Fullerene lipids: Synthesis of dialkyl 1,2-[6,6]-methano-[60]-fullerene dicarboxylate derivatives (original) (raw)
Related papers
Lipids, 1999
Tris(hydroxymethyl)aminomethane was successfully esterified with saturated and unsaturated long-chain fatty acids. The resulting amino-triester intermediates were successively reacted with chloroacetyl chloride, sodium azide, and C 60 fullerene. Spectral evidence showed that the aziridine ring is joined to the junction of [6,6]-fused rings of the fullerene. The structures of the various C 60 fullerene derivatives bearing a long-chain saturated or unsaturated triester system were characterized by spectroscopic and spectrometric methods.
New developments in the organic chemistry of fullerenes
Journal of Physics and Chemistry of Solids, 1997
Since the discovery and isolation of macroscopic quantities of the fullerenes, the preparation of derivatives has grown rapidly over the last few years [1-3]. Functionalization of C6o in our group has been done primarily by cycloaddition reactions; particularly the 1,3-dipolar addition of diazoalkanes and alkyl azides. rt
Preparation and Characterization of Fulleroid and Methanofullerene Derivatives
The Journal of Organic Chemistry, 1995
We describe the synthesis and complete characterization of soluble derivatives of C 60 for applications to physics and biology. The goal of the strategy was to have a "modular" approach in order to be able to easily vary a functional group attached indirectly to the cluster. The functionality could be hydrophilic (e.g., histamide) or hydrophobic (e.g., cholestanoxy). The former was prepared for biological studies and the latter for photophysical studies toward improvement of photoinduced electron transfer efficiencies in the fabrication of photodetectors and photodiodes. An important intermediate, a carboxylic acid, was found to be recalcitrant to characterization by the usual mass spectroscopic and elemental analysis techniques. This problem was solved by the use of MALDI-MS. The carboxylic acid was easily converted to the key intermediate acid chloride, which in turn was convertible to a large variety of derivatives. Both isomeric forms ([5,6], fulleroid and [6,6], methanofullerene) of the C 61 clusters were prepared. The fulleroid formation could have given rise to a 50:50 mixture of phenyl-over-former pentagon phenyl-over-former hexagon isomers but, remarkably, afforded a 95:5 mixture of these isomers, respectively. The fulleroid and methanofullerene gave different cyclic voltammograms, with the former being reduced at 34 mV more positive potential than the latter.
Covalent and Non-Covalent Derivatives of Fullerene C60 and Its Biological Activity
ChemInform, 2003
I'll' nil's /io/wr present: 1!IC basic c!ICJI1ico! characteristics ofbuckniiustcrfullcrenc-molecule Cfd) ((JU! sonic of 11.1' liiologicctllv active derivatives. This newform 0/ carbon with unique pro/Jeri ICS, disco vcrcc! ill /1)85, is II I'en' react ivc species IIlldc/going 0 variety o] chem ICO! reactions !codlllg 10 a wide spcctntni ofpossible covalent derivatives. Besides covalent co-JI1/)OIl/U!S, [ullercuc reacts with di/li>I'ellt dopants toforni non-covalent complexes. illc!lIi!ln,l!, cndohcdral, exohcdral systems (intercalates]. The review ofth« most significant papers Oil non-covalent aiu! covalent derivatives and their biological activity is given, as wei! as our results ill this [ield. Formution 0/ intercalates offullerenc with small molecules oialipliatic O/CO/IO!S is described and the illl/)III'IOIICC oj'to/)%gy and size ofdopants atul the role ojsolvents ill [ormation II/ intercalates is explained. Original synthesis IIf bromine derivative Cwnr c / and water-soluble polvhvdrox» derivative C(,J()H)~4 is described. Antioxidative e/k!'IS ojtlic latter C(}}Il/)IIII/II! \Val' investigator! in chemical model system and ill vitro .I'\'sICIII lI(h1l1110/l ncoplasuuttic cc!!s. The IUI/w/' 0/.1'11 gives theoretical explanation ofculdttion C(,()R l l derivatives touethcr with OS.I'III1I/)liol1 IIhUIII antioxidative activit» ujO/it/!cm!. I<LY WUI{DS: lullcrcnc C w ' covalent derivatives, intercalate. fullcrol, antioxidant activity, conformation C(,oR 2 1 DISCOVERY 01" BUCKMINSTERFULLERENE Discovery of icosahedral buckminsterfullerene molecule has a long and very exciting his" tory. l-or the experimental proof of the existence of fullcrcnc molecule, in I 90() Nobel prize was awarded to Harold Croto. Richard Smelley and Robert Curt, leaders ofAmerican-English research tc.un that in !lJX5 synthesized this molecule LIS the most perfect symmetry form existing in nature (1). Ful lcrcnc mulccu!c possesses gl'olllciry of truncated icosahedron, which was already known tu Leonardo~ll]d Duhrcr back in IS(JO, Fig. I. (2),
Biological applications of fullerene derivatives: a brief overview
Starting soon after the production of fullerenes in 1990, many efforts have been devoted to the application of C 60 and its derivatives. In fact, [60]fullerene possesses a variety of interesting biological properties, such as HIV-P inhibition, DNA photocleavage, neuroprotection, apoptosis, etc. Unfortunately, the low solubility in biological fluids limits the use of these compounds as new pharmacophores for structure-activity relationship studies in medicinal chemistry. This article briefly summarizes recent studies on the functionalization of C 60 aimed at increasing water solubility as well as the preliminary studies performed on biological targets. In particular, the HIV-P inhibition, DNA photocleavage and antibacterial activity are discussed.
A Convenient Synthesis of Novel Meldrum's Acid C60 Fullerene Derivatives
Chinese Journal of Chemistry, 2007
A series of novel Meldrum's acid C 60 derivatives were prepared in moderate yields from a convenient one-pot reaction of C 60 , the Meldrum's acid derivatives, I 2 and 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) in toluene at room temperature under nitrogen atmosphere. All the new compounds were fully characterized by the spectral data and elemental analysis. A carbene intermediate mechanism was proposed for this reaction.
Compositions for medicinal Chemistry of fullerenes
2010
The paper presents a quantum-chemical approach to t wo aspects of fullerene nanomedicine related to the oxidative and antioxidant actions of fullerene. The first topic is concerned in regards photodynamic therapeutic effect of fulleren e solutions. A new mechanism of the effect is proposed. The second aspect is exemplified by th e consideration of two fullerene-silica complexes, namely, fullerosil and fullerosilica gel .