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Organic near-infrared two-photon fluorescent dye

A two-photon fluorescence and near-infrared technology, applied in the chemical field, can solve the problems of two-photon fluorescence characteristics of carbocyanine dyes, and achieve the effects of improved two-photon fluorescence efficiency, good water solubility, and stable chemical properties

Inactive Publication Date: 2013-05-29
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] So far, there has been no report on the two-photon fluorescence characteristics of carbocyanine dyes

Method used

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  • Organic near-infrared two-photon fluorescent dye
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  • Organic near-infrared two-photon fluorescent dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] In the present invention, the near-infrared fluorescent compound has the structure of formula I:

[0051]

[0052] Formula I

[0053] Wherein, X is chlorine or bromine or iodine or ClO 4 - ; 1 is no substituent or alkyl or chlorine or nitro or sulfonate or carboxyl; R 2 is chlorine or bromine; n is 1 or 2 or 3 or 4 or 5 or 6 or 7 or 8 or 9 or 10 or 11 or 12;

[0054] Its synthetic route is shown in formula II,

[0055]

[0056] Formula II.

[0057] Among the present invention, the structural formula of preferred embodiment compound is as shown in Table 1,

[0058] Table 1

[0059]

[0060]

Embodiment 2

[0061] Embodiment 2 synthesizes dialdehyde

[0062]

[0063] 7.2mL POCl 3 and 2g cyclohexanone dissolved in 10mL CH 2 Cl 2 Add it dropwise to 8mL DMF and 8mL CH in an ice-water bath and magnetic stirring 2 Cl 2 in the mixed solution. After the dropwise addition, it was moved to room temperature and heated to reflux in an oil bath at 65°C for 3h. After cooling, the reaction solution was poured into 50°C ice water, left at room temperature to melt, and then transferred to a separatory funnel for static layering. After removal of the lower organic solution, a yellow precipitate was obtained by filtration in the upper aqueous phase. After repeated washing with ice water and vacuum drying, 2.5 g of the reactant was obtained with a yield of 71.8%.

Embodiment 3

[0064] Embodiment 3 synthetic compound 1

[0065]

[0066] 198 mg (1.25 mmol) of 2,3,3-trimethylindole and 0.56 g (4 mmol) of butane sultone were dissolved in 5 ml of o-dichlorobenzene. Under nitrogen atmosphere, 120°C oil bath with magnetic stirring, reflux reaction for 12h. After the reaction solution was cooled to room temperature, it was dropped into 50 ml of glacial diethyl ether at 0°C. After the red precipitate precipitated, it was suction filtered, redissolved in 10ml of distilled water, and washed with CHCl 3 Extraction and freeze-drying gave 1284 mg of the compound with a yield of 76.9%.

[0067]

[0068] Dissolve 241mg (1.25mmol) of 2,3,3-trimethyl-5-chloroindole and 0.56g (4mmol) of butane sultone in 5ml of o-dichlorobenzene, in a nitrogen atmosphere, in an oil bath at 120°C Magnetic stirring, reflux reaction for 12h. After the reaction solution was cooled to room temperature, it was dripped into 50ml of glacial ether at 0°C, a red precipitate precipitate...

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Abstract

The invention belongs to the field of chemistry and relates to an organic near-infrared two-photon fluorescent dye with a structure in a formula I in the specification. The organic near-infrared two-photon fluorescent dye has the beneficial effects that after being excited, the organic near-infrared two-photon fluorescent dye simultaneously shows stronger luminous efficiency of single-photon near-infrared fluorescence and two-photon fluorescence; the efficiency of two-photon fluorescence is obviously improved compared with that of other carbocyanine dyes; living cell fluorescence microscope experiments show that probes prepared from the fluorescent dye can enter tumor cell lysosome through endocytosis and can be imaged and simultaneously monitored by single-photon fluorescence and two-photon fluorescence microscopes; the dye can achieve synchronous single-photon near-infrared fluorescence and two-photon fluorescence imaging in the in-vivo and in-vitro states; and the fluorescent dye has the characteristics o good water solubility and stable chemical properties, can be used or bio-macromolecular markers and in the field of medical image diagnosis and especially has strong application value in optical image guided tumor excision.

Description

technical field [0001] The invention belongs to the field of chemistry, and relates to an organic near-infrared two-photon fluorescent dye, in particular to an organic near-infrared two-photon fluorescent dye with specific reactivity that can be used for biomacromolecule labeling; the organic near-infrared two-photon fluorescent dye is water-soluble Good, stable chemical and optical properties, high luminous efficiency of single-photon near-infrared fluorescence and two-photon visible fluorescence. Background technique [0002] Optical imaging is a non-invasive medical imaging technology that has emerged in recent years. It has the advantages of no ionizing radiation, low cost, easy operation, and long-term dynamic monitoring [Koo, V.et al, Cell Oncol.2006, 28(4), 127-139]; the optical imaging technology has become a cancer One of the key technologies for the diagnosis and adjuvant treatment of major diseases. In addition, optical imaging technology can also monitor import...

Claims

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Application Information

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IPC IPC(8): C09B23/10C09K11/06A61K49/00C12Q1/02
Inventor 李聪陈溪山王璐
Owner FUDAN UNIV
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