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Asymmetric cyanine dye compound and application thereof

A technology of compounds and cyanine dyes, applied in the field of compounds, can solve the problems of insufficient quenching efficacy and limitation of signal kinetic characteristics

Active Publication Date: 2014-02-05
上海辉睿生物科技有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, known non-fluorescent quenchers have the disadvantage of insufficient quenching efficacy, which leads to high background signal, which in turn leads to limited signal kinetics

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

[0037] Embodiment 1: 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 at 110°C overnight, 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 2 hours, the product precipitated, filtered , and dried to obtain 6.4 g of the product.

[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 2

[0041] Embodiment 2: Synthesis of compound (I-1)

[0042]

[0043] 3-Methyl-2-methylthiobenzothiazole p-toluenesulfonate (5g, 0.014mol) and compound (II) (6.33g, 0.01mol) were dissolved in 20ml DMF, and 3.9ml of Triethylamine, then stirred overnight, after the reaction, pour the product into water, add 5% hydrochloric acid dropwise, filter the product after precipitation, dissolve the filtered product in 30ml of 1:1 methanol and water, add 5.6g of hydrogen Sodium oxide was hydrolyzed. After hydrolysis, concentrated hydrochloric acid was added dropwise again. After the product was precipitated, it was filtered and dried to obtain the final product.

[0044] Product NMR data 1 H NMR: 1.46 (s, 3H), 3.7 (m, 1H), 4.39 (s, 3H), 5.95 (s, 2H), 6.77 (s, 1H), 7.5-8.6 (m, 13H).

Embodiment 3

[0045] Embodiment 3: the synthesis of compound (I-2)

[0046]

[0047] Compound (I-1) (30mg, 0.056mmol) was dissolved in 0.5ml DMF, 0.05ml DIEA was added and TSTU (34mg, 0.12mmol) was added. The mixture was stirred at room temperature for 2-3 hours, and the reaction was monitored by TLC. After the reaction, 2ml of 5% HCl was added, and the precipitate was washed with dilute hydrochloric acid, filtered, and dried to obtain 30 mg of the product.

[0048] NMR data 1 H NMR: 1.46 (s, 3H), 2.64 (m, 4H), 3.7 (m, 1H), 4.39 (s, 3H), 5.95 (s, 2H), 6.77 (s, 1H), 7.5-8.6 (m , 13H).

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Abstract

The invention provides an asymmetric cyanine dye compound (I) and application of the same as a quenching agent. The invention provides the asymmetric cyanine dye fluorescence quenching compound which can effectively quench fluorescence of FAM and stabilize DNA double strands, enables melting temperature in the PCR process to increase 2 to 3 DEG C, is applicable to a conventional real time fluorescence quantification PCR detection method and can be effectively applied to the field of analysis of single nucleotide polymorphism.

Description

(1) Technical field [0001] The present invention relates to a compound used as a quenching agent in FRET. Further, the present invention relates to a cyanine dye compound as a quenching agent, a reagent and its application in FRET. (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 desi...

Claims

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Application Information

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IPC IPC(8): C07D417/06C07D417/14G01N33/52C12Q1/68
CPCC07D417/06C07D417/14C09B23/04G01N21/6428G01N2021/6432
Inventor 李辉金大智方维佳王尧柯炳欣
Owner 上海辉睿生物科技有限公司
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