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Rare earth complex with near infrared pH intensity and life response

A technology of rare earth complexes and rare earth ions, which can be applied to organic compounds of group 3/13 without C-metal bonds, compounds containing elements of group 3/13 of the periodic table, organic chemistry, etc., which can solve the problem of short life and limited applications , Low luminous quantum yield and other issues, to achieve the effect of near-infrared intensity imaging and lifetime imaging

Active Publication Date: 2018-08-21
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported dyes in the second near-infrared region have only realized the research of fluorescence intensity imaging, and the luminescence quantum yield is low and the lifetime is short, which limits their application as near-infrared biological probes (Wan H, Yue J, Zhu S, et al. Nat. Commun. 2018, 9, 1171; I,Eliseeva S V,Nguyen T N,et al.J.Am.Chem.Soc. 2017,139,8388-8391; Lei Z,Li X,Luo X,et al.Angew.Chem.Int.Ed.2017,56 ,2979-2983)

Method used

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  • Rare earth complex with near infrared pH intensity and life response
  • Rare earth complex with near infrared pH intensity and life response
  • Rare earth complex with near infrared pH intensity and life response

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The synthesis of embodiment 1 complex 1:

[0038]

[0039] The first intermediate product was obtained by mixing the corresponding fluorinated tetrapyrrole ligand and ytterbium acetylacetonate salt in trichlorobenzene and reacting at 200° C. under nitrogen atmosphere. The resulting first intermediate and the corresponding deuterated The tripod ligand was reacted in chloroform to obtain a second intermediate product. Then react the second intermediate product in sulfuric acid to obtain complex 1. For the location of the main emission peak, see figure 1 : 920nm, 950nm, 980nm, 1000nm, 1020nm, 1050nm; main excitation peak position: 418 nm, 560nm, 620nm; lifetime: about 170μs.

Embodiment 2

[0040] The synthesis of embodiment 2 complex 2:

[0041]

[0042] The first intermediate product was obtained by mixing the corresponding fluorinated tetrapyrrole ligand and ytterbium acetylacetonate salt in trichlorobenzene and reacting at 200° C. under nitrogen atmosphere. The resulting first intermediate and the corresponding deuterated The tripod ligand was reacted in chloroform to obtain a second intermediate product. Then the second intermediate product was hydrolyzed by potassium hydroxide in methanol and tetrahydrofuran to obtain complex 2. Main emission peak position: 920nm, 950nm, 980nm, 1000nm, 1020nm, 1050nm; main excitation peak position: 416nm, 546nm, 592nm; lifetime: about 150μs.

Embodiment 3

[0043] The synthesis of embodiment 3 complex 3:

[0044]

[0045] The first intermediate product was obtained by mixing the corresponding fluorinated tetrapyrrole ligand and ytterbium acetylacetonate salt in trichlorobenzene and reacting at 200° C. under nitrogen atmosphere. The resulting first intermediate and the corresponding deuterated The tripod ligand was reacted in chloroform to obtain a second intermediate product. Then react the second intermediate product in (trimethylsilyl)phosphite to obtain complex 3. Main emission peak position: 920nm, 950nm, 980nm, 1000nm, 1020nm, 1050nm Excitation main peak position: 416nm, 546nm, 592nm; lifetime: about 140μs.

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Abstract

The invention discloses a rare earth complex capable of performing intensity and life response on pH in a near infrared area (800-1600 nm) as well as preparation and application thereof. The compoundcomprises a tetrafluoropyrrole organic ligand, rare earth ions and an axial ligand. The compounds have excellent biocompatibility; the light intensity and the life are obviously changed along with thechange of pH; and the compounds are a potential living body intensity and life imaging reagent and a pH detection medicine.

Description

technical field [0001] The invention relates to the field of biological imaging and probes, in particular to a rare earth complex that responds to pH in the second near-infrared region and its preparation method and biological application, which can effectively realize near-infrared intensity and lifetime imaging, and to Effective detection of intracellular pH changes. Background technique [0002] Compared with the traditional dyes in the first near-infrared region (700-900nm), dyes in the second near-infrared region (900-1200nm) can achieve deeper tissue imaging (Cheng Z, et al.Chem.Soc.Rev., 2018, DOI: 10.1039 / c8cs00234g; Dai H, et al. Nat. Biomed. Eng., 2017, 1, 0010). However, the reported dyes in the second near-infrared region have only realized the research of fluorescence intensity imaging, and the luminescence quantum yield is low and the lifetime is short, which limits their application as near-infrared biological probes (Wan H, Yue J, Zhu S, et al. Nat. Commun....

Claims

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Application Information

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IPC IPC(8): C07F19/00C07F5/00C09K11/06G01N21/64
CPCC07F5/003C07F17/02C09K11/06C09K2211/182C09K2211/187G01N21/6486
Inventor 张俊龙宁莹莹
Owner PEKING UNIV
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