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Preparation and application of naphthalimide-amino acid compound and modified quantum dot

A naphthalimide and compound technology, applied in the field of medicinal chemistry, to improve water solubility and biological properties, reduce false positive results, and the method is simple and easy to implement

Active Publication Date: 2014-04-23
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the tumor-targeting quantum dots in the prior art still have problems such as wide emission spectrum, uneven size distribution, and low fluorescence quantum yield.

Method used

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  • Preparation and application of naphthalimide-amino acid compound and modified quantum dot
  • Preparation and application of naphthalimide-amino acid compound and modified quantum dot
  • Preparation and application of naphthalimide-amino acid compound and modified quantum dot

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052]Preparation of n = 2, x = 1, when the quantum dots (QDs) are CdSe, the synthesis steps of naphthalimide-amino acid compound and its modified quantum dots:

[0053] 1) Preparation of compound a: Add 1.97 g (10 mmol) of 1,8-naphthalimide ( ), 4.14 g (30 mmol) of anhydrous K in a 100 mL round bottom flask 2 CO 3 , 0.249 g (1.5 mmol) KI, 1.20 g (3.3 mmol) cetyltrimethylammonium bromide and 50 mL acetone, then added dropwise 6.48 g (30 mmol) 1,4-dibromobutane at 20 °C Stir the reaction for 3 days, conduct thin-layer chromatography (TCL) on a silica gel plate, discard the solid in the upper layer by suction filtration, evaporate the solvent under reduced pressure, and elute the residue with petroleum ether and ethyl acetate through flash column chromatography to obtain yellow-white crystals a;

[0054] 2) Preparation of compound b: Take lysine as an example, dissolve 1.46 g (10 mmol) lysine () in 5 mL of water, add 2 mL of saturated NaHCO 3 solution, cooled to 0°C, and slow...

Embodiment 2

[0064] Preparation of n = 2, x = 1, when the quantum dot is CdSe / CdS, the synthesis of quantum dots modified by naphthalimide-amino acid compound:

[0065] 1) Preparation of compound a: Add 1.97 g (10 mmol) of 1,8-naphthalimide ( ), 4.14 g (30 mmol) of anhydrous K in a 100 mL round bottom flask 2 CO 3 , 0.166 g (1.0 mmol) KI, 0.91 g (2.5 mmol) cetyltrimethylammonium bromide and 50 mL acetone, then 4.32 g (20 mmol) 1,4-dibromobutane was added dropwise at 30 °C Stir the reaction for 2 days, detect by thin-layer chromatography (TCL) on a silica gel plate, discard the solid in the upper layer by suction filtration, evaporate the solvent under reduced pressure, and elute the residue with petroleum ether and ethyl acetate by flash column chromatography to obtain yellow-white crystals a;

[0066] 2) Preparation of compound b: Take lysine as an example, dissolve 1.46 g (10 mmol) lysine () in 5 mL of water, add 2 mL of saturated NaHCO 3 solution, cooled to 5°C, and slowly added 1.47...

Embodiment 3

[0074] Preparation of n = 2, x = 1, when the quantum dot is CdSe / ZnS, the synthesis of quantum dots modified by naphthalimide-amino acid compound:

[0075] 1) Preparation of compound a: Add 1.97 g (10 mmol) of 1,8-naphthalimide ( ), 4.14 g (30 mmol) of anhydrous K in a 100 mL round bottom flask 2 CO 3 , 0.498 g (3 mmol) KI, 1.82 g (5 mmol) cetyltrimethylammonium bromide and 50 mL acetone, then added dropwise 10.8 g (50 mmol) 1,4-dibromobutane, stirred at 45 °C Reaction for 3 days, silica gel thin-layer chromatography (TCL) detection, suction filtration discarded the upper solid, evaporated the solvent under reduced pressure, and the residue was eluted with petroleum ether and ethyl acetate by flash column chromatography to obtain yellow-white crystals a;

[0076] 2) Preparation of compound b: Take lysine as an example, dissolve 1.46 g (10 mmol) lysine () in 5 mL of water, add 2 mL of saturated NaHCO 3 solution, cooled to -5°C, slowly added 0.733 g (3.3 mmol) of di-tert-buty...

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Abstract

The invention belongs to the pharmaceutical chemistry field, and concretely relates to a naphthalimide-amino acid compound, its preparation method and an application, and simultaneously relates to a quantum dot modified by the naphthalimide-amino acid compound and its application. The naphthalimide-amino acid compound has a general formula of (img file='2013106912783100004dest_path_image002. TIF' wi='261' he='86' / ). The provided naphthalimide-amino acid compound and its modified quantum dot is the nano-material with high biology targeting and singularity, can realize anti-tumour targeting effect, and make the contribution for the development of new drugs.

Description

[0001] technical field [0002] The invention belongs to the field of medicinal chemistry, and specifically relates to a naphthalimide-amino acid compound and its preparation and application, and also relates to a naphthalimide-amino acid compound modified quantum dot and its application. [0003] Background technique [0004] Due to the differences between cancer cells and normal cell DNA, it is an ideal choice to use DNA as the target of anti-tumor drugs. DNA intercalators play a significant role in the treatment of tumors, and naphthalimide derivatives can be used as cutting agents and intercalating agents to produce anti-tumor activity. Most of the naphthalimide derivatives have a DNA intercalation effect. After intercalating DNA, it can be seen that the DNA double helix is ​​elongated, and the viscosity of the DNA solution increases, thereby further producing obvious biological activity. The structural modification and physiological activity research of natural product...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/88C09K11/02A61K47/48A61K31/473A61K49/00A61P35/00
CPCC07D221/14C09K11/025C09K11/883G01N33/57484
Inventor 赵美霞王超杰李洋
Owner HENAN UNIVERSITY
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