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Dye and fluorescent probe for detecting singlet oxygen and manufacturing method of dye and fluorescent probe

A fluorescent probe and singlet oxygen technology, applied in chemical instruments and methods, fluorescence/phosphorescence, dibenzoanthone/isodibenzoanthrone dyes, etc., can solve highly sensitive and selective fluorescence quenching Solve the problems of scarcity of reagents, difficulty in synthesis, and low sensitivity, and achieve the effects of reducing synthesis cost, expanding application range, and high sensitivity

Inactive Publication Date: 2017-08-29
NAT UNIV OF SINGAPORE SUZHOU RES INST +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In summary, the fluorescent probes for singlet oxygen detection in the prior art face the problems of difficult synthesis, high cost and low sensitivity.
In addition, fluorescent quenchers with high sensitivity and selectivity to singlet oxygen are also scarce.
These defects limit the 1 o 2 Applications of Probes in Chemical and Biological Systems

Method used

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  • Dye and fluorescent probe for detecting singlet oxygen and manufacturing method of dye and fluorescent probe
  • Dye and fluorescent probe for detecting singlet oxygen and manufacturing method of dye and fluorescent probe
  • Dye and fluorescent probe for detecting singlet oxygen and manufacturing method of dye and fluorescent probe

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Experimental program
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Effect test

Embodiment 1

[0052] Embodiment 1: the synthesis of formula I probe

[0053] Such as figure 1 As shown, using 9,10-dioxo-9,10-dihydroanthracene-1,4-dicarboxychloride (for example, as shown in CAS No. 6937-78-6) as a raw material, the compound of formula I was prepared and synthesized. Alternatively, in order to obtain 9,10-dioxo-9,10-dihydroanthracene-1,4-dicarboxychloride, commercially available or synthetic 9,10-dioxo - 9,10-dihydroanthracene-1,4-dicarboxylic acid (eg, CAS No. 54292-11-4), subjecting it to a chlorination reaction with a chlorinating agent (eg, thionyl chloride).

[0054] For example, 9,10-dioxo-9,10-dihydroanthracene-1,4-dicarboxylic acid can be synthesized first: prepare 1,4- Dimethylanthraquinone (1.3g, 5.51mmol) suspension, add active MnO in batches while stirring at 80°C 2 (6.88 g, 79.1 mmol). After 15 minutes, heat to 110°C and hold for 4 hours. Then, after the reaction mixture had cooled, it was slowly poured into cold water. The resulting solid was isolated, ...

Embodiment 2

[0064] Embodiment 2: the piperazine derivative of formula I compound is synthesized

[0065] Such as figure 2 As shown, piperazine derivatives of compounds of formula I were prepared. For example, piperazine (5.31mg, 0.062mmol) was dissolved in dry dichloromethane (DCM) (6mL), then benzotriazole-N,N,N',N'-tetramethyluronium hexafluoro Phosphate (HBTU) 34.3mg, 0.091mmol), N, N-diisopropylethylamine (DIPEA) (31μl, 0.184mmol), and compound 1 (34mg, 0.062mmol) stirred overnight at room temperature, namely The crude product of the piperazine derivative of the compound of formula (I) (ie compound 5) was obtained. The product can be purified with HCl (1M, 10mL) and NaHCO 3 Aqueous solution (2X 10 mL) washed the reaction mixture. The organic phase was collected and rotovaped to dryness. By silica gel column chromatography (eluent: CH 2 Cl 2 / MeOH, v / v=97: 3)) purify the crude product to obtain pure purple piperazine derivatives of the compound of formula (I) (wherein R 1 is m...

Embodiment 3

[0070] Embodiment 3: the synthesis of formula IIa singlet oxygen probe

[0071] Such as figure 2 As shown, according to the following steps, the singlet oxygen fluorescence detection probe of formula IIa was synthesized.

[0072] Synthesis of Compound 3: According to the description in Sunahara et al. 2007 (Sunahara, H.; Urano, Y.; Kojima, H.; Nagano, T.J.AM.CHEM.SOC.2007, 129, 5597-5604), the compound was prepared 3. Its chemical structure is as figure 2 Compound 3 in.

[0073] Synthesis of Compound 4 ： To a solution of compound 3 (35 mg, 0.10 mmol) in anhydrous dichloromethane (8 mL) was added chloroacetyl chloride (30 μL, 0.41 mmol, dissolved in 1 mL of dichloromethane) and triethylamine (30 μL, 0.215 mmol). Stir the reaction at room temperature for 2 hours, then wash with NaHCO 3 The reaction mixture was washed with aqueous solution (3 x 10 mL) and deionized water (3 x 10 mL). The organic phase was collected and rotovaped to dryness, then used further in the next s...

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Abstract

The application discloses a synthetic method of a dye compound used for sensitive detection of singlet oxygen. Furthermore, a fluorescent probe having a part of different fluorescent groups of the dye compound is designed and is synthesized through a new synthetic method. The fluorescent probe can well react with singlet oxygen. The probe can be used for detecting singlet oxygen in fields of environment, food and bio-medical treatment. The probe can be used for making molecular probes, researching singlet oxygen and disease photodynamic therapy and manufacturing a singlet oxygen kit.

Description

technical field [0001] The invention relates to the field of singlet oxygen detection, in particular to a compound for detecting singlet oxygen, a probe containing the compound, a synthesis method thereof and an application in detecting singlet oxygen. Background technique [0002] Singlet Oxygen (Singlet Oxygen, 1 o 2 ), which is different from the stable ground-state oxygen molecule oxygen that is usually breathed, is a form of existence of oxygen molecules in an excited state. Compared with the ground state, the chemical properties of singlet oxygen are more active, less stable, and highly oxidizing, which can lead to the oxidation of various substances. Singlet oxygen can participate in a variety of biochemical reactions and physiological processes in the body, such as signal transduction, enzyme reactions, cell division, tissue peroxidation, inflammation, aging, phagocytosis, tumors and chemical poisoning, and has multiple complex dual effects on the body. On the one...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B3/24C09B3/72C09K11/06G01N21/64
CPCC09B3/24C09B3/72C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088G01N21/643
Inventor 黄德建沙兰根·克里希纳库马尔吴海霞陈代郭晶晶
Owner NAT UNIV OF SINGAPORE SUZHOU RES INST
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