The Associative Properties of Some Amphiphilic Fullerene Derivatives

Angelini, Guido; Cusan, Claudia; Maria, Paolo De; Fontana, Antonella; Maggini, Michele; Pierini, Marco; Prato, Maurizio; Schergna, Stefano; Villani, Claudio

doi:10.1002/ejoc.200400699

Cited by 19 publications

(15 citation statements)

References 30 publications

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“…The synthesis of 2-[2-(2-fulleropyrrolidin-1-ylethoxy)ethoxy]-ethanol (FPE) was based on a 1,3-dipolar cycloaddition reaction as previously reported. 10 The rate of release of CF entrapped into liposomes, the polarity and the viscosity measurements were carried out by a Jasco FP-6200 spectrofluorimeter, with a band-pass of 5 nm.…”

Section: Methodsmentioning

confidence: 99%

Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes

et al. 2006

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Membrane stability of extruded large unilamellar vesicles (LUV) formed by 1-palmitoyl-2oleoylphosphatidylcholine (POPC) containing fullerene C 60 or an amphiphilic fullerene derivative, 2-[2-(2-fulleropyrrolidin-1-ylethoxy)-ethoxy]-ethanol (FPE), has been investigated by spectrofluorimetrically monitoring the spontaneous release of entrapped carboxyfluorescein (CF). Under controlled conditions of temperature, osmolarity and pH, these guests increase the stability of the liposomal membrane as shown by the decrease in the rate of outflux of CF. The stability conferred to the POPC liposomes by C 60 and FPE has been compared with that conferred by the well-known stabilizing guest 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy-(polyethylene glycol)-2000] ammonium salt (PEG). The addition of amphiphilic molecules, such as non-ionic surfactants, which intercalate into the membrane bilayer, and of sucrose or NaCl, which induce a hyposmotic stress, has been extensively investigated in order to get information on how to modulate the release of entrapped CF. This information could hopefully be useful in the formulation of new drug delivery systems as well as for getting a deeper understanding of the mechanisms of the formation/enclosure of channels through the membrane. The viscosity and the micropolarity of the membrane have been measured fluorimetrically by using pyrene as the probe. An interesting increase of the gel-liquid crystal phase transition temperature has been observed for POPC liposomes hosting C 60 .

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Section: Methodsmentioning

confidence: 99%

Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes

et al. 2006

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“…The cyclen-C 60 -1 and its intermediates were confirmed by 1 H NMR, 13 C NMR and HRMS. The 1 H NMR and 13 C NMR of bis(cyclen)-C 60 -2 did not give meaningful results, 28,29 but its TOF-MS spectrum showed the expected molecular ions peaks in high intensity (Fig. 1, m/z 1203.4613).…”

Section: Resultsmentioning

confidence: 91%

Synthesis of Water-Soluble Cyclen-Functionalised Fullerene C₆₀ Derivatives

Yan

Liu

et al. 2014

Journal of Chemical Research

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The fullerene family has interesting photophysical, electrochemical and mechanical properties with applications in organic solar cells, nanotechnology, superconductivity, chemosensors and biomedicine. Water-soluble cyclen-functionalised fullerene derivatives cyclen-C 60 -1 and bis(cyclen)-C 60 -2 have been synthesised. The whole synthetic routes are simple and the total yields are relatively high.

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“…For this purpose, the concentration of R1 was kept at a constant value of 3.2 × 10 −5 M. The self-association process was monitored by registering the changes in the UV-absorbance difference at the wavelengths of 350 and 400 nm ( ΔABS 350–400 ) as a function of the δ H value of the corresponding solvent system. The scatter plot of ΔABS 350–400 vs δ H was further fitted by using the following equation [ 29 , 40 ]: ΔABS 350–400 = b/(1 + 10 (−( δH − API )/ a ) with b and a parameters representing the maximum value assumed by ΔABS 350–400 and the slope of the sigmoidal curve, respectively. As depicted in Figure 5 , the self-aggregation of R1 is featured by an API value of 17.3 which corresponds to a water amount of 57.3% (with a = 0.42).…”

Section: Resultsmentioning

confidence: 99%

Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates

Buonsenso

Ghirga

Romeo

et al. 2021

IJMS

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Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of the host-guest complex by using calixarene-based macrocycles (i.e., resorcinol-derived cyclic oligomers) with a good solubility profile can improve solubilization of hydrophobic drugs. Herein, we explore the ability of resorc[4]arenes to self-assemble in polar solutions, to form supramolecular aggregates, and to promote water-solubility of an isoflavone endowed with anti-cancer activity, namely Glabrescione B (GlaB). Accordingly, we synthesized several architectures featuring a different pattern of substitution on the upper rim including functional groups able to undergo acid dissociation (i.e., carboxyl and hydroxyl groups). The aggregation phenomenon of the amphiphilic resorc[4]arenes has been investigated in a THF/water solution by UV–visible spectroscopy, at different pH values. Based on their ionization properties, we demonstrated that the supramolecular assembly of resorc[4]arene-based systems can be modulated at given pH values, and thus promoting the solubility of GlaB.

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The Associative Properties of Some Amphiphilic Fullerene Derivatives

Cited by 19 publications

References 30 publications

Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes

Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes

Synthesis of Water-Soluble Cyclen-Functionalised Fullerene C₆₀ Derivatives

Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates

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The Associative Properties of Some Amphiphilic Fullerene Derivatives

Cited by 19 publications

References 30 publications

Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes

Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes

Synthesis of Water-Soluble Cyclen-Functionalised Fullerene C60 Derivatives

Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates

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Synthesis of Water-Soluble Cyclen-Functionalised Fullerene C₆₀ Derivatives