 10928
页数：6
相关论文
共 30 条
  • [1] Structure-activity relationships in platinum-acridinylthiourea conjugates: effect of the thiourea nonleaving group on drug stability, nucleobase affinity, and in vitro cytotoxicity
    Ackley, MC
    Barry, CG
    Mounce, AM
    Farmer, MC
    Springer, BE
    Day, CS
    Wright, MW
    Berners-Price, SJ
    Hess, SM
    Bierbach, U
    [J]. JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2004, 9 (04): : 453 - 461
  • [2] Multivalent glycoconjugates as anti-pathogenic agents
    Bernardi, Anna
    Jimenez-Barbero, Jesus
    Casnati, Alessandro
    De Castro, Cristina
    Darbre, Tamis
    Fieschi, Franck
    Finne, Jukka
    Funken, Horst
    Jaeger, Karl-Erich
    Lahmann, Martina
    Lindhorst, Thisbe K.
    Marradi, Marco
    Messner, Paul
    Molinaro, Antonio
    Murphy, Paul V.
    Nativi, Cristina
    Oscarson, Stefan
    Penades, Soledad
    Peri, Francesco
    Pieters, Roland J.
    Renaudet, Olivier
    Reymond, Jean-Louis
    Richichi, Barbara
    Rojo, Javier
    Sansone, Francesco
    Schaeffer, Christina
    Turnbull, W. Bruce
    Velasco-Torrijos, Trinidad
    Vidal, Sebastien
    Vincent, Stephane
    Wennekes, Tom
    Zuilhof, Han
    Imberty, Anne
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (11) : 4709 - 4727
  • [3] Antiadhesive Properties of Glycoclusters against Pseudomonas aeruginosa Lung Infection
    Boukerb, Amine M.
    Rousset, Audric
    Galanos, Nicolas
    Mear, Jean-Baptiste
    Thepaut, Marion
    Grandjean, Teddy
    Gillon, Emilie
    Cecioni, Samy
    Abderrahmen, Claire
    Faure, Karine
    Redelberger, David
    Kipnis, Eric
    Dessein, Rodrigue
    Havet, Stephane
    Darblade, Benoit
    Matthews, Susan E.
    de Bentzmann, Sophie
    Guery, Benoit
    Cournoyer, Benoit
    Imberty, Anne
    Vidal, Sebastien
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (24) : 10275 - 10289
  • [4] CAMARASA MJ, 1984, SYNTHESIS-STUTTGART, P509
  • [5] Glycomimetics versus Multivalent Glycoconjugates for the Design of High Affinity Lectin Ligands
    Cecioni, Samy
    Imberty, Anne
    Vidal, Sebastien
    [J]. CHEMICAL REVIEWS, 2015, 115 (01) : 525 - 561
  • [6] Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm
    Cecioni, Samy
    Praly, Jean-Pierre
    Matthews, Susan E.
    Wimmerova, Michaela
    Imberty, Anne
    Vidal, Sebastien
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) : 6250 - 6263
  • [7] Structural basis of calcium and galactose recognition by the lectin PA-IL of Pseudomonas aeruginosa
    Cioci, G
    Mitchell, EP
    Gautier, C
    Wimmerová, M
    Sudakevitz, D
    Pérez, S
    Gilboa-Garber, N
    Imberty, A
    [J]. FEBS LETTERS, 2003, 555 (02) : 297 - 301
  • [8] Synthesis of porphyrin glycoconjugates bearing thiourea, thiocarbamate and carbamate connecting groups: Influence of the linker on chemical and photophysical properties
    Dallagnol, Juliana C. C.
    Ducatti, Diogo R. B.
    Barreira, Sandra M. W.
    Noseda, Miguel D.
    Duarte, Maria Eugenia R.
    Goncalves, Alan Guilherme
    [J]. DYES AND PIGMENTS, 2014, 107 : 69 - 80
  • [9] Multivalency as a Chemical Organization and Action Principle
    Fasting, Carlo
    Schalley, Christoph A.
    Weber, Marcus
    Seitz, Oliver
    Hecht, Stefan
    Koksch, Beate
    Dernedde, Jens
    Graf, Christina
    Knapp, Ernst-Walter
    Haag, Rainer
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) : 10472 - 10498
  • [10] Fernández JMG, 2000, ADV CARBOHYD CHEM BI, V55, P35
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