CLICK MULTIVALENT GLYCOMATERIALS: GLYCOCLUSTERS, GLYCODENDRIMERS, GLYCOPOLYMERS, HYBRID GLYCOMATERIALS, AND GLYCOSURFACES - Click Chemistry in Glycoscience: New Developments and Strategies - page 161

O

O

O O

O

O

O O

O

O

O O

OO O O

O

O

O O

O

O

97 O O

O O

N 3 N 3 O O

O O

N 3

N 3 O O

O O

O O

O O

OO

98

N 3 O O N 3

O

O

O

O

O N 3

N 3 O

O O

O O

O O

O O

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N 3 N 3

99

FIGURE 6.7 Representative clickable poly(propargyl)-functionalized fullerene scaffolds.

of the key polyaromatic platform glycoconjugates suitable for CNT surface coating.
Bertozzi and coworkers [144] prepared octavalent mannose-, galactose-, and lactose-
conjugated click glycodendrimers with a terminal pyrene-bearing segment at the
focal point from the alkyne derivative 100 . Khiar and coworkers proposed, instead,
the azide-armed butterfly-like tetrabenzo[ a,c,g,i ]fluorene polyaromatic platform 101
[145], whereas Star and coworkers used the tetraalkynyl porphyrine scaffold 102
[146]. In all cases, the resulting glycoconjugates self-organized on the CNT surface
to form the corresponding multivalent click glyco-CNTs (Scheme 6.18).
Metal glyconanoparticles are probably the glyconanomaterials that have raised
the highest expectations in nanomedicine [147-149]. Examples of click-chemistry-
based glycocoating of either azide (TiO 2 ) [150] or alkyne functional metal nanoparti-
cles (Au) [151] have been reported. Interestingly, ZnS/CdSe glyconanoparticles 103
(Fig. 6.8), obtained by thiol coupling of trivalent galactosyl click glycodendrons
with preformed pyridine-capped nanoparticles were shown to be selectively uptake
by lung cancer cells enriched with membrane-bound asialoprotein receptors [152].