Near-infrared fluorescence dye for targeting tumor tissue as well as preparation method and application
A technology for tumor tissue and fluorescent staining, which is applied in the field of near-infrared fluorescent dyes, can solve the problems of tumor tissue metastasis cannot be detected, tumor tissue cannot be completely removed, and the local recurrence rate of cancer cells is high, achieving convenient commercial production, The effect of eradicating tumor residues and broad application prospects
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Embodiment 1
[0033] The structure of the near-infrared fluorescent dyeing agent of the present embodiment is as formula I:
[0034]
[0035] The preparation method of the near-infrared fluorescent dyeing agent of the present embodiment comprises the following steps:
[0036] Step 1. Preparation of 2,3,3-trimethyl-1-[3-(trimethylamino)propyl]-3H-indole-5-potassium sulfonate: with toluene as solvent, 2,3, 3-Trimethylindole-5-sulfonic acid potassium salt and (3-bromopropyl) trimethylammonium bromide were dissolved in the solvent toluene according to the molar ratio of 1:1.1, under the protection of nitrogen, at 130 ° C The reaction was refluxed and stirred for 72 hours, and the solvent was removed after cooling to obtain a crude product; then, the crude product was recrystallized using a mixed solvent of methanol and methyl tert-butyl ether at a volume ratio of 1:1 to obtain a pink compound having the structural formula II Chromatic crystal 2,3,3-trimethyl-1-[3-(trimethylamino)propyl]-3H-...
Embodiment 2
[0052] The structure of the near-infrared fluorescent dyeing agent of this embodiment is the same as that of Embodiment 1.
[0053] The preparation method of the near-infrared fluorescent dyeing agent of the present embodiment comprises the following steps:
[0054] Step 1. Preparation of 2,3,3-trimethyl-1-[3-(trimethylamino)propyl]-3H-indole-5-potassium sulfonate: with toluene as solvent, 2,3, 3-Trimethylindole-5-sulfonic acid potassium salt and (3-bromopropyl)trimethylammonium bromide were dissolved in the solvent toluene according to the molar ratio of 1:1, under the protection of nitrogen, at 120 ° C Reflux and stir the reaction for 80 hours, remove the solvent after cooling to obtain a crude product; then use a mixed solvent of methanol and methyl tert-butyl ether according to a volume ratio of 1:1.2 to recrystallize the crude product to obtain pink Chromatic crystal 2,3,3-trimethyl-1-[3-(trimethylamino)propyl]-3H-indole-5-potassium sulfonate, yield 56.5%; reaction equat...
Embodiment 3
[0063] The structure of the near-infrared fluorescent dyeing agent of this embodiment is the same as that of Embodiment 1.
[0064] The preparation method of the near-infrared fluorescent dyeing agent of the present embodiment comprises the following steps:
[0065] Step 1. Preparation of 2,3,3-trimethyl-1-[3-(trimethylamino)propyl]-3H-indole-5-potassium sulfonate: with toluene as solvent, 2,3, 3-Trimethylindole-5-sulfonic acid potassium salt and (3-bromopropyl)trimethylammonium bromide were dissolved in the solvent toluene according to the molar ratio of 1:1.2, under the protection of nitrogen, at 140 °C Reflux and stir the reaction for 60 hours, remove the solvent after cooling to obtain a crude product; then use a mixed solvent of methanol and methyl tert-butyl ether according to a volume ratio of 1:1.1 to recrystallize the crude product to obtain pink Chromatic crystal 2,3,3-trimethyl-1-[3-(trimethylamino)propyl]-3H-indole-5-potassium sulfonate, yield 57.2%; reaction equa...
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