Folate-targeted fat-water-amphiphilicity benzylidene cyclopentanone photosensitizer, preparation method thereof and application of folate-targeted fat-water-amphiphilic benzylidene cyclopentanone photosensitizer in preparation of photosensitive drugs for photodynamic therapy
A targeting technology of benzylidene cycloalkane ketone and folic acid, which is applied in the application of photosensitizing drugs for two-photon photodynamic therapy, folic acid targeting lipid-water amphiphilic benzylidene cycloalkane ketone photosensitizer, preparation of single photon field , can solve problems such as limiting curative effect
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Embodiment 1
[0142] (1) synthetic C2-1, reaction equation is as follows:
[0143]
[0144] Specific steps are as follows:
[0145] Dissolve 8.0 g (54 mmol) of 2,2'-(ethylenedioxy)bis(ethylamine) in 500 ml of dichloromethane, cool in an ice bath to 0-5°C; add 6.0 g (60 mmol) of triethylamine to it , and make the system stir evenly; After adding dropwise the dichloromethane solution of 4.0 grams (18mmol) di-tert-butyl dicarbonate in the above-mentioned system, continue to react for 12 hours; The final reaction solution is extracted 3 times with dichloromethane, and water After washing 3 times, drying, filtering, and rotary evaporation to remove dichloromethane, 3.3 g of C2-1 was obtained (yield 75%).
[0146] (II) Synthesis of C6-1, the reaction equation is as follows:
[0147]
[0148] Specific steps are as follows:
[0149] Dissolve 17.3 grams (0.1mol) of C3-1 in 50 milliliters of ethanol-water solution (wherein the volume percentage of ethanol is 50%); slowly add 20 grams (0.5mol...
Embodiment 2
[0181] (1) Example 1 was repeated, the difference being that cyclopentanone was changed to cyclobutanone in the above step (V), and other conditions were unchanged to obtain target photosensitizer M-2 (yield 20%). HR-MS(ESI):m / z[M+H]:Calcd.for[C 70 h 101 N 11 o 19 ] + 1398.7191; found 1398.7229.
[0182]
[0183] (II) With reference to the operation of (IX) in Example 1, it is proved that the solubility of M-2 is greater than 2mg / mL; and there is a strong absorption peak in the 350-600nm wavelength range, see attached Figure 4 .
[0184] (III) With reference to the operation of Example 1 (X), the results have also proved that the target photosensitizer M-2 can produce active oxygen species under 473nm laser irradiation, see the attached Figure 5 .
[0185] (IV) With reference to the operation of Example 1 (XI), the result also proves that the photosensitizer has a larger two-photon absorption cross section in the wavelength range of 720-880nm, and can use two-photo...
Embodiment 3
[0187] (1) With reference to the operation of (I) in Example 1, synthetic C2-2, reaction equation is as follows:
[0188]
[0189] Specific steps are as follows:
[0190] Dissolve 4.0 g (45 mmol) of C1-2 in 100 ml of dichloromethane, and cool in an ice bath to 0-5° C.; add 5.8 g (45 mmol) of N, N-diisopropylethylamine (DIEA), and Stir the system evenly; add dropwise 0.9 g (4.5 mmol) of di-tert-butyl dicarbonate in dichloromethane solution to the above system, and continue the reaction for 12 hours; extract the final reaction solution 3 times with dichloromethane, and wash with water 0.7 g of C2-2 (yield 80%) was obtained after three times of drying, filtering, and rotary evaporation to remove dichloromethane.
[0191] (II) Referring to the operation of (V) in Example 1, the intermediate product C11-2 was prepared by reacting C10-1 with cyclohexanone, the basic catalyst was lithium hydroxide, and the molar weight was 0.01 times that of the reactant. (yield 30%)
[0192] ...
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