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Asymmetric cyanine dye compound and application thereof

A technology of compound and cyanine dye, which is applied in the application field of 650nm channel fluorescence quencher, which can solve the problems of insufficient quenching efficiency and limitation of signal kinetic characteristics, etc.

Inactive Publication Date: 2014-10-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the disadvantage of known non-fluorescent quenchers is their insufficient quenching efficacy, which leads to high background signal, which in turn leads to limited signal kinetic characterization

Method used

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  • Asymmetric cyanine dye compound and application thereof
  • Asymmetric cyanine dye compound and application thereof
  • Asymmetric cyanine dye compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the synthesis of compound (III)

[0034]

[0035] 2,3-Dimethylbenzothiazole p-toluenesulfonate (180mg, 0.52mmol), benzamidine (160mg, 0.8mmol) and 2ml of acetic anhydride were refluxed for 30 minutes, and after cooling, they were dropped into diethyl ether to obtain 170mg of the product .

[0036] Product NMR data 1 H NMR: 1.82 (s, 3H), 2.34 (s, 3H), 6.06 (m, 1H), 7.6 (m, 1H), 4.39 (s, 3H), 7.5-8.6 (m, 13H).

Embodiment 2

[0037] Embodiment 2: the synthesis of compound (II)

[0038]

[0039] 4-Methylquinoline (4.8ml, 0.0363mol) with methyl 2-(4-(bromomethyl)-2-nitrophenyl)propionate (according to Naoki Yamakawa et al., Bioorganic & Medicinal Chemistry 19(2011) 3299 -3311 preparation) (16.44g, 0.05445mol) were mixed, reacted overnight at 110°C, after cooling, added 20ml of methanol to dissolve, suspended and steamed to obtain a viscous solid, then added 200ml of acetone and stirred, after stirring for 2h, the product precipitated, filtered , dried to obtain product 6.4g.

[0040] Product NMR data 1 H NMR: 1.51 (s, 3H), 2.66 (s, 3H), 3.6 (d, 3H), 3.7 (m, 1H), 5.95 (s, 2H), 7.5-8.6 (m, 9H).

Embodiment 3

[0041] Embodiment 3: the synthesis of compound (I-1)

[0042]

[0043] Compound III (60mg0.13mmol) and compound (II) (89mg, 0.2mol) were dissolved in 2ml of pyridine, heated to reflux for 30 minutes, after the reaction was completed, the pyridine was removed by rotary evaporation, the residue was poured into water, and 5% hydrochloric acid was added dropwise , filter after the product is precipitated, dissolve the product obtained by filtration in 30ml of 1:1 methanol and water, add 80mg of sodium hydroxide for hydrolysis, after hydrolysis, drop concentrated hydrochloric acid again, after the product precipitates, filter and dry to obtain the final product.

[0044] Product NMR data 1 H NMR: 1.56(m, 3H), 3.82(m, 1H), 4.39(s, 3H), 5.5(m, 3H), 6.65(m, 1H), 6.71(m, 1H), 8.54(m, 1H ), 7.3-8.6(m, 12H),

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PUM

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Abstract

The invention provides an asymmetric cyanine dye compound (I) and an application of the cyanine dye compound as a quenching agent. By virtue of the asymmetric cyanine dye fluorescence quenching agent compound provided by the invention, 650nm-channel fluorescence can be effectively quenched and the melting temperature of stable double strands of DNA is increased by 2-3 DEG C in the PCR (Polymerase China Reaction) process. The asymmetric cyanine dye compound can be used for a conventional real-time fluorescent quantitative PCR detection method and can be also effectively used in the field of single nucleotide polymorphism analysis.

Description

(1) Technical field [0001] The invention relates to an asymmetric cyanine dye compound and its application as a fluorescence quencher, especially a 650nm channel fluorescence quencher. (2) Background technology [0002] Nucleic acid hybridization technology is one of the basic techniques of molecular biology, which can be used for diagnosis of genetic diseases, human body identification, microbial identification, paternity identification, and is gradually being used for specific, sensitive and rapid diagnosis of viruses in recent years. [0003] An important aspect of nucleic acid hybridization techniques is the detection of hybridization. A frequently used tool is the fluorescent oligonucleotide probe. A particularly useful type of fluorescent probe is the self-quenching probe, which includes a reporter The dye and the quencher dye interact through the process of fluorescence resonance energy transfer (FRET). Although the design of different probes using this motif may dif...

Claims

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Application Information

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IPC IPC(8): C09B23/06C12Q1/68G01N21/64
Inventor 方维佳郑怡
Owner ZHEJIANG UNIV
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