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Probe for a biological specimen and labelling method and screening method using the probe

Inactive Publication Date: 2011-10-06
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0004]It is an object of the present invention to provide a novel probe for a biological specimen, which has excellent spectral characteristics and also exhibits excellent storage stability.
[0014]The present invention provides a probe for a biological specimen for labelling a biological specimen in a simple manner and with high sensitivity, the probe exhibiting high storage stability and having a large Stokes' shift. Further, the labeling of a cell or a cell organ with high sensitivity enables the imaging of morphological features such as size and shape. In particular, the progression and cure of a disease can be objectively evaluated by imaging a disease-related site and monitoring its time-dependent change. The probe is also applicable to a technology of selectively imaging a specific body tissue at a molecular level. Further, the speed of drug development including screening becomes faster, with the result that a cost reduction can be achieved. The probe is also applicable to the high precision diagnosis of new diseases and the development of treatment method for the new diseases. Further, the probe is expected to be used as an index in screening for safety evaluation of a chemical substance. In addition, the probe may be used, for example, for life science research to understand unexplained phenomena, and thus, may become an effective basic technology that dramatically develops the industry.

Problems solved by technology

However, there has been a problem that the fluorescence sensitivity is not sufficient, and a stained site cannot clearly detected owing to scattering by a body tissue.
Further, there has been a problem that indocyanine green as a cyanine-based dye does not exhibit sufficient fluorescence intensity in many cases in the above-mentioned applications (see SPIE, 2389, pp.
789-797, 1995), and hence needs to be used in a large amount to increase the sensitivity, with a result that an unnecessary portion may be stained.
In addition, there has been a problem that the compound has low light fastness, and hence tends to be discolored during observation.

Method used

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  • Probe for a biological specimen and labelling method and screening method using the probe
  • Probe for a biological specimen and labelling method and screening method using the probe
  • Probe for a biological specimen and labelling method and screening method using the probe

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of Staining Compound (1)

[0150]To a solution obtained by dissolving 3.0 g (11.4 mmol) of an aldehyde derivative (A-2) in 20 mL of acetic acid, added were 2.2 g (11.5 mmol) of a compound (B-20) and 0.9 g of ammonium acetate, followed by stirring under reflux for 2 hours. After completion of the reaction, 50 mL of water were slowly added dropwise thereto while cooling, and the mixture was cooled to room temperature. A solid precipitate was filtrated, washed with 100 mL of water twice, and further washed with 50 mL of 2-propanol, to thereby afford 3.2 g (yield: 64.4%) of a target product (1).

Analysis Result of Compound (1)

[0151][1]1H NMR (400 MHz, DMSO-d6, room temperature): δ [ppm]=1.36-1.40 (m, 1H), 1.63-1.81 (m, 4H), 2.04-2.08 (m, 1H), 3.89 (t, 1H, J=8.47 Hz), 4.73 (s, 2H), 5.06 (t, 1H, J=7.10 Hz), 6.93 (d, 1H, J=8.24 Hz), 7.15 (t, 1H, J=7.10 Hz), 7.38-7.46 (m, 6H), 7.74 (s, 1H).

[0152]FIG. 1 illustrates a spectrum thereof.

[0153][2] Mass spectrometry (ESI-TOF): m / z=435.0859 ...

synthesis example 2

Synthesis of Staining Compound (7)

[0154]To a solution obtained by dissolving 3.43 g (10.0 mmol) of an aldehyde derivative (A-16) in 20 mL of toluene, added were 1.13 g (10.0 mmol) of a compound (B-7) and 2.5 g (30.0 mmol) of piperidine, followed by stirring under reflux for 2.5 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with 100 mL of toluene, supplemented with 100 mL of water, and stirred. After the whole had been left to stand still, an organic layer was separated and dried over anhydrous sodium sulfate. After filtration, toluene was distilled off under reduced pressure, and recrystallization of the residue from ethanol afforded 1.3 g (yield: 31.7%) of a target product (7)

[Analysis Result of Compound (7)]

[0155][1]1H NMR (400 MHz, DMSO-d6, room temperature): δ [ppm]=1.36-1.47 (m, 1H), 1.64-1.81 (m, 4H), 2.04-2.13 (m, 1H), 3.90 (t, 4H, J=8.93 Hz), 5.18 (s, 1H), 6.89 (d, 1H, J=8.24 Hz), 7.19 (dd, 1H, J=2.52, 8.93 Hz), 7.34 (d, 1H, J=2...

example 1

In vivo Labelling with Probe for Biological Specimen

[0158]Five juveniles of Zebrafish were put into one well of a well plate together with rearing water. After rearing water had been discharged, 1 mL of distilled water was added to the well, and a solution of a staining compound (1) in DMSO was further added thereto so as to achieve a concentration of 10 ng / mL, followed by gentle stirring (pipetting). Further, Egg Water was prepared by dissolving artificial seawater SEALIFE (manufactured by Marinetech Co., Ltd.) in distilled water at a concentration of 60 mg / L. After the whole had been left to stand for 1 hour, distilled water in the well was discharged and replaced by 1 mL of fresh Egg Water. In addition, such an operation that Egg Water was discharged and replaced by 1 mL of fresh Egg Water was repeated twice. One of the juveniles was taken out from the well onto a dish, supplemented with 100 μL of a 3% methylcellulose aqueous solution to fix the movement of the juvenile, and phot...

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Abstract

Provided is a novel probe for a biological specimen for labelling by itself and clearly visualizing one of a specific cell and a specific cell organ in a living body, the probe having excellent spectral characteristics and exhibiting excellent storage stability. The probe for a biological specimen contains, as an active agent, at least one kind of compound represented by a general formula (I).

Description

TECHNICAL FIELD[0001]The present invention relates to a probe for a biological specimen for labelling a biological specimen in a simple manner and with high sensitivity, and a labelling method and a screening method using the probe.BACKGROUND ART[0002]Molecular imaging is means for forming an image for observing a biological activity at cellular and molecular levels. The advances in molecular imaging technologies of recent years allow various cellular and molecular behaviors in a living body to be observed from the outside (captured as images), resulting in that the molecular imaging becomes important means for a diagnostic technology in a medical area and for research in a life science area.[0003]Magnetic resonance imaging (MRI), positron emission tomography (PET), and optical topography are mainly studied as techniques of the molecular imaging, and widely utilized in the medical area and in the life science area depending on the purposes. Of those, a molecular imaging technology w...

Claims

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Application Information

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IPC IPC(8): A61K49/00C07D417/10C07D417/14C07D209/94C07D403/10C07D413/10C07D409/10C07D401/10C07D405/10G01N1/30
CPCA61K49/0002G01N2500/10A61K49/0021A61K49/006C07D209/08C07D209/86C07D209/94C07D401/08C07D403/06C07D403/08C07D413/08C07D417/06C07D417/14C09B23/0091C09B23/04C09B23/105G01N33/582G01N2333/4603A61K49/0008A61K49/10A61K51/0453
Inventor SHINTOU, TAICHIMIYAZAKI, TAKESHIHIROSE, MASASHIOKUBO, TAKETOSHIWATANABE, KOHEINOMOTO, TSUYOSHITANAKA, TOSHIONISHIMURA, YUHEISHIMADA, YASUHITONISHIMURA, NORIHIRO
Owner CANON KK
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