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New compounds and uses thereof for detection of target molecules in a sample

A technology of fluorophore, alkyl, applied in the field of profluorophore

Active Publication Date: 2019-06-04
UNIVERSITY OF GENEVA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of another known dye viologen (e.g. paraquat) commonly used as a redox indicator is limited in food applications due to its toxicity and its low sensitivity requiring high concentrations to achieve visual detection

Method used

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  • New compounds and uses thereof for detection of target molecules in a sample
  • New compounds and uses thereof for detection of target molecules in a sample
  • New compounds and uses thereof for detection of target molecules in a sample

Examples

Experimental program
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example

[0177] The following abbreviations refer to the following definitions, respectively:

[0178] bp (base pair), COI (cytochrome c oxidase), DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone), DIAD (diisoazodicarboxylic acid Propyl ester), DMF (dimethylformamide), DMSO (dimethyl sulfoxide), dsDNA (double-stranded DNA), EtOH (ethanol), LED (light-emitting diode), LNA (locked nucleic acid), PBS (phosphate buffered saline), m-CPBA (m-chloroperoxybenzoic acid), PNA (peptide nucleic acid), TsOH (toluenesulfonic acid), MS (ESI) (mass spectrometry (electrospray ionization)), NaAsc (sodium ascorbate), NMR (NMR), QR TM Code (Quick Response Code), RP-HPLC (Reverse Phase High Performance Liquid Chromatography), Ru(bpy) 3 Cl 2 (tris(bipyridyl)ruthenium(II) chloride), Ru(bpy) 2 Phen (bis(bipyridyl)ruthenium(II)phenanthroline (Ru(bpy)2Phen).

example 1

[0179] Example 1: Synthesis of profluorophores of the invention

[0180] Profluorophores of the invention can be synthesized according to general scheme 1. The following profluorophores have been synthesized according to the following method of Scheme 2, wherein R is selected from H (intermediate (iva), (va) and compound (1)) and N 3 (Intermediate (ivb), (vb) and compound (2)).

[0181] Step 1 - Formation of intermediate (iiia)

[0182] 5-chlorosalicylaldehyde (491mg, 3.13mmol) (intermediate (ia)) and potassium carbonate (K 2 CO 3 , 1306mg, 9.4mmol) was dissolved in 8ml dimethylformamide (DMF). The mixture was heated to 80°C and solid (Intermediate (iia) (800mg, 3.13mmol) was added portionwise. The resulting mixture was stirred for 6 hours. Then the solvent was added and evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 365mg The desired intermediate product (iii), as a yellow solid. Yield: 47%. 1 H NMR (nuclear...

example 2

[0227] Example 2: Preparation of probes for target molecules according to the methods of the invention

[0228] In the method according to the invention, the target molecule in the sample can be detected by detecting the formation of an insoluble fluorophore once the corresponding profluorophore is in the vicinity of the photoredox catalyst bound to the target molecule in the sample, enabling the detection and Quantify the target molecule.

[0229] probe

[0230] In order for a photoredox catalyst to bind to a target molecule, the probe labeled with the photoredox catalyst needs to have a specific affinity for the target molecule.

[0231] In order for a target molecule to bind to an anchoring matrix that may be photoreactive, the anchoring matrix should have a specific affinity for the target molecule (e.g. a matrix containing probes with specific affinity for the target molecule) or a label that binds to the target molecule (a streptavidin group that can react with a bioti...

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Abstract

The present invention relates to new profluorophores and conjugates thereof and their use for the detection of target molecule in a sample, in particular nucleic acid target molecules. The invention relates to new profluorophores and new fluorophores and methods of use thereof particularly useful in the fields of diagnostics and quality control.

Description

technical field [0001] The present invention relates to profluorophores precipitated under photoredox catalysis at sites of reaction with target molecules and their use for the detection of said target molecules in a sample. Background technique [0002] There is an increasing demand for signal detection in diagnostics and quality assurance (monitoring traceability, shelf life, procurement, security, counterfeit, compliance) applications. In particular, in the field of the food industry, there is an increasing need for the detection of ingredients and the presence of bacteria to immediately verify the authenticity, compliance and quality of food products. Customer demand comes especially from food manufacturers, retailers, trade organizations and government agencies that control the integrity of the supply chain. This integrity is especially important for end consumers, such as people who cannot eat a particular food due to medical (eg allergies, diet) or personal reasons (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C08G63/48C12Q1/00
CPCC07D401/12C08G63/48C12Q1/00C08L71/02C08L77/00C12Q1/6816C07C205/56C07C205/57C07F9/65522C09B29/0813G01N21/00G01N21/62G01N21/63G01N21/64G01N21/6428C12Q2565/113C12Q2565/501C12Q2563/107
Inventor 詹保罗·兰多尼古拉斯·文森格埃里克·林德贝格马尔塞洛·安左拉
Owner UNIVERSITY OF GENEVA