Hypochlorite-responsive dihydrazine linker and its application
A hypochlorite and fluorescent probe technology, which is applied in the fields of biomedicine and disease diagnosis and treatment, can solve the problems of poor specificity and low sensitivity of hypochlorite-responsive linkages
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Embodiment 1
[0074] OCl ˉ Fluorescent probe Cou-dhz-Ph-NO 2 design and application
[0075] Synthetic route: First, the compound 7-(diethylamino)coumarin-3-carboxylate was synthesized from 4-diethylaminosalicylaldehyde and diethylmalonate by Knoevenagel condensation reaction, and the latter was combined with hydrazine hydrate. The reaction produces compound 7-(diethylamino)coumarin-3-carboxylhydrazide. Cou-dhz-Ph-NO 2 From p-nitrobenzoyl chloride and 7-(diethylamino) coumarin-3-formyl hydrazide reaction derived. The specific route is as follows:
[0076]
[0077] Synthesis of ethyl 7-(diethylamino)coumarin-3-carboxylate: Dissolve 4-diethylaminosalicylaldehyde (3.86 g, 20 mmol) in 60 mL of ethanol, add 6 mL of diethyl malonate ( 40 mmol) and 2 mL of piperidine. Under nitrogen protection, it was heated to 80°C and refluxed for 24h. At the end of the reaction, the solution turned black. The solvent was removed by rotary evaporation, and the remaining viscous liquid was poured into ...
Embodiment 2
[0092] OCl ˉ Responsive novel phospholipid SA-dhz-His(C 38 H 55 N 7 O 4 ) design and application
[0093] Synthetic route: First, p-nitrobenzoyl chloride reacts with hydrazine hydrate to generate p-nitro-N'-p-nitrobenzoyl-benzoyl hydrazide, which reacts with hydrazine hydrate to generate compound p-amino-N'-p-amino Benzoyl-Benzohydrazide. Continue to react with stearoyl chloride to obtain SA-dhz, and connect the water-soluble amino acid L-histidine through EDC / NHS reaction on the other side of SA-dhz to obtain the amphiphilic molecule SA-dhz-His. The specific route is as follows:
[0094]
[0095] Synthesis of p-nitro-N'-p-nitrobenzoyl-benzoyl hydrazide: take 0.38 mL of 85% hydrazine hydrate (10 mmol) and dissolve it in 30 mL of 95% ethanol, slowly add 1.9 g of p-nitrobenzoyl chloride ( 10 mmol). 10 mL of sodium carbonate solution (containing 1.06 g of sodium carbonate, 10 mmol) was added dropwise with stirring, followed by another 1.9 g of p-nitrobenzoyl chloride. ...
Embodiment 3
[0110] OClˉ responsive crosslinker N-acryloylacrylohydrazide (C 6 H 8 N 2 O 2 ) design and application
[0111] Synthetic route: Acryloyl chloride and hydrazine hydrate react in 95% ethanol to generate N-acryloylacrylohydrazide, which can be used for gel formation. The specific synthetic route is as follows:
[0112]
[0113] Synthesis of N-acryloylacryloyl hydrazide: 0.38 mL of 85% hydrazine hydrate (10 mmol) was dissolved in 30 mL of 95% ethanol, and 905.1 mg of acryloyl chloride (10 mmol) was slowly added. 10 mL of sodium carbonate solution (containing 1.06 g of sodium carbonate, 10 mmol) was added dropwise with stirring, followed by another 905.1 mg portion of acryloyl chloride. Continue to stir the reaction for 12h. The product was purified by column chromatography and dried in vacuo to obtain 1.15 g of a white solid with a yield of 82.1%.
[0114] 1 H NMR (DMSO-d 6 ,300MHz),δ(ppm):11.23(s,2H),6.36(m,2H),5.92(m,,2H),5.20(m,2H).
[0115] 13 C NMR (DMSO-d 6 ,...
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