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Synthesis and application of double-function water-soluble perylene bisimide derivative

A perylene imide and derivative technology, applied in the field of chemical synthesis, can solve problems such as safety problems, low gene transfection efficiency, and limited application range, and achieve good detection, excellent water solubility, and good selectivity

Active Publication Date: 2014-04-30
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the commonly used gene vectors mainly include viral and non-viral types. Viral gene transfection vectors have safety issues and limitations of low gene transfection efficiency, which limits their scope of application.

Method used

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  • Synthesis and application of double-function water-soluble perylene bisimide derivative
  • Synthesis and application of double-function water-soluble perylene bisimide derivative
  • Synthesis and application of double-function water-soluble perylene bisimide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1. Add 212mg (0.25mmol) of perylene derivatives 4Cl-PDI and 366mg (3mmol) of 4-hydroxybenzaldehyde into two reaction tubes, then add 138mg (0.1mmol) of K 2 CO 3 , then dissolved with 4mL of DMF, stirred evenly under a nitrogen atmosphere, and then reacted at 100°C for 72h; after the reaction was complete, cooled to room temperature, washed with dilute hydrochloric acid, filtered, and then washed with deionized water until the solid product was neutral, and purified on a silica gel column , the obtained product is denoted as CHO-PDI1, and the yield is 60.8%;

[0043] 1 H NMR (400MHz, CDCl3) δ9.95(s, 4H), 8.35(s, 4H), 7.85(d, J=8.7Hz, 8H), 7.48(t, J=7.8Hz, 2H), 7.32(d ,J=7.8Hz,4H),7.09(d,J=8.6Hz,8H),2.70(dt,J=13.6,6.8Hz,4H),1.15(d,J=6.8Hz,24H).

[0044]

[0045] 2. Add 12mg (0.01mmol) of the product CHO-PDI1 of step 1 and 27mg (0.24mmol) of 2-aminoethanethiol hydrochloride into the reaction tube, add 2mL of DMF to dissolve it, and use 2mL of dichloromethane to disso...

Embodiment 2

[0051] 1. Add 424mg (0.5mmol) perylene derivative 4Cl-PDI and 750mg (5mmol) 4-formaldehyde phenylboronic acid to the reaction tube, then add 2mL K 2 CO 3 (1M) solution, then dissolve with the toluene of 6ml, freeze the air in the pumping reaction tube in the nitrogen atmosphere 3 times, add the catalyst Pb (PPh) of 200mg (0.17mmol) in the nitrogen atmosphere 3 ) 4 ;Finally placed in a dark room at 80°C for 48h; the product was purified by a silica gel column, recorded as CHO-PDI2, with a yield of 30.2%;

[0052]

[0053] 2. Add 11mg (0.01mmol) of the product CHO-PDI2 of step 1 and 27mg (0.24mmol) of 2-aminoethanethiol hydrochloride into the reaction tube, add 2mL of DMF to dissolve it, and use 2mL of dichloromethane to dissolve 34mg (0.24mmol) Catalyst BF 3 ·Et 2 O, then added to the reaction tube, reacted at 40°C for 4 days, centrifuged, dissolved the precipitate with methanol (0.5-1mL), and then precipitated with ether (30-50mL), and finally dissolved the product in d...

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Abstract

The invention discloses preparation of a double-function water-soluble perylene bisimide derivative and an application of the derivative to a mercury ion probe and a gene carrier. A perylene fluorescent core CHO-PDI carrying four formyl groups is utilized, and a protection reaction is carried out on the formyl groups by sulfydryl to obtain the double-function water-soluble perylene bisimide derivative. On basis of de-protection reaction of mercury ions to the formyl groups of the double-function water-soluble perylene bisimide derivative, the aim of highly-sensitively and highly-selectively rapidly detecting the trace mercury ions in water is realized; the double-function water-soluble perylene bisimide derivative has very good biocompatibility and very low cytotoxicity; an amino with a positive charge is carried at the periphery of a molecule, can enter a live body culture cell and can be combined with DNA (Deoxyribonucleic Acid) or RNA (Ribonucleic Acid) with a negative charge to form a stable compound which is used as a carrier for carrying and protecting an exogenous nucleic acid to enter the live body culture cell. In combination with the two functions, the double-function water-soluble perylene bisimide derivative can be applied to biological cell imaging to detect the mercury ions in the cells.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to the preparation of a bifunctional perylene imide derivative and its application on mercury ion probes and gene carriers. Background technique [0002] Pure mercury is a common toxic metal, its vapor is highly toxic, and most of its compounds and salts are very toxic, which can cause brain and liver damage after oral administration, inhalation or contact, among which the most dangerous mercury organic compound is di Methylmercury (C 2 h 6 Hg), only a few microliters can be fatal in contact with the skin. Although mercury has a high boiling point, mercury vapor saturated at room temperature has reached several times the poisoning dose. Since pure mercury is easily oxidized to form compounds, only a very small amount of mercury exists in the state of pure metal in nature. Therefore, the selective and high-sensitivity recognition of mercury ions has importan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/64C12N15/63
CPCC07D471/06C09K11/06C09K2211/1029C12N15/87G01N21/33G01N21/6402G01N21/6428C09B5/62C12N15/63
Inventor 尹梅贞刘柯兰许泽军何碧程沈杰
Owner BEIJING UNIV OF CHEM TECH
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