Recent trends in glycodendrimer syntheses and applications

被引:192
作者
Chabre, Yoann M. [1 ]
Roy, Rene [1 ]
机构
[1] Univ Quebec, Dept Chem, Montreal, PQ H3C 3P8, Canada
关键词
adhesin; antigen; click chemistry; DC-SIGN; dendrimer; dendron; galectin; glycodendrimer; glycomimetics; glycopeptide; glycopolymer; hemagglutination; lectin; multivalency; triazole;
D O I
10.2174/156802608785848987
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Carbohydrate protein interactions are at the front of several biological interactions spanning from cell growth and differentiation, cell signaling, apoptosis, cancer, and microbial infections. Classical medicinal glycochemistry has so far concentrated on designing glycosyl transferase and glycohydrolase inhibitors for which only handful candidates have emerged. Added to the complexity of drug resistances, drugs in development have rapidly witnessed this limitation as well. New approaches are therefore highly encouraged. Amongst these, blocking pathogen adhesions to host tissues as an early preventive mechanism is a foreseeable potentiality. It has the clear advantage that the pathogens are unlikely to mutate their anchoring motifs without upsetting their own binding to host tissues. An added dilemma is that these binding interactions are usually too weak to provide suitable drug candidates. As a consequence, the community has successfully come up with multivalent glycoconjugates having greatly enhanced avidity. An alternative strategy in which both monovalent ligands as well as the multivalent scaffolds undergoing QSAR improvement is thus suggested. This review will highlight recent trends toward the design of multivalent glycodendrimers and their biological applications.
引用
收藏
页码:1237 / 1285
页数:49
相关论文
共 191 条
[81]   Glycodendrimer synthesis without using protecting groups [J].
Kieburg, C ;
Lindhorst, TK .
TETRAHEDRON LETTERS, 1997, 38 (22) :3885-3888
[82]   Supramolecular one-pot approach to fluorescent glycodendrimers [J].
Kikkeri, Raghavendra ;
Hossain, Laila H. ;
Seeberger, Peter H. .
CHEMICAL COMMUNICATIONS, 2008, (18) :2127-2129
[83]   Neoglycopeptide dendrimer libraries as a source of lectin binding ligands [J].
Kolomiets, Elena ;
Johansson, Emma M. V. ;
Renaudet, Olivier ;
Darbre, Tamis ;
Reymond, Jean-Louis .
ORGANIC LETTERS, 2007, 9 (08) :1465-1468
[84]   Multivalent ligands for the mannose-specific lectin on type 1 fimbriae of Escherichia coli:: syntheses and testing of trivalent α-D-mannoside clusters [J].
Kötter, S ;
Krallmann-Wenzel, U ;
Ehlers, S ;
Lindhorst, TK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (14) :2193-2200
[85]   Fully synthetic carbohydrate HIV antigens designed on the logic of the 2G12 antibody [J].
Krauss, Isaac J. ;
Joyce, Joseph G. ;
Finnefrock, Adam C. ;
Song, Hong C. ;
Dudkin, Vadim Y. ;
Geng, Xudong ;
Warren, J. David ;
Chastain, Michael ;
Shiver, John W. ;
Danishefsky, Samuel J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :11042-+
[86]   Dependence of effective molarity on linker length for an intramolecular protein-ligand system [J].
Krishnamurthy, Vijay M. ;
Semetey, Vincent ;
Bracher, Paul J. ;
Shen, Nan ;
Whitesides, George M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1312-1320
[87]  
Lahm Harald, 2004, Glycoconj J, V20, P227
[88]   Prevention of influenza pneumonitis by sialic acid-conjugated dendritic polymers [J].
Landers, JJ ;
Cao, ZY ;
Lee, I ;
Piehler, LT ;
Myc, PP ;
Myc, A ;
Hamouda, T ;
Galecki, AT ;
Baker, JR .
JOURNAL OF INFECTIOUS DISEASES, 2002, 186 (09) :1222-1230
[89]   Mannosyl glycodendritic structure inhibits DC-SIGN-mediated Ebola virus infection in cis and in trans [J].
Lasala, F ;
Arce, E ;
Otero, JR ;
Rojo, J ;
Delgado, R .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2003, 47 (12) :3970-3972
[90]   Syntheses of glycodendrimers having scyllo-inositol as the scaffold [J].
Lee, NY ;
Jang, WJ ;
Yu, SH ;
Im, J ;
Chung, SK .
TETRAHEDRON LETTERS, 2005, 46 (36) :6063-6066