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Compound for detecting tumor hypoxia and preparation method thereof

A compound and selected technology, applied in the field of fluorescent probes, can solve the problems of small changes in fluorescence and complex probe synthesis

Active Publication Date: 2015-09-30
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These fluorescent probes can distinguish hypoxic cells from normal cells to a certain extent, but at the same time, there are problems such as small changes in hypoxic / aerobic fluorescence and complex probe synthesis.

Method used

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  • Compound for detecting tumor hypoxia and preparation method thereof
  • Compound for detecting tumor hypoxia and preparation method thereof
  • Compound for detecting tumor hypoxia and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0068] The preparation method of fluorescent probe of the present invention comprises:

[0069] (1) In the presence of a solvent and a catalyst, 4-aminonaphthalene anhydride is prepared from 4-nitronaphthalene anhydride;

[0070] (2) In the presence of a solvent, from 4-aminonaphthalene anhydride and R 2 -NH 2 Compounds of the following formula II were prepared:

[0071]

[0072] (3) making the compound of formula II react in an ice bath in the presence of hydrochloric acid and sodium nitrite;

[0073] (4) Add the compound of the following formula III to the reaction solution of step (3) and react in an ice bath:

[0074]

[0075] (5) Remove the ice bath in step (4) to adjust the pH to about 6, and continue the reaction, so as to prepare the compound of formula I of the present invention that does not contain B.

[0076] To prepare a compound containing B, the method further comprises:

[0077] (6) In the presence of dichloromethane, triethylamine and HBTU (benzotri...

Embodiment 1

[0089] Embodiment 1: the synthesis of 4-aminonaphthalene anhydride

[0090]

[0091] Add 4-nitronaphthalene anhydride (980mg, 4mmol), 10mL absolute ethanol, stannous chloride (5.4g, 24mmol) and 6mL concentrated hydrochloric acid into a 25mL flask respectively, and heat to reflux for 5h under magnetic stirring. After the reaction, the heating was stopped, cooled naturally to room temperature, filtered with suction, washed with 5% dilute hydrochloric acid, washed with water, and dried by infrared to obtain 560 mg of a yellow solid with a yield of 65%. Solubility is too poor, no NMR. HRMS(ES-)calcd.for C 12 h 7 NO 3 [M-H]-212.0348,found212.0344.

Embodiment 2

[0092] Example 2: Synthesis of N-n-butyl-4-amino-1,8-naphthalimide

[0093]

[0094]Add 4-aminonaphthalene anhydride (430mg, 2mmol), 4mL DMF and n-butylamine (150mg, 2mmol) respectively into a 25mL flask, and heat to 110°C for 5h under magnetic stirring. Stop heating after the reaction is over, cool to room temperature naturally, pour the reaction solution into 100mL of potassium bisulfate solution (5%, m / m), filter with suction, wash with water, and dry by infrared. Separation by column chromatography (dichloromethane: methanol = 100:1) gave 390 mg of an orange solid, with a yield of 74%. 1 H NMR (CDCl 3 ,400MHz)δ8.59(d,1H,J=8.4Hz),8.39(d,1H,J=7.2Hz),8.17(d,1H,J=8.0Hz),7.62(dd,1H,J 1 =7.6Hz,J 2 =8.4Hz),7.40(s,2H),6.83(d,1H,J=8.4Hz),3.99(t,2H,J=7.6Hz),1.53–1.60(m,2H),1.27–1.36(m ,2H),0.90(t,3H,J=7.2Hz);HRMS(ES+)calcd.for C 16 h 16 N 2 o 2 [M+H] + 269.1290,found269.1292.

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Abstract

The invention relates to a compound for detecting tumor hypoxia disclosed as Formula I, a preparation method and application thereof, and a kit containing the compound. The groups in the formula are disclosed in the specification. The compound can be used for detecting hypoxia of tumor tissues, can respond to changes of partial oxygen pressure and reducibility of partial tissues, and provides conditions for early detection of cancers. The compound has the advantages of novel structure, simple synthesis process, high detection sensitivity, high fluorescence enhancement multiple, no trauma and the like, and can be used for cell detection and even living body detection.

Description

technical field [0001] The invention belongs to the field of fluorescent probes. Specifically, the present invention relates to a fluorescent probe for the detection of tumor hypoxia using 1,8-naphthoimideazobenzene as a parent and a preparation and detection method thereof. Background technique [0002] Fluorescent molecular imaging is one of the most promising, hottest and most important directions in optical imaging. It mainly uses fluorescent molecular probes to specifically mark target cells or target molecules in vivo, and the marked target parts emit fluorescent signals under the excitation of external light sources. Dynamic and real-time tracking of biological processes at the horizontal level. Molecules (including small molecules, polymers, and nanoparticles) that transmit the interaction between molecules through fluorescent signals are called fluorescent molecular probes or fluorescent molecular sensors. As a microanalysis technique with high sensitivity, good ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07F5/02C07D405/12C09K11/06G01N21/64
Inventor 朱维平余涛徐玉芳钱旭红
Owner EAST CHINA UNIV OF SCI & TECH
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