Water-soluble C <sub> 60 </ Sub> - The Dehydroabietylamine Derivatives And Their Biological Activity Study

Buckyminiterfullerene is the third allotrope of carbon, fullerene and its derivatives have widespread and prospective application in chemistry, biology, material and medicine for their particular three-dimensional structures. Fullerene[60], the most representative compound, has particular efficacy and bioactivity in anti-HIV, antibacterial, antitumor, inhibition of enzymatic activity, antioxidation, neuroprotective and so on. Dehydroabietylamine which is the derivative of abietic acid, with a steroid-like tricyclic diterpene structure, has sterilization and other biological activities. C₆₀-dehydroabietylamine derivatives which were synthesized by our early research have low solubility in water, the study of their bioactivity is limited. It is significant to increase their water-soluble by modify C₆₀-dehydroabietylamine derivatives chemically and to do bioactivity researches on these novel compounds.The hydroxylation on fullerene was studied first in this paper. Water-soluble C₆₀-dehydroabietylamine fullerenol derivatives(XY-OH and G-OH)were synthesized by reaction of C₆₀-dehydroabietylamine derivatives(fulleropyrrolidine dehydroabietylamine derivative and C₆₀-dehydroabietylamine nitrene [5,6] opencyclo-monoaddition derivative)and NaOH, in toluene/water mixed solution at reflux temperature, with TBAH and H2O2 as the catalysts. The target compounds, which were the mixture of different addition degrees of hydroxyl group, were c h a r a c t e r i z e d b y T E M , F T- I R , E S I - M S , 1 H N M R a n d H P L C . The addition reaction of fullerene and glycine was also studied in this paper.Water-soluble C₆₀-dehydroabietylamine glycine derivatives(XY-gly and G-gly)were synthesized by reaction of C₆₀-dehydroabietylamine derivatives and glycine, in the mixed solution of toluene and water/ethanol at reflux temperature, with ultrasonic assistance. The target compounds, which were the mixture of different addition degrees of glycine group, were characterized by TEM, FT-IR, ESI-MS, 1H NMR and HPLC. Then, the bioactivity of four water-soluble C₆₀-dehydroabietylamine derivatives which were synthesized in this paper was investigated in this paper. We tested them on inhibition of rTaq DNA polymerase activity, in vitro anti-HIV-1 reverse transcriptase activity and anti-ovarian cancer(Hey 1B cells)activity. We come to a conclusion by the preliminary test result , the four water-soluble C₆₀-dehydroabietylamine derivatives displayed different degree of inhibition to rTaq DNA polymerase and HIV-1 reverse transcriptase, and with no regularity. The lowest concentration range of inhibition to rTaq DNA polymerase are 0.05⁰.1μg / m L ( X Y- g l y ) , 0 . 0 5 0 . 1μg / m L ( G - g l y ) , 2 2 . 2μg / m L ( X Y- O H ) , 1 2μg/mL(G-OH),respectively; The median inhibitory concentration(IC50) of HIV-1 reverse transcriptase are 70.64μg/mL(XY-gly),25.70μg/mL(G-gly),198.26μg/mL(XY-OH),16.28μg/mL(G-OH), respectively; and they displayed few inhibition to ovarian cancer(Hey 1B cell).