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Labelling reagents, method for synthesis of said reagents and methods for detecting biological molecules

A technology of labeling reagents and reagents, applied in the application of labeling biomolecules, 4] Finally, in the field of new reagents, it can solve problems such as background noise and double-stranded DNA cannot work effectively

Inactive Publication Date: 2009-07-08
比奥・麦利尤股份有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, a large excess of labeling reagent must be added relative to the RNA to achieve efficient labeling, which leads to the problem of background noise from excess labeling
Finally, the method does not work efficiently on double-stranded DNA

Method used

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  • Labelling reagents, method for synthesis of said reagents and methods for detecting biological molecules
  • Labelling reagents, method for synthesis of said reagents and methods for detecting biological molecules
  • Labelling reagents, method for synthesis of said reagents and methods for detecting biological molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0463] Embodiment 1: Synthetic reagent with biotin:

[0464] General synthesis process:

[0465]

Embodiment 11

[0466] Example 1.1: Synthesis of Inter-BioPMDAM:

[0467] ● Compound biotin-meta-acetophenone 1a:

[0468] D-biotin (1.0 grams (g), 4.1 millimoles (mmol)) was dissolved in 45 milliliters (ml) of hot anhydrous DMF. The mixture was cooled to 0 °C under argon, and then N-methyl mol morphine (590 microliters (μl), 5.33mmol) and isobutyl chloroformate (840μl, 6.60mmol).The mixture was stirred for 30 minutes (min), and then 3-aminoacetophenone (824mg , 6.10mmol) and N-methylmorpholine (480μl, 4.35mmol). The solution was stirred at 0°C for 2 hours (h), then evaporated to dryness. The residue was dissolved in 3ml MeOH, then 50ml of water was added. The resultant was filtered precipitation, water, CH 2 Cl 2 Washing with ether gave 1.2 g (80%) of crude product 1a. From MeOH-H 2 Recrystallization from O gave 1a (1.01 g, 70%) as a white powder.

[0469] The melting point is 145°C. -IR(KBr): 3280, 2931, 2857, 1691, 1590, 1540, 1487, 1434, 1298, 1266cm -1 .- 1 H NMR (300MHz, DMSO...

Embodiment 12

[0476] Embodiment 1.2: to the synthesis of-BioPMDAM:

[0477] ● Compound biotin p-acetophenone 1b:

[0478] D-biotin (1.0 g, 4.1 mmol) was dissolved in 45 ml of hot anhydrous DMF. The mixture was cooled to 0 °C under argon, then N-methylmorpholine (590 μl, 5.33 mmol) and isobutyl chloroformate (840 μl, 6.60 mmol) were added successively. The mixture was stirred for 30 min, then 4-aminoacetophenone (824 mg, 6.10 mmol) was added. The solution was stirred at 0 °C for 2 h, then evaporated to dryness. The residue was dissolved in 50ml of water. The resulting precipitate was filtered, washed with water and then with 50 ml of hot MeOH. The white precipitate was dissolved in DMF while heating, then the resulting solution was filtered and washed with MeOH. The filtrate was recovered and evaporated to dryness to give 888 mg of 1b (2.46 mmol, 60%).

[0479] The melting point is 260°C. -IR(KBr): 3260, 2930, 2358, 1706, 1673, 1610, 1526, 1401, 1380, 1322, 1257, 1150cm-1.-1H NMR (2...

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Abstract

The invention concerns a temperature-stable labelling reagent of formula (I), wherein: R<1> represents H or an alkyl, aryl or substituted aryl group; R<2> represents a detectable marker or at least two detectable markers linked together by at least a multimeric structure; L is a linking arm comprising a linear catemer concatenation of at least two covalent bonds; and n is an integer equal to 0 or 1; R<3> and R<4> represent, independently of each other: H, NO2, Cl, Br, F, I, R<2>-(L)n-Y-X-, OR, SR, NR2, R, NHCOR, CONHR, COOR with R = alkyl or aryl, A is a linking arm comprising at least a double bond enabling the conjugation of the diazo function with the aromatic cycle; and u is a whole number between 0 and 2, preferably between 0 and 1; and -Y-X- represents -CONH-, -NHCO-, -CH2O-, -CH2S-. The invention also concerns a method for the synthesis of said markers and uses for labelling biological molecules, in particular nucleic acids, with a labelling reagent bearing the diazomethyl function. The invention is particularly applicable in the field of diagnosis.

Description

Background of the invention [0001] The present invention relates to novel reagents for labeling biomolecules, to methods for the synthesis of said labels and to the use of labeled biomolecules, especially in the field of diagnosis with nucleic acid probes. [0002] Description of prior art [0003] The prior art shows various methods for labeling nucleotides, oligonucleotides or nucleic acids. [0004] The first method involves attaching a label to the base, whether the latter is a natural base or a modified base. The second method attaches the label to the sugar, again, whether the latter is a natural sugar or a modified sugar. The third method attaches the label to the phosphoric acid. [0005] Labeling at bases is particularly useful for labeling nucleic acids by direct incorporation of labeled nucleotides. [0006] Labeling on sugars is often used in the case of nuclear probes prepared by chemical synthesis. [0007] Labeling on phosphates has also been used to introd...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/14C07C245/18C07D209/14C07D495/04C07D311/82C12Q1/68G01N33/58C07D209/08C07D311/90C07H21/04C12N15/09G01N33/50G01N33/533
CPCC07D495/04C07C245/14C07D209/08C07D311/90C07C245/18
Inventor C·鲍格特J·洛姆A·拉扬M·柯特拉E·特里维希奥L·梅诺E·博纳门德兹
Owner 比奥・麦利尤股份有限公司
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