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Oxazine near-infrared fluorescent dye as well as preparation method and application thereof

A fluorescent dye and near-infrared technology, which is applied in the direction of oxazine dyes, organic dyes, luminescent materials, etc., can solve the problem of high non-specific tissue uptake, and achieve the effect of improving specificity and improving specificity

Pending Publication Date: 2022-04-26
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all nerve-specific contrast agents suffer from high non-specific tissue uptake

Method used

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  • Oxazine near-infrared fluorescent dye as well as preparation method and application thereof
  • Oxazine near-infrared fluorescent dye as well as preparation method and application thereof
  • Oxazine near-infrared fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of YQN-3 (i.e. compound I-1)

[0032] 1. Take 1.50g of m-bromoanisole, 0.73g of cyclopropylamine, 1.36g of potassium tert-butoxide, and 0.05g of tetrakis(triphenylphosphine)palladium in toluene (8ml) and heat to reflux at 80°C for 8h. After the reaction, the solution was spin-dried, and the remaining solid was purified by column chromatography to obtain N-cyclopropyl-3-methoxyaniline as a brown oily liquid. m / z: 164.14.

[0033] 2. Dissolve 200 mg of N-cyclopropyl-3-methoxyaniline in 2M ice-cold dilute hydrochloric acid solution (5 ml), add 103 mg of sodium nitrite into the solution while keeping the solution temperature below 5°C. After the addition, the solution was stirred for another 2 h, then it was dropped into a saturated potassium carbonate solution, extracted with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate, and spin-dried to obtain a yellow-green solid N-cyclopropyl-3-methoxy Base-4-nitrosoaniline. m / z: 192.09.

[003...

Embodiment 2

[0036] Synthesis of YQN-4 (i.e. compound I-2)

[0037] The synthesis of YQN-4 refers to Example 1. Its mass spectrometry and H NMR spectrum are as figure 2 As shown, the specific data are as follows: m / z: 322.21, 1H NMR (400MHz, DMSO-d6) δ9.67 (d, J=6.4Hz, 1H), 7.79 (d, J=9.4Hz, 1H), 7.73 ( d, J=9.3Hz, 1H), 7.46-7.31(m, 1H), 7.15(d, J=9.3Hz, 1H), 6.97(s, 1H), 6.67(s, 1H), 4.43-4.25(m , 1H), 3.74(q, J=7.1Hz, 4H), 2.47(d, J=9.3Hz, 2H), 2.09(p, J=9.6Hz, 2H), 1.84(q, J=8.6Hz, 2H ), 1.25(t, J=7.0Hz, 6H).

Embodiment 3

[0039] Synthesis of YQN-5 (i.e. compound I-3)

[0040] The synthesis of YQN-5 refers to Example 1. Its mass spectrometry and H NMR spectrum are as image 3 As shown, the specific data are as follows: m / z: 336.22, 1H NMR (400MHz, DMSO) δ9.31 (s, 1H), 7.79 (d, J=9.5Hz, 1H), 7.72 (d, J=9.4Hz, 1H), 7.37(d, J=8.6Hz, 1H), 7.17(d, J=10.0Hz, 1H), 7.11-6.96(m, 1H), 6.95(d, J=16.1Hz, 1H), 3.73( dd, J=14.0, 6.9Hz, 4H), 1.95(d, J=9.9Hz, 2H), 1.76(d, J=13.2Hz, 2H), 1.64(d, J=13.7Hz, 1H), 1.36( dt, J=22.3, 11.5Hz, 4H), 1.23(t, J=7.0Hz, 6H).

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Abstract

The invention discloses an oxazine near-infrared fluorescent dye as well as a preparation method and application thereof, the oxazine near-infrared fluorescent dye comprises a compound as shown in a formula I, and X is selected from naphthenic bases. The oxazine near-infrared fluorescent dye is targeted to nerves after intravenous injection, shows a relatively high signal background ratio, can realize rapid and long-term nerve visualization, has certain clinical application prospects, and is used for reducing intraoperative nerve injury in a fluorescence-guided surgical operation.

Description

technical field [0001] The invention relates to a fluorescent dye and its preparation method and application, in particular to an oxazine near-infrared fluorescent dye and its preparation method and application. Background technique [0002] Surgery remains the most effective treatment option for many diseases and injuries, with more than 300 million surgical procedures performed each year worldwide. The ultimate goal of surgery is to remove or repair tissue while minimizing complications by preserving vital structures such as nerves and blood vessels. Iatrogenic neurological injury is one of the most feared surgical complications, resulting in chronic neurological disease that limits patients' quality of life and increases medical costs. [0003] Despite advances in surgical techniques and equipment, intraoperative identification and preservation of nerves has been difficult due to changes in anatomy and limited ability to directly visualize nerves during surgery. Current...

Claims

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Application Information

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IPC IPC(8): C07D265/38C09K11/06C09B19/00A61K49/00
CPCC07D265/38C09K11/06A61K49/0028C09B19/00C09K2211/1033C09K2211/1007
Inventor 包瑞楚顾月清李昌盛
Owner CHINA PHARM UNIV
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