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Naphthalimide two-photon fluorochrome and preparation method and application thereof

A two-photon fluorescence, naphthalimide technology, applied in naphthalimide compounds and their preparation, fluorescent dyes in biological dyeing, naphthalimide two-photon fluorescent dyes, and imaging applications, can solve the problem of cytotoxicity , poor water solubility, etc., to achieve the effect of improving water solubility, good water solubility, and good transfection efficiency

Active Publication Date: 2016-05-04
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Two-photon fluorescent probes using naphthalimide as a fluorophore have attracted more and more attention. However, most naphthalimide compounds have poor water solubility and still need to be dissolved in a mixed solvent of water and organic solvents. Cytotoxicity

Method used

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  • Naphthalimide two-photon fluorochrome and preparation method and application thereof
  • Naphthalimide two-photon fluorochrome and preparation method and application thereof
  • Naphthalimide two-photon fluorochrome and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: 4-branched PEI-N-butyl-1,8-naphthalimide (T-1)

[0045] The present embodiment provides a kind of naphthalimide compound 4-branched PEI-N-butyl-1,8-naphthalimide (represented by T-1 below), its structure is shown in the following formula; Wherein, PEI Be the branched PEI of molecular weight 2000;

[0046]

[0047] Its preparation method is as follows:

[0048] 1) Add 4-bromo-1,8-naphthalene anhydride (542mg, 2mmol) and n-butylamine (205μl, 2.1mmol) into ethanol (150ml) in a round-bottomed flask, heat at reflux at 80°C for 3h, and react The liquid was concentrated and precipitated, and filtered to obtain a yellow solid, which was the intermediate M-1, with a molecular weight of 331 and a yield of 90%; 1 The HNMR data are as follows:

[0049] 1 HNMR (400MHz, CDCl 3 )δ (ppm) 8.65 (dd, J = 8.0Hz and 0.8Hz, 1H), 8.56 (d, J = 8.0Hz, 1H), 8.41 (d, J = 8.0Hz, 1H), 8.03 (d, J = 8.0Hz, 1H), 7.84(t, J=8.0Hz, 1H), 4.18(t, J=8.0Hz, 2H), 1.74–1.68(m, 2H), 1.45–1.4...

Embodiment 2

[0055] Example 2: 4-branched PEI-N-(N,N-dimethylethylenediamine)-1,8-naphthalimide (T-2)

[0056] This embodiment provides a naphthalimide compound 4-branched PEI-N-(N,N-dimethylethylenediamine)-1,8-naphthalimide (hereinafter represented by T-2), Its structure is shown in the following formula; wherein, PEI is a branched PEI with a molecular weight of 2000;

[0057]

[0058] Its preparation method is as follows:

[0059] 1) Add 4-bromo-1,8-naphthalene anhydride (542mg, 2mmol) and N,N-dimethylethylenediamine (230μl, 2.1mmol) to ethanol (150ml) in a round-bottom flask, 80°C After heating to reflux for 3 hours, the reaction solution was concentrated and precipitated, and filtered to obtain a yellow solid, which was intermediate M-2, with a yield of 88%; M-2 1 The HNMR data are as follows:

[0060] 1 HNMR (400MHz, CDCl 3 )δ (ppm) 8.66 (dd, J = 7.2Hz and 1.2Hz, 1H), 8.57 (dd, J = 8.0Hz and 0.8Hz, 1H), 8.41 (d, J = 8.0Hz, 1H), 8.04 (d ,J=8.0Hz,1H),7.84(t,J=8.0Hz,1H),4.32(t,...

Embodiment 3

[0064] Example 3: 4-branched PEI-N-n-hexadecylamino-1,8-naphthalimide (T-3)

[0065] This embodiment provides a naphthalimide compound 4-branched PEI-N-n-hexadecylamino-1,8-naphthalimide (hereinafter represented by T-3), its structure is shown in the following formula; Wherein, PEI is the branched PEI of molecular weight 2000;

[0066]

[0067] Its preparation method is as follows:

[0068] 1) Add 4-bromo-1,8-naphthalene anhydride (542mg, 2mmol) and n-hexadecylamine (507mg, 2.1mmol) into ethanol (150ml) in a round bottom flask, heat at reflux at 80°C for 3h, The reaction solution was concentrated and precipitated, and filtered to obtain a yellow solid, which was intermediate M-3, with a yield of 85%; M-3 1 The HNMR data are as follows:

[0069] 1 HNMR (400MHz, CDCl 3 )δ (ppm) 8.67 (d, J = 6.4Hz, 1H), 8.57 (d, J = 8.4Hz, 1H), 8.41 (d, J = 7.6Hz, 1H), 8.04 (d, J = 8.0Hz, 1H), 7.84(t, J=7.6Hz, 1H), 4.16(t, J=7.6Hz, 2H), 1.76–1.26(m, 28H), 0.88(t, J=6.4Hz, 3H).

[0070] ...

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Abstract

The invention belongs to the field of fine chemical engineering, and discloses naphthalimide two-photon fluorochrome and a preparation method and application thereof. The naphthalimide two-photon fluorochrome is a naphthalimide compound of which the 4-bit is coupled with low molecular weight PEI (polyethyleneimine) and the N-bit is substituted by alkane or aliphatic amine disclosed in the formula. The naphthalimide two-photon fluorochrome has the advantages of two-photon adsorption characteristics, good water solubility, good biocompatibility, small toxicity and short dyeing time, can be used for cell nucleus and lysosome imaging and can realize nonstationary living cell dyeing and imaging, and no leakage phenomena appear when imaging is carried out in a cell.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and relates to a naphthalimide two-photon fluorescent dye, specifically a naphthalimide compound with two-photon absorption characteristics and a low-molecular-weight PEI substitution at the 4-position and a preparation method thereof, and the Application of quasi-fluorescent dyes in biological staining and imaging. Background technique [0002] Two-photon fluorescence microscopy imaging is excited by near-infrared light, which can penetrate specimens and realize tissue and animal imaging; compared with single-photon imaging, it can avoid phototoxicity, fluorescence bleaching, reduce damage to cells, and have high lateral resolution It has the advantages of vertical and horizontal resolution, reduced biological tissue absorption coefficient and autofluorescence interference, and improved imaging effect. Two-photon fluorescent dyes are needed to achieve two-photon microscopy imaging. Therefore, two-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/04C09B57/08C09K11/06
CPCC08G73/0206C09B57/08C09K11/06C09K2211/1029C09K2211/14
Inventor 解丽娟
Owner HUAQIAO UNIVERSITY
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