In dry DMSO and the mixture Vascular-targeting Agent 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 Themixture 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  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: d1.85 1.88, 2.25, 2.69 2.84, 3.11 3.98, 4.26 4.37, 4.89 5.09, 6.56 6.66, 7, 55 7.57, 8.47 8.55 ppm, 13C NMR: d28.5, 32.3, 43.4, 44.8, 46.0, 48.7, 53.7, 60.0 , 70, 4, 72.1, 72.5, 73.2, 81.6, 83.2, 102.0, 111.4, 122.1, 128.0, 128.7, 148.4, 150 , 7, 154.8, 156.4, 162.0, 165.6, 172.7, 175.6 ppm, elemental analysis calculated for C63H93N9O39 鈥 H2O: C 42.93, H 6.35, N 7.15, found: C 42.97, H 6.34, N 7.30, MALDI-TOF-MS: m / z: 1600.56, 1622, 56, 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, NDicyclohexylcarbodiimide 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 of S Receive column chromatography to claim 2 as a purple solid. 1H NMR: d2.77, 1.73 1.83, 2.09, 3.35, 6.47, 7.73 7.81, 8.16, 8.22, 8.31, 8.80 8 , 87 ppm, 13C NMR: d28.4, 34.3, 37.1, 40.6, 51.7, 118.8, 120.5, 120.7, 125.4, 126.9, 127, 9, 134.5, 134.68, 134.8, 142.2, 145.6, 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 IGF-1 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.