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Synthesis and application of photosensitive medicament taking folic acid as targeted group

A photosensitive and targeted technology, which can be used in drug combinations, medical preparations without active ingredients, and medical preparations containing active ingredients, etc. It can solve problems such as hindering application, limited ability of Pyro tumor localization, and tissue damage.

Active Publication Date: 2017-01-04
康宏药源(河南)科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Pyro's limited tumor localization ability and poor water solubility make it cause damage to normal tissues, resulting in severe phototoxicity, which hinders its clinical application (Jasinski, 2009)

Method used

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  • Synthesis and application of photosensitive medicament taking folic acid as targeted group
  • Synthesis and application of photosensitive medicament taking folic acid as targeted group
  • Synthesis and application of photosensitive medicament taking folic acid as targeted group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The compound that is called for short Pyro-Maleimide and the compound that is called FA-Pyro for short (attachment figure 1 ).

[0036] The synthesis process integrates the solid-phase synthesis method and the liquid-phase synthesis method, and facilitates large-scale preparation on the basis of simplifying the post-treatment process. Among them, the synthesis of FA-Pyro adopts the classic reaction method of thiol and maleimide, which greatly improves the yield of the compound.

[0037] 1. Synthesis of a compound called FA-Cys-SH for short

[0038] FA-Cys-SH is synthesized by Fmoc-based solid phase synthesis. Weigh 1g of 2-chlororitylchloride resin (1g, 0.5mmol, 1.0eq) into a solid-phase synthesizer, add 10ml of dichloromethane (DCM) to swell for 20min. Fmoc-Cys(Trt)-OH (351mg, 0.6mmol, 1.2eq) and N,N-diisopropylethylamine (DIEA, 198μl, 1.2mmol, 2.4eq) were dissolved in 8ml DCM and added to the solid-phase synthesis Reactor at room temperature for 4h. Configure a b...

Embodiment 2

[0047] Spectral properties of FA-Pyro and Pyro (attached figure 2 ).

[0048] (1) UV-Vis spectrum

[0049] The absorption spectra of FA-Pyro and Pyro were scanned with USA Cary 5000 in the wavelength range 300–850. The concentrations of FA-Pyro and Pyro were 10 μM, respectively.

[0050] (2) Fluorescence excitation and emission spectra

[0051] The fluorescence emission spectrum uses 665nm as the excitation light, and the recording spectrum ranges from 600-900nm. The fluorescence excitation spectrum uses 675 as the emission light, and the recording excitation light range is 450-800nm. The concentration of FA-Pyro and Pyro was recorded as 5 μM. The photomultiplier tube (PMT) voltage is 700V, and the scanning speed is 2400nm / min.

[0052] Experimental results and conclusions:

[0053] The spectral properties of FA-Pyro and Pyro are the absorption spectrum and fluorescence spectrum properties such as figure 2 As shown in A and 2B: in DMSO, the spectral properties of FA-...

Embodiment 3

[0055] Compound FA-Pyro's ability to kill tumor cells (attached image 3 ).

[0056] 1) Culture of KB (human oral epidermal carcinoma cell) and A549 (human lung bronchial carcinoma cell) cell lines

[0057] The cells were taken out of liquid nitrogen, placed in a 37°C water bath to thaw quickly, and then centrifuged at 1000rpm / min for 5min. Replace the supernatant, add preheated complete medium, and place in a 5% CO2, 37°C incubator to culture overnight. The medium was changed the next day. Continue to culture until the cells cover the bottom of the dish. Subculture 2-3 times.

[0058] 2) drug and cell incubation

[0059] Take the cells in the logarithmic phase, with 5×10 3 Add 100 μL of cell suspension to a 96-well plate at a cell density of 1 cell / well, and incubate for 24 hours in a 37°C incubator. After aspirating the medium, add fresh medium containing different FA-Pyro concentrations to continue culturing for 6 hours, use 660nm, 40-mW / cm 2 Give different light do...

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Abstract

The invention discloses synthesis and application of a photosensitive medicament taking folic acid as a targeted group. Micro-molecular folic acid is selected to serve as the targeted group to link Pyro. Because of the water solubility of the folic acid and a hydrophilic group in a linker, the linker can improve the water solubility and the pharmacokinetic characteristics of the Pyro so as to improve a photodynamic treatment effect.

Description

technical field [0001] The present invention relates to the synthesis of photosensitive drug called FA-Pyro for short and its application in tumor photodynamic therapy. Background technique [0002] At present, the clinical methods for treating cancer mainly include radiotherapy, chemotherapy and surgery. However, while these traditional treatment methods kill tumor tissues, they also damage normal tissues of the body and cause systemic toxicity. Photodynamic therapy (Photodynamic Therapy, PDT), as a minimally invasive treatment strategy for clinical application, has attracted more and more attention. [0003] The therapeutic effect of PDT needs to be combined with the following three elements: 1. A photosensitizer that can be enriched in tumor tissue; 2. Light of a specific wavelength required to excite the photosensitizer; 3. Oxygen (O 2 ). When the photosensitizer is excited by light of a specific wavelength, it utilizes the O in the tissue 2 Singlet oxygen is generat...

Claims

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Application Information

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IPC IPC(8): C07D519/00A61K41/00A61K47/48A61P35/00
CPCA61K41/0071C07D519/00
Inventor 洪章勇黄伟强
Owner 康宏药源(河南)科技有限公司
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