TPE-2'-deoxynucleoside, fluorescent gel, and preparation methods and application of TPE-2'-deoxynucleoside and fluorescent gel
A TPE-2, deoxynucleoside technology, applied in the field of nucleoside derivatives, to achieve the effects of stable fluorescence intensity, high fluorescence intensity and high product yield
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Embodiment 1
[0061] Synthesis of TPE-2'-deoxyuridine, its molecular formula: C 44 h 41 N 5 o 5 , molecular weight: 719.84, the structural design is as follows:
[0062]
[0063] (1) Synthesis of 5-octadiyne-2'-deoxyuridine
[0064] Add 5-iodo-2'-deoxyuridine (0.531g, 1.50mmol), tetrakistriphenylphosphine palladium (0.173g, 0.15mmol), cuprous iodide (0.058g, 0.30mmol) into 15mL of anhydrous N, Dissolve in N-dimethylformamide, then add 0.5mL anhydrous triethylamine and 1,7-octadiyne (0.800g, 7.5mmol), stir overnight at room temperature, column chromatography (dichloro Methane→dichloromethane:methanol 92:8, volume ratio) After separation and purification, a light yellow powder was obtained with a yield of (0.391 mg, 78.6%). 1 H-NMR (DMSO-d 6 ): 1.55-1.57 (m,2CH 2 ), 2.11(m,2 H-C(2')), 2.19(m,CH 2 ), 2.38 (m, CH 2 ), 2.74(s,C≡CH), 3.55-3.60(m,2H-C(5')), 3.77(m,H-C(4')), 4.22(m,H-C(3')), 5.06( t,OH-C(5')), 5.21(d,OH-C(3')), 6.10(t,6.6,H-C(1')), 8.10(s,H-C(6')), 11.53( s, NH).
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Embodiment 2
[0078] Synthesis of TPE-2'-deoxycytidine, its molecular formula: C 44 h 44 N 6 o 4 , Molecular weight: 720.86, the structural design is as follows:
[0079]
[0080] (1) Synthesis of 5-octadiyne-2'-deoxycytidine
[0081] Add 5-iodo-2'-deoxycytidine (0.530g, 1.50mmol), tetrakistriphenylphosphine palladium (0.173g, 0.15mmol), cuprous iodide (0.058g, 0.30mmol) into 15mL of anhydrous N, Dissolve in N-dimethylformamide, then add 0.5mL anhydrous triethylamine and 1,7-octadiyne (0.800g, 7.5mmol), stir overnight at room temperature, column chromatography (dichloro Methane→dichloromethane:methanol 92:8, volume ratio) After separation and purification, a light yellow powder was obtained with a yield of (0.391 mg, 78.6%).1 H-NMR (DMSO-d6): 1.55-1.57 (m,2CH 2 ), 2.11(m,2 H-C(2')), 2.19(m,CH 2 ), 2.38 (m, CH 2 ), 2.74(s,C≡CH), 3.55-3.60(m,2H-C(5')), 3.77(m,H-C(4')), 4.22(m,H-C(3')), 5.06( t,OH-C(5')), 5.21(d,OH-C(3')), 6.10(t,6.6,H-C(1')), 8.10(s,H-C(6')), 11.53( s, NH).
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Embodiment 3
[0086] The application of TPE-2'-deoxyuridine in Hela cell imaging is as follows:
[0087] (1) Prepare the solution
[0088] Weigh 10 μmol of TPE-2'-deoxyuridine compound and dissolve it in 1 mL DMSO to prepare a 10 mM mother solution, and store it at 4°C for future use.
[0089] (2) Cell culture
[0090] Take a certain concentration of digested cells, add culture medium to dilute the cells to 1×10 4 cells / mL (the cell concentration should not exceed 3×10 4 cells / mL), transferred to the culture vessel, and filled with 5% CO at 37°C 2 Under these conditions, culture overnight to ensure that the cells adhere to the wall and have good viability.
[0091] (3) Fluorescence imaging of cells
[0092] Remove the old culture medium of overnight cultured cells, wash with PBS twice and add new culture medium, slowly add a certain amount of TPE-2'-deoxyuridine mother solution into the culture system to make the final concentration reach 5 μM or 10 μM, The cells were cultured statica...
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