JPH023448A - Fluorescent acrylamide compound - Google Patents
Fluorescent acrylamide compoundInfo
- Publication number
- JPH023448A JPH023448A JP63147772A JP14777288A JPH023448A JP H023448 A JPH023448 A JP H023448A JP 63147772 A JP63147772 A JP 63147772A JP 14777288 A JP14777288 A JP 14777288A JP H023448 A JPH023448 A JP H023448A
- Authority
- JP
- Japan
- Prior art keywords
- fluorescent
- compound
- equivalent
- formula
- triethylamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 acrylamide compound Chemical class 0.000 title claims abstract description 10
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims abstract description 3
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 claims abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 2
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 229920002401 polyacrylamide Polymers 0.000 abstract description 6
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 3
- CSJXLKVNKAXFSI-UHFFFAOYSA-N n-(2-aminoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NCCN CSJXLKVNKAXFSI-UHFFFAOYSA-N 0.000 abstract description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000706 filtrate Substances 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000000499 gel Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 7
- 238000001962 electrophoresis Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Peptides Or Proteins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規で有用なケイ光化合物に関し、特に電気
泳動用媒体として有用なケイ光性アクリルアミド化合物
に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to novel and useful fluorescent compounds, and particularly to fluorescent acrylamide compounds useful as electrophoretic media.
本発明は、電気泳動用媒体として用いられるポリアクリ
ルアミドゲルをケイ光化するために使用できる新規で有
用なケイ光化合物およびその合成法に関するものである
。The present invention relates to a new and useful fluorescent compound that can be used to fluoresce polyacrylamide gel used as an electrophoretic medium, and a method for synthesizing the same.
従来、各種のゲルを媒体とする電気泳動法が生体分子の
分離精製・検出を目的として多数開発されてきた。その
中でもポリアクリルアミドゲル電気泳動法は、広範に使
用されている。このポリアクリルアミドゲルは、アクリ
ルアミドとＮ、Ｎ’−メチレンビスアクリルアミドから
製造される。Conventionally, many electrophoresis methods using various gels as media have been developed for the purpose of separating, purifying, and detecting biomolecules. Among them, polyacrylamide gel electrophoresis is widely used. This polyacrylamide gel is made from acrylamide and N,N'-methylenebisacrylamide.
これに関しては、Ｔ、Ｊｏｖｉｎらの論文に詳細な記載
がある。Regarding this, there is a detailed description in the paper by T. Jovin et al.
しかし、従来のポリアクリルアミドゲルを電気泳動媒体
として使用した場合、生体分子の分離精製・検出に関し
て化学的操作を必要とする。たとえば、電気泳動前のサ
ンプルの標識又は、電気泳動後のゲルの色素染色および
脱色などである。However, when conventional polyacrylamide gel is used as an electrophoresis medium, chemical operations are required for separation, purification, and detection of biomolecules. For example, labeling of samples before electrophoresis or dye staining and decolorization of gels after electrophoresis.
このような操作は、分析の簡便性かつ迅速性の面で大き
な障害となっていた。Such operations have been a major obstacle in terms of simplicity and speed of analysis.
上記問題点を解決するためには、電気泳動媒体であるポ
リアクリルアミドゲルとサンプルとの間で生じる弱い相
・夏作用を増幅して検出できることが重要となる。たと
えば、ゲルに色素団を共有結合させ、泳動サンプルとそ
の色素団との相互作用を色素団の色調変化として検出す
るという方法も考えられる。すなわち、新規な機能性ゲ
ルの開発が必要である０本発明では、その第１歩として
、ケイ光性ゲルを製造するために必要となる新規なケイ
光性アクリルアミド化合物とその合成法を提供するもの
である。In order to solve the above-mentioned problems, it is important to be able to amplify and detect the weak phase effect that occurs between the polyacrylamide gel, which is an electrophoresis medium, and the sample. For example, a method can be considered in which a chromophore is covalently bonded to the gel and the interaction between the electrophoresis sample and the chromophore is detected as a change in the color tone of the chromophore. In other words, it is necessary to develop a novel functional gel.As a first step, the present invention provides a novel fluorescent acrylamide compound necessary for producing a fluorescent gel and a method for synthesizing the same. It is something.
上記のようなケイ光性アクリルアミド化合物は、Ｎ、Ｎ
’ −アルキルビスアクリルアミドとの架橋反応によ
って、ケイ光性ポリアクリルアミドゲルを得ることがで
きる。The fluorescent acrylamide compound as mentioned above is N,N
A fluorescent polyacrylamide gel can be obtained by crosslinking reaction with '-alkylbisacrylamide.
以下、実施例に基づいて本発明を説明する。 Hereinafter, the present invention will be explained based on Examples.
〔実施例１〕
次式で表せられるケイ光性アクリルアミド化合物の合成
法：
ＣＨｔ ”” ＣＨ−ＣＯ−Ｎ ＨＫ
上式で表せるケイ光化合物の基本的合成法をアミノフル
オレセインアクリレートの合成を例として示す。[Example 1] Method for synthesizing a fluorescent acrylamide compound represented by the following formula: CHt "" CH-CO-NHK The basic method for synthesizing a fluorescent compound represented by the above formula will be shown using the synthesis of aminofluorescein acrylate as an example. .
アミノフルオレセインとトリエチルアミンを１当量ずつ
含む無水アセトン溶液をアクリロイルクロライド１当量
を含む無水アセトン溶液へ水冷下ゆっくり滴下する。３
時間攪拌後、副生ずるトリエチルアミン塩酸塩を濾過に
より除去し、ろ液を減圧濃縮し、結晶化させる。オレン
ジ色結晶。収率９０％。An anhydrous acetone solution containing 1 equivalent each of aminofluorescein and triethylamine is slowly added dropwise to an anhydrous acetone solution containing 1 equivalent of acryloyl chloride under water cooling. 3
After stirring for a period of time, the by-produced triethylamine hydrochloride is removed by filtration, and the filtrate is concentrated under reduced pressure to crystallize. orange crystals. Yield 90%.
同様の方法によって、ローダミン、ベンゾフラザン誘導
体を高収率で得ることができる。Rhodamine and benzofurazan derivatives can be obtained in high yields by similar methods.
〔実施例２〕
次式で表せられるケイ光性アクリルアミド化合物の合成
法：
ＣＨ，冨ＣＨ−ＣＯ−ＮＨ−Ｒ−ＮＨ−Ｘ上式で表せる
ケイ光化合物の基本的合成法をＮ−ダンシルエチレンジ
アミンアクリレートの合成を例として示す。[Example 2] Method for synthesizing a fluorescent acrylamide compound represented by the following formula: CH, TomiCH-CO-NH-R-NH-X A basic method for synthesizing a fluorescent compound represented by the above formula was performed using N-dansylethylenediamine. The synthesis of acrylates is shown as an example.
まず、Ｎ−ダンシルエチレンジアミンの合成から始める
。First, we begin with the synthesis of N-dansylethylenediamine.
エチレンジアミンと炭酸水素ナトリウムを１当量ずつ含
む６０％エチルアルコール水溶液にダンジルクロライド
１当量を含む６０％エチＪレアルコールを室温でよく攪
拌しながらゆっくり滴下する。さらに４時間攪拌後、減
圧上濃縮乾固する。乾固した化合物を無水エチルアルコ
ールに加え、不溶の塩化ナトリウムを濾過により除去し
、Ｎ−ダンシルジアミンのエチルアルコール溶液を減圧
上濃縮し、結晶化させる。To a 60% ethyl alcohol aqueous solution containing 1 equivalent each of ethylene diamine and sodium hydrogen carbonate, 60% ethyl alcohol containing 1 equivalent of danzyl chloride is slowly added dropwise at room temperature with thorough stirring. After further stirring for 4 hours, the mixture was concentrated to dryness under reduced pressure. The dried compound is added to absolute ethyl alcohol, insoluble sodium chloride is removed by filtration, and the ethyl alcohol solution of N-dansyldiamine is concentrated under reduced pressure to crystallize.
次にＮ−ダンシルジアミンとトリエチルアミンを１当量
ずつ含む乾燥アセトン溶液をアクリロイルクロライド１
当量を含む乾燥−アセトン溶液に水冷下、攪拌しなから
ゆっ（り滴下する。析出したトリエチルアミン塩酸塩を
ろ別後、析出物が生ずるまで濃縮し、結晶化させる。黄
色結晶、収率９３％。Next, add 1 equivalent of acryloyl chloride to a dry acetone solution containing 1 equivalent each of N-dansyldiamine and triethylamine.
It is slowly added dropwise to a dry acetone solution containing the same amount under water cooling without stirring. After the precipitated triethylamine hydrochloride is filtered off, it is concentrated until a precipitate is formed and crystallized. Yellow crystals, yield 93%. .
同様に、クロロベンゾフラザン系化合物をダンジルクロ
ライドの代わりに用いることによって、Ｎ−ベンゾフラ
ザンエチレンジアミンアクリレート誘導体を高収率で得
ることができる。Similarly, by using a chlorobenzofurazane compound in place of danzyl chloride, an N-benzofurazane ethylenediamine acrylate derivative can be obtained in high yield.
以上の説明から明らかなように、ケイ光性アクリルアミ
ド化合物の合成法の確立によって、これを用いたケイ光
性アクリルアミドゲルの製造が可能となった。As is clear from the above explanation, the establishment of a method for synthesizing fluorescent acrylamide compounds has made it possible to produce fluorescent acrylamide gels using the same.
（１１Ｔ、 Ｊｏｖｉｎ、 Ａ、Ｃｈｒａｂａｃｈ ａ
ｎｄ Ｒ，Ｒ，Ｒｕｅｃｋｅｔ。(11T, Jovin, A, Chrabach a
nd R, R, Ruecket.
＾ｎａ１． Ｂｉｏｃｈｅａ＋、 １１．３４２ （１
９６５）以上
出願人 セイコー電子工業株式会社^na1. Biochea+, 11.342 (1
965) Applicant: Seiko Electronic Industries Co., Ltd.
Claims (1)
化合物： ＣＨ＿２＝ＣＨ−ＣＯ−ＮＨ−Ｘ ＣＨ＿２＝ＣＨ−ＣＯ−ＮＨ−Ｒ−ＮＨ−Ｘ式中、Ｘは
フルオレセイン、ローダミン、ダンシル、ベンゾフラザ
ンを含むケイ光原子団；Ｒは炭素数約１０までのメチレ
ン鎖であることを特徴とするケイ光性アクリルアミド化
合物。[Claims] A fluorescent acrylamide compound represented by any of the following formulas: CH_2=CH-CO-NH-X CH_2=CH-CO-NH-R-NH-X where X is fluorescein, rhodamine, A fluorescent acrylamide compound characterized in that a fluorescent atomic group includes dansyl and benzofurazan; R is a methylene chain having up to about 10 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63147772A JPH023448A (en) | 1988-06-15 | 1988-06-15 | Fluorescent acrylamide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63147772A JPH023448A (en) | 1988-06-15 | 1988-06-15 | Fluorescent acrylamide compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH023448A true JPH023448A (en) | 1990-01-09 |
Family
ID=15437833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63147772A Pending JPH023448A (en) | 1988-06-15 | 1988-06-15 | Fluorescent acrylamide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH023448A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112812229A (en) * | 2020-12-31 | 2021-05-18 | 中国科学院苏州纳米技术与纳米仿生研究所 | fluorescence/MRI dual-mode probe and preparation method and application thereof |
-
1988
- 1988-06-15 JP JP63147772A patent/JPH023448A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112812229A (en) * | 2020-12-31 | 2021-05-18 | 中国科学院苏州纳米技术与纳米仿生研究所 | fluorescence/MRI dual-mode probe and preparation method and application thereof |
| CN112812229B (en) * | 2020-12-31 | 2022-03-04 | 中国科学院苏州纳米技术与纳米仿生研究所 | fluorescence/MRI dual-mode probe and preparation method and application thereof |
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