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Method for detecting content of free tryptophan in tryptophan and serum sample

A detection method and tryptophan technology are applied in the detection field of free tryptophan content, can solve problems such as unfavorable detection application, urgency of biological small molecule probes, irreversible identification process, etc., and achieve simple synthesis, easy large-scale preparation, The effect of real-time field detection

Active Publication Date: 2013-02-06
DALIAN UNIV OF TECH
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  • Abstract
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Problems solved by technology

[0004]1. The recognition of amino acids based on the weak interaction recognition process, in which improving the selectivity of the recognition process is the focus, because amino acids and their derivatives have similar structures, so Recognition of a single amino acid molecule with the same weakly acting recognition site has yet to be resolved in the current study
[0005]2. Most of the highly selective amino acid probes are based on the covalent bond reaction mechanism. change, the identification process is irreversible, which is not conducive to the detection application in the practical sense
[0006]3. The interference of small peptides and proteins on the amino acid recognition process is currently less studied. Most biological samples contain amino acids, small peptides and proteins. The real construction Probes for studying biological small molecules in living systems are urgently needed

Method used

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  • Method for detecting content of free tryptophan in tryptophan and serum sample
  • Method for detecting content of free tryptophan in tryptophan and serum sample
  • Method for detecting content of free tryptophan in tryptophan and serum sample

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1 (synthesis of probe material)

[0038] Add 4,4',4''-triphenylamine hydrazide (0.76 g, 1.8 mmol) and salicylaldehyde (0.80 g, 6.6 mmol) to the methanol solution, and add 5 drops of glacial acetic acid as a catalyst. Reflux under stirring for 24 hours, filter and dry to obtain 1.06 g of yellow solid, yield: 80.0%. 1 H NMR (400 MHz, DMSO- d 6 , ppm ): δ 12.10 (s, 3H, H -NH- ), 11.33 (s, 3H, H -OH ), 8.65 (s, 3H, H -CH=N ), 7.97 (d, 6H, J = 7.5Hz, H Ar ), 7.55 (d, 3H, J = 7.2 Hz, H Ar ), 7.31 (s, 3H, H Ar ), 7.24 (m, 6H, H Ar ), 6.93 (m, 6H, H Ar ). 13 C NMR (100 MHz, DMSO- d 6 , ppm ): δ 162.1 ( C -C=O ), 157.5 ( C -OH), 149.2 ( C Ar ), 148.2 ( C -CH=N ), 131.3 ( C Ar ), 129.6 ( C Ar ), 129.5 ( C Ar ), 127.8 ( C Ar ), 123.7 ( C Ar ), 119.3 ( C Ar ), 118.7 ( C Ar ), 116.4 ( C Ar ). Anal. Calc. for C 42 h 33 N 7 o 6 : H 4.55, C 68.94, N 13.40. Found: H 4.68, C 68.51, N 13.12.

Embodiment 2

[0039] Example 2 (synthesis of metal-organic tetrahedron as probe material)

[0040] Ce(NO 3 ) 3 ·6H 2 O (44.2 mg, 0.15 mmol) and the material of Example 1 (73.0 mg, 0.10 mmol) were dissolved in DMF, stirred for 2 hours, filtered, and diffused with methanol to obtain black crystals, which were filtered and dried with a yield of 65%. 1 H NMR (400 MHz, DMSO- d 6 , ppm ): δ 13.17 (s, 8H, H -NH- ), 8.61 (s, 12H, H -CH=N ), 8.09 (s, 12H, 5 ), 7.41–7.18 (m, 48H, H Ar ), 6.56 (s, 24H, H Ar ), 5.66 (s, 12H, H Ar ). 13 C NMR (100 MHz, DMSO- d 6 , ppm ): δ 166.8 ( C -C=O ), 157.4 ( C -OH ), 152.5 ( C Ar ), 132.6 ( C -CH=N ), 129.5 ( C Ar ), 129.3 ( C Ar ), 124.0 ( C Ar ), 123.3 ( C Ar ), 122.9 ( C Ar ), 119.4 ( C Ar ), 117.2 ( C Ar ), 116.6 ( C Ar ). Anal. Calc. for Ce 4 (C 42 h 29 N 7 o 6 )4: H 3.37, C 58.13, N 11.30; Found: H 3.85, C 57.35, N 11.26. ESI-MS: m / z: 1155.7824[Ce 4 (HTTS) 3 (H 2 TTS)] 3- ,1734.1365[Ce 4 (HTTS) 2 (H 2...

Embodiment 3

[0041] Embodiment 3 (fluorescence intensity and concentration intensity working curve)

[0042] Weigh the probe material and prepare 15 100 ml DMF / H of M 2 O=9 / 1 standard probe solution, then configure 2.0×10 -2 M tryptophan DMF / H 2 O=1 / 1 solution. Measure 2 ml of the standard probe solution, add the calculated amount of tryptophan solution, and prepare the standard test solution. Excited at 350 nm, the fluorescence emission spectrum was measured, and then the addition of tryptophan was taken as the abscissa, and the relative fluorescence intensity was taken as the ordinate to obtain a standard curve. The test results are as follows figure 2 shown.

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Abstract

The invention provides a method for detecting content of free tryptophan in a tryptophan and serum sample, which relates to a method for detecting the content of free tryptophan. The invention provides a method for identifying and detecting free tryptophan in the natural amino acid and serum sample by using a metal organic tetrahedral compound based on fluorescence functionalization and for achieving biological cell imaging application. In the method, a tetrahedral compound, which is obtained by self-assembling a three-tooth ligand constructed by using triphenylamine as a parent body and cerous nitrate, is used as a material; the material can high-selectively identify the tryptophan in 20 types of natural amino acid, and a response range is 0-0.1 mM; in addition, the material can also effectively distinguish free and combined tryptophan, so that the content of free tryptophan in the serum sample is detected and the application on living cell imaging is also preferably achieved. Therefore, the material provides a method for testing the content of free tryptophan in the serum sample, and the method has the advantages of high sensitivity and simplicity in operation.

Description

technical field [0001] The present invention relates to a method for detecting the content of free tryptophan, more specifically, to a method for detecting the content of free tryptophan in tryptophan and serum samples. Background technique [0002] Among the 20 natural amino acids, tryptophan is of vital importance. For example, the abnormally high content of tryptophan in serum is considered to be a key factor affecting certain diseases, such as chronic hepatitis, Parkinson's disease, Aplastic anemia and muscle atrophy, etc. Therefore, it is of clinical significance to develop effective in vivo identification and detection of tryptophan content, especially for the detection of tryptophan content in serum samples. [0003] However, designing and synthesizing probes with high selectivity and effective recognition of such important biological small molecules is currently a very challenging task. After decades of unremitting efforts by scientists, fluorescent probes for amino...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C07F5/00C09K11/06
Inventor 何成王健武鹏彦刘晓花段然
Owner DALIAN UNIV OF TECH
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