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Indocyanine green compound for treating early brain glioma, and preparation method and application thereof

A technology for indocyanine green and glioma, which is applied in the field of indocyanine green compounds and their preparation, can solve the problems of low drug efficiency, cannot realize the integration of diagnosis and treatment, and achieves biological safety and biocompatibility. The effect of good sex and enhancing the ability of aggregation

Active Publication Date: 2020-04-14
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The technical problem to be solved by the present invention is to overcome the defects and insufficiencies of existing drugs that cross the blood-brain barrier, such as low efficiency and inability to realize the integration of diagnosis and treatment, and provide an indocyanine green compound for the treatment of early brain glioma, which has Good biocompatibility, high efficiency, can meet clinical needs, and can realize the integration of diagnosis and treatment

Method used

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  • Indocyanine green compound for treating early brain glioma, and preparation method and application thereof
  • Indocyanine green compound for treating early brain glioma, and preparation method and application thereof
  • Indocyanine green compound for treating early brain glioma, and preparation method and application thereof

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Embodiment 1

[0083] An indocyanine green compound for treating early-stage glioma, named iRGD-ILD, has a molecular structure shown in formula (I):

[0084]

[0085] The preparation method of above-mentioned indocyanine green compound, comprises the steps:

[0086] S1. Preparation of carboxylated indocyanine green (ICG-COOH):

[0087] Stir 4-hydrazinobenzoic acid, methyl isopropyl ketone, and sodium acetate at a molar ratio of 30:42:60 in 50 mL of glacial acetic acid for 1 hour, then heat to reflux for 12 h. After vacuum removal of acetic acid, 80 mL of 10% methanol was added to the residue, filtered and dried to obtain a brown solid product (27.12 mmol, yield 90%);

[0088] The above product and 1,4-butane sultone with a molar ratio of 9.84:57.36 were heated to reflux in 40 mL of 1,2-dichlorobenzene for 12 h to form a red precipitate, which was filtered, washed with acetone, and dried to obtain a red solid ( 9.37mmol, yield 95%);

[0089] Add the above product with a molar ratio of 5...

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Abstract

The invention discloses an indocyanine green compound for treating early brain glioma, and a preparation method and an application thereof. The compound has a molecular structure represented by formula (I) described in the specification. The preparation method comprises the following steps: synthesizing a derivative of near-infrared fluorescent molecule indocyanine green (ICG) with a carboxyl group, then connecting Gd-DTPA to the ICG, and finally connecting a targeting cyclic peptide iRGD to obtain the compound. The addition of the iRGD enables the compound to have the capability of targetingvascular endothelial cells and tumor cells at the same time; the size is extremely small, and the efficiency is high; in the early stage of brain glioma, the ICG fragment can efficiently pass throughthe blood brain barrier, target tumor tissue and perform MR / fluorescence bimodal imaging, and the ICG fragment can also realize photothermal and photodynamic therapy.

Description

technical field [0001] The invention relates to the technical field of treating glioma, and more specifically, relates to an indocyanine green compound for treating early glioma, a preparation method and application thereof. Background technique [0002] Glioblastoma (Glioblastoma multiforme, GBM) is a very fatal disease of the central nervous system, due to the existence of the blood-brain barrier (Blood-Brain Barrier, BBB) hinders 100% of macromolecular drugs and more than 98% of small molecules Drugs pass from the blood into the brain. At present, surgical resection is still the mainstream method for the treatment of glioma, but the incomplete resection of the tumor and the trauma caused by the operation itself make surgical resection accompanied by high risks. [0003] In addition, magnetic resonance imaging (MRI) has been regarded as one of the most effective means for diagnosing various diseases, and the most commonly used MRI contrast agent, Magnevist, has been comme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/107C07D209/42C07D403/14A61K49/00A61K49/14A61K41/00A61K47/64A61P35/00
CPCC07K7/06C07D209/42C07D403/14A61K49/0034A61K49/0056A61K49/14A61K49/0002A61K41/0052A61K41/0057A61K47/64A61P35/00A61K2300/00
Inventor 帅心涛李博李晓霞蔡宇骏陈亚丽
Owner SUN YAT SEN UNIV
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