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Rhodol derivative dye and application thereof

A technology of derivatives and dyes, applied in the directions of organic dyes, styryl dyes, methine/polymethine dyes, etc., can solve the problems of high photostability, low contrast ratio of probe imaging, and low quantum yield, etc. The effect of excellent photophysical properties and excellent photostability

Active Publication Date: 2019-11-08
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most probes have low imaging contrast due to relatively small shifts in absorption spectra or quantum yields induced by targeting molecules
However, the rational design of activated PA probes with excellent photophysical properties, such as large absorption shifts, strong near-infrared absorption, low quantum yield, and high photostability, and finally probes that provide high-contrast PA signals is still a challenge. Difficult to achieve
[0004] The common spirocyclic anthracene dye, Rhodol, because it has a large extinction coefficient, ideal photostability and unique analyte-responsive ring-opening characteristics, after hydroxyl acetylation, it forms a spironolactone structure and is in a closed-loop state. It is often used as an activation Formula fluorescent reporter group, but its maximum absorption wavelength is only 550nm, and its maximum fluorescence emission is only 580nm, which limits its application range
And Rhodol only has an absorption band in the visible region and has a relatively large quantum yield, which is not suitable for in vivo PA imaging, let alone PA / NIRF dual-mode imaging

Method used

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  • Rhodol derivative dye and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Design and Synthesis of Rhodol Derivative Dyes--Rhodol-NIR.

[0058] Freshly distilled cyclohexanone (3.3 mL, 31.9 mmol) was added dropwise to concentrated H 2 SO 4 (35 mL) and the mixture was cooled to 0 °C. Then, 4-diethylaminoketoacid (16 mmol) was added portionwise with stirring. After reacting at 90°C for 1.5 hours, the mixture was poured into ice (150 g). Perchloric acid (70%, 3.5 mL) was then added, and the resulting precipitate was filtered and washed with cold water (50 mL) to give 9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3, 4-Tetrahydrooxyalkyl (2a), using 9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3,4-tetrahydrooxyalkyl (237.6mg, 0.5mmol ) and 3,5-difluoro-4-hydroxybenzaldehyde (118.5mg, 0.75mmol), refluxed in acetic acid at a high temperature of 110°C, and spin-dried through a silica gel column to obtain Rhodol-NIR as a blue solid (89.2mg, yield 29%), the specific synthesis process is as follows:

[0059]

[0060] The structural formula of Rhodol-NIR ...

Embodiment 2

[0064] Photophysical Properties of Rhodol-NIR

[0065] Steps:

[0066] In order to determine the pKa value of Rhodol-NIR, use NaOH and hydrochloric acid to adjust the pH, prepare phosphate buffer solution containing 0.5% DMSO as a co-solvent and have different pH values, mix Rhodol-NIR (15 μ M) with different buffer systems, use The absorption spectrum of Rhodol-NIR in different pH buffer systems was measured by UV-1800 spectrophotometer, and the fluorescence spectrum of Rhodol-NIR in different pH buffer systems was measured by FS5 fluorometer, and the excitation wavelength was 620nm. The pH curve was then plotted using absorbance at 650 nm and fluorescence intensity at 720 nm. Calculate the pKa of the compound according to the Henderson-Hasselbach equation, the specific results are as follows figure 1 shown.

[0067] Rhodol-NIR has an absorption maximum at 630nm, but it produces a significantly enhanced absorption band in the broad NIR region from 620nm to 700nm. from fi...

Embodiment 3

[0077] Design and Synthesis of PA Probe Based on Rhodol-NIR

[0078] The specific synthesis process is:

[0079] B. Synthesis of trimethyl-locked quinonepropionic acid: 3,3-dimethacrylate (1.60mL, 12mmol) was added to 2,3,5-trimethyl-1,4-benzenediol (1.52 g, 10 mmol) and methanesulfonic acid (15 mL), the mixture was stirred at 70°C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with water to 150 mL and extracted three times with 70 mL of dichloromethane. Extract with saturated NaHCO 3 solution and NaCl solution, washed with anhydrous Na 2 SO 4 Dry and concentrate in vacuo. with 30% CHCl 3 Recrystallization in petroleum ether afforded 6-hydroxy-3,3,5,7,8-pentamethylcyclolactone-2-one as a white solid (1.85 g, 79.2% yield).

[0080]To a solution of 6-hydroxy-3,3,5,7,8-pentamethylcyclic lactone-2-one (1.17 g, 5 mmol) in acetonitrile (60 mL) and water (25 mL) was added NBS (0.98 g, mmol). The reaction mixture was then stirred at room temp...

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Abstract

The invention relates to a Rhodol derivative dye and a photoacoustic imaging PA (polyamide) probe and in particular to preparation and application of the Rhodol derivative dye and the photoacoustic imaging PA probe. A novel Rhodol derivative dye Rhodol-NIR is designed and synthesized, has novel Rhodol-NIR chromophore which has a large mole extinction coefficient, excellent photostability and an ideal quantum yield, and has excellent optical physical properties when a high-contrast activated PA probe. Tests prove that the Rhodol-PA probe designed and synthesized by the invention has high sensitivity and high selective detection on hNQO1 in in-vitro PA absorption and fluorescent measurement. By adopting the Rhodol derivative dye, the high-contrast activated PA probe is developed through a spirolactone open-loop conversion policy in China for a first time. The related policy of the invention is a generally applicable design, and a new platform can be provided for developing the high-contrast activated PA probe.

Description

technical field [0001] The invention relates to a Rhodol derivative dye and a photoacoustic imaging PA probe, in particular to the preparation and application of the Rhodol derivative dye and a photoacoustic imaging PA probe. Background technique [0002] Photoacoustic (PA) imaging is a powerful biomedical imaging modality that enables the noninvasive visualization of biological processes at the molecular and cellular levels in deep tissues with high spatial resolution. Utilizing a near-infrared (NIR) operating window, the PA can provide a penetration depth of several centimeters with a resolution of about 100 μm. Due to its advantages, it provides a useful tool for clinical imaging of various diseases including cancer diagnosis, metastasis assessment and treatment monitoring. [0003] Molecular probes are essential in PA imaging because they can confer molecular or cellular specificity and enhance imaging contrast. PA probes typically rely on designs that allow selective ...

Claims

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Application Information

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IPC IPC(8): C09B23/14A61K49/22A61K49/00
CPCA61K49/0002A61K49/0021A61K49/221C09B23/145
Inventor 蒋健晖汪凤林刘锋唐丽娟
Owner HUNAN UNIV
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