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Single-photon up-conversion pentamethine cyanine photosensitive dye as well as preparation method and application thereof

A technology for pentamethyl tetracyanine and photosensitizing dyes, which is applied in the field of single photon up-conversion pentamethyl tetracyanine photosensitive dyes, and can solve the problem of limited quantum yield of reactive oxygen species.

Active Publication Date: 2022-02-15
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing PDT photosensitizers have the disadvantages of relying on heavy atoms and upconversion excitation to generate reactive oxygen species with limited quantum yields.

Method used

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  • Single-photon up-conversion pentamethine cyanine photosensitive dye as well as preparation method and application thereof
  • Single-photon up-conversion pentamethine cyanine photosensitive dye as well as preparation method and application thereof
  • Single-photon up-conversion pentamethine cyanine photosensitive dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1. Synthesis of photosensitive molecule XAN-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 H NMR (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 XAN-Cy5:

[0063] Dissolve 3 (0.1g, 0.16mmol), 4 (0.084g, ...

Embodiment 2

[0064] Example 2. Singlet oxygen performance test of photosensitive molecule XAN-Cy5

[0065] Add 2μM photosensitive molecule XAN-Cy5 to the test quartz dish containing 3mL dichloromethane solution, adjust the absorbance at 415nm to about 1 through DPBF solution, place the dish at 760nm, 500mW / cm 2 The absorption spectrum of the solution was recorded every 120 seconds. The test results are collated and displayed in figure 1 In , the absorption of the solution decays at a certain value with the increase of the irradiation time, indicating that the solution produces singlet oxygen under the irradiation of the light source of this wavelength.

Embodiment 3

[0066] Example 3. XAN-Cy5 up-conversion excitation fluorescence test

[0067] 2 μM of compound XAN-Cy5 was placed in 3 mL of dichloromethane solution. Excitation at 760nm is used and fluorescence emission at 630-700nm is captured. Such as figure 2 is the upconversion fluorescence excitation map of the photosensitive molecule XAN-Cy5

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Abstract

The invention provides a single-photon upconversion pentamethine cyanine photosensitive dye as well as a preparation method and application thereof. The photosensitive dye has a structure as shown in a general formula I. The pentamethine cyanine photosensitive dye without heavy atom modification and with the single photon up-conversion property has high singlet oxygen generation capacity under excitation of light longer than the maximum absorption wavelength of the pentamethine cyanine photosensitive dye. By means of the photosensitive dye, under the excitation of up-conversion light, effective photodynamic killing can be performed on cancer cells under deep tissues, and the up-conversion light-induced cancer cell can be used for photodynamic therapy of solid tumors in vivo and has a good application prospect in inhibition of growth of deep tumors.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a class of single-photon up-conversion pentamethine photosensitive dyes, 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 wavelength of light emitted by the light source largely determines the treatment depth of photodynamic therapy for solid tumors. Therefore, the development of photosensitive dyes that can be excited by long-wavelength light has always been a research hotspot. Although incre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C09K11/06A61K41/00A61K49/00A61P35/00
CPCC09B23/083C09K11/06A61K41/0057A61K49/0032A61P35/00C09K2211/1029
Inventor 樊江莉赵学泽杜健军彭孝军
Owner DALIAN UNIV OF TECH
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