In dry DMSO and the mixture 5 α reductase was stirred in the absence of light at 30 8C in a N 2 atmosphere for 1 h and then re End added compound 3 in anhydrous DMSO. The pH of the reaction mixture was adjusted to 9 by addition of triethylamine. The reaction in the absence of light occurred at 308C under an atmosphere of N 2 for 48 re h The mixture was then poured into acetone and the yellow precipitate filtered off. The crude product was purified by column chromatography S With nPrOH/H2O/25 cleaned 鈥  2O% NH3 as eluent. The resulting product is then purified by MPLC eluting with a water / ethanol and then compound 1 was obtained as a yellow solid. 1H NMR: 1638.51. Adamantane-modified porphyrin: 5 and 1 10,15,20 triphenylporphyrin hydroxybenzotrizole were dissolved in dry DMF st and in an ice bath for 0.5 hours. An L Solution of 1 adamantanemethylamine and N, N Dicyclohexylcarbodiimide in dry DMF was added dropwise.
The reaction mixture was stirred in the absence of light at 08C under N 2 atmosphere re overnight and then at room temperature for another 48 hours. The mixture was filtered and the filtrate was dried under reduced pressure to remove the L Solvent. The residue was dissolved in chloroform St and washed with water, then the organic phase was dried over MgSO 4. The L Solvent was removed under reduced pressure and the crude product was washed with hexane and then by means IkB Pathway of S Receive column chromatography to claim 2 as a purple solid. 1H NMR: 168.0 ppm, ESI-MS: m / z: 828.37, calculated elemental analysis for C56H47N5O: C 83.45, H 5.88, N 8.69, found: C 83.26, H 6, 00, N 8.46. Complex 2/GO: Compound 2 was dissolved in DMSO and added dropwise to a st w added dropwise ssrigen suspension of GO and then deionized water was added.
Filtered the mixture was stirred for 24 h, then through a 450 nm filter and the residue was dispersed in deionized water to remove ultrasonic DMSO. Then the suspension at 4000 rpm for 5 min on unsolved Centrifuged to remove ste porphyrin and chunks of GO. Procedure was repeated nine times to obtain a suspension of 2/GO, the resulting complex was stored at 48C. Complex DOX / GO: DMSO was added to a suspension of w ssrigen GO and DOX added added Cl, then the pH of the final mixture was was adjusted to 8 with triethylamine and stirred for 24 h. The mixture is then filtered through a 450 nm filter and the residue was dispersed in demineralised water to the ultrasonic DMSO and to eliminate free DOX. The suspension was then centrifuged at 4000 rpm for 5 minutes, remove to large E pieces of GO. The procedure was repeated nine times to form a suspension of DOX / GO, the resulting complex was obtained at 4 8C stored data. DOX/2/GO Complex: Compound 2 was dissolved in DMSO and st.