Cationic lipid compounds and compositions and uses for delivery of nucleic acids
A cationic lipid and nucleic acid delivery technology, applied in the field of cationic lipid compounds and compositions, and cationic lipid compounds, can solve the problems of short circulating time of naked mRNA, easy to be degraded, difficult to enter target cells, etc., and achieve less residue in the body , Improve the clearance rate in the body, and the effect of low carrier toxicity
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Embodiment 1
[0061] Example 1 Synthesis of Compound 1
[0062]
[0063]
[0064]
[0065] step 1:
[0066] To a solution of 2-hexyldecanoic acid (1-1, 2.00 g) in DCM (20 mL) was added 4-dimethylaminopyridine (DMAP, 95 mg) followed by 6-bromohexanol (1.68 g). After the mixture was stirred at 25°C for 5 minutes, 1-ethyl-(3-dimethylaminopropyl) (EDCl, 1.45 g) was added and the reaction mixture was stirred at 25°C for 12 hours, then TLC showed complete disappearance of the starting alcohol. The reaction mixture was diluted with DCM (30 mL) and washed with saturated NaHCO 3 (100 mL) and brine (100 mL). The organic layers were combined with Na 2 SO 4 Drying and removal of the solvent in vacuo gave the crude product, which was purified by column chromatography (silica gel column, eluent 0-1% EA (v / v) in n-hexane) and the pure fractions were evaporated, Compound 1-2 was obtained (2.00 g, 58% yield).
[0067] Step 2:
[0068] To a solution of compound 1-2 (2.00 g) in ethanol (20 mL) w...
Embodiment 2
[0077] Example 2 Synthesis of Compound 2
[0078]
[0079]
[0080]
[0081] step 1:
[0082] To a solution of 2-hexyldecanoic acid (1-1, 2.00 g) in DCM (20 mL) was added 4-dimethylaminopyridine (DMAP, 95 mg) followed by 6-bromohexanol (1.68 g). After the mixture was stirred at 25°C for 5 minutes, 1-ethyl-(3-dimethylaminopropyl) (EDCl, 1.45 g) was added and the reaction mixture was stirred at 25°C for 12 hours, then TLC showed complete disappearance of the starting alcohol. The reaction mixture was diluted with DCM (30 mL) and washed with saturated NaHCO 3 (100 mL) and brine (100 mL). The organic layers were combined with Na 2 SO 4 Drying and removal of the solvent in vacuo gave the crude product, which was purified by column chromatography (silica gel column, eluent 0-1% EA (v / v) in n-hexane) and the pure fractions were evaporated, Compound 1-2 was obtained (2.01 g, 56% yield).
[0083] Step 2:
[0084] To a solution of compound 1-2 (2.01 g) in ethanol (20 mL)...
Embodiment 3
[0093] Example 3 Synthesis of Compound 3
[0094]
[0095]
[0096]
[0097] step 1:
[0098] To a solution of compound 3-1 (2.00 g) in DCM (20 mL) were sequentially added 4-dimethylaminopyridine (DMAP, 84 mg) and 7-bromoheptanol (2.05 g). After the mixture was stirred at 25°C for 5 minutes, 1-ethyl-(3-dimethylaminopropyl) (EDCl, 1.29 g) was added and the reaction mixture was stirred at 25°C for 12 hours, then TLC showed complete disappearance of the starting alcohol. The reaction mixture was diluted with DCM (30 mL) and washed with saturated NaHCO 3 (100 mL) and brine (100 mL). The organic layers were combined with Na2 SO 4 Drying and removal of the solvent in vacuo gave the crude product, which was purified by column chromatography (silica gel column, eluent 0-1% EA (v / v) in n-hexane) and the pure fractions were evaporated, Compound 3-2 was obtained (2.06 g, 59% yield).
[0099] Step 2:
[0100] To a solution of compound 3-2 (2.06 g) in ethanol (20 mL) was add...
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