Chapter 10. Biological Applications of Fullerenes

Bianco, Alberto; Ros, Tatiana Da

doi:10.1039/9781847557711-00301

Cited by 6 publications

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“…Nearly 30 years after their discovery, fullerenes, the third allotrope of carbon, still attract the attention of many researchers worldwide due to their unique properties and their applications in a wide range of fields such as materials science or medicine. [1][2][3] Nowadays, one of the most active fields in fullerene chemistry is the search for molecular receptors capable to form stable associates with them. These receptors not only are useful for isolating fullerenes of the soot, but also for developing new materials for solar energy conversion, optoelectronics, catalysis and switching.…”

Section: Introductionmentioning

confidence: 99%

Fullerene recognition with molecular tweezers made up of efficient buckybowls: a dispersion-corrected DFT study

Josa

Rodrı́guez-Otero

Cabaleiro‐Lago

2015

Phys. Chem. Chem. Phys.

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In 2007, Sygula and co-workers introduced a novel type of molecular tweezers with buckybowl pincers that have attracted the substantial interest of researchers due to their ideal architecture for recognizing fullerenes by concave-convex π∙∙∙π interactions (A. Sygula et al., J. Am. Chem. Soc., 2007, 129, 3842). Although in recent years some modifications have been performed on these original molecular tweezers to improve their ability for catching fullerenes, very few improvements were achieved to date. For that reason, in the present work a series of molecular tweezers have been devised and their supramolecular complexes with C60 studied at the B97-D2/TZVP//SCC-DFTB-D and B97-D2/TZVP levels. Three different strategies have been tested: (1) changing the corannulene pincers to other buckybowls, (2) replacing the tetrabenzocyclooctatetraene tether by a buckybowl, and (3) adding methyl groups on the molecular tweezers. According to the results, all the three approaches are effective, in such a way that a combination of the three strategies results in buckycatchers with complexation energies (with C60) up to 2.6 times larger than that of the original buckycatcher, reaching almost -100 kcal mol(-1). The B97-D2/TZVP//SCC-DFTB-D approach can be a rapid screening tool for testing new molecular tweezers. However, since this approach does not reproduce correctly the deformation energy and this energy represents an important contribution to the total complexation energy of complexes, subsequent higher-level re-optimization is compulsory to achieve reliable results (the full B97-D2/TZVP level is used herein). This re-optimization could be superfluous when quite rigid buckycatchers are studied.

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Section: Introductionmentioning

confidence: 99%

Fullerene recognition with molecular tweezers made up of efficient buckybowls: a dispersion-corrected DFT study

Josa

Rodrı́guez-Otero

Cabaleiro‐Lago

2015

Phys. Chem. Chem. Phys.

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“…In this chapter we consider, above all, the most recent developments of biological and toxicological aspects of fullerene and related compounds of the last few years, considering that many reviews and books cover this topic up to 2006 (Jensen et al, 1996;Nakamura et al, 1996;Da Ros and Prato, 1999;Tagmatarchis and Shinohara, 2001;Bosi et al, 2003;Nakamura and Isobe, 2003;Sarova et al, 2006;Bianco and Da Ros, 2007).…”

Section: Introductionmentioning

confidence: 99%

Twenty Years of Promises: Fullerene in Medicinal Chemistry

Ros

2008

Medicinal Chemistry and Pharmacological Potential of Fullerenes and Carbon Nanotubes

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Many biological activities have been envisioned for fullerenes and some of them seem to be very promising. The lack of solubility in biologically friendly environments is the major obstacle in the development of this field. The possibility of multiple fuctionalization can be exploited to get more soluble compounds but, up to now, only a few polyadducts, presenting perfectly defined geometry, can be selectively prepared avoiding long purification processes.The toxicity of this third allotropic form of carbon is an aspect related to application in medicine and biology, while the concern about the environmental impact is due to the industrial production of fullerenes. Many studies are dedicated to both aspects and, so far, it is not possible to have a definitive answer although the current findings allow some optimistic vision.In this chapter the main biological applications of fullerene and fullerene derivatives will be reviewed, with special attention to the most recent advances in this field. Antiviral and antibacterial activity, enzymatic inhibition, and DNA photocleavage are some aspects considered herein, together with the use of these nanostructures as possible vectors for drug and gene delivery. The most promising applications include the use of endohedral fullerenes, filled by gadolinium, in magnetic resonance imaging (MRI) and the antioxidant capacity exploitation of some tris-adducts and fullerols.

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The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

Durka

Buffet

Iehl

et al. 2011

Chemistry A European J

101

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L,D-Heptosides (L-glycero-D-manno-heptopyranoses) are found in important bacterial glycolipids such as lipopolysaccharide (LPS), the biosynthesis of which is targeted for the development of novel antibacterial agents. This work describes the synthesis of a series of fullerene hexa-adducts bearing 12 copies of peripheral sugars displaying the mannopyranose core structure of bacterial L,D-heptoside. The multimers were assembled through an efficient copper-catalyzed alkyne-azide cycloaddition reaction as the final step. The final fullerene sugar balls were assayed as inhibitors of heptosyltransferase WaaC, the glycosyltransferase catalyzing the incorporation of the first L-heptose into LPS. Interestingly, the inhibition of the final molecules was found in the low micromolar range (IC(50) =7-45 μM), whereas the corresponding monomeric glycosides displayed high micromolar to low millimolar inhibition levels (IC(50) always above 400 μM). When evaluated on a "per-sugar" basis, these inhibition data showed that, in each case, the average affinity of a single glycoside of the fullerenes towards WaaC was significantly enhanced when displayed as a multimer, thus demonstrating an unexpected multivalent effect. To date, such a multivalent mode of inhibition had never been evidenced with glycosyltransferases.

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Chapter 10. Biological Applications of Fullerenes

Cited by 6 publications

References 0 publications

Fullerene recognition with molecular tweezers made up of efficient buckybowls: a dispersion-corrected DFT study

Fullerene recognition with molecular tweezers made up of efficient buckybowls: a dispersion-corrected DFT study

Twenty Years of Promises: Fullerene in Medicinal Chemistry

The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

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