This tutorial review surveys and highlights the integration of different molecular wires-in combination with chromophores that exhibit (i) significant absorption cross section throughout the visible part of the solar spectrum and (ii) good electron donating power-into novel electron donor-acceptor conjugates. The focus is predominantly on charge transfer and charge transport features of the most promising systems.
The covalent connection of the electron acceptor C 60 to p-quinonoid pi-extended tetrathiafulvalenes (exTTFs) has allowed for the preparation of new photo- and electroactive conjugates able to act as artificial photosynthetic systems and active molecular materials in organic photovoltaics. The gain of aromaticity undergone by the pi-extended TTF unit in the oxidation process results in highly stabilized radical ion pairs, namely, C 60 (*-)/exTTF (*+). Lifetimes for such charge-separated states, ranging from a few nanoseconds to hundreds of microseconds, have been achieved by rationally modifying the nature of the chemical spacers. These long-lived radical pairs are called to play an important role for the conversion of sunlight into chemical or electrical power.
Fullerene hexakis-adducts bearing 12 peripheral carbohydrate moieties have been prepared by grafting sugar derivatives onto the fullerene core through the copper mediated Huisgen 1,3-dipolar cycloaddition of azides and alkynes.
After
the last epidemic of the Zika virus (ZIKV) in Brazil that
peaked in 2016, growing evidence has been demonstrated of the link
between this teratogenic flavivirus and microcephaly cases. However,
no vaccine or antiviral drug has been approved yet. ZIKV and Dengue
viruses (DENV) entry to the host cell takes place through several
receptors, including dendritic cell-specific intercellular adhesion
molecule-3-grabbing nonintegrin (DC-SIGN), so that the blockade of
this receptor through multivalent glycoconjugates supposes a promising
biological target to inhibit the infection process. In order to get
enhanced multivalency in biocompatible systems, tridecafullerenes
appended with up to 360 1,2-mannobiosides have been synthesized using
a strain-promoted cycloaddition of azides to alkynes (SPAAC) strategy.
These systems have been tested against ZIKV and DENV infection, showing
an outstanding activity in the picomolar range.
Water-soluble glycofullerenes based on a hexakis-adduct of [60]fullerene with an octahedral addition pattern are very attractive compounds providing a spherical presentation of carbohydrates. These tools have been recently described and they have been used to interact with lectins in a multivalent manner. Here, we present the use of these glycofullerenes, including new members with 36 mannoses, as compounds able to inhibit a DC-SIGN-dependent cell infection by pseudotyped viral particles. The results obtained in these experiments demonstrate for the first time that these glycoconjugates are adequate to inhibit efficiently an infection process, and therefore, they can be considered as very promising and interesting tools to interfere in biological events where lectins such as DC-SIGN are involved.
The infection of humans by lethal pathogens such as Ebola and other related viruses has not been properly addressed so far. In this context, a relevant question arises: What can chemistry do in the search for new strategies and approaches to solve this emergent problem? Although initially a variety of known chemical compounds-for other purposes-proved disappointing in tests against Ebola virus (EBOV) infection, more recently, specific molecules have been prepared. In this Perspective, we present new approaches directed at the design of efficient entry inhibitors to minimize the development of resistance by viral mutations. In particular, we focus on dendrimers as well as fullerene C-with a unique symmetrical and 3D globular structure-as biocompatible carbon platforms for the multivalent presentation of carbohydrates. The antiviral activity of these compounds in an Ebola pseudotyped infection model was in the low micromolar range for fullerenes with 12 and 36 mannoses. However, new tridecafullerenes-in which the central alkyne scaffold of [60]fullerene is connected to 12 sugar-containing [60]fullerene units (total 120 mannoses)-exhibit an outstanding antiviral activity with IC in the sub-nanomolar range! The multivalent presentation of specific carbohydrates by using 3D fullerenes as controlled biocompatible carbon scaffolds represents a real advance, being currently the most efficient molecules in vitro against EBOV infection. However, additional studies are needed to determine the optimized fullerene-based leads for practical applications.
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