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Asymmetric near-infrared organic fluorescent probe as well as synthesis method and application thereof
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A technology of fluorescent probes and synthesis methods, applied in the fields of material chemistry and biology, to achieve multifunctional convenience and expand the scope of practical applications
Pending Publication Date: 2022-06-24
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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[0004] The main purpose of the present invention is to provide a class of asymmetric near-infrared organic fluorescent probes that are easy to multi-functional modification, have a long emission wavelength and are easy to prepare for the deficiencies in structure and performance of existing fluorescent probes.
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[0041] As another aspect of the technical solution of the present invention, what it relates to is a method for synthesizing a class of asymmetric near-infrared organic fluorescent probes, comprising:
[0042] A kind of probe skeleton with bifunctional structure is provided, and its general structural formula is shown in formula (II):
[0043]
[0044] Wherein, n is selected from 0, 1 or 2, and R is a halogen atom, which can include: F, Cl, Br, I, etc.;
[0045] R 3 for -H or X - is an anion and can include Cl - , Br - , I - , NO 3 - , ClO 4 - , CH 3 COO - , CH 3 SO 3- or CF 3 SO 3 - Wait;
[0046] A first intermediate terminated with an aldehyde group is provided, and its structural formula is:
[0089] Dissolve probe skeleton A with 20 mL of toluene and n-butanol (3:1) mixed solvent 1 (0.5mmol) and B 1 (0.5mmol), under nitrogen protection, heated to 90°C for reaction for about 2h, after the reaction, HPLC was used to separate, purify and dry to obtain intermediate C 1 ; Dry the flask, then add Intermediate C to the flask 1 (0.1mmol), the response group D 1 (0.1mmol), palladium acetate (0.0001mmol), triethylamine (0.1mmol) and dry DMF, under nitrogen protection, 140 ℃ sealed reaction 12h, finally rotary evaporation, purification and drying to obtain black powder (denoted as Dye 1 ), and its characterization data are as follows: HRMS(M+)=829.85. The UV absorption spectra of probe framework A before and after synthesis are shown in figure 1shown.
Embodiment 2
[0091]
[0092] Dissolve probe skeleton A with 20 mL of toluene and n-butanol (2:1) mixed solvent 2 (0.5mmol) and B 1 (1.0 mmol), heated to 100 °C for about 3 h under nitrogen protection, after the reaction was completed, separated, purified and dried by HPLC to obtain intermediate C 2 ; Dry the flask, then add Intermediate C to the flask 2 (0.1mmol), the response group D 1 (0.2mmol), palladium acetate (0.0002mmol), triethylamine (0.2mmol) and dry DMF, under nitrogen protection, 110 ℃ sealed reaction 13h, finally rotary evaporation, purification, drying to obtain black powder (represented as Dye 2 ), and its characterization data are as follows: HRMS(M+)=843.88.
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Abstract
The invention discloses an asymmetric near-infrared organic fluorescent probe as well as a synthesis method and application thereof. The structural general formula of the asymmetric near-infrared organic fluorescent probe is shown in the specification. The synthesis method comprises the following steps: in a system in which methylbenzene and n-butyl alcohol exist, carrying out condensation reaction on a probe skeleton and a first intermediate of which the tail end is an aldehyde group; then, a mixed reaction system containing the reaction product, a second intermediate with double bonds at the tail end, a catalyst and an organic solvent is subjected to a ligation reaction, and the asymmetric near-infrared organic fluorescent probe is obtained. The absorption / emission wavelength of the asymmetric near-infrared organic fluorescent probe is located in a near-infrared region, and the asymmetric near-infrared organic fluorescent probe can be used for diagnosis and treatment guided by near-infrared fluorescence imaging and fluorescence images. According to the asymmetric near-infrared organic fluorescent probe, the modifiability of the near-infrared organic fluorescent probe can be greatly improved, the multi-functional application of the probe can be realized, and the asymmetric near-infrared organic fluorescent probe has a wide application prospect in the fields of biological imaging and detection.
Description
technical field [0001] The invention relates to an organic fluorescent probe, in particular to a kind of asymmetric near-infrared organic fluorescent probe constructed based on a bifunctional probe skeleton based on a xanthene structure, a synthesis method and biological application thereof, and belongs to the fields of material chemistry and biology technical field. Background technique [0002] In situ biopsy methods based on visual imaging technology are widely used in clinical diagnosis and treatment. Compared with traditional magnetic resonance imaging (MRI), ultrasound imaging, CT imaging, PET imaging and other technologies, fluorescence imaging has higher sensitivity and specificity, and can achieve rapid real-time feedback at a lower cost. Surgical navigation, treatment effect, and prognosis evaluation have received more and more attention. [0003] Among various fluorescent imaging reagents, organic fluorescent materials have received great attention due to their ...
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