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Fluorescent compound, and fluorescently-labeled biological substance using same

A compound and fluorescent technology, used in the field of fluorescent compounds and fluorescently labeled biological substances, can solve the problems of low light resistance, deterioration, and insufficient biological observation of organic fluorescent pigments

Pending Publication Date: 2021-01-08
FUJIFILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, organic fluorescent dyes have low light resistance and are degraded by excitation light irradiation, so that desired biological observations may not be sufficiently performed.

Method used

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  • Fluorescent compound, and fluorescently-labeled biological substance using same
  • Fluorescent compound, and fluorescently-labeled biological substance using same
  • Fluorescent compound, and fluorescently-labeled biological substance using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0435] Hereinafter, the present invention will be described in further detail based on examples, but the present invention is not limited thereto.

[0436] Compounds (1) to (24) and comparative compounds (1) to (2) used in Examples and Comparative Examples are shown below. In addition, [] in the structural formula of compound (14) represents a repeating structure.

[0437] [chemical formula 47]

[0438]

[0439] [chemical formula 48]

[0440]

[0441] Comparative compound (1) is compound A described in paragraph [0052] of International Publication No. 2013 / 035303.

[0442] The comparative compound (2) is BODIPY (registered trademark) 496 / 512 (manufactured by Invitrogen Japan K.K., product name).

[0443] Hereinafter, the synthesis methods of compounds (1) to (24) and labeled antibodies (1) to (12) used in each example will be described in detail, but the starting materials, dye intermediates, and synthesis routes are not limited to These.

[0444] Unless otherwise s...

Synthetic example 1

[0491] Compound (1) was synthesized based on the following scheme.

[0492] 1) Synthesis of compound (1-C)

[0493] The following compound (1-A), compound (1-B) and compound (1-C) were respectively according to the method described in Chem.Eur.J.2016,22,93-96, Org.Process Res.Dev. It was synthesized by the method described in 2015, 19, 1774-1783.

[0494] [chemical formula 49]

[0495]

[0496] 2) Synthesis of compound (1)

[0497] [chemical formula 50]

[0498]

[0499] 2-1) Synthesis of compound (1-D)

[0500] To 11 ml of a CPME solution of 112 mg of compound (1-C), 0.02 ml of water, 76 mg of 2-(hydroxymethyl)phenylboronic acid [Wako Pure Chemical Industries, Ltd.], PdCl 2 (dtbpf) 16 mg [Tokyo Chemical Industry Co., Ltd.] and cesium fluoride 152 mg [Wako Pure Chemical Industries, Ltd.] were stirred under reflux for 90 minutes. Next, after cooling the reaction liquid to room temperature, saturated sodium bicarbonate water was added to the reaction liquid, extracti...

Synthetic example 2

[0508] Compound (2) was synthesized based on the following scheme.

[0509] [chemical formula 51]

[0510]

[0511] In the synthesis method of compound (1), 2-(hydroxymethyl)phenylboronic acid was changed to 4-fluoro-2-(hydroxymethyl)phenylboronic acid [Combi-Blocks Inc.], and Compound (2) 1 mg (reddish-brown solid) was obtained in the same manner as the synthesis method of compound (1).

[0512] MS (ESI m / z): 557 (M+H)

[0513] RT(min): 1.28

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Abstract

Provided are: any one of the following fluorescent compounds; and a fluorescently-labeled biological substance having the compound. X represents CR5 or N, and R1-R7, Q1, Q2, L1, and L2 represent specific groups. The number of ring members in ring beta1 and ring beta2 are 5-8. At least one among R1-R7, Q1, Q2, L1, and L2 has a specific hydrophilic group. When the number of ring members in ring beta1 and ring beta2 is 6, and L1 and L2 are arylene groups, R5 is not a C18 or higher linear alkyl group-substituted aryl group. In addition to said definitions of ring beta1, ring beta2, L1, and L2, when R5 has a substituent having a dipyrometheneboron complex structure, the dipyrometheneboron complex structure has a structure in which a dipyrromethene skeleton is coordinated to a boron atom in a tridentate or tetradentate configuration.

Description

technical field [0001] The present invention relates to a fluorescent compound and a fluorescently labeled biological substance using the fluorescent compound. Background technique [0002] Bioimaging technology that analyzes the dynamics and functions of biomolecules, cells, tissues, etc. in a living body is used in the diagnosis of various diseases. In recent years, as a new technology for living body observation, biofluorescent imaging in which a specific part of a living body is visualized and observed with a fluorescent dye is expected. [0003] In this biological fluorescence imaging, organic fluorescent dyes are generally used. However, organic fluorescent dyes have low light resistance and are degraded by excitation light irradiation, so that desired living body observations may not be sufficiently performed. [0004] The dipyrromethene boron complex is known as a fluorescent dye with a high quantum yield and clear luminescent properties, and is used in various fie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B23/00C09K11/06G01N21/64
CPCC09K11/06C07F5/022C09K2211/1055G01N33/533C09B23/04C09B55/009C09B23/0008C09B69/00C09B23/06C09K2211/1029G01N21/6428G01N33/582G01N2021/6439
Inventor 中田飞翼渡边康介朝仓彰洋牧田庆子金泽吉宪金子和平
Owner FUJIFILM CORP
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