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A man in his 60s with severe trismus was referred to our hospital. Based on computed tomography (CT), positron emission tomography/computed tomography (PET/CT), and biopsy, his initial diagnosis at another hospital was oropharyngeal cancer with cervical lymph node and distant metastases. After the review of the contrast-enhanced CT and reevaluated PET/CT images, we updated his diagnosis to left primary lung cancer that had metastasized to the cervical lymph nodes, bones, and skeletal muscles including the right medial pterygoid muscle. Since metastasis from primary lung cancer to the contralateral cervical lymph node is relatively rare, cervical lymph node metastases were thought to have originated from the metastatic lesion in the right medial pterygoid muscle. As metastases in the masticator muscles from lung cancer are rare, it is sometimes necessary to differentiate from primary head and neck lesions. Here, we report a rare case of lung cancer with the onset of trismus due to metastasis to the masticator muscle and perineural spread along the mandibular nerve.

A lithium-encapsulated fullerenol Li@C60(OH)18, as an example of a polar solvent-soluble endohedral fullerene derivative, has been synthesized and fully characterized by infrared spectroscopy, nuclear magnetic resonance spectroscopy, UV spectroscopy, electron spin resonance (ESR) spectroscopy, matrix-assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF-MS), elemental analysis, thermogravimetric analysis, and inductively coupled plasma-atomic emission spectroscopy (ICP-AES), and the particle size was determined using the induced grating (IG) method, and scanning probe microscopy. The encapsulated Li+ was clearly detected by 7Li NMR at very high field in the range −15 to −19 ppm, an intermediate lithium-encapsulated fullerenol was detected by MALDI-TOF-MS, and the molar ratio of lithium-encapsulated fullerenol to empty fullerenol was quantitatively determined to be 12:88 by ICP-AES. The solid-state ESR and particle size measurements using the IG method showed the characteristic anionic behavior with no external counter cations, in what can be called a “cation-encapsulated anion nanoparticle”, revealing the drastic differences between its properties and those of empty C60(OH)16. Open image in new window

A water-soluble polyhydroxylated fullerene, i.e. a fullerenol, with 44 hydroxyl groups and 8 secondary bound water molecules, C60(OH)44·8H2O (estimated average structure), has been synthesized in a facile one step reaction from pristine C60 by hydroxylation with hydrogen peroxide in the presence of a phase-transfer catalyst, tetra-n-butylammonium hydroxide (TBAH), under organic/aqueous bilayer conditions. The fullerenol exhibited high water solubility, up to 64.9 mg/mL, under neutral (pH = 7) conditions. Dynamic light-scattering (DLS) analysis showed a narrow particle size distribution, of 1–2 nm, indicating that the fullerenol had high dispersion properties in water. The results of particle size analyses, which both focused on a single nanoregion and were conducted using a novel induced grating (IG) method and a scanning probe microscope (SPM), were consistent with the DLS results. A plausible reaction mechanism, which includes fullerene oxide intermediates detected by liquid chromatography-mass spectrometry (LC-MS), has been proposed.

Due to the spherical shape with a diameter of ca. 1 nm, the aggregation behaviour of fullerene C60 is very interesting in view of the possible formation of magic number particle in a similar manner as metal cluster in gas phase. Herein, we report for the first time the magic number aggregation behaviours of polyhydroxylated fullerenol C60(OH)36 in water–alcohol (methanol, ethanol and 1-propanol) binary solution with increasing alcohol component. The diameters of particle were ca. 6–8 nm depending on the alcohol used. The particle sizes were precisely measured by the novel-induced grating method which is superior for the particle-size measurement in single-nano region (1–10 nm). The magic number cluster was also detected by scanning probe microscopy observation. However, such aggregation behaviours were not found in DMSO–alcohol system or for the use of less hydroxylated C60(OH)10.

We have developed a facile synthetic method for highly water-soluble, hollow carbon nanoparticles with a diameter of ∼1 nm, as a so-called fullerenol. The method was extended to fullerene soot to obtain the corresponding hydrophilic carbon materials, and the products were subjected to IR and elemental analysis. Particle size analysis demonstrated the relatively high dispersion of particles with diameters of ∼70 nm, in water. The surface analysis using FE-SEM showed the difference in morphology between fullerene soot and activated carbon as well as between before and after hydrophilic treatment of the soot with hydrogen peroxide. Moreover, this hydrophilic fullerene soot exhibited high antioxidant activity as compared with fullerenol and C60.

Treatment of [Li+@C60](PF6–) with 30% fuming sulfuric acid and subsequent hydrolysis gave hydroxylated derivative Li+@C60O–(OH)7. Its structure was deduced by IR, NMR, MALDI-TOF/FAB MS, and elemental analysis. Notably, the reaction of [Li+@C60](PF6–) was site-selective, giving a single major isomer (ca. 70%) with two minor isomers, in marked contrast to the case of empty C60. Furthermore, the results clearly indicate that the internal Li cation was strongly shielded by the surface dipolar hydroxyl groups, and thus it appears that the properties of endohedral fullerenes can be controlled by the external modification of the fullerene cage. Whereas Li+@C60 is relatively insoluble, Li+@C60O–(OH)7 was found to be highly soluble in polar solvents such as DMSO and DMF. The increased solubility is especially desirable for biological/medicinal assays and applications in such research fields.