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A cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect and its preparation method

A technology of fluorescent molecules and push-pull electrons, applied in the field of biochemical detection, can solve problems such as poor signal-to-noise ratio, limited application, limited sensitivity, etc., and achieves the effects of mild conditions, simple preparation process, and stable fluorescent properties

Active Publication Date: 2021-08-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, xanthene fluorescent dyes such as fluorescein and rhodamine have the disadvantage of pH dependence due to the tautomerization between the quinone and spironolactone structures. Its application in acidic synthetic environment
In addition, fluorescent dyes such as fluorescein, rhodamine, oxazine, and anthocyanin exhibit a Stokes shift of less than 30 nm, and this severe crosstalk between excitation and emission spectra often results in poor signal-to-noise ratios and Self-quenching due to backscattering from biological samples

Method used

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  • A cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect and its preparation method
  • A cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect and its preparation method
  • A cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] This embodiment provides a cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect, and its structural formula is: Among them, R 1 Hydrogen, fluorine, chlorine, bromine, iodine, methoxyl, hydroxyl, diethylamine, piperidine, tetrahydropyrrole, nitro, aryl or cyano connected to the 5, 6, 7, 8 positions of the 10π electron ring A kind of R 2 A five-membered aromatic ring with no substituents or 1-4 substituents or a six-membered aromatic ring with no substituents or 1-4 substituents, a nitrogen-containing heterocycle, an oxygen-containing heterocycle or a sulfur-containing heterocycle , the R 3 p-toluenesulfonyl, methanesulfonyl, alkyl, unsubstituted or a five-membered aromatic ring with 1-4 substituents, or a six-membered aromatic ring with no substituent or 1-4 substituents, nitrogen-containing Heterocycle, oxygen-containing heterocycle or sulfur-containing heterocycle.

[0041] The fluorescent molecule is obtained by reacting differently sub...

Embodiment 2

[0057] This embodiment provides a cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect, and its structural formula is: It is prepared from N-sulfonyltriazolebenzaldehyde and o-toluidine, and its preparation method is basically the same as that of Example 1.

[0058] The NMR spectrogram of the cyclic amidinyl fluorescent molecule described in the present embodiment is as follows Figure 8-9 As shown, the test data is as follows:

[0059] 1 H NMR (400MHz, CDCl 3 ):δ8.34(s,1H),8.02(s,1H),7.67(d,J=8.2Hz,2H),7.63–7.48(m,3H),7.44(dd,J=10.8,4.1Hz, 1H), 7.41–7.32(m,2H), 7.25–7.08(m,4H), 2.34(s,3H), 2.02(s,3H).

[0060] 13 C NMR (100MHz, CDCl 3 ): δ152.6, 142.0, 142.0, 141.5, 141.2, 141.0, 134.3, 134.0, 131.2, 129.9, 128.8, 127.7, 127.2, 126.4, 126.2, 125.9, 125.3, 120.0, 111.5, 21.3, 17.6

[0061] In the infrared (IR) spectrum of the fluorescent molecular product, the positions of the absorption peaks are respectively located at: 2922, 1640, 1600, ...

Embodiment 3

[0065] This embodiment provides a cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect, and its structural formula is: It consists of N-sulfonyltriazole benzaldehyde and Prepared, its preparation method is basically the same as that of Example 1.

[0066] The NMR spectrogram of the cyclic amidinyl fluorescent molecule described in the present embodiment is as follows Figure 11-12 As shown, the test data is as follows:

[0067] 1 H NMR (400MHz, CDCl 3 ): δ8.45(s,1H),7.95(s,1H),7.74(d,J=8.2Hz,2H),7.59(d,J=8.6Hz,1H),7.52(d,J=3.4Hz ,2H),7.38(dt,J=11.8,4.1Hz,6H),7.25–7.18(m,1H),7.11(ddd,J=9.8,8.4,4.9Hz,3H),7.00(t,J=2.2 Hz, 1H), 6.92 (dd, J=7.8, 1.2Hz, 1H), 4.97 (s, 2H), 2.36–2.26 (m, 3H).

[0068] 13 C NMR (100MHz, CDCl 3 ): δ159.3, 152.4, 142.6, 141.8, 141.5, 141.1, 136.3, 134.1, 130.2, 128.9 128.7, 128.2, 127.9, 127.6, 126.2, 125.8, 125.3, 119.9119.0, 116.4, 110.13.1

[0069] In the infrared (IR) spectrogram of the fluorescent molecular pr...

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Abstract

According to the cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect described in the present invention, the structural formula of the fluorescent molecule is: the cyclic amidinyl fluorescent molecule contains both an electron-pushing group (EDG) and an electron-withdrawing group (EWG). ), thereby constructing a novel skeleton molecule with a 10π electron structure, in which the electron-pushing group and the electron-withdrawing group are on the same side of the π electron, and this structure has a large Stokes shift (approximately 100nm), excellent acid-base stability, and stable fluorescent properties in the pH range of 2.8-11.4. At the same time, the fluorescent molecule has no obvious cytotoxicity and has broad biological application prospects. A preparation method of the fluorescent molecule is also disclosed. The method has simple process, mild conditions and is suitable for industrial batch production.

Description

technical field [0001] The invention belongs to the technical field of biochemical detection, and relates to a fluorescent molecular probe and a preparation method thereof, in particular to a cyclic amidinyl fluorescent molecule with the same-side push-pull electron effect and a preparation method thereof. Background technique [0002] With the rapid development of life science research, fluorescent molecular probes have become more and more widely used in cellular immunology, molecular biology, molecular genetics, etc., and have become one of the important tools for life science research. Among many fluorescent molecular probe materials, organic small molecule fluorescent dyes have been widely used in the fields of chemistry and biology due to their high sensitivity, diverse structures, and good specificity, especially low-molecular-weight organic fluorophores. It has good performance, little interference to living systems, high sensitivity, and fast response, and has signi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/22C09K11/06
CPCC07D217/22C09K11/06C09K2211/1029
Inventor 洪亮李国锋赵漫
Owner SUN YAT SEN UNIV
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