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Method for detecting cancer cell using fluorescently labeled L-glucose derivative, and cancer cell-imaging agent comprising fluorescently labeled L-glucose derivative

A technology of a glucose derivative and a detection method, which is applied in the field of detecting cancer cells or cells that may have cancer, and can solve the problems of difficulty in diagnosing diabetes patients and the like

Active Publication Date: 2014-01-08
ORBIO CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, it has to be admitted that as long as the fluorescently labeled D-glucose derivative is used, it is limited to determine whether there are tumor cells with good accuracy.
In addition, the FDG method is difficult to diagnose diabetic patients, but there is a problem that the cancer-prone age overlaps with the onset age of diabetes, and imaging using 2-NBDG may also be restricted

Method used

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  • Method for detecting cancer cell using fluorescently labeled L-glucose derivative, and cancer cell-imaging agent comprising fluorescently labeled L-glucose derivative
  • Method for detecting cancer cell using fluorescently labeled L-glucose derivative, and cancer cell-imaging agent comprising fluorescently labeled L-glucose derivative
  • Method for detecting cancer cell using fluorescently labeled L-glucose derivative, and cancer cell-imaging agent comprising fluorescently labeled L-glucose derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Embodiment 1: the synthesis of compound

[0112] (1) Synthesis of fluorescently labeled L-glucose derivatives

[0113] (1-1) Synthesis of 2-NBDLG

[0114] 2-NBDLG is synthesized from L-glucose as follows.

[0115]

[0116] 3,4,6-Tri-O-acetyl-L-glucal

[0117] L-glucose (20 g) was dissolved in pyridine (262 ml), and cooled to 0°C. Add anhydrous acetic acid (171ml) dropwise, and stir overnight at room temperature. Concentration under reduced pressure followed by azeotropic operation with toluene was repeated three times. Ethyl acetate was added to the residue, washed with saturated sodium bicarbonate water and saturated brine, and the organic layer was dried over sodium sulfate. Sodium sulfate was filtered off, and the organic solvent was removed by concentration under reduced pressure. The obtained residue was dissolved in dehydrated dichloromethane (115 ml) under an argon atmosphere, and cooled to 0°C. A 30% hydrobromide acetic acid solution (61 ml) was adde...

reference example 1

[0211] Reference Example 1: Synthesis of Comparative Compounds

[0212] (1) Synthesis of fluorescently labeled D-glucose derivatives

[0213] (1-1) Synthesis of 2-NBDG

[0214] 2-NBDG can be synthesized according to the method described in Non-Patent Document 5.

[0215] (1-2) Synthesis of fluorescently labeled L-mannose

[0216] In the present invention, as the sugar skeleton bound to the fluorescent group, the mirror-image isomer of the natural 6-carbon sugar D-glucose that exists in large quantities in nature can be used, that is, the non-natural L-glucose that is not found in nature. On the other hand, as a fluorescently labeled L-mannose derivative whose backbone is the mirror image isomer of the 6-carbon sugar D-mannose that exists in large quantities in nature, that is, unnatural L-mannose, the inventors newly synthesized 2-Deoxy-2-[N-(7-nitrobenzo-2-oxa-1,3-oxadiazol-4-yl)amino]-L-mannose (2-NBDLM).

[0217]

[0218] Benzyl 4,6-O-benzylidene-α-L-glucopyranosid...

Embodiment 2

[0239] Example 2: Studies Using Mice Transplanted with Tumor Cells (C6 Glioma)

[0240] (experimental method)

[0241] (1) Preparation of rat glioma cells (C6) for transplantation

[0242] According to the conventional method, the number of cells was 2×10 7 cells / mL to prepare C6 cells.

[0243] (1-1) Cultivation of C6 cells

[0244] Transplant the C6 cells into a 10cm culture dish in CO 2 Let stand in the incubator and cultivate at 37°C. The culture medium was changed every 2 days.

[0245] (1-2) Composition of culture medium for culturing C6 cells

[0246] Add Fetal Bovine Serum (Equitech-Bio SFBM) to Dulbecco's modified Eagle's Medium (DMEM) (Nacalai No.08456-65) containing 1g / L glucose to make the final concentration 10%, and add penicillin-chain Mycin (Nacalai No. 26253-84) was used at a final concentration of 1%, and the above culture solution was used.

[0247] (2) Production of tumor model mice

[0248] For 5-6 week-old thymus-deficient nude mice (BALB / cAJcl-...

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Abstract

The purpose of the present invention is to provide a method for highly accurately detecting a cancer cell. The method of the present invention is characterized by comprising imaging with the use of a fluorescently labeled L-glucose derivative. By using the method and imaging agent according to the present invention, a high contrast between a cancer cell and a normal cell can be obtained compared with the case wherein imaging is conducted with the use of a fluorescently labeled D-glucose derivative. According to this method, moreover, no fasting is needed for the determination. Thus, the imaging can be quickly carried out without imposing a burden on a patient.

Description

technical field [0001] The present invention relates to a method for detecting cancer cells or cells that may be cancerous using fluorescently labeled L-glucose derivatives. The present invention also relates to an imaging agent for cancer cells or potentially cancerous cells containing fluorescently labeled L-glucose derivatives. Background technique [0002] It is important to detect cancer with good precision for the discovery or treatment of cancer. Usually, cancer tissue is not a collection of cells showing the same properties, but a collection of cells showing various morphological or functional characteristics and degrees of differentiation. In addition, sometimes mixed in normal cells. Therefore, in cancer diagnosis, it is necessary to evaluate abnormal cells at the cellular level in order to confirm the diagnosis and conduct pathological diagnosis of biopsy specimens. However, in the pathological diagnosis of biopsy specimens, especially in the case of early-stag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12Q1/04A61B10/00A61K49/00G01N21/64G01N33/48G01N33/52
CPCA61K49/0054G01N21/6428G01N33/5091A61K49/0052G01N2800/7028G01N33/574G01N33/582A61B10/00A61K49/00C12Q1/04G01N21/64G01N33/48
Inventor 山田胜也尾上浩隆丰岛正山本敏弘
Owner ORBIO CORP
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