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Application of a kind of highly charged cationic porphyrin in the preparation of pdt nano photosensitizer

A photosensitizer and cationic technology, which is applied in the application field of highly charged cationic porphyrins in the preparation of PDT nano photosensitizers, can solve the problems of reducing potential treatment of deep tumors, low tissue penetration ability, and short wavelength of light absorption, and achieve high photoinduced Effects of cytotoxicity, low dark toxicity, phototoxicity, and simple preparation method

Active Publication Date: 2021-12-07
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently clinically used photosensitizers still have defects such as low cellular uptake, strong dark toxicity, poor targeting, and short wavelengths of light absorbed (resulting in low tissue penetration and reduced potential for treating deep tumors).

Method used

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  • Application of a kind of highly charged cationic porphyrin in the preparation of pdt nano photosensitizer
  • Application of a kind of highly charged cationic porphyrin in the preparation of pdt nano photosensitizer
  • Application of a kind of highly charged cationic porphyrin in the preparation of pdt nano photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A kind of preparation of PDT nano photosensitizer:

[0039] (1) Fmoc-H / Zn 2+ Preparation of:

[0040] Fluorenylmethoxycarbonyl-L-histidine (hereinafter referred to as Fmoc-H) was dissolved in 50mM HCl to prepare a Fmoc-H solution with a concentration of 10mg / mL; then, the Fmoc-H solution and ZnCl 2 The solution was added to water to prepare a final concentration of 0.5 mM ZnCl 2 and an aqueous mixture of Fmoc-H at 1 mg / mL; the pH of the mixture was adjusted to neutral by adding 1M Tris solution, and self-assembled to form nanospherical particles Fmoc-H / Zn 2+ .

[0041] (2) Fmoc-H / Zn 2+ Preparation of / OMHEPzEOPP:

[0042] Dissolve the porphyrin OMHEPzEOPP in a Tris solution with a concentration of 50mg / mL 2M as a stock solution of porphyrin; to the Fmoc-H / Zn prepared above 2+ Add OMHEPzEOPP dissolved in 2M Tris-HCl buffer to the final concentration of OMHEPzEOPP to 1mg / mL to obtain a mixture; mix this mixture and place it in a centrifuge for centrifugation, remove...

Embodiment 2

[0047] (1) Cellular uptake and confocal microscopy imaging.

[0048] (A) Cell culture. The incubator was maintained at 37 °C, 5% CO 2 , HeLa cells were cultured in DMEM containing 10% fetal bovine serum and 1% double antibody.

[0049] (B) Adding nanocomposite photosensitizer. Fmoc-H / Zn 2+ / OMHEPzEOPP / AS1411 (the concentration of OMHEPzEOPP is 0.5μM) was co-incubated with Hela cells for 1h, 4h, 12h, and 24h, respectively recorded as samples 1, 2, 3, and 4, and washed 3 times with PBS to remove uningested drugs , and then fix the cells with 4% paraformaldehyde for 15 min.

[0050] (C) Experimental results obtained using laser confocal imaging. Olympus IX-81 microscope was used for laser confocal imaging, and 458nm was selected as the excitation wavelength of the diode-pumped laser. Obtain nanocomposite photosensitizer Fmoc-H / Zn 2+ Confocal fluorescence microscopy images of / OMHEPzEOPP / AS1411 co-incubated with HeLa cells for 1h, 4h, 12h, 24h. (See Figure 4a to Figure 4...

Embodiment 3

[0061] Preparation of a highly charged cationic porphyrin:

[0062] Highly charged cationic porphyrin chemical name: octaiodide 5,10,15,20-tetra{4-[2-[1,4-dimethyl-4-(2-hydroxyethyl)piperazine-1- base] ethoxy] phenyl} porphyrin. (OMHEPzEOPP for short), see figure 1 .

[0063] (1) Synthesis of 5,10,15,20-tetrakis[4-(2-bromoethoxy)phenyl]porphyrin

[0064] Add 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin 0.23mM, 36mM K 2 CO 3 , 40mL N,N-dimethylformamide, magnetic stirring at room temperature. Then, 23mM 1,2-dibromoethane was diluted with 10mL DMF under the condition of avoiding light, and added dropwise into the three-necked flask through a constant pressure separating funnel, and stirred evenly by magnetic force at room temperature. After the dropwise addition was completed, the reaction temperature was adjusted to 60° C. and stirred for 8 h. After the reaction was completed, the temperature was lowered to room temperature, filtered under reduced pressure, and potassiu...

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Abstract

The invention discloses the application of a highly charged cationic porphyrin in the preparation of a PDT nano-photosensitizer. The invention utilizes an eight-charged water-soluble porphyrin compound——octaiodide 5,10,15,20-tetra{4-[2- [1,4‑Dimethyl‑4‑(2‑hydroxyethyl)piperazin‑1‑yl]ethoxy]phenyl}porphyrin (OMHEPzEOPP) 8+ 8I ‑ (hereinafter referred to as OMHEPzEOPP) combined with polypeptide nano-carriers, and applied to prepare nano-PDT photosensitizers that can specifically recognize tumor cells.

Description

technical field [0001] The invention belongs to the fields of photodynamic therapy (PDT), chemical analysis and biochemistry, and in particular relates to the application of a highly charged cationic porphyrin in preparing a PDT nano photosensitizer. Background technique [0002] From ancient times to the present, cancer has been a persistent disease and has seriously threatened human health and social development. Common cancer treatment methods include: surgery, chemotherapy, radiotherapy, ultrasound therapy, gene therapy, immunotherapy, magnetic hyperthermia, photothermal therapy, and photodynamic therapy. At present, in the treatment of cancer, traditional methods such as radiotherapy and chemotherapy have some disadvantages. In the course of treatment, it not only kills cancerous tissues and cells, but also causes serious side effects due to loss of function of normal organs, and long-term drug use can lead to multi-drug and drug resistance of tumors. Photodynamic the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0071A61P35/00C07D487/22
Inventor 朱莉娜楚俊卿李永晖
Owner TIANJIN UNIV
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