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Dual-mode imaging probe with pH response as well as preparation method and application thereof

A dual-mode imaging and probe technology, which is applied in the field of bioluminescence analysis, can solve the problems of short pH probe wavelength, strong background interference, and low signal-to-noise ratio. less distracting effect

Active Publication Date: 2016-06-08
SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Compared with other pH measurement methods, the use of fluorescent probes for pH detection has the advantages of high sensitivity and good selectivity, but most of the current pH probes have short wavelengths, which cannot avoid tissue self-absorption and autofluorescence, background interference Strong, small displacement of some stocks, large overlap of ultraviolet absorption spectrum and fluorescence spectrum, low signal-to-noise ratio, high toxicity, and cannot be used for pH detection of cells and living bodies
At the same time, a single pH fluorescent probe is only limited to imaging tissues close to the skin surface by imaging the fluorescence emitted by characteristic molecules in the tissue, and is not suitable for capturing information about tissues and organs in the body.

Method used

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  • Dual-mode imaging probe with pH response as well as preparation method and application thereof
  • Dual-mode imaging probe with pH response as well as preparation method and application thereof
  • Dual-mode imaging probe with pH response as well as preparation method and application thereof

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Experimental program
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Embodiment 1

[0063] A method for preparing a dual-mode imaging probe with pH response, comprising the following steps:

[0064] (1) Preparation

[0065] 34.4mg (0.4mmol) of and 63.8 mg (0.1 mmol) of the compound Dissolve in 2ml of anhydrous DMF solvent, under argon gas atmosphere, react at 80°C for 1h, remove the solvent by rotary evaporation, vacuum dry for 12h, pass through a silica gel column, the volume ratio of eluent dichloromethane and methanol is from 40 :1 is changed to 20:1 and carry out gradient elution, remove solvent, obtain blue solid product 55mg, productive rate 80%, the structural formula of this blue solid product is

[0066] (2) Preparation of dual-mode imaging probes with pH response:

[0067] The chemical formula will be 34.4mg (0.05mmol, molecular weight 688.3) and 48.76mg (0.25mmol) Put it into a three-necked flask, add 2 mL of anhydrous DMF as a solvent, then add 40 μL (0.2886 mmol) of triethylamine as an acid-binding agent, under the protection of argo...

Embodiment 2

[0072] A method for preparing a dual-mode imaging probe with pH response, comprising the following steps:

[0073] 25.8mg (0.3mmol) of and 34.4 mg (0.05 mmol) of the compound Dissolve in 2ml of anhydrous DMF solvent, under argon gas atmosphere, react at 70 °C for 1.5h, remove the solvent by rotary evaporation, vacuum dry for 12h, pass through a silica gel column, the volume ratio of eluent dichloromethane and methanol from Change 40:1 to 20:1 and carry out gradient elution, remove solvent, obtain blue solid product 28mg, productive rate 81%, the structural formula of this blue solid product is

[0074] (2) Preparation of dual-mode imaging probes with pH response:

[0075] The chemical formula will be 34.4mg (0.05mmol) and 39mg (0.2mmol) of Put it into a three-necked flask, add 2mL of anhydrous DMF as a solvent, then add 40μL of triethylamine as an acid-binding agent, under the protection of argon, react at a temperature of 60°C for 4h, remove the solvent by rotary ev...

Embodiment 3

[0077] A method for preparing a dual-mode imaging probe with pH response, comprising the following steps:

[0078] (1) 31.6mg (0.37mmol) of and 70.47 mg (0.11 mmol) of the compound Dissolve in 2.5ml of anhydrous DMF solvent, react at 60°C for 2h under argon gas atmosphere, remove the solvent by rotary evaporation, dry in vacuum for 12h, pass through a silica gel column, and carry out gradient washing with a mixed solution of dichloromethane and methanol Remove, the volume ratio of eluent dichloromethane and methanol is changed from 40:1 to 20:1, remove solvent, obtain blue solid product 60mg, productive rate 81%, the structural formula of this blue solid product is

[0079] (2) Preparation of dual-mode imaging probes with pH response:

[0080] The chemical formula will be 68.8mg (0.1mmol) and 78mg (0.4mmol) of Add it into a three-necked flask, add 3mL of anhydrous DMF as a solvent, then add 70μL (0.5mmol) of triethylamine as an acid-binding agent, under the protection...

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Abstract

The invention provides a dual-mode imaging probe with pH response. The chemical structural formula of the dual-mode imaging probe is as shown in the formula (I). In the formula (I), X represents -C(CH3)2-, -O-, -S- or -Se-; Y represents F, Cl, Br or I; R1 and R2 are independently selected from H atom, C1-18 alkyl or -SO3R5; R5 represents C1-18 alkyl or benzyl; R3 and R4 are independently selected from C1-18 alkyl or benzyl. When a pH of the probe is 3.5-10.0, the fluorescence intensity ratio of emission light at 760nm and 670nm is gradually enhanced along with the reduction of the pH; the absorption intensity ratio at 760nm and 680nm is gradually enhanced along with the reduction of the pH; 760nm / 680nm photo-acoustic signals are gradually enhanced along with the reduction of pH; the obvious pH-depended photo-acoustic signal variability is shown; pKa is 6.2. The dual-mode imaging probe is very applicable to detection of tumor pH I in both a fluorescence mode and a photo-acoustic mode. The invention also provides a preparation method and application of the probe.

Description

technical field [0001] The invention relates to the technical field of bioluminescent analysis, in particular to a pH-responsive dual-mode imaging probe and its preparation method and application. Background technique [0002] Intracellular pH plays a crucial role in a series of tissue activities such as enzyme activity, cell proliferation and apoptosis, drug resistance, ion transport, endocytosis, and muscle contraction. For example, intracellular pH changes when tumors develop. The delicate relationship between cell function and pH value means that as long as the change of intracellular pH value can be mastered, it can provide important information for the study of related physiological and pathological processes. Therefore, how to accurately detect the change of intracellular pH is very important. [0003] Compared with other pH measurement methods, the use of fluorescent probes for pH detection has the advantages of high sensitivity and good selectivity, but most of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/14A61K49/00
CPCA61K49/0032C07D209/14C09K11/06C09K2211/1044
Inventor 蔡林涛吕亚琳龚萍孟晓青张利周理华李三朋
Owner SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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