2. Academic Validation
  3. Synthesis, optical properties and preliminary in vitro photodynamic effect of pyridyl and quinoxalyl substituted chlorins

Synthesis, optical properties and preliminary in vitro photodynamic effect of pyridyl and quinoxalyl substituted chlorins

  • Bioorg Med Chem. 2015 Apr 15;23(8):1684-90. doi: 10.1016/j.bmc.2015.03.021.
Jiazhu Li 1,  Xin Zhang 2,  Yang Liu 3,  Il Yoon 4,  Dong-Kyoo Kim 5,  Jun-Gang Yin 3,  Jin-Jun Wang 3,  Young Key Shim 6
Affiliations

Affiliations

  • 1 College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China. Electronic address: jiazhu82@ytu.edu.cn.
  • 2 School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang 110016, China.
  • 3 College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
  • 4 PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea.
  • 5 Department of Biomedicinal Chemistry and Institute of Basic Science, Inje University, Gimhae 621-749, Republic of Korea.
  • 6 PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea. Electronic address: ykshim@inje.ac.kr.
PMID: 25797162 DOI: 10.1016/j.bmc.2015.03.021
Abstract

A series of chlorophyll a-based chlorins conjugated with pyridyl or quinoxalyl group at different positions were synthesized, characterized and evaluated for their photodynamic effect in vitro. It was found that all the pyridyl and quinoxalyl chlorins showed promising photocytotoxicities but nontoxic without irradiation in HeLa cells, and the substituted types and positions had a significant influence on the photocytotoxicities of the chlorophyll a-based chlorins. All the chlorins with a pyridyl group at the C-D ring end exhibited relatively high photocytotoxicity as compared to those with 3(2)-pyridyl. Among them, compound 12 conjugated with a pyridyl group at its C12 position showed the best photodynamic effect in HeLa cells with an IC50 value of 0.033μM. These facts, associated with the relative high long wavelength absorptions of those chlorins may provide valuable ways to design and prepare promising photosensitizers for application in photodynamic therapy.

Keywords

Chlorophyll a; Photodynamic therapy; Photosensitizer; Pyridyl chlorin; Quinoxalyl chlorin.

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