title: Synthesis, optical properties and preliminary in vitro photodynamic effect of pyridyl and quinoxalyl substituted chlorins.
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.
authors: College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China. Electronic address: jiazhu82@ytu.edu.cn.
authors: Jiazhu
authors: J
authors: Li
authors: School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors: Xin
authors: X
authors: Zhang
authors: College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
authors: Yang
authors: Y
authors: Liu
authors: PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea.
authors: Il
authors: I
authors: Yoon
authors: Department of Biomedicinal Chemistry and Institute of Basic Science, Inje University, Gimhae 621-749, Republic of Korea.
authors: Dong-Kyoo
authors: DK
authors: Kim
authors: College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
authors: Jun-Gang
authors: JG
authors: Yin
authors: College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
authors: Jin-Jun
authors: JJ
authors: Wang
authors: PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea. Electronic address: ykshim@inje.ac.kr.
authors: Young Key
authors: YK
authors: Shim
mesh_terms: D002734:Chlorophyll / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000077194:Chlorophyll A; D006367:HeLa Cells; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D017319:Photosensitizing Agents; D011166:Porphyrins; D011725:Pyridines; D011810:Quinoxalines; D002734:Chlorophyll; C006969:chlorin; D000077194:Chlorophyll A
keywords: Chlorophyll a; Photodynamic therapy; Photosensitizer; Pyridyl chlorin; Quinoxalyl chlorin