Near infrared fluorescent compounds of porphyrins connected with alkynyl and preparation method

A fluorescent compound, near-infrared technology, applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of limiting the sensitivity of fluorescent probes, unsatisfactory photophysical properties, and reducing background interference.

Inactive Publication Date: 2008-12-31
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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Problems solved by technology

For biological samples, the sample matrix and some impurities will also absorb or fluoresce in this area, and the influence of light scattering often produces more serious background interference, which limits the improvement of fluorescent probes in molecular imaging applications. Sensitivity
Compared with conventional fluorescence (λ600nm) light region, the light absorption or fluorescence intensity of the biological sample matrix is ​​very small, so the background interference is greatly reduced, and due to the difference between the intensity of scattered light and the wavelength Inversely proportional to the fourth power, with the increase of wavelength, the Raman scattering decreases rapidly, so that the scattering interference is also greatly reduced; in addition, the commonly used fluorescent molecular probes have poor photophysical properties due to their poor biocompatibility, and Not suitable for large-scale synthesis, thus limiting its development
[0004] Designing and synthesizing a near-infrared fluorescent molecular compound with good biocompatibility and photophysical properties, and using it as a fluorescent molecular probe is a very challenging research, but it is of great practical significance

Method used

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  • Near infrared fluorescent compounds of porphyrins connected with alkynyl and preparation method
  • Near infrared fluorescent compounds of porphyrins connected with alkynyl and preparation method
  • Near infrared fluorescent compounds of porphyrins connected with alkynyl and preparation method

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preparation example Construction

[0045] In the preparation process of the present invention, the input involved is only the ratio of the amount of one of the substances. In a specific reaction, we can enlarge or reduce the ratio of the amount of this substance.

[0046]

[0047] The preparation method of two{[5,5'-10,20-diphenyl-15-(4-pyridyl)porphyrin]Zn(II)]}butadiyne

Embodiment 1

[0050] Synthesis of 5-Phenyldipyrromethane (Compound 3)

[0051] Add (150 ml, 2.16 mol) freshly distilled pyrrole and (6.0 ml, 59 mmol) benzaldehyde in a 250 ml two-neck round bottom flask, protect with nitrogen for 15 minutes, add (0.45 ml, 5.8 mmol) three Fluoroacetic acid, continue to react for 15 minutes, and distill off excess pyrrole under reduced pressure to obtain dark yellow oil, which is dissolved in dichloromethane, purified by silica gel column chromatography, and eluted with dichloromethane to obtain 5-phenyldipyrrole 8.6 grams of methane, yield 65%. 1 HNMR (300MHz, CDCl 3)δ: 5.44 (s, 1H), 5.83 (br, s, 2H), 6.15 (d, 2H), 6.69 (br, s, 2H), 7.20-7.34 (m, 5H), 7.90 (br s, 2H ); ESI-MS (CHCl 3 ): 223.3 ([M+H] + ).

Embodiment 2

[0053] Synthesis of 5-Phenyldipyrromethane (Compound 3)

[0054] Add (150 ml, 2.16 mol) freshly distilled pyrrole and (6.0 ml, 59 mmol) benzaldehyde in a 250 ml two-necked round bottom flask, react at 20°C, protect with nitrogen for 40 minutes, add (0.45 ml , 5.8 mmol) trifluoroacetic acid, continued to react for 10 minutes, and removed excess pyrrole by distillation under reduced pressure to obtain dark yellow oil, which was dissolved in dichloromethane, purified by silica gel column chromatography, and eluted with dichloromethane to obtain 5-Phenyldipyrromethane.

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Abstract

The invention discloses an IR fluorescent porphyrins connected by alkynyls and a preparation method thereof. The IR fluorescent porphyrins connected by alkynyls has above general formula(I) and can be used as IR fluorescent molecule probes.

Description

technical field [0001] The invention relates to a class of porphyrin-based near-infrared fluorescent compounds linked by alkyne groups and a preparation method. Background technique [0002] In recent years, with the advancement of molecular and cell biology techniques and the completion of the Human Genome Project, the importance of non-invasive, high-resolution, real-time, in vivo molecular and gene imaging techniques has become increasingly prominent, and molecular imaging has come into being. And born. Molecular medical imaging technology is a medical imaging method that displays human life information that cannot or is difficult to recognize with the naked eye or other technologies. In contrast to general clinical imaging, it detects the molecular abnormalities underlying the disease rather than imaging the end result of those molecular alterations. First, molecular imaging can improve the level of clinical diagnosis and treatment of diseases. In addition, molecular ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
Inventor 刘天军陈国辉李迪潘雯瑛陈魏
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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