The water-soluble β-cyclodextrin–[60]fullerene complex

Murthy, C. N.; Geckeler, Kurt E.

doi:10.1039/b102142g

Cited by 141 publications

(107 citation statements)

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“…B uckminsterfullerene (C 60 ), commonly known as the buckyball, has been the focus of many experimental and theoretical studies because of its promise in both biomedicine and nanomaterials (1)(2)(3)(4)(5)(6)(7)(8). Carbon nanotubes, a nanomaterial similar to fullerenes, exhibit unique mechanical properties, electrical and heat conductivity; they are often hailed as a twenty-first century material that could revolutionize a number of industries (2).…”

mentioning

confidence: 99%

Remarkable patterns of surface water ordering around polarized buckminsterfullerene

Chopra

Levitt

2011

Proc. Natl. Acad. Sci. U.S.A.

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Accurate description of water structure affects simulation of protein folding, substrate binding, macromolecular recognition, and complex formation. We study the hydration of buckminsterfullerene, the smallest hydrophobic nanosphere, by molecular dynamics simulations using a state-of-the-art quantum mechanical polarizable force field (QMPFF3), derived from quantum mechanical data at the MP2/aug-cc-pVTZ(-hp) level augmented by CCSD(T). QMPFF3 calculation of the hydrophobic effect is compared to that obtained with empirical force fields. Using a novel and highly sensitive method, we see polarization increases ordered water structure so that the imprint of the hydrophobic surface atoms on the surrounding waters is stronger and extends to long-range. We see less water order for empirical force fields. The greater order seen with QMPFF3 will affect biological processes through a stronger hydrophobic effect.B uckminsterfullerene (C 60 ), commonly known as the buckyball, has been the focus of many experimental and theoretical studies because of its promise in both biomedicine and nanomaterials (1-8). Carbon nanotubes, a nanomaterial similar to fullerenes, exhibit unique mechanical properties, electrical and heat conductivity; they are often hailed as a twenty-first century material that could revolutionize a number of industries (2). The behavior of fullerenes in water is of special interest for biosensors (9). Moreover, water-soluble buckyball derivatives could potentially be used for a wide variety of medical applications, including HIV protease inhibition, DNA photoclevage, antibacterial activity, and photocytotoxicity for cancer treatment (10).The interaction of water with hydrophobic surfaces is responsible for many biological processes, such as protein folding, substrate binding and biological self-assembly of micelles, lyotropic mesophases, and lipid membranes. The molecular surface of proteins can have extended hydrophobic patches, so that buckyballs, graphite surfaces, and carbon nanotubes provide model systems for study of water molecules near large hydrophobic surfaces. An accurate description of interactions between water and its surrounding environment is essential for understanding and simulating such processes. Molecular dynamics (MD) simulations are used to study the behavior of water molecules next to hydrophobic surfaces at atomic detail and subpicosecond time resolution. The hydration structure of nonpolar solutes of varying size has been studied extensively in the past (11-22) using empirical force fields. Work from our lab has used empirical potential energy functions with popular water models to model the effect of a single molecule of benzene, cyclohexane (18, 21), methane, and C 60 (22) on the structural details of water around these solutes. All these studies used force fields with nonpolarizable fixed point charge water models and analyzed water structure with a low-sensitivity method unable to detect the effect of solute surface "roughness" on water structure.Polarization, which allows the ef...

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confidence: 99%

Remarkable patterns of surface water ordering around polarized buckminsterfullerene

Chopra

Levitt

2011

Proc. Natl. Acad. Sci. U.S.A.

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“…Koizumi et al recently demonstrated that the chemical shifts of all glucose carbons were practically unvarying for DP9 and DP31 in 13 C-NMR measurements. 19) In addition, we have reported the solubilities, specific rotations and surface tensions of largering cyclodextrins with DP ranging from 10 to 17.…”

Section: Enhancement Of Water Solubility Of Fullerene By Cogrinding Withmentioning

confidence: 99%

“…[9][10][11][12] On the other hand, solubilization of fullerenes into water also has been investigated extensively, since their applicability was strictly limited due to poor solubility to polar solvent. In addition to developing chemically modified hydrophilic fullerene derivatives, fullerene (C 60 ) has been solubilized into water combined with b-cyclodextrin, 13) g-cyclodextrin, 14,15) polyvinylpyrrolidone 16) and fluoroalkyl oligomer. 17) Complexation between C 60 and each solubilization agent was usually performed in the aqueous solution or organic solvent i.e.…”

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confidence: 99%

Enhancement of Water Solubility of Fullerene by Cogrinding with Mixture of Cycloamyloses, Novel Cyclic .ALPHA.-1,4-Glucans, via Solid-Solid Mechanochemical Reaction

Fukami

Mugishima

Suzuki

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Improvement of solubility for fullerene (C 60 ) was studied by cogrinding with cycloamyloses using a ball mill in the solid state. Cycloamylose is a novel cyclic a a-1,4-glucan produced from synthetic amylose by enzymatic reaction. Although sample solutions showed a pale yellow for the initial period of cogrinding with cycloamyloses and C 60 , the color varied to brown after 48 h. Subsequently, the solubility of C 60 was improved markedly to 560 (m mg/ml) at 96 h. From powder X-ray diffraction analysis, the peak intensity of crystalline C 60 decreased as the cogrinding time was extended. The UV-VIS absorption spectrum of C 60 shows absorption bands at 262 and 340 nm in water with cycloamyloses, and 258 and 328 nm in n-hexane. These results suggested that C 60 molecules were dispersed into cycloamyloses micellar system and the red-shift of the UV-VIS spectra was due to an intermolecular interaction between C 60 and cycloamyloses.

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“…But, the low solubility of fullerenes in aqueous media limits their biological applications. To overcome this problem, several strategies have been developed such as the preparation of water soluble fullerene complexes with macrocyclic host systems [101,102]. Therefore, Rio and Nierengarten synthesized water soluble supramolecular cyclotriveratrylene- [60]fullerene complexes for biological applications [103].…”

Section: Cyclotriveratrylenesmentioning

confidence: 99%