Issue 39, 2018

Highly efficient green synthesis and photodynamic therapeutic study of hypericin and its derivatives

Abstract

A highly efficient synthetic pathway for hypericin (7a) was achieved under mild conditions with an overall yield over two steps of 92% using emodinanthrone as a starting material, where protohypericin, a key precursor of hypericin, was synthesized in water with microwave assistance, which was then photocyclized to hypericin with a high yield via 1 h irradiation in a visible light reactor equipped with 575 nm monochromatic lamps. In addition, the method could be used to synthesize hypericin derivatives (7b–d) with similar overall yields. Furthermore, their effects of photodynamic therapy (PDT) were evaluated on A431, HepG-2, and MCF-7 cell lines. The PDT of 7b was better than that of 7a, whereas 7c and 7d were worse. Unlike other cell lines, MCF-7 was not sensitive to any of 7a–d at the same concentrations.

Graphical abstract: Highly efficient green synthesis and photodynamic therapeutic study of hypericin and its derivatives

Supplementary files

Article information

Article type
Paper
Submitted
01 Maijs 2018
Accepted
02 Jūn. 2018
First published
13 Jūn. 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 21786-21792

Highly efficient green synthesis and photodynamic therapeutic study of hypericin and its derivatives

Y. Zhang, K. Shang, X. Wu, S. Song, Z. Li, Z. Pei and Y. Pei, RSC Adv., 2018, 8, 21786 DOI: 10.1039/C8RA03732A

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