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Ph-sensitive probe comprising polymer and fluorescent dye

A technology of polymers and fluorescent dyes, applied in the field of fluorescent probes and new polymers, can solve problems such as difficulty in distinguishing high-grade malignant tumors

Inactive Publication Date: 2010-02-03
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore it is difficult to distinguish between high-grade malignant tumors (pH value: about 5.5) and normal sites (pH value: about 7.4)

Method used

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  • Ph-sensitive probe comprising polymer and fluorescent dye
  • Ph-sensitive probe comprising polymer and fluorescent dye
  • Ph-sensitive probe comprising polymer and fluorescent dye

Examples

Experimental program
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Effect test

Embodiment 1

Embodiment 1-1

[0061] A total of 1 g of sodium salt of poly-L-glutamic acid (PGA; molecular weight 41,000, Peptide Research Institute) was dissolved in 100 ml of distilled water, followed by stirring while adding hydrochloric acid dropwise, and the desalted PGA was precipitated. The resulting desalted PGA was washed thoroughly with acetone and then with diethyl ether, then dried in vacuo. The washed and dried PGA (150 mg) was then dissolved in 1 ml anhydrous DMSO, N-hydroxysuccinimide (NHS; 13.5 mg) and 1-ethyl-3-dimethylaminopropylcarbodiimide were added hydrochloride (EDC; 22.2 mg), and shake overnight at room temperature. Succinimidization was performed at a ratio of 10% to the total COOH. After this reaction, reprecipitation was performed with anhydrous acetone to remove unreacted EDC and the reaction product of NHS and EDC, 1-ethyl-3-(3-dimethylaminopropyl)urea. It was then centrifuged and washed two more times by decanting. The succinimidized PGA was then obtained by washing with he...

Embodiment 1-2

Modification of succinimidized PGA with anilinonaphthalimide

[0062] Succinimidized PGA (150 mg) prepared according to Example 1-1 above was dissolved in anhydrous DMSO (5 ml). Then, N-(1-anilinonaphthyl-4-)-maleimide (anilinonaphthylimide: ANM) (21 mg) and 6-amino-1-hexanethiol (11 mg ), add 1.5ml of DMSO solution which has been stirred overnight, and stir overnight at room temperature in the dark. The reaction solution was reprecipitated with acetone, and then washed twice by pouring. Then, 136 mg of anilinonaphthalimine-modified PGA (PGA-AN1) was obtained by washing with hexane, replacing with ether, and drying in vacuo (90% yield). By measuring the absorbance (350 nm) and anilinonaphthyl (AN) of the obtained PGA-AN1, it was confirmed that the modification rate of the AN group with respect to the total COOH of the PGA was 0.006. The structural formula of the obtained PGA-AN1 is shown in Formula 3 above. In this formula, m is 316, and N is 1.9.

[0063] Succinimidized P...

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Abstract

A polymer has a fluorescent dye sensitive to a hydrophobic environment. When a pH around the polymer decreases within a range of pH of equal to or greater than 5.5 and less than 7.4, and a secondary structure of the polymer changes from a random coil to a helix.

Description

technical field [0001] The present invention relates to novel polymers and fluorescent probes having said novel polymers. Background technique [0002] Detection of lesion sites in diseases such as tumors and inflammations is a very important task in the fields of biology and medicine, especially clinical medical research and internal imaging diagnosis. Therefore, there is a need for molecular probes that can detect lesion sites with high sensitivity and specificity to perform such high-sensitivity and high-precision detection. [0003] Sites of disease such as tumors and inflammation differ in pH from the normal tissue environment. Tumors or sites of inflammation (pH around 5-6) are known to have a lower pH than normal tissue (pH around 7.4). It is also known that the pH of some high-grade malignant tumors can even drop to about 5.5. Therefore, pH-responsive compounds are expected to be candidates for molecular probes that can detect cancer and inflammation. [0004] Ja...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B69/10C09K11/06C09K9/02G01N21/64
CPCA61K49/0021A61K49/0054A61K47/645
Inventor 山内文生
Owner CANON KK
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