Hypocrellin derivative substituted both in a peri-position and in 2-position by amino, preparation method, and application thereof

US11439707B2 · kind B2 · utility

Assignee

• Technical institute of physics and chemistry of the chinese academy of sciences · CN

Inventors

• Pengfei Wang · Shanghai, CN
• Jiasheng Wu · Reading, US
• Weimin Liu · Sandy Hook, US
• Xiuli Zheng · Beijing, CN
• Ying Gu · Fujian, CN

Key dates

• Filing date: Sep 5, 2018
• Grant date: Sep 13, 2022
• Expiry date: Nov 19, 2038

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/54
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention discloses a hypocrellin derivative substituted both in a pen-position and in a 2-position by an amino, and a preparation method and use thereof. A general structural formula of the derivative is as represented by formulas I-a to I-d:The hypocrellin derivative substituted both in a peri-position and in a 2-position by an amino prepared in the present invention has a maximum absorption wavelength of 600-650 nm and a molar extinction coefficient reaching about 20000-40000 M−1cm−1. Compared with unmodified hypocrellin or hypocrellin having only a 2-position modified, an absorption spectrum of the derivative is significantly red-shifted and the molar extinction coefficient is greatly improved, and the derivative can efficiently produce reactive oxygen species such as singlet oxygen in a photosensitive condition. In the same condition, the hypocrellin derivative substituted both in a pen-position and in a 2-position by an amino involved in the present invention, when used as a photosensitizer, has a stronger ability to photo-dynamically inactivate tumor cells than the first and second generation commercial photosensitizers.