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Fluorogenic pH-sensitive dyes and their methods of use

A fluorescent dye and sensitive technology, applied in chemical instruments and methods, peptide preparation methods, triarylmethane dyes, etc., can solve the problems of unstable compounds and unadjustable pKa

Inactive Publication Date: 2015-03-25
LIFE TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this would limit the applicability of the dyes described in WO2005 / 098437 at physiological pH (eg pH 6-7), especially in biological systems
An additional disadvantage of these dyes is that their pKa is not adjustable
Furthermore, we have found that these compounds are unstable in solution

Method used

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  • Fluorogenic pH-sensitive dyes and their methods of use
  • Fluorogenic pH-sensitive dyes and their methods of use
  • Fluorogenic pH-sensitive dyes and their methods of use

Examples

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preparation example Construction

[0482] Preparation of peptide or protein conjugates typically involves first dissolving the protein to be conjugated at about 1-10 mg / mL in an aqueous buffer at room temperature or below. Bicarbonate buffer (approximately pH 8.3) is especially suitable for reacting with succinimide esters, phosphate buffer (approximately pH 7.2-8) is especially suitable for reacting with thiol-reactive functional groups and carbonate or borate The buffer (about pH 9) is especially suitable for reactions with isothiocyanates and dichlorotriazine. The appropriate reactive compound is then dissolved in a non-hydroxylic solvent (usually DMSO or DMF) in an amount sufficient to produce the appropriate degree of binding when added to the solution of the protein to be bound. The appropriate amount of compound for any protein or other component is preferably predetermined by experiments wherein variable amounts of a dye compound are added to the protein, the conjugate is purified by chromatography to s...

example

[0648] Referring to the following examples, the pH sensitive fluorescent dye compounds disclosed herein were synthesized using the methods described herein or other methods known in the art.

[0649] It will be appreciated that organic compounds according to the present invention may exhibit tautomerism. Since the chemical structures within this specification may represent only one possible tautomeric form, it is understood that the invention encompasses any tautomeric form of the drawn structures.

[0650] Chemical Synthesis of Fluorescent pH Sensitive Dye Compounds Disclosed herein :

example 1

[0651] Example 1: Preparation of compound (5):

[0652]

[0653] Compound (5) can be obtained from compound (4) via a multi-step synthesis according to US Patent Publication No. 2008 / 076524, which is incorporated herein by reference in its entirety.

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Abstract

Disclosed herein are compounds, compositions, methods and kits for detecting pH in samples using pH-sensitive fluorescent dyes. The compounds disclosed herein are novel xanthene-derivative dyes comprising an aniline moiety with one or more electron donating groups, which dyes are for detecting pH in samples either in vitro or in vivo. Also described herein are processes for preparing said dyes for use in the disclosed compositions, methods and kits.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of priority to U.S. Provisional Application No. 61 / 653,333, filed May 30, 2012, and U.S. Provisional Application No. 61 / 653,616, filed May 31, 2012, which are filed as Incorporated by reference in its entirety. technical field [0003] Uncovers novel pH-sensitive fluorescent dyes and assays for a variety of applications including monitoring intracellular processes. Background technique [0004] pH-sensitive fluorescent dyes used in biological research and medical diagnostics fall into two groups that differ in the origin of the fluorescent response to pH changes. The first group includes compounds with fluorescence controlled by ionization of the phenolic hydroxyl group in the fluorophore. Examples include fluorescein, carboxyfluorescein, and HPTS indicator. [0005] US Patent Publication No. 2006 / 0051874 describes fluorescein-like structures incorporated into fluorescence dete...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B11/24C07K1/13G01N33/52
CPCC09B11/24A61K49/0041C07D311/90G01N33/5005G01N33/582G01N33/84
Inventor K. 吉U. 辛赫A. 鲁卡维什尼科夫D. 比查姆S-J. 黄M. 简斯W. 周J. 贝利埃
Owner LIFE TECH CORP
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