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Pentamethine-cyanine-dye photosensitive dye with long lifetime of excited state, and preparation method and application thereof

A photosensitive dye and excited state technology, applied in organic dyes, medical preparations containing active ingredients, azo dyes, etc., can solve the problems of fluorescence quenching, short life, shortened state life, etc.

Active Publication Date: 2021-09-14
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, strong spin-spin exchange interactions between radicals and fluorophores can also lead to significant fluorescence quenching and T 1 State life shortened
[0005] In addition, due to the complex bond isomerization process, cyanine dyes usually have low radiation quantum yield and short excited state lifetime, which affect the anticancer effect

Method used

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  • Pentamethine-cyanine-dye photosensitive dye with long lifetime of excited state, and preparation method and application thereof
  • Pentamethine-cyanine-dye photosensitive dye with long lifetime of excited state, and preparation method and application thereof
  • Pentamethine-cyanine-dye photosensitive dye with long lifetime of excited state, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] The synthesis of embodiment 1. photosensitive molecule ANOMe-Cy5:

[0059]

[0060] (1) Synthesis of intermediate compound 3:

[0061] Compound 2 (0.34g, 1mmol), quaternary ammonium salt 1 (0.63g, 2mmol) and anhydrous sodium acetate (0.2g, 2.5mmol) in absolute ethanol were stirred under reflux for 2h. After cooling, the ethanol was spin-dried by a rotary evaporator, and the crude product was purified by silica gel column chromatography (dichloromethane / methanol=10:1, v / v) to obtain compound 3 as a blue powder (0.53 g, 71.8%). 1 HNMR (400MHz, MeOD): 8.41 (d, J = 13.3Hz, 2H, CH), 7.56 (d, J = 7.4Hz, 2H, ArH), 7.46 (t, J = 7.6Hz, 2H, ArH), 7.40 (d, J=7.8Hz, 2H, ArH), 7.33(t, J=7.4Hz, 2H, ArH), 6.49(d, J=13.3Hz, 2H, CH), 4.24(q, J=7.2Hz, 4H,CH 2 ),1.76(s,12H,CH 3 ), 1.45(t, J=7.2Hz, 6H, CH 3 ).ESI-MS (C 29 h 34 BrN 2 I) m / z: [M–I] - calcd.489.19; found, 489.28.

[0062] (2) Synthesis of photosensitive molecule ANOMe-Cy5:

[0063] Dissolve 3 (0.1g, 0.16mmol), ...

Embodiment 2

[0064] Embodiment 2. Singlet oxygen performance test of photosensitive molecule ANOMe-Cy5

[0065] Add 1.5μM photosensitive molecule ANOMe-Cy5 to the test quartz dish containing 3mL dichloromethane solution, adjust the absorbance at 415nm to about 1 through the DPBF solution, place the dish at 660nm, 10mW / cm 2 Irradiate under a xenon light source, and record the absorption spectrum of the solution every 15 seconds. The test results are collated and displayed in figure 1 In , the absorption of the solution attenuates at a certain value as the irradiation time increases, indicating that the solution produces singlet oxygen under the irradiation of the light source of this wavelength.

Embodiment 3

[0066] The test of embodiment 3.ANOMe-Cy5 excited state lifetime

[0067] 5 μM of compound ANOMe-Cy5 was placed in 3 mL of dichloromethane solution. The fluorescence lifetime and triplet lifetime of the two compounds were tested by flash photolysis and time-resolved spectroscopy. The results are reflected in figure 2 Figures C and D.

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Abstract

The invention provides a pentamethine-cyanine-dye photosensitive dye with a long lifetime of excited state and a preparation method and application thereof. The photosensitive dye has a structure shown in a general formula I. The pentamethine-cyanine-dye photosensitive dye with long lifetime of excited state can have relatively high singlet oxygen quantum yield and relatively long lifetime of excited state. Under the excitation of near-infrared light, the photodynamic killing can be carried out on normoxic and hypoxic cancer cells. Meanwhile, the pentamethine-cyanine-dye photosensitive dye with a long lifetime of excited state possesses a good application prospect in the aspects of treating solid tumors in vivo and inhibiting lung metastasis of cancer cells.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a class of pentamethylcyanine dye photosensitizers with long excited state lifetime, a preparation method and application thereof. Background technique [0002] Photodynamic therapy (Photodynamic Therapy, PDT) is a method that applies the principles of photochemistry, photophysics and photobiology to the diagnosis and treatment of diseases. It is the fourth therapy after surgery, chemotherapy and radiotherapy. It shows great application potential in malignant diseases such as cancer and various benign diseases. [0003] The three elements of photodynamic therapy are: light source, photosensitizer and oxygen. The photosensitizer is the most important component among the three elements of PDT. At present, commercial photosensitizers such as porphyrin derivatives chlorin (ce6), phthalocyanine, and indocyanine green have played an important role in photodynamic therapy. Howev...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61K49/00A61P35/00C07D209/12C09B57/00
CPCA61K41/0057A61K49/0021A61P35/00C07D209/12C09B57/00
Inventor 樊江莉赵学泽姚起超龙飒然孙文彭孝军
Owner DALIAN UNIV OF TECH
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