Photothermal reagent for identifying tumor cells through pH control and preparation method and application thereof

A technology of photothermal reagents and tumor cells, which can be applied in the direction of antineoplastic drugs, pharmaceutical formulations, medical preparations containing active ingredients, etc., and can solve problems such as poor photostability, low photothermal conversion efficiency, and variable structure

Inactive Publication Date: 2016-06-22
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(4) Organic dyes, such as: indocyanine green, Prussian blue, polyaniline, etc., have the advantage of variable structure, and the current discovery is that the light-to-heat conversion efficiency is low and the photostability is not good

Method used

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  • Photothermal reagent for identifying tumor cells through pH control and preparation method and application thereof
  • Photothermal reagent for identifying tumor cells through pH control and preparation method and application thereof
  • Photothermal reagent for identifying tumor cells through pH control and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of 2-chloro-3-hydroxymethyl-cyclohex-1-ene carboxaldehyde: Prepare 40 mL of ice-cold N,N-dimethylformamide and dichloromethane mixed solution with a volume ratio of 1:1, under nitrogen protection , slowly add 20mL of phosphorus oxychloride solution dropwise, react for 30 minutes, add 20mL of cyclohexanone, stir vigorously and heat up to 80 o C reaction. After the reaction is complete, pour it into a large amount of ice water and let it stand overnight. A large amount of yellow solids are produced, and the product is obtained by filtration and washing. 1 H-NMR (300MHz, CDCl 3 ):1.57(m,2H),2.35(t,4H,J=6.3Hz),2.5(s,1H),10.10(s,1H).

Embodiment 2

[0043] Preparation of 1-(2-carboxyethyl)-2,3,3-trimethyl-4,5-phenylindole: measure 80 ml of 1,2-dichlorobenzene, add 10 mmol of 2,3,3 -Trimethyl-4,5-phenylindole and 10mmol of 3-bromopropionic acid, the mixture was stirred and heated to 80 o C, react for 20-30 hours, after the reaction is completed, filter to obtain a solid, wash with ether, and dry to obtain a solid for subsequent use; 1 HNMR (DMSO-d 6 ,400MHz):δ8.36(d,1H,J=8.37),8.273(d,1H,J=8.28),8.206(dd,2H,J=8.20),7.765(t,1H,J=7.78), 7.706(t,2H,J=7.72),4.761(t,2H,4.78),3.029(t,2H,3.05),2.97(s,3H),1.75(s,6H).

Embodiment 3

[0045] Preparation of compound PTT-pH: Dissolve 10 mmol of 2-chloro-3-hydroxymethyl-cyclohex-1-enecarboxaldehyde in 20 mL of acetic anhydride, add 10 mmol of 1-(2-carboxyethyl)-2,3 , 3-trimethyl-4,5-phenylindole and 10 mmol of 2,3,3-trimethyl-4,5-phenylindole, heat to 70 o C, react for 24 hours, extract the aqueous phase several times with dichloromethane, combine the organic phases, and dry the organic phases with anhydrous magnesium sulfate. The above solution was filtered, the filtrate was removed, and the solvent was removed in vacuo to obtain the crude product. The pure product was obtained by thin layer chromatography. 1 HNMR (DMSO-d 6 ,400MHz):δ8.42(d,1H,J=8.37),8.26(m,3H),8.05(t,4H,J=8.20),7.72(d,1H,J=7.78),7.62(t, 3H,J=7.72),7.50(t,3H,J=7.78),6.43(d,1H,J=7.05),6.29(d,1H,J=7.56),4.49(s,2H),2.74(s ,6H),1.95(s,8H),1.78(t,6H,J=8.05),ESIm / z(C 41 H 40 ClN 2 O 2 + ):calc:627.2772;found:627.2773.

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Abstract

The invention belongs to the technical field of photothermal reagents, and particularly relates to a photothermal reagent and synthesis thereof and application of serving as the photothermal reagent under the excitation of a near-infrared 808-nm laser.The designed compound has a property of pH sensitivity and can identify tumor cells by responding to a cellular microenvironment.In the tumor cells, the compound in a weak acid environment can serve as the photothermal reagent to achieve a photothermal therapy under the induction of near-infrared light.In normal cells, due to the fact that the normal cells are alkalescent, a photothermal reaction almost does not exist under the induction of the near-infrared light.

Description

technical field [0001] The invention belongs to the technical field of photothermal reagents, and in particular relates to a photothermal reagent and its synthesis, as well as its application as a photothermal therapeutic reagent excited by near-infrared 808nm laser. Background technique [0002] Photothermal therapy is to use materials with high photothermal conversion efficiency, inject them into the human body, use targeted recognition technology to make them gather at the tumor site, and convert light energy into heat energy under the irradiation of external near-infrared light. A therapeutic method in which locally generated high temperatures are used to kill tumor cells. The advantages of photothermal therapy are: (1) reduce the pain experienced by patients; (2) the treatment time is short, only a few minutes, and the treatment effect is obvious; (3) the material is non-toxic and harmless, and has little toxic and side effects on the human body. [0003] At present, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/10A61K41/00A61K31/404A61P35/00
CPCA61K31/404A61K41/0052C07D209/10
Inventor 易涛薛峰峰温莹魏鹏李若涵
Owner FUDAN UNIV
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