Porphyrin compound with good water solubility and near-infrared absorption and its preparation method and application

A porphyrin compound, water-soluble technology, applied in the field of water-soluble, near-infrared-absorbing porphyrin compound and its preparation, can solve unsolved problems such as porphyrin solubility, achieve high singlet oxygen yield, low dark toxicity, phototoxic short effect

Active Publication Date: 2019-04-19
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Agnieszka Nowak-Król et al. (Agnieszka Nowak-Król, Craig J.Wilson, Mikhail Drobizhev, et al.ChemPhysChem, 2012,13,3966-3972) designed a class of Trans-A 2 B 2 Type porphyrin, through the introduction of benzyne to enhance the absorption of porphyrin in the infrared and near-infrared region, but did not solve the problem of poor solubility of porphyrin in water

Method used

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  • Porphyrin compound with good water solubility and near-infrared absorption and its preparation method and application
  • Porphyrin compound with good water solubility and near-infrared absorption and its preparation method and application
  • Porphyrin compound with good water solubility and near-infrared absorption and its preparation method and application

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Embodiment 1

[0064] with R 1 structured as R 2 The structure is R 2 = R 1 or choose n 1 =3, M=Zn as an example. Its specific synthetic route is as follows:

[0065] a, the preparation of aldehyde

[0066]

[0067] Take triethylene glycol monomethyl ether (4.4mL, 27.6mmol) and p-toluenesulfonyl chloride (5.7g, 30mmol) and dissolve in 80mL of dichloromethane, and place in a 250mL round bottom flask, then add triethylamine (11.1 mL, 82.5mmol), the mixed solution was stirred and reacted at room temperature for 12h. After the reaction was completed, the solvent was removed by rotary evaporation to obtain an oily mixture. Using ethyl acetate:petroleum ether=2:1 (V / V) as eluent, the product was purified by column chromatography to obtain 9 g of a colorless oily liquid (88 %). 1 HNMR (CDCl 3 ,500MHz): δ=7.81(d,J=10.0Hz,2H),7.34(d,J=10.0Hz,2H),4.17(t,J=5.0Hz,2H),3.69(t,J=5.0Hz ,2H),3.63-3.60(m,6H),3,54(t,J=4.0Hz,2H),3.38(s,3H),2.45(s,3H).MALDI-TOF MS:m / z calcd for C 14 h 22 o 6...

Embodiment 2

[0088] with R 1 structured as R 2 The structure is R 2 = R 1 or choose n 2 =3; M=Zn as an example. Its specific synthetic route is as follows:

[0089] a, the preparation of aldehyde

[0090]

[0091] Weigh 3,4-dihydroxybenzaldehyde (2.76g, 20mmol) and tosylate triethylene glycol monomethyl ether (8.06g, 48mmol) and dissolve in 120mL DMF solution, and place in a 500mL round-bottomed flask, and then Join K 2 CO 3 (8.28g, 60mmol) and LiBr (1.74g, 20mmol), the mixture was heated to 100°C in an oil bath and stirred for 48h. 2M H ​​was added after the reaction 2 SO 4 (200mL) to quench the reaction, after 30min to finish the reaction cooling, extract the organic layer with dichloromethane and deionized water; the organic layer was washed with anhydrous MgSO 4 Dry, filter and remove the solvent by rotary evaporation. Using dichloromethane:methanol=99:1 (V / V) as eluent, the product was purified by column chromatography to obtain 6.6 g (62%) of light yellow oily prod...

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Abstract

The invention belongs to the field of organic synthesis and drugs, and more specifically relates to a porphyrin compound which is high in water solubility and is capable of absorbing near infrared ray, and a preparation method and applications thereof. According to the preparation method, the water solubility of the porphyrin compound is improved via introducing PEG chains and adjusting PEG chain length, and the absorption wavelength of porphyrin photosensitizer molecules is adjusted via introducing acetylene bonds or other conjugate groups. The porphyrin compound possesses relatively high singlet oxygen productive rate, low phototoxicity, and low dark toxicity, and is promising to be applied in photodynamic therapy.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicine, and specifically relates to a water-soluble, near-infrared-absorbing porphyrin compound, a preparation method and application thereof. Background technique [0002] Photodynamic therapy (Photodynamic therapy, PDT) is a new technology that uses cold photochemical reactions for disease diagnosis and treatment, and its basic elements are oxygen, photosensitizers and light sources (commonly used lasers). It excites the photosensitizer absorbed by the tissue through laser irradiation, and the photosensitizer in the excited state transfers energy to the oxygen molecules in the surrounding tissue to generate highly active substances such as singlet oxygen or superoxide free radicals, which are separated from the adjacent Oxidation of biomacromolecules produces cytotoxins, which cause local photodamage of cells, induce cell death or inactivate microorganisms, thereby exerting therapeutic eff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61K31/409A61K31/555A61P31/00
CPCA61K41/0071C07D487/22
Inventor 杨洲钟祥敏潘东王冬曹晖何万里
Owner UNIV OF SCI & TECH BEIJING
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