Chlorofullerene C60Cl6: a precursor for straightforward preparation of highly water-soluble polycarboxylic fullerene derivatives active against HIV.
We report for the first time the application of chlorofullerene C60Cl6 as a substrate for straightforward preparation of highly water-soluble fullerene derivatives, promising compounds for investigation of the biological action of fullerenes in vitro and in vivo. Methyl esters of phenylacetic and benzylmalonic acids were used as reagents in the Friedel-Crafts arylation of C60Cl6 that resulted in the corresponding C60(Ar)5Cl compounds with 50-60% yields. The following cleavage of ester groups in phenylacetic and benzylmalonic residues was accomplished almost quantitatively to yield the corresponding fullerene-based acids bearing 5 and 10 carboxylic groups, respectively. The relatively-low solubility of these acids in water can be strongly enhanced (up to 150-200 mg ml(-1)) by their conversion to salts with alkali metal cations. These fullerene salt derivatives showed pronounced anti-HIV action and low toxicity; these two findings point to the necessity for further investigation of the biological properties of the here-reported compounds.
Troshina
Olesya A
OA
Institute of Problems of Chemical Physics of Russian Academy of Sciences, Semenov Prospect 1, Chernogolovka, Moscow region 142432, Russia.
Troshin
Pavel A
PA
Peregudov
Alexander S
AS
Kozlovskiy
Viacheslav I
VI
Balzarini
Jan
J
Lyubovskaya
Rimma N
RN
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D002264:Carboxylic Acids / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry* / Q000633:toxicity*; D015497:HIV-1 / Q000187:drug effects; D015498:HIV-2 / Q000187:drug effects; D021621:Imaging, Three-Dimensional; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D012492:Salts / Q000737:chemistry; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry*
D019380:Anti-HIV Agents; D002264:Carboxylic Acids; D037741:Fullerenes; D012492:Salts; D014867:Water